Chapter 7 - ITS: Tasks, Schedules, Resources, and other Non-Human Components

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Chapter 7 - ITS: Tasks, Schedules, Resources, and other Non-Human Components

The Its is the quadrant most of us think of and work with first before any other quadrant.

This is where the disciplines of project management and system design tend to work.

The Its quadrant is all the resources, materials, costs, processes, tools, and other things that we may need to make our desired change real and sticky.

The Project Management Body of Knowledge (fondly called the PMBOK by practitioners) defines multiple control areas to consider when planning and executing a project: scope, procurements, stakeholders and communications, work/tasks, schedule, costs, quality, resources and procurement, and risks.

For large and complex projects, all these areas require consideration.

Thankfully, we don’t need to worry about all these things all at once. We also have significantly more control over these areas. Unlike corporate projects, YOU are the one defining what needs to happen in each area. Furthermore, the level of complexity is under your control.

In this chapter, as we consider all of the materials and systems that our change impacts, we are going to look at the following:

  • Scope – Do we know what our desired outcome is? Are we certain about which direction we are marching?

  • Tasks – Is what we are doing moving us towards our desired outcome? Do we know what that desired outcome is? Are we making things more complicated than we need to?

  • Schedule – Are we performing the tasks when we said we were going to? Are tasks taking more or less time than we anticipated? Do we have the time in our day or week to do the task? Are we able to maintain the boundary around this time?

  • Resources – What resources do you need (tools, materials, skills) for this change to be successful?

  • Costs – How much is all this costing – in time, personal energy, and money?

    The PMBOK is concerned about money in the Budget/Cost Management work area. Time cost is in the Schedule Management work area. I invite you to consider the time and personal energy you spend on an activity as “paid by the hour.” For example, if you make $65/hr at work – use this for your time/energy cost calculation on your change activity. Your “investment” is the number of hours you spend (or think you will spend) on this activity X $65. I find this exercise eye-opening.

We are going to address each area based on the type of change we are trying to make. You define the change you intend to make in Chapter 5.

  • Permanent habit – A concentrated short-term effort to establish the habit

  • Implementation - A short-term push to get things moving, then an operations component that differs from both your current state and from that short-term push.

  • Impermanent Push – A change effort focused with a specific event, goal, and/or date in mind. Our planning will also define an off-ramp.

This chapter will look at scope, tasks, schedules, costs, resources as they appear in each type of change.


Scope Clarity

When a project manager talks about scope, they are talking about what is and is NOT included in the project. In a project manager’s utopian fantasyland – scope is well-defined with solid boundaries. In real life, this seldom (if ever) happens.

Thankfully, in personal change initiatives, we don’t need to worry so much about maintaining solid boundaries around scope. We are making changes to our life.

The key here is to make sure you define what you intend to do, what you WON’T do, and that your activities (or lack thereof) move you in your desired direction.

We spent chapters 4 and 5 starting to refine the scope of the change you wish to make.

Thankfully, in personal change, the scope of your effort is, fundamentally, the goals you set.

The trick is to do the dead minimum it takes to achieve those goals.


Permanent Habit Scope

Remember, permanent habits are set with a concentrated, short-term effort to establish the habit. Much of that effort consists of being mindful of your decision-making, finding time to execute the habit, and tracking whether you are performing the habit.

For example: a change effort of “establish a regular meditation practice” has a scope of “sit down to meditate x minutes per day.” Within the scope are considerations such as:

  • How many minutes per day do you wish your final practice to take?

  • What type of meditation do you want to practice?

  • Do other mindfulness practices – such as yoga – count towards “meditation”?

  • What are your expectations of this practice when it comes to outcomes? This question speaks specifically to Why you want to establish this practice.

Your scope is found within the lag and lead metrics for this initiative that you defined in Chapter 6.

Actions that help you move towards the desired goal are within scope.

  • If you include “yoga” in your meditation count, then “yoga” is within scope. If you have specifically excluded “yoga,” and insist that your meditation practice needs to be separate, then “yoga” is not in scope.

  • If you choose to do transcendental meditation one day, mantra meditation a second day, and mindfulness meditation a third day, and sitting with your eyes closed letting your brain wander about – each for the 15 minutes you defined – if you have not specifically defined what type of meditation you intend to do, these are be in scope.

  • Even “failed” attempts can be in scope. Such as those days that you sit to meditate, then get interrupted 5 minutes later by your kids.

Actions that have nothing to do with the desired goal are not within scope.

  • Going vegan because you feel it will help is not in scope. That’s another initiative.

  • Attending a meditation retreat is a related project (impermanent push). 5 days with 30 people doing nothing but meditation is not necessary to establish a daily meditation practice – therefore I would consider it out of scope. I would treat a multi-day meditation retreat a separate project. Meditation retreats can be expensive and often require clearing out your schedule and arranging to not be disturbed or distracted.

  • You may decide “establishing a yoga practice” is specifically out of scope. Some of us (myself included) treat the last 10 minutes of yoga practice (where you lie on the ground – otherwise known as savasana) as part of meditation practice. Again, it depends upon why you are meditating and what you hope to accomplish with meditation.


Exercise: Permanent Habit Scope

Pull out the lag and lead metrics you defined in Chapter 6 for your project. Also pull out your “Why” from Chapter 3. This information provides reference.

Answer the following questions:

  • What is the habit I am trying to establish?

  • What activities are specifically in-scope?

  • What activities are specifically “out-of-scope?”

  • What guidelines do I want to set for a practice session to “count?”

  • When do I want to evaluate my progress? Do I want to do this evaluation weekly? Monthly? Other?

  • What are the criteria where I can consider myself “successful” at establishing this habit?

    • Note: Give yourself at least 12 weeks of regular practice before “success.” You want to both establish the habit and show that you can keep that habit going. Remember – habits take months to become habitual enough that you don’t have to think about them.

  • What should I look out for to tell me that this habit isn’t working or providing the results I expected?

    • You may want to get information from a friend or expert with experience in the change you are wishing to make. They can help you discern the difference between a common challenge and a reason to quit.

Knowing what your scope and guardrails are as you establish a new habit helps provide that certainty that your brain craves.

Personal permanent habit changes, especially in the longer term, will shift and change as you look for ways to keep your habit fresh and interesting. Knowing what your guardrails are will help you with decision-making as you integrate this new habit into your life.


Implementation Scope

Implementation projects, either personal or professional, can go off-the-rails very quickly without clear guardrails focused on what you are trying to accomplish and what is in and out of scope.

If there are other people involved in your change effort, scope can change very quickly. Especially if you have “idea people” involved.

If this is a personal project with no others involved, the only threat to your scope definition is you. Depending upon your attention-span, this may not be an advantage.

More than any other type of change effort, it is important that you keep the goal the goal.

For example: if you are trying to start a business, you have the short-term push that involves:

  • developing the business plan

  • getting the licensing and legal requirements completed

  • creating the branding

  • establishing the systems

  • sourcing the administrative tools

  • building a marketing strategy and infrastructure

  • and determining the daily operational habits (among other things)

required to establish your business.

Once the business gains clients and starts developing its own rhythm, you then need to define what operations looks like and the guardrails for decision-making in the long-term.


Exercise: Implementation Scope

Pull out the lag and lead metrics you defined in Chapter 6 for your project. Also pull out your “Why” from Chapter 3.

If this is a large project and something you have not done before, I strongly recommend recruiting help or doing some research as you answer these questions. This guidance will help you determine an appropriate scope for your project.

Like any change initiative, the goal is to focus your efforts on the activities that lead towards your goal and minimize any activities that won’t help or will actively distract you.

Answer the following questions:

  • What am I trying to establish?

  • What activities, in the short-term, are specifically in-scope?

    • Implementation projects can be complex. It’s good to make sure that you are clear on what you expect to be doing as part of this effort. We will break down our tasks further later in this chapter.

    • This is

  • What is the best order of prioritization? How do you want to define your sprints or phases?

    • With this question, I am asking what you need to focus on during each period. This approach is particularly handy for complicated change efforts such as starting a business. The first phase could be: creating a business plan. Focus activities would emphasize the research required to create that business plan. The second phase could be: Product or Service creation and the activities around that. The third phase could be: Marketing Strategy and Execution and those activities.

      • What activities are specifically “out-of-scope” for each sprint.

      • What activities become “in-scope” later in the effort or in another sprint?

      • What activities stay “out-of-scope” for this effort? For example, I may come up with 3 different business plans to pursue. 2 of those plans become “out-of-scope” as I attempt to execute on 1 plan.

    • Work with someone who is an expert or who has done the activity before to help you with prioritizing your efforts.

  • What guidelines do I want to set for intaking new activities related to this goal?

  • When do I want to evaluate my progress? Do I want to do this evaluation weekly? Monthly? Other?

  • What are the criteria where I can consider each phase complete?

  • What are the criteria where I can consider the short-term phase complete and ready to move to operations?

  • How long do I anticipate the short-term phase to last?

  • What should I look out for to tell me that this effort isn’t providing the results I expected?

    • Get information from a friend or expert with experience in the change you are wishing to make. They can help you discern the difference between a common challenge and a reason to quit.


Impermanent Push Scope

Impermanent Push efforts have scopes that are easy to define. There is usually an event, goal, or date in mind.

Examples: Lose 30 pounds by my 30th high school reunion next year. Or… Run the Cherry Blossom 10 Miler in May in under 2 hours.

All activities should work toward that goal. Anything that doesn’t help you towards that goal is out-of-scope.

For example: Any training plan I decide to follow if I’m going to run the Cherry Blossom 10 Miler is in scope. This includes sprinting, stair running, weight-lifting, and training miles. Any social media posts I make as I train is out of scope because it doesn’t directly help me run the race. Those posts could help keep me motivated since I will feel accountable to an “audience.” I may have a coach watching these posts and adjusting my training as a result. Still, for me, social media participation is optional when I am training for a race.

I am not actually training to run 10 miles. This is just an example.


Exercise: Impermanent Push Scope

Pull out the lag and lead metrics you defined in Chapter 6 for your project. Also pull out your “Why” from Chapter 3. This information provides reference.

Answer the following questions:

  • What is my goal and deadline?

  • What activities directly help me achieve this goal?

  • What activities are specifically “out-of-scope?”

  • What guidelines do I want to set to determine if an activity is in-scope?

  • When do I want to evaluate my progress? Do I want to do this evaluation weekly? Monthly? Other?

  • What are the criteria where I can consider myself “successful?”

  • Are there criteria where I am still happy with what I accomplished even if I don’t reach my goal?

  • What should I look out for to tell me that this effort isn’t working or providing the results I expected?

    • You may want to get information from a friend or expert with experience in the change you are wishing to make. They can help you discern the difference between a common challenge and a reason to quit.

In an impermanent push, it is good to know your outs. For example, getting injured while training for your race is an “out.”

It is also good to be ok with partial success. For example: losing 20 pounds instead of 30 before the reunion – but I’ve gone down 3 dress sizes. I would consider that a success, even if I didn’t necessarily reach the goal.


Inventory in the Its – what you have

Now that we have defined our scope, let’s look at what we are working with in our current state. This inventory will provide us with an idea of the tasks we will need to complete for our change effort.

As we begin to plan our project, we are looking to minimize our effort. We want to leverage our prior experience and maximize the resources we currently have available. The more we are able to take advantage of our current resources, the less costly – in both energy and money – the change is.


Exercise: SWOT Analysis – Its (resources and materials)

When performing this SWOT Analysis, I invite you to write down the assumptions you are making as you engage with this analysis. Leverage the information you gathered during Pass 3 (What I have) and Pass 4 (What I need).

  • What resources, processes, and systems do you have that will help with this change? What money do you currently have available to fund this change? How do you want to leverage these strengths to be successful?

  • What materials need to be purchased? What processes and systems are you missing? How much money do you need to fund your effort? What can you do to mitigate these weaknesses?

  • What opportunities might surface as you execute on this change? Is there anything on the horizon that could help you with this change? Think both short-term and long-term.

  • What threats might you encounter that could derail us? Are there particular resources that you need that, if they aren’t available or don’t exist, would prevent the execution of your change effort? Is there a risk that something you currently have might not be available? Again, think both short-term and long-term.

The picture below is a brief example based on this book project.


Tasks - Breaking down your tasks

Once I’ve taken the time to figure out the opportunity costs of particular scenarios and a decision regarding direction has been made, I start breaking down what needs to happen to get from here to there.
A valuable skill I learned while working on my Master’s Thesis is how to break down a large effort into manageable chunks.

My Master’s Thesis, was 96 pages and 3 chapters. I started with….well.. nothing.

The deadline I set for myself was May 1994.
I was starting in September 1992.

A Master’s Thesis is a classic example of an Impermanent Push – A clear goal, a clear deadline, a distinct beginning, middle, and end that can stand alone. The “off-ramp” for the Master’s Thesis was graduation with the degree and figuring out what I was going to do now that I had the diploma.
I had a rough idea of what I was going to do for my thesis. I needed to know this to get accepted to a degree program and so that I could put together a committee.

Because I was going in with a rough idea of what I wanted to accomplish and the time I wanted to accomplish it in, I could project plan.

– Leverage coursework assignments as research. This made every individual assignment an opportunity to complete the research portion of the project – as much as possible. I considered this a mini-phase. Also – the course attendance time was used as what I would now consider as Initiating and Planning phases. I figured out the true scope of the project, confirmed my topic/goal, and put together my plan and deadlines during the phase I spent attending classes.

– For the Execution phase – I separated the thesis into the 3 main chapters plus the introduction and conclusion. Dr. Lester Stephens, my advising professor and the committee lead, and I set deadlines (milestones) for each phase.

– Closing – the phase closures were the reviews of the individual chapters. Final closure of project was the Master’s defense, formatting and submission to the library.

This is an example of classical project planning. Agility occurred within the execution of each phase (eg – writing). What I wrote and how I wrote it varied according to what I encountered in the research and the feedback I received from my professors.

Quality was the primary fixed point of the project. The project had to look like a Master’s Thesis and meet the approval of my graduate committee.

Time was secondary and more flexible - May 1994 since this was the deadline to get the thesis defended for a June graduation.

Cost was third – though if I missed the May 1994 date, cost was going to become a HUGE issue since I would have had to pay for another semester or two and ran the risk of not getting the degree.


The Power of Task Breakdowns in Accommodating Variable Energy

Early in 2019, at a beachfront house outside Jacksonville, Florida, my cousin Mary and I were catching up on life since we last saw each other.

Suddenly, she jabbed her finger at me, “About your business….”


Thankfully, the story gets good…

Mary lost her mother (my Aunt Barbara) and one of her sisters (my cousin Karen) in 2018. As a result, Mary has become the de-facto matriarch of her family. It’s a responsibility that can weigh heavy.

I thought about some of the exercises you provided and stuff you have been writing and decided to put it into practice!”

After last spring’s funerals, Mary created a goal for herself – create 100 hat/scarf sets for the homeless this past winter.

“I needed to do something to get out of this funk.”

This is a classic example of a SMART goal – measurable, a bit of a stretch, and attainable with careful marshaling of the resources she had available.

Mary already knew the material requirements for each hat/scarf set. She had built them before for family members and friends.

After purchasing multiple bolts of Polarfleece and other supplies, she broke down the process into discrete steps. Mary has rheumatoid arthritis, so once she broke down the process, she identified which steps would require a “good hand day” to complete.

Mary began to execute the plan, creating the hats and scarves in batches.

On “good hand days” she would take a batch of hats and scarves and put that batch through the step requiring a “good hand day,” then setting them aside for later.

On “bad hand days” she would take a batch at a step that could be done on a “bad hand day” and get that batch as far as she could get. She would then set that batch aside for the next “good hand day.”

As a result of this batching process, she was able to create 50 hat/scarf sets for the homeless community this winter. Pretty impressive for less than 6 months of work and working around a chronic health issue.

“I should be able to do 100 for next winter if I start when I get back from Florida.”

Mary’s example demonstrates the importance of task breakdowns and task analysis – especially when energy is unpredictably variable due to chronic illness.

She asked a very specific question during planning:

“Which tasks require a resource (in her case, a “good hand day”) that comes and goes during the duration of the project?”

Mary then planned her process to take advantage of this variability.

We tend not to consider variable resources and energy enough in our planning.

Most of us assume we are going to have “good days” during the entire project.

We all know that’s not going to be the case for 95% of us.

Kids get sick, we get sick, some of us grapple with chronic illness, bad days happen.

Identifying which tasks require “good days” and batching our project (if it is a project that lends itself to this sort of batching) is a great way to ensure that progress continues – even if we encounter “bad hand days.”


Considerations for breaking down your tasks

Are you clear on what type of change you are making?

  • Permanent Habit – Remember, permanent habit changes are about creating a habit you can sustain long-term. The planning for this type of change consists of identifying a target habit and the smaller iterations of that habit to get you there.

For example, if you want to develop a 20 minute per day meditation habit, and you have a hard time sitting still for 60 seconds, you can outline how you can nudge yourself towards a 20 minute habit based on what you have a 90% chance of succeeding at now. For the first month, try a 1-minute meditation each day. When you are successful at that – go to 5-minutes per day. Once that stabilizes, try 10-minutes per day.

  • Implementation – Implementation changes are those changes that can be complex and often are life-changing. Planning for this type of change is best done by considering the effort in phases or sprints with key milestones and decision points for your “outs.”

For example, if you are starting a side-hustle business, you need to determine what you need to focus on for each phase, the concrete steps you need to take during that phase, and when you need to have that step completed to move forward.

  • Impermanent Push – Impermanent Push changes look like the classical definition of “project” – a temporary effort with a beginning and an end.

For example, if you are planning to run a 5K 3 months from now, consider where you are currently and what your criteria for success is during that 5K 3 months from now. Start from the end-date and work backwards to your current date. Determine what your training plan needs to look like.

Do you have a clear “definition of done” for each task, as well as for your change effort?

Are your tasks measurable and specific? Do you know what a completed task looks like?

You want to be able to answer the question “Is this task finished?” with a yes/no answer. “Well, it’s kinda finished. I just need to…” is not an appropriate answer. If you can’t answer “Is this task finished?” with a yes/no answer – break it down further.

Example Task: I will contact 5 potential clients each week. The breakdown of the task will be “Did I contact a potential client – yes/no?”

Is each task stated positively?

Moran and Lennington, The 12 Week Plan, pg 95

“Today I will drink 5 16 oz glasses of water” is much better than “Today I won’t drink coffee.” Nature abhors a vacuum. Your “not doing” can easily be replaced by something equally undesirable.

Example: “Today I won’t drink coffee” can be replaced by “Instead, I’ll drink a 24 oz Monster Energy drink – full sugar please.” You didn’t drink the coffee, but you also didn’t do yourself any favors.

Is each task a realistic stretch?

Remember: You want your tasks to have a 90% certainty of success. You are trying to hit that sweet spot between “this is a no-brainer” and “there is no way this is going to happen without a miracle.”

For longer-term efforts, you want each step to build on each other. Steps that are going to be more difficult for you, consider ways to make it easier.

Do certain tasks require the completion of other tasks?

In project management, this is called task dependency. As we make our plans, we ask the following questions:

  • What are the steps you need to take to complete the task?

  • What order do these steps need to be in?

  • Does step order make a difference?

  • Will you need to iterate on your activities?


Recruiting help for task breakdowns

If you are trying to do something you haven’t done before, it is trickier to figure out what you need to do.

This is where getting help from someone who has done it before is crucial.

You can ask your friends or find experts through doing some research.

I would venture to guess that for the change you wish to make, someone, somewhere, has done it before. You may even have someone who has done whatever you are trying before near you.

In today’s environment, we have more access to more expertise than ever before. If anything, the challenge is to differentiate the quality of that expertise.

For this book, I had people who had written books in my network. I had also written a master’s thesis before – which is not quite a book, but still requires that multiple pages of content become a cohesive whole.

Early in the process, I asked for some advice from my network about book writing and publication.

To a person, they insisted that I need to be clear about my expectations for the book. I received great advice on outlining, drafting, and finding a good partner. I also received advice about publishers and the need to keep my expectations realistic about marketing and marketing support.

As I continued my research and broadened my network of authors, I learned about tasks that I wouldn’t had thought of when writing – ISBN codes, various forms of publication and their specific needs, graphical design, layout, cover design and selection, copywriting, the list sometimes feels endless.

Before engaging any expert – make sure you are clear on your intentions for your project and what you wish to learn from that expert. Stay open to the response – it might not be what you want to hear, but it will provide important information for you to move forward.

Some of the questions I make sure I ask any expert in any field where I am making a change:

  • Why did you engage in this effort? What were your motives? What did you hope to accomplish?

  • Where did you encounter challenges? What did you do to overcome them?

  • What surprised you about the process?

  • What advice would you give to someone starting out?

Have specific questions prepared if there is something you want to learn about your specific change effort.

If you are looking for more help from this expert – such as mentoring or consulting – work with the expert to determine whether they have the time and the bandwidth, how much time they have to work with you, what they will and won’t help you with, what that help will look like, and how frequently you will touch base.

Make sure you are both clear about the boundaries of the engagement.

Respect that expert’s time, knowledge, and energy. What they are providing you is a gift.


Overall Planning Steps – Our Goal

Our goal in planning – for any type of change – is to establish our next steps in small enough chunks so that we can concentrate on the task at hand. Smaller chunks provide clarity and immediate feedback regarding your progress towards those goals. Because of that immediate feedback, you gain a sense of control over the task.

In a small enough chunk, the task can be assigned, if the change effort accommodates this. The small chunks also allow you to better establish the appropriate balance between the challenge of the task and the skills of the individual.

What we are trying to do is plan for flow. If we get task definition right – the person doing the task should experience timelessness, the experience feeling intrinsically rewarding, effortless and easy and being able to lose self-consciousness. Remember Csiksentmihalyi’s characteristics of Flow state:

This is what we are going for when we are planning our change efforts.

We want this change to feel as easy and effortless as possible.


Overall Planning Steps – From High-Level to Yes/No

Dependent upon the complexity of your change effort, you may have to consider your to-do list at various levels:

  • High-Level activities.

  • Mid-Level activities – specific, assignable – if necessary.

  • Yes/No activities – Did I do this or not?

For example: The activity – Create a Business Plan is a high-level activity with multiple steps. Each of those steps has steps within that.

The high-level activity is Create a Business Plan. After talking to the experts around me, I have decided to use the Business Plan Canvas out of Business Model You.

The mid-level activity is to execute the smaller steps within that model. The components of the Business Plan Canvas include:

  • Identifying Key Partners

  • Defining Key Activities

  • Identifying Key Resources

  • Determining the Value provided

  • Deciding which Customers you will serve

  • Clarifying the purpose and type of Customer Relationships

  • Researching potential Channels

  • Estimating the Costs and expenses incurred with acquiring Key Resources, performing Key Activities, and working with Key Partners

  • Determining what Value Customers are willing to pay for and how they prefer to pay

  • Deciding what Revenue types you will develop and sell.

    Tim Clark, Alexander Osterwalder, Yves Pigneur, Business Model You: A One-Page Method for Reinventing Your Career, 2012, pg 32-33

Each one of these mid-level activities has its own activities within them. Let’s tackle the steps within identifying Key Activities. For this exercise, the steps look like a series of questions:

  • What do you plan to “Make”? This includes designing and manufacturing products; designing, developing and delivering services; and solving problems.

    • Each item you “make” will have its own set of steps. If I am creating a new service, I have a set of steps I need to follow to make that service into something I can sell.

  • How do you intend to Sell your service or product? This includes promoting, advertising, or educating potential Customers about the Value your service or product provides.

    • Each strategy you develop has its own set of steps – planning and executing advertisements or promotions; planning and executing educational webinars; planning and executing content

  • How do you intend to Support your business? This is all the tasks that keep the organization running smoothly – such as bookkeeping, license administration, etc.

    Clark, Osterwalder, and Pigneur, Business Model You, pg 43

We need to take our high-level activities and divide them into actionable, assignable steps.

We want to be able to see the path we need to take and easily discern the “next step.”

It’s the ability to see the next step that provides the sense of certainty. Seeing the next step makes it easier to act.

The task should have a definitive definition of “done.”

The definition of done is important. You want to be able to see immediate feedback – is it done or not?

This helps to provide a feeling of control and “completion.”

The example I provided is an implementation change. Starting a business is no joke and can be a very complex endeavor. The administrative odds and ends involved can be overwhelming.

The more complex the change you are trying to make, the more time you want to take on this process.

Just understand that the plan is just a baseline. The plan will change as you execute.

And, fortunately, most personal change efforts do not require this level of complexity.

The simpler, the better.


Planning based on the type of change

How you plan and determine the steps of your tasks is dependent upon the type of change you are making.

Some change efforts require more detailed planning and scheduling than others.

We’re looking for the appropriate balance between knowing what we need to do next to be successful and being flexible enough to adjust based on what we learn and changes in our environment.


Permanent Habit Planning

Planning for permanent habit change is about identifying the habit you wish to practice, then practicing it.

As you practice, you will discover the obstacles and challenges to completing that practice.

In your scope, you defined the “ideal” version of the habit you wish to establish.

What we want to do is to determine the version of the habit that we have a 90% chance of practicing successfully RIGHT NOW!

As we get more comfortable with the habit and have the early success, we can nudge ourselves towards the “ideal” version.

It may feel slower. However, by building on these early wins, we are more likely to successfully make a change that sticks.

The great thing about permanent habit changes is that we aren’t on deadlines. We are looking at the long-term.


Exercise: Permanent Habit Planning

Pull out your Permanent Habit Scope exercise.

  • Identify a version of your habit that you have a 90% chance at succeeding at.

  • How do you want to track your progress on this habit?

    • There are many habit trackers available online – many of them currently allow you to track a simple question, “Did you practice the habit, Yes/No.”

    • I found that I am personally more successful with habit tracking when the tracking solution is embedded in my daily life. As I write this, I am using my analog daily planner to track a habit I am trying to establish. I reserved a section to track that habit. I have also used my online calendar to do this at other times – leveraging the private, separate calendar function such that I can see what’s happening, but anyone else with access to my calendar cannot.

  • Clarify what “success” looks like with this initial attempt

  • Identify when you are going to evaluate how you are doing and make the decision to stop, roll back to something easier, maintain your current state, or up the challenge to be closer to your goal.

  • As you practice, determine what the next 90% success version of the habit looks like.

  • Rinse and repeat until you are happy.


Implementation and Impermanent Push Planning – Short-term

Implementation and Impermanent Push changes can be incredibly complex, especially in the short-term

There may or may not be other people involved. This includes the gatekeepers for the resources you need to acquire.

There may or may not be a series of specific steps that need to occur for your change to happen.

I recommend recruiting expert help to confirm that you are taking the right approach and have considered everything that needs to happen to be successful.


Remember, we are trying to minimize the amount of work we need to do to be successful.

As we create and execute on these plans, keep in the back of your head the question – “Does it need to be done?”

We don’t lack great ideas. We lack the time, energy, and resources to execute.

You want to make sure you “keep the goal the goal.”


Determining the planning approach

Let’s look at your change effort and confirm what we are working with. Pull out the Scope for your change effort and answer these questions.

  • Do you have a specific, clear, defined goal or is the outcome nebulous and unclear?

  • Does your change effort have clear steps that others have used to accomplish the same thing or is your change effort more exploratory and uncertain?

    PMI, Agile Practice Guide, pg7

In a personal context, much of what we are trying to do is uncertain (to us) and requires a level of flexibility to adjust and adapt as you learn what works and what doesn’t as you move towards your goals.

Even in change efforts that appear to have clear steps, there is a level of uncertainty around execution and what may come up as we attempt to make change.

How’s your health? How’s your mindset? How’s your motivation? How many distractions do you have? How shifty are your priorities? How supportive is your environment?

These things may change almost hourly.

Because of this level of uncertainty, and that we are delivering against our life vs. delivering value to customers, we’re going to lean towards more Agile forms of planning.


Since the Agile Manifesto’s publication in 2001, and with time out in the field, the Project Management Institute, in partnership with the Agile Alliance, have identified 4 general project approaches:

PMI, Agile Practice Guide, pg18

These project approaches are on a continuum from the low degree of change and low frequency of delivery that predictive approaches leverage to the high degree of change and high frequency of delivery of true Agile life cycles.

  1. Predictive approaches to project management, such as “Waterfall,” work best when the possibility of change during the project is low and the requirements are well understood. Any activities will happen only once during the project. Delivery typically happens at the end of the project. The goal is to manage costs. This technique is best used when the requirements are known and stable.

    • Predictive approaches, which is what many people think of when they think of project management and planning. This approach requires that all planning happens up front. The goal is to work to the plan with minimal deviation.

    • In a personal context, even if you decide to use a Predictive approach to planning, it is good to make sure that you have room where you can adapt the plan to better map to reality and change.

    • For example, a project of “remodeling the bathroom” is often planned using a predictive approach. Contractors tend not to be crazy about clients changing their mind mid-way through a project.

  2. Incremental approaches allow you to finish activities quickly by dividing the activity into smaller chunks that can be released as they are finished. A common example is releasing a stand-alone chapter to potential customers as you write your book.

    • Incremental approaches plan up front, but per chunk or segment.

    • There might be a rough overall plan, but you are working as close to the plan as possible within the segment, then reprioritizing after that segment ships.

    • For example, a large email upgrade project can be divided into more manageable chunks by department. Each departmental roll-out has its own plan. The team works the plan for that department.

    • Personal example: I planned authoring this book using an incremental approach. I did not write the initial drafts in sequential order. I prioritized based on the information I had access to and where the muse took me. The goal was to get this information into book form as quickly as possible – then use later drafts to integrate the information into an actual book.

  3. Iterative approaches encourage prototyping. Many people have a hard time visualizing what they want or how your plan will work until they see it in action. By using an Iterative project approach, you are planning for those prototypes.

    • Iterative approaches change the plan based on regular feedback. Each output and round of feedback modifies the plan.

    • Permanent Habit changes are planned using an Iterative approach. We create a small experiment (meditate 5 minutes), see whether it works (did I successfully meditate 5 minutes every day?) and adjust.

    • You can also try an iterative approach with Implementation and Impermanent Push approaches. Is there an “experiment” available within your effort?

    • Example: The project is an Impermanent Push to run a 5K in less than 30 minutes 3 months from now. Month 1 – train following a sprinting plan. After an “evaluation” 5K training run, I can either change my approach for the next month or increase the training difficulty.

  4. Agile combines Incremental and Iterative approaches – allowing you to deliver results in small chunks that can be prototyped in a way that delivers maximum value quickly.

    • Agile approaches leverage the chunking of incremental approaches and the regular feedback rounds of iterative approaches. Planning occurs throughout the project and how often you down to plan will vary. Many Agile teams in the corporate environment plan daily.

    • The basic questions in an Agile planning session are:

      • What have I done?

      • What do I intend to do today?

      • Where am I encountering obstacles or issues I need to address?

      • What changes do I need to consider?

    • Example: The project is an Implementation effort to build a new web site for my business. As I put together the website, I asked the questions above daily. I did have a rough list of “story points” to determine what I needed to have in place. These were placed in a “backlog.” The goal, in planning, was to get something resembling a home page up as quickly as possible, then add other pages and features over time – prioritizing based on what would provide maximum value to the web site audience. I make adjustments to individual features or pages as needed. Each requested adjustment goes to the backlog for prioritization. Since I’m the owner, I am the one who prioritizes.

  5. Hybrid combines approaches based on what is appropriate for your change effort. So – part of your project may be planned as a Predictive project, another part of your project may lend itself to an iterative approach.

    • Example: Let’s say I want to open a hair salon. The construction of the interior of the salon will likely require a predictive approach to get the sinks, electric, and stationary fixtures in place. Once we get the infrastructure of the salon completed and all licenses, permits, and approvals completed, we can use an Incremental approach for creating our processes (scheduling appointments, receiving payments and tips, ordering materials) and Iterative approaches for our marketing, hiring, and customer outreach.

Let me offer a few questions as you plan your projects:

1) Can you deliver your project in increments? For example, a web site development project is the perfect opportunity to deliver in increments. The home page can be one increment, About Us can be another increment etc.

2) How do you want to address requirements changes? When planning any new project – you need to assume requirements WILL change. Thankfully, YOU are the one defining requirements in this case. If you are working with others, do you want to assume iteration and plan the time for receiving feedback and making adjustments?

3) Do you tend towards change-averse with a low risk and failure tolerance?

Your risk and failure tolerance tells you whether prototyping and iteration is seen as a positive request for feedback or a demonstration of sloppy work. The more perfectionistic you are, the more likely there will be an underlying fear of feedback.

Even the most change-tolerant of us may have a clear boundary where risk and failure is unacceptable. Make sure you know where that boundary is and what your guardrails are.

I ask these questions because I want to encourage you to plan in chunks as much as possible and plan for drafts as much as you can.

Even if you take a Predictive planning approach, within each activity and task is an opportunity to be flexible.

The key is to be focused on the desired result and why you are doing this.


Accommodating Flexibility

The planning technique I like to use leverages the concept of Sprints.

I am defining a sprint as “a defined period of time within a project where we focus on completing a particular activity or set of activities.”

We may or may not have a releasable product or clearly observed results at the end of it, but we should have a milestone deliverable or an important part of the whole complete.

I’m going to use a corporate example to illustrate. Let’s say I am planning a learning management solution replacement project.

At a very high level, within that project I need to

  • Set up a development site

  • Inventory courses within the current solution

  • Test whether the current files work in the new solution

  • Transfer the courses

  • Launch the site

I can use the concept of sprints to make sure that the team is focused on the most important thing that needs to be done during that short period of time. I try to keep this down to a week. Two weeks at most.

This also does not mean that we do those activities exclusively. Other tasks may need to happen at the same time. We are just focused on completing that specific task during a short timeframe.

You don’t need to do sprints throughout a project. Some projects and organizations won’t lend themselves to that.

You can, however, look at certain activities and times as good candidates for “sprints.”

  • Key milestones and deliverables. Consider using a “sprint week” prior to the milestone date to make sure deliverables are ready

  • Any task on the critical path. The critical path contains the tasks that must happen on-time, otherwise the deadline slips. This is not a big deal for many personal change efforts, but if you are trying to meet a specific deadline, knowing which tasks will impact your ability to meet your goal is critical. You want to make sure that you are setting aside concentration time for tasks that require focus and take up significant cognitive load. Set aside a week or two in your plan as a sprint to make sure these tasks get done.

  • Tasks that need to be finished before other tasks start. The more activities that are dependencies to that task, the more important it is that the task gets done.

  • Short tasks requiring significant concentration. Some change projects have what I call a “whack-a-mole” component. These are all the small odds and ends that need to get done. None of the odds and ends take up much time in and of themselves, but between the task switching costs and having those tasks take up room in your brain, having a “whack-a-mole” sprint can be a useful way to reduce stress.

See what other tasks you can move during those sprint weeks. Also look at how you can deflect distractions from outside the project.

You want to be able to concentrate as much as possible and get the activity done.

There are some benefits to using sprints as a technique within a more traditionally planned project:

  • You can quickly see the “most important” activity at any given time

  • The focus makes it easier to complete important tasks

You can uncover challenges to your focus as you execute your project. This will help you on your next planning cycle. Where are you getting interrupted? What situations tend to derail you from your desired change?


Planning Small-Scale Experiments

One of my favorite things to do is to go to the local international supermarket and find unfamiliar foodstuffs to experiment with.

I can tell how risky the “experiment” is based on certain criteria:

  • How close is this item to something I already know? If it seems familiar, it is lower risk than something I’ve never encountered before. If I happen to like the familiar item, my risk is even lower. Example: eating a donut peach (Obviously a peach, just donut shaped) is less risky than eating an octopus (Uh…is this a fish? Is this even edible? Will I die if I eat it? What part do I eat? How do I prepare it?)

  • What are the chances of this item behaving wildly differently from the familiar item? This question is harder to figure out. Experience with a wide array of items helps with this question. Being able to estimate risk based on prior experience often helps. However, it can also hinder if you insist on the new item behaving in ways based on your prior experience without experimenting.

Let’s use Taiwanese spinach as an example.

I picked this up at the International Grocery store. I assumed that it was both edible and non-poisonous since it was in the produce section (vs. the floral department).

Upon investigation, I was able to discern that yes, this is spinach. I’ve got a rough idea of how to cook greens, but I have no idea how this is going to behave when I cook it and I don’t particularly know what it tastes like.

I tasted the Taiwanese Spinach raw to start. Despite my familiarity with greens, I didn’t want to make any assumptions about this new item. I can only determine what it tastes like by actually tasting it.

Without cooking – Taiwanese Spinach tastes like spinach with a little bit of soap. Probably not a repeat purchase. When I put it in a strongly flavored, spicy soup – the leaves cooked down like spinach, with slightly stronger stems. The Taiwanese Spinach added a nice texture to the soup. The spices masked any soapiness.

This really speaks to risk and taking risks and trying new things. It could be as simple as doing this in your personal life first were and in a small scale like going to the grocery store and picking up something brand new that you’ve never tasted before or never tried before.

You don’t have to buy a ton of it. You don’t even really have to eat all of it. You could taste it and come up with a calculated reason why you don’t like it.

One, you can now say you’ve tried it and you don’t like it, and two, you can explain why that is.

Or you’ve discovered something that you really enjoy.

You can do the same thing in your business – find a small technique that you’ve never tried before.

When you’re managing your project or you’re working with your team, take something really low risk and experiment with it. Talk to your team afterwards. Then you’ll have an educated reason as to why you did like the technique or you didn’t like the technique.

For example, you can try holding standup meetings at work where you have your developers lead those meetings. With that small experiment, you can see what’s working, what’s not and why.

And if you decide to not do that again, you’ll at least know why you didn’t want to do it again.


Exercise: Planning – Task Breakdowns

What we are going to do is develop what, in Project Management parlance, is called a Work Breakdown Structure.

PMBOK v6, pg159

The work breakdown structure will give us an idea of what needs to happen at each stage in the process as we do our initial setup. Even Agile projects have an early planning session where the team identifies tasks and when, approximately, these tasks will need to happen.

The Task Breakdown we are developing is going to serve as a baseline. As we execute on the plan, expect this to change. New tasks may appear. Other tasks may not need to be done.

This exercise is to help you see what needs to be done and provide clarity on what next steps are along the way.

  • Identify your high-level activities

    • What order do these activities need to be in?

    • Are there any activity dependencies? Does one activity need to be finished before another activity starts?

    • Will you be bringing in other resources and/or people to help you? If so, for which activity?

    • What is your “definition of done” for each activity?

      • If there is a dependency, at what point can you move to the next activity?

  • Identify your mid-level activities

    • What are the general steps to complete your high-level activity?

    • Are there any activity dependencies? Is there an activity that needs to be finished before another activity starts?

    • Will you be bringing in other resources and/or people to help you for this activity?

    • What is your “definition of done?”

  • Identify your tasks within each mid-level activity

    • What are the specific steps you need to take to complete your mid-level activity?

      • You want to break this down to a level where you know what you need to do to complete the task.

      • Example: If I am writing a book – I could choose “Write Chapter 7” as a task and be happy with it. If Chapter 7 is going to take me 1 month to write, I might want to break it down further into “Write Section 1”. If I am feeling easily distractible, I could break it down even further so that I have achievable, daily tasks.

    • Are there any task dependencies? Is there a task that needs to be finished before another task starts?

    • Do you need another resource and/or people to help you with this task? When is this resource or person available? You will need this information for scheduling.

You may want to take a few days with this exercise.

After you have a Work Breakdown Structure that provides you with enough information to get started, look at the tasks within that structure.

Does that task need to be done?

Remember: we are trying to accomplish our goals with the least amount of effort.

You want to remove any tasks that are “optional.” Or, at least, mark them as such if you are concerned that they will become mandatory as you move through the process.

If you discover 3 different ways to do a task, choose one and mark the other 2 as “option 1, option 2, etc.” You might find, as you move through your short-term effort, that another option works better. Still, you only want to execute ONE option.

With this plan, you should have a good idea of what needs to happen right now and what can wait until later. You are also going to have a great starter map.


Exercise: Update Your Kanban Board and Backlog

Back in Chapter 4, we did a prioritization activity. The result of the prioritization activity was a Kanban board where you could see your work in progress.

If you have not been keeping your Kanban board updated, I’d like you to do the following:

  • Update your Kanban board with your current activities.

    • What work do you currently have “in progress”?

  • Update your backlog with activities you have agreed to since we started this journey

    • Color-code your activities into any programs you had set up.

  • Identify any deadlines for these new activities and whether they are “hard” or “soft” deadlines

  • Identify the importance of these activities (remember, importance is whether they are important to YOU)

We want to get an accurate idea of what you have in progress. This will help us see how much room we have for your change effort.

If you have already started – that is AWESOME!

If not, we need to figure out how to make room.


Incorporating your change effort into your current efforts

I have a challenging question for you:

How bad do you want it?

If you are staring at your Kanban board and thinking “I don’t have time,” my next question is How do you want to make time?

If you are not willing to make time for this change, the truth is that it is not important to you.

Your “Why” isn’t compelling enough.

It’s OK – but you need to be honest with yourself.

Are you willing to work through the inevitable challenges to get to your goal?

Are you willing to set boundaries and change your agreements with others?

Are you willing to say “No” to opportunities that do not align with your goals?

If the answer is “No” – you might as well abandon the effort now.

If the answer is “Yes” – let’s figure out how we can make space.


Exercise: Evaluate Your Existing Tasks

Remember in Chapter 4 we talked about the Eisenhower Matrix and the difference between important and urgent? Let’s see if there is anything we can clear off your plate.

We want any task that is not important and not urgent off our to-do list.

We want to reduce the number of tasks that are not-important and urgent. Most of those tasks are probably someone else’s made up urgency anyway.

  • Identify the Not Important and Not Urgent. Is someone else relying on you to complete this task? What is the next step you need to take to get this task off your plate?

    • If this is a task you developed for yourself, can you let this task go altogether?

    • If you can’t let this task go – how does it fit into your life plan? If it doesn’t let it go.

    • If you STILL can’t let the task go – what do you think this task will allow you to do in the future? What is so compelling about this task?

  • Identify the Not Important and Urgent. Is someone else relying on you to complete this task? What is the next step you need to take to get this task off your plate? What agreement do you need to make to reduce this type of request in the future?

    • If this is a task you have agreed to that is important to the other person, and that other person is able to explain WHY it is important – is there a way you can make the task less urgent?

    • If the other person is not able to explain why the task is important, is there a way you can get this task off your plate?

    • If this is a task you developed for yourself, can you let this task go altogether?

    • If you can’t let this task go – how does it fit into your life plan? If it doesn’t let it go.

    • If you STILL can’t let the task go – what do you think this task will allow you to do in the future? What is so compelling about this task?

  • Identify the Important and Not Urgent

    • Does it need to be done right now? If not, stick it in your backlog.

  • Identify the Important and Urgent

    • Does each task have a clear “Definition of Done?”

      • If not, create a “Definition of Done” for the task.

    • Does each task have a deadline?

      • Is that deadline “hard” or “soft”?

      • What are the consequences for missing the deadline?

We will talk about ways to approach the tasks others put on your plate in Chapter 8.

In the meantime, focus on finishing what you currently have in progress.

The goal, as you work, is to minimize your Work in Progress.

Each unfinished task in progress is a burden on your cognitive load and your focus.



Once you know what needs to be done, you can then schedule those activities.

When I schedule, I typically ask the following questions:

  • Is there an activity that is important AND urgent? And does it have a hard deadline? These activities will be my first, most immediate priority for both planning and execution

  • Are there tasks that are dependent upon other tasks to complete? I do this with the important and urgent task streams first

  • What resources do I have available and when are they available? Here I am including people, money and materials. I ask this during scheduling because resource availability often determines when I can actually schedule the task.


Basic Steps for Scheduling a Project

The Kingwood, Texas Rotary Club has a program called Flags Across Kingwood. Club members place flags around Kingwood Texas for major holidays. They use this service as a fundraiser for their chapter.

First – they broke the activity down into steps. These are roughly the high-level steps they take.

Next, they determined their final date. This effort is what we would call an Impermanent Push. For this project, the activity had a hard deadline of July 4th – American Independence Day.

From here, they can figure out when they need to perform the tasks to meet the deadline.

They determine the deadlines for each task based on what order it needs to be done in and how much time it will take to perform each task.

For example, putting out flags needs to be done in one day. The activity can’t happen sooner than July 3rd.

Assigning volunteers might take a week or so. You need to get people’s availability and the amount of time they are willing to give to the effort.

Assigning volunteers needs to be done before you put out flags, otherwise, there isn’t anyone to put out the flags. A task that needs to happen before another task can start is known as a dependency.

Other tasks can happen at the same time, otherwise known as parallel. The requirement for having parallel tasks is having the resource (often human) to do that task.

For instance, they can inventory the flags and determine the locations for the flags at the same time. The Kingwood Rotary can do so because they have the people available.

In many personal change efforts, you might not have that option since you are doing everything yourself. If you have friends who are helping you, however, you have more options for multi-tasking.

In summary, your basic questions for project scheduling are:

  • What needs to be done and when does it need to be done by?

  • What are the steps I need to take to to get to the goal?

  • Which tasks must finish before others start?

  • Which tasks can happen at the same time if I have the resources available?

  • How long will each task will take?

In this example, we are working backwards from when the project needs to be done through each task, accommodating dependencies. So if we know we are starting to put out flags on July 3, we need to know which volunteers are doing what by July 1 so we can notify them of their assignments.

The Kingwood Rotary had a good idea of what needs to be done and how long each task will take.

For many of us, time estimation may not be so clear.


Time Estimates and SMART Goals

“Most people overestimate what they can do in one year and underestimate what they can do in ten years.”

Bill Gates

We can only act in the present moment.

We only have certainty right now.

We can only decide what to do next from where we currently stand.

We can base our decisions on where we want to go in the future.

If I take this next step – will this move me towards or away from my desired destination?

Clarity only exists in the immediate.

I only have certainty that I will perform the next task.

I can plan my to-do list for today. Whether I am successful in crossing anything off may be another story – and that’s OK.

Slightly more challenging is figuring out what I need to get done this week. I can set time aside in my schedule and try to scope the work to fit the time I have. A lot can happen in a week that we don’t expect.

Same thing with the month, the quarter, the year, and other, longer periods of time.

We lose clarity the farther out we go on the time scale.

That’s OK.

More importantly is whether you are headed in the direction you desire and that you are clear on why you are headed in that direction.

As much as we wish that our dreams would manifest instantaneously – creation takes time. Often more time than we would wish.

Life happens, energy fluctuates, we make our estimates based on our best-case scenario with our current environment staying static.

This is why we tend to over-estimate what we can accomplish in a year and under-estimate what we can accomplish in 10 years.

We feel we can get more “done” than we actually can. We over-estimate our time and energy and under-estimate the amount of change in our immediate environment.

However, if we continue to move forward, weaving between the trees and finding the shallow spots in the creeks, we can find ourselves having accomplished more than we ever dreamed of.


Most of us are LOUSY at estimating how much time a task will take.

If I plan to spend 1 hour at the gym, I also need to allocate time for changing into workout clothes, the commute time, locker-room time, and showering afterwards.

15 minutes of meditation still requires a few moments of setting yourself up to meditate and starting the timer before, and easing out of the meditation after the 15 minutes are up.

Creative projects are notorious for taking significantly longer than we expect. Most of us only account for the time spent creating. We don’t think about the time spent contemplating how you are going to approach the project or problem, gathering and preparing the materials, and cleaning up afterwards. If it is a creative work that potentially has multiple drafts or approvals – it gets worse.

Creating time estimates for your personal projects is a GREAT way to practice creating accurate time estimates for your professional projects.

Unlike in a personal project, where the only person you may have to worry about disappointing is yourself, corporate projects have higher stakes and other people relying on you to finish your piece on time.

If you ever find yourself working with me – either as a coaching client or as a corporate client – and we are estimating time, you will hear the following questions:

  • How long do you think it will take you to complete this task?

  • Does this number include time for design (or…figuring out how you are going to approach the task)?

  • Is this number based on your best self or is this an average of how long this type of task typically takes you?

  • How many other things are you doing along with this task? How much other work do you have in progress?

I usually assume that the person, when they tell me this is an average, is still giving me a number based on their best self. If I am reliant upon them giving me an accurate estimate, such as when I am running a project, I will ask these follow-on questions:

  • What is the longest amount of time this task has taken you? Why did it take this long?

  • What is the shortest amount of time this task has taken you? What allowed this task to move so quickly?

  • What is the likelihood of you being distracted from this task?

What I am doing, somewhat informally, is a form of three-point estimating.


Three-Point Time Estimates and Duration Estimates

Three-point estimates provides a planner an approximate range for how long a task will take to do.

As a project manager, when I am doing scheduling and time estimates during the planning process, I am looking for three numbers:

  • Most likely – A time estimate based on the amount of time it will most likely take a resource to perform a task. For your change, that resource is likely you.

    • Have you done this task before? If not, expect it to take longer.

    • How available are you for the task? If you can only perform the task in short bursts, expect it to take longer.

    • How focused are you able to be on the task? If you are forced to “multi-task,” expect it to take longer.

  • Optimistic – A time estimate based on the best-case scenario. You know what you are doing (or the task is easier than anticipated), you have lots of energy, you are able to set aside a significant amount of time where you can concentrate on the task, and you aren’t interrupted.

  • Pessimistic – Everything that can go wrong will go wrong.

You can then average the three numbers to come up with an estimate of how long it will take to perform a task.

PMBOKv6, pg 201. Finding the average of most likely, optimistic, and pessimistic is known as Triangular Distribution. There are other ways to estimate time. This just happens to be one of my favorites. It provides me with more information and better surfaces assumptions about what is realistically involved in executing the task and the number of distractions we expect to surface as we execute. In corporate environments, time estimates are aggressively optimistic. The person doing the work wants to impress. The manager is under tight time constraints from above. In a personal context, we don’t need to put ourselves under that type of pressure.

If you have a long history of missing deadlines (self-imposed or otherwise) – use the Pessimistic number.

If other people are relying on you, it is much better to under-promise and over-deliver than the other way around. Plus, using the Pessimistic number provides you with some wiggle room if the task proves larger than anticipated or a distraction surfaces.


The Consequence of Bad Time Estimates

How long do you think it will take you to complete this task?

I should have it done in a couple of days.

Are you sure? I know you have (list activities here) due or on-deck.

Yeah – shouldn’t be a problem. I’ll get it knocked out in a couple of hours.

We set a mutually agreed-upon due date.

Meanwhile – I check my project plan to see when the “panic date” should be.


I venture back to the project team member the day before our mutually agreed-upon due date.

How’s it going?

Um…not quite done yet. (add excuse here – often the other activities due or on-deck took time and energy the team member didn’t account for, they are waiting for a piece of information from someone else, or they mis-calculated how much time it REALLY takes to complete a task).

We set a mutually agreed-upon due date.

I double-check the impact and make sure I didn’t agree to something based on the assumption of the first due date.


Typically, the above scenario will repeat for a few rounds. We start having harder conversations as we get closer to the panic date.

I feel like a negative nellie when I question my project team member’s time estimates.

But I’ve lived through the above scenario way too many times to count.

From what I’ve seen, project team members regularly under-estimate how much time it will take to perform a task.

Common reasons:

  • Accounting only for the time it actually takes to do the task, but NOT the thinking and design work that also needs to occur. Don’t be surprised if you hear “So is that just the time it takes to do it or does that include design time?” from my lips.

  • Forgetting to set aside time for information collection. Especially if they need that information from others. If they are working in an environment where “knowledge is power” – that time needs to be extended even further.

  • Forgetting to set aside time for approvals. I tend to work in politically sensitive environments, so I’ll often ask if there is anyone who needs to see their work before it gets turned in.

  • Forgetting they are human. I’ve been fortunate enough to work with some great people who want to be superheros. They will agree to do anything on the most impossible timelines. They don’t want to disappoint.

    • These are the people who tend to be the most over-burdened. As a project manager, I frequently don’t have visibility into the resource’s other tasks. Often, these folks don’t feel like they have the power or right to say “no.” Asking for help feels like failure.

    • Things will slip through the cracks, and it becomes tricky to determine the cause and how to help. The team member feels bad, I get stressed, and things don’t get done. No one wins.


When estimating task times, I will often set two dates:

  • The due date the project team member and I agree to.

    • It’s important we both agree to the date. It’s part of establishing a feeling of ownership around the project for the team member. Furthermore, I often won’t have visibility into the team member’s other activities – so their honesty is critical.

    • I don’t need a superhero. I just need to know when a task will get done and trust it will be done when they say it will.

  • The panic date – often the date the task needs to be complete before impacting other tasks on the plan.

    • The only time I tell people outright when the task is due is when we are under a really tight timeline and that task impacts other tasks on the critical path.

    • The only other time – when that team member has proven repeatedly that they will miss dates for a wide array of lame reasons.

If that task is on the critical path – missing the panic date means impacting the project go-live date.

Thankfully, in personal change, we set our own dates and deadlines.

If your project is an Impermanent Push with a hard deadline, you will be able to see whether you are going to make that deadline by seeing whether you are meeting the deadlines of your tasks.


Exercise: Estimating Task Durations

This is an exercise for Implementation and Impermanent Push change efforts.

Pull out the Work Breakdown Structure you created.

For each task:

  • Estimate how long you think it will take you to perform that task.

  • Write down any assumptions you are making.

    • Have you done this task (or something similar) before?

    • Does this estimate include research and design time?

    • Are you anticipating interruptions?

  • For the mid-level activity – add up the time for each task within that activity. That is how long it will take for you to complete the entire activity.

  • Repeat for the high-level activity – add up the time each mid-level activity will take. That is how long it will take for you to complete the entire activity.

  • Repeat for the overall effort – add up the time each high-level activity will take.

As we do this, I am assuming that you are the only human resource on the effort.

As you look at your time estimates – if you have set a deadline for yourself, is that deadline realistic?

If it is not a hard deadline, consider pushing it back. You are making this change for YOU. You probably have enough unrealistic deadlines at work. No need to do this in your personal life.

If it is a hard deadline, are there tasks and activities that you can cut and still get the same result?

Do you need to find help? Do you need to reduce your scope? Is there another opportunity at a later date?

Make any necessary adjustments.

If, no matter how you look at it, the amount of time your tasks will take is more than the amount of time you have available before the deadline, you have the choice to abandon the effort.

You may be able to try again at another time after you have gained experience elsewhere (to speed up the task), found help (that will help you perform tasks in parallel), and/or reduced distractions (such as the kids starting school or finishing a major work project).



In this picture, Brian and I are picking through the priorities Advocates set and discussing the level of effort needed.

This discussion is important because as with Advocates, his time on the project is limited and somewhat unpredictable.

Now, in the ideal Agile world, all members of the project are solely on that one project.

The closest I’ve seen to that ideal in real life was in the Data Whisperer’s implementation of Agile – and that took 3 years, a new VP, and probably 5 years off his life to achieve.

In the Advocate’s Agile-style implementation, the most important thing we had to accommodate was the wild variance of team availability.

Brian is a pro-bono volunteer. As am I.

The Advocates staff needs to prioritize their time towards fulfilling their mission.

The tools that helped us here are the Scrum concepts of projected work capacity and story points.

For each 2-week sprint – Advocates will predict their projected work capacity by the number of hours available for the effort for those 2 weeks. We anticipate that for some sprints, the number of hours may be zero. That’s ok – though I am hoping that is NEVER the case, for fear that they will lose focus and drop the project. That’s on them.

In the meantime, Brian predicts his projected work capacity for the project for the sprint, also by the number of hours he will have available for the effort.

Each card has an estimated number of hours (the story points) it will take to complete. If the item requires feedback or a decision from outside the project team, I asked them to double the number of hours. I suspect that they are better about talking to each other than most organizations, but it’s been my experience that it takes a lot longer to get an external decision than one predicts.

The estimation of the number of hours/story points occurs when Advocates moves the card from the backlog to Prioritized.

That estimation also occurs when Advocates moves the card from the sprint to “Ready for Development” – Brian needs to identify the amount of time he has available and when he will have something for testing.

Something Advocates made very clear on this effort is that there is no set deadline. They just need to show regular progress to the Board. Since the velocity will be wildly variable from sprint to sprint, this is good news. They are not setting an unrealistic deadline for themselves. As long as they set regular bi-weekly milestones and keep an eye on their goal, I think they will be ok.


Accommodating Ambiguity

In Wendy’s Utopian Fantasyland– there would be no uncertainty or ambiguity.

Every decision, every plan, will be made within clear, stable environments.

Priorities would be unchanging.

Markets and competition would be understood and predictable.

And all stakeholders agree on the scope, desired results and importance of the project.

You can stop laughing now…


Kailash Awati, at 8 to Late, recently identified some issues with common decision and estimation techniques.

The distinction between uncertainty and ambiguity points to a problem with quantitative decision-making techniques such as cost-benefit analysis, multicriteria decision making methods or analytic hierarchy process. All these methods assume that decision makers are aware of all the available options, their preferences for them, the relevant evaluation criteria and the data needed. This is almost never the case for consequential decisions.

Options are emergent rather than fully articulated from the beginning; there is no agreement around decision criteria among the stakeholders; and even if they DID agree on the decision criteria it would still be difficult to rank the relative importance of each identified item.

Nevermind that there is often not enough information available to make the decision in the first place.

Or a common understanding of the problem to be solved.

Or, even with a common understanding of the problem to be solved, an agreement about how best to approach the solution.

You can see how it then becomes difficult to create project plans and time estimates.

  • Is there a shared agreement and understanding of what needs to be done? Not just the desired end-result, but the steps it will take to get there?

  • Is everyone clear on the scope of the activity during the time allotted? (Yes – even Agile projects have scope, if only during the sprint)

  • Do you really have enough information to know how much time it will take someone to perform a task? Have they over or undersold their expertise? Assumed they would not run into problems? Account for other tasks and the task-switching cost? Accommodated the research and design time in their statement – not just the development time?

    • Even within a PERT range – are you sure of your best case, worst case and probability?

  • Are you aware of the entire environment that might impact the execution of that task? Not just organizational, but also that resource’s personal world?

Kailash’s observation –

…In an ambiguous situation, a good decision – whatever it might be – is most likely to be reached by a consultative process that synthesizes diverse viewpoints rather than by an individual or a clique. However, genuine participation … in such a process will occur only after participants’ fears have been addressed.

And those fears will only surface in a safe “holding environment.” If you have no idea what a stakeholder’s real concerns are, it is impossible to address them.


In my projects, I do my best to create those “holding environments” or safe zones – often with 1-on-1 conversations. And not just for politically important stakeholders. It also needs to happen for project team members. Maybe ESPECIALLY for project team members.

That way, we can get more accurate plans and time estimates.

It makes it easier to identify risks and resource constraints.

And it makes it easier to identify the fear points a team member may have around the success of the project.

  • Are they concerned about how their job is going to change if the project is successful? Or if they will have a job at all at the end of it?

  • Is the project replacing something they spent their career perfecting? Something they have taken ownership of and pride in?

  • Are the activities they are being asked to perform in alignment with what they want to do? How does the project impact their career trajectory?

  • Are they being asked to spend more time at work? How does this impact their personal life (what little of it is left)?

  • Are they even being given the space to do this project? How much is on their plate already?

  • Are they being set up to fail? What is the political climate?

The answers to these questions impact the quality and time it takes to perform tasks, the probability of meeting deadlines, and the overall success of the project.

The upshot of all this is that any approach to tackle ambiguity must begin by taking the concerns of individual stakeholders seriously. Unless this is done, it will be impossible for the group to coalesce around a consensus decision. Indeed, ambiguity-laden decisions in organisations invariably fail when they overlook concerns of specific stakeholder groups. The high failure rate of organisational change initiatives (60-70% according to this Deloitte report) is largely attributable to this point – Kailash Awati

Projects and project decisions are generally awash in ambiguity. If it wasn’t, you likely wouldn’t need a project manager.

As Kailash argues, if you recognize the existence of ambiguity and the attendant negative emotions it can bring up, you are more likely to make a sound decision.


The Importance of Rest Stops

I make it a point to design “rest stops” in my projects.

These rest stops aren’t necessarily milestones (though milestones make good rest stops).

Rest stops are places within the execution of the project where you can take a breather and evaluate what you need.

  • Do you have the resources to continue?

  • What changes have occurred in the environment since you started?

  • Are there new resources available?

  • How are you feeling and what do they need to recharge?

  • Are you on the right path? If not – how do you get back on the right path?

  • Should you even keep going?

If I don’t plan these rest stops, it’s easy for me to get lost in my “to-do” list and project plan.

I get so busy “doing” that I totally lose track as to whether I am even headed in the right direction.

I also don’t see where I am making real progress because I get so fixated on the unfinished tasks.

Without those rest stops, I get frustrated (because I don’t see progress), burned out (because I keep grinding), and, often, off-track (because I am not reflecting upon whether my current actions are working and not accommodating changes to my environment).

For all your change efforts, purposefully schedule times when you are going to take a rest stop.


Exercise: Scheduling - Permanent Habit

Permanent Habit changes are about finding time to perform the habit and determining how often you are going to review your progress.

  • Schedule time each day or as appropriate to execute your new habit. Include in this block any prep or commute time.

    • If you are blocking this time on a public calendar, mark as busy and use a private calendar to identify what that busy time is for.

  • Identify how you are going to keep track of whether you performed the habit.

    • I recommend using a solution that you are already looking at every day – such as your calendar.

      • If you look at an online calendar daily, use that.

      • If you have an analog planner you carry around and use for your daily to-do list, use that.

    • Determine how you are going to mark success. In the picture below, I changed color. If you are using color-coding for something else, you can edit the header with another marker.

  • Select a regular cadence for reviewing results and schedule your review. (The Rest Stop)

    • The appropriate review cadence may vary based on what you are trying to do.

      • I find that for a meditation practice or minor dietary change, reviewing my progress weekly is helpful.

      • For weight loss or fitness, I found a monthly review was more helpful – it was enough time to see results but not so frequent that I got freaked out by setbacks.

    • Work with experts or do research to determine a baseline for an appropriate review cadence. Adjust for yourself as necessary.

  • Schedule a date for adjustment of your practice.

    • You can do this during your review, or you can decide to go through a few review cycles before making adjustments.

    • During the adjustment, decide whether you are ready to take the next step, stay the course, make your task easier (90% likely that you will successfully do the habit), or abandon the effort.

From here, practice your habit.

You will learn quickly what is working and where challenges lie.

My only ask is that you don’t beat yourself up if you “fail” to practice a habit on a given day.

Reflect on what happened, learn from it, and adjust as necessary.


Exercise: Scheduling – Impermanent Push and Implementation Efforts.

With an Impermanent Push or Implementation Effort, earlier in the chapter you put together a Work Breakdown Structure for your change effort and estimated the amount of time the tasks are going to take.

You will work with the following:

  • Your Work Breakdown Structure

  • Your Backlog

  • Your Kanban board (to do, doing, done)

  • Your Calendar

You can do this using post-it notes (recommended) or a project management tool with backlog and Kanban functionality.

The pictures are from my Teamwork installation (circa April 2019). Asana and MS Office are other good options.

Our goal is to get a visual of EVERYTHING we are currently doing, what is upcoming, and what we need to focus on this week.

We then want to get what we need to focus on this week in our calendar and the time blocked so that we have the space to do the work.

Before starting, make sure your backlog and Kanban are up do date. Be honest about everything you currently have in your “Doing” column.

Remember: We want to minimize Work in Progress. Each task that is currently “In Progress” is taking up valuable cognitive space.

1) Put your tasks for your change effort in your backlog.

  • Make sure the tasks for your project have clearly marked deadlines, as needed.

2) Does the task need to be done (or start) this week? If so, stick that task in your to-do.

2a) (optional) Stick the next task in a Next Sprint if you like having visibility into what is coming.

3) Schedule time for doing the task in your calendar.

Anticipate that your biggest challenge will be keeping this time unscheduled.

It is too easy to over-ride the time you want to spend on change efforts that are important to YOU with other people’s priorities.

Your ability to maintain those boundaries and be disciplined in doing the tasks during the time you scheduled them are the keys to success.

4) Determine your Rest Stop cadence. Add these rest stops to your calendar.

The complexity of the project determines how much time you need to set aside for analysis.

My personal practice, for complex projects, is to perform a brief review at the end of each sprint and a major review upon completion of a milestone.

For all review sessions, I use the following questions:

  • Am I on the right track?

  • What minor adjustments do I need to make?

  • What is my next step?

This process generally takes me 5-15 minutes, dependent upon the complexity of the effort.

For the major review sessions, I add the following questions:

  • Do I have the resources to continue?

  • What changes have occurred in the environment since I started?

  • How do these changes impact my plan?

  • Are there new resources available?

  • How am I feeling and what do I need to recharge?

  • Am I on the right path? If not – what do I need to do to get back on the right path?

  • With what I know, should I continue?

  • If I continue, what are my next steps for the next phase of my effort? What do I need to focus on? For how long?

  • Do I need to adjust my review cadence?

Schedule your next review sessions.

I set aside 30 minutes or more for the major review sessions. During these sessions, I am updating my budget and resources, making decisions about the next few sprints, and updating my plan.

The more complex and resource-intensive your change effort, the more time you should take in review.


Common Pitfalls when creating your plan

As you begin to develop your task breakdown and schedule – do you see any of the following issues?

Moran and Lennington, The 12 Week Plan, pg 103.

  • Your plan does not align with your long-term vision.

    • Have you added extra tasks that are unnecessary for achieving your goals? They seem like a “good idea?”

    • Do the actions you have identified move you towards that long-term vision?

    • Does your overall change effort move you towards your long-term vision?

  • You aren’t staying focused.

    • Are there too many priorities, too many goals, and too many activities scheduled during a time period?

    • Does your change effort align with where you are in life right now? Do you have the right focus?

  • You don’t make the tough choices.

    • Are you experimenting with 5 ways of doing things when you need to choose 1 or 2?

    • Are there old initiatives that you need to let go of?

    • Are there activities that are no longer aligned to your vision that you need to stop doing?

  • Your plan is too complex.

    • If you gave your plan to a friend, would they be able to execute on the plan as it is written?

    • Does your plan feel complicated? If it feels complicated to you – simplify it.

  • You don’t make it meaningful.

    • Is the “Why” attached to your change effort strong enough?

    • Do the activities and tasks make sense to you?

    • Does the plan feel like you can execute on it? How confident are you?

    • Do the activities feel meaningful to you? Can you see how if you execute the plan, you make progress towards your goals?

Keep your plans simple.

Focus on the day-to-day and small steps.

Stay clear on your lead metrics.

Keep track of your lag metrics to ensure that your actions move you toward your goals.

Don’t be afraid to adjust as you execute.



For our purposes, I am defining resources as any materials or software applications you need for your change effort.

The PMBOKv6 includes Personnel in their definition of “Resources” -equivalent to a hammer or a server. I have deep-seated concerns about this definition. The Project Team should get just as much consideration as the Stakeholders and should become a separate Knowledge Area and not divided and hidden under Resources and Stakeholders.

My bias – use what you have first and get creative before you go out and buy anything.

I have found that if the effort is important enough to me, I get VERY creative with the resources at my immediate disposal.

By using what you have, you get a clearer idea of what you REALLY need and a stronger set of requirements when you go out and purchase something.


How to do Major Change with minimal available resources

In 2014, I was in the middle of a high-stakes Unified Communications implementation at a large university. This project was a game-changer – both for how faculty could teach and how everyone could communicate internally.

That project changed not only the phone system, but also provided video teleconferencing, integration between our classrooms and mobile laptops (a trickier thing to do back in 2014 – conference room video teleconferencing used a completely different set of standards than laptop video teleconferencing), advanced and integrated chat functionality, and many other goodies that could be helpful to students, faculty, and staff.

Though this is a corporate example, the same techniques I am sharing apply to personal change efforts.

You may not need to talk to as many people as I did during this project. Feedback from others can be helpful.

The goal is to maximize what you have to work with RIGHT NOW.
The Unified Communications project had the following problems / issues that needed to be solved.

1) This is a major assumption shift. We asked people to think about how they communicate with others at work. THIS WAS NOT A PHONE REPLACEMENT!

2) The entire project team needed to be on-board with that assumption shift.

3) The solution had a LOT of pieces. We’re not just messing with one workflow (picking up the phone and calling someone), we were messing with a bunch of them (chat, voice, person to person video teleconferencing, one-to-many video teleconferencing, desktop share….)

4) It would be very difficult to cover all the details of those pieces in one training event.

5) And even if we were able to do that – no one would remember how to do anything.

6) The system was also “unstable” during this section of the project. The pilot was to help identify better configurations. We asked a lot of the pilot participants – who I fondly refered to as “the 300.”

7) We wouldn’t have much documentation until after the pilot.
Activity 1: Go talk to people.
I went around to my team-mates, the experienced sub-contract trainer that has been assigned to us for the project, the pilot coordinators and members of the 300 and kicked around some possible solutions.

I had a number of conversations around materials that were available from the vendor and others “right now” and decided that curated link lists of how-to’s would be useful for this section of the project. At least until we had enough of a system to start testing and developing more specific content. The folks I talked to liked that idea.

Activity 2: Scavenge for materials
I talked around the IT department to see what else was available. We
have a SharePoint implementation underway. I knew that SharePoint had
all the features that I wanted for this project. Unfortunately – I
also discovered that the team would not be ready for me and for this

I thanked them profusely and looked elsewhere.
No one has a monopoly on tools.

A positive takeaway from this conversation, I became involved in the SharePoint project – so I’ll be looking at this solution more closely for future efforts.

Sometimes no = not yet.
For the curated link lists – I just dumped them into the University’s Google Docs installation. This way, I could give people permission to add and I knew that everyone at the University could access the materials.

Besides – I really didn’t want to spend a ton of time and effort over-engineering a web site that was only going to be used for a few months. And the sites were way too complicated to just point users to.

I also gained access to a free demo of a tool called IdeaScale. This tool would help us collect feedback.

Activity 3: Figure out how to use the materials you scavenged
I knew how to use most of the materials I scavenged. I used GoogleDocs daily and had already been messing with SharePoint for other tasks.

IdeaScale was pretty straightforward. The big trick with that solution was the human process. How do I get people engaged? Since this was free and low-profile, I have room and space to experiment with some things.

Activity 4: Take what you have found and go solve the problem
(see above)

Activity 5: Repeat Activity 1 (Go talk to people) with the thing you created to solve the problem. Get feedback.
The link list has already gotten positive feedback from the project team and pilot coordinators.

I am still in the process of putting together the rest of the solution.

Activity 6: Repeat activities 4 and 5 until either
– the problem is solved (often the jury-rigged solution you just created is good enough)
– you got the information you needed from your proof-of-concept and now have leverage to go ask for money / resources / people
– you realize you have completely mis-identified the problem and need to
chuck everything and start over (this is not a bad thing – just a
learning thing)


Considerations for Purchasing Tools and Materials

By creating a prototype using what I have lying around first, I am able to:

  • Get clear on the problem I am trying to solve without worrying about others’ expectations and opinions.

  • Identify the real gap in my resources – not what I (or marketers) THINK my gap in resources are.

  • Save money – I am not spending because I “think” something will help. When I spend, I know exactly why I am spending. Using what I have allows me to reduce “shiny object syndrome.” It also stops me from buying solutions to problems I don’t have.

  • Get creative about solutions. Both personally and professionally, my most satisfying solutions have occurred when I have had restricted resources.

Unlike professional projects, the source of resources and money is likely going to be you or whatever you can convince others to give you.

The connection between costs/resources and your project, therefore, is more direct.

If you are using what you have – that is personal money, tools, and energy that cannot be used for other things. You have likely obtained that resource as a result of past energy expenditures (working a job, investment research, relationships, etc).

If someone gives you a resource (money, tools, or materials), you are entering a relationship and a contract. There is an (often unspoken) expectation attached that you will use that resource wisely.

My general steps are as follows:

  • Attempt to make the change with the resources I have quickly at hand.

  • If I find I am missing something, determine whether I can do one of the following:

    • Rent or borrow the resource short-term. Here, I am entering a relationship with the “owner.” The expectation is that I take care of that resource and bring it back to them as good, or better, than they gave it to me.

    • Find a free or very inexpensive resource. This allows me to prototype on the cheap and the “relationship” involves an exchange of money or information (such as your email address). I will personally tend towards this option first.

      • The risk with this approach is clutter – both analog and digital.

      • Many “free” digital tools are on subscription models. It is important you keep track of the due dates and cancellation policies. Otherwise, you will wind up with a bunch of money being sucked out of your pockets by a gang of vendors.

  • If I am clear that I require a pricy resource, I make sure I know why I am buying the resource and what my intentions for that resource are.

    • For digital tools and other subscriptions, if there is a free trial period, I try to take advantage of it to make sure that the resource does what it claims.

    • I have been burned in this area too many times to count. Don’t get wedded to a solution.

    • If something critical is missing in your trial and the vendor says it is available in a paid version – tread carefully and do more research before shelling out the money.

  • Make sure you add the cost of the resource to your budget.

    • For Implementation and Permanent Change habits – add any subscription or ongoing costs to your operational budget.

    • For Impermanent Change habits – make sure you schedule cancellations in your calendar, so you don’t wind up with a collection of expensive subscriptions.


Replacing Resources

If I’ve been prototyping a solution in my change effort, I will typically upgrade or change out resources in one of the following scenarios:

  • The new resource fills a gap that the current resource just can’t fill.

    • For example, I replaced MailChimp (free) with Kartra (pricy) because I was beginning to have difficulty with the integrations and, after pricing all the pieces of my marketing architecture and the personal cost of maintaining those integrations, saw that the longer-term operational costs were lower. This is absolutely nothing against MailChimp – it’s a great tool.

  • The new resource is less expensive (both short and long-term) and does the same thing.

    • There is a switching cost to changing resources – both in energy and, often, financially.

    • Switching between resources needs to be considered a task that takes time – you have to learn how to use the new resource, switch over any old materials, and integrate the new resource into your processes.

  • The environment or my circumstances as I execute have changed and I require a different resource.

    • This is part of what happened in my MailChimp example. I was building out some paid courses and discovered multiple gaps. The workflow started to get too complicated.

  • The resource I have doesn’t do what it said it was going to do – despite multiple attempts at making it work.

    • I ran into this problem when looking at webinar solutions. Great marketing, but when I tried to use the product in real-life it was garbage. I spent too much time working around the product and finally gave up.

      It has been a few years, so I do not know whether this webinar application is still running or if they finally managed to resolve its multiple issues.

    • To help you avoid “sunk cost fallacy” – remember to “price” your time. Then, calculate how many hours you have spent trying to work around the resource. Add extra hours for the time taken off your life from the frustration.

  • “Scheduled” upgrades. These days, much of our hardware (computers, cell phones, and cars seem to be headed this direction) requires regular upgrades to keep running. If your Implementation or Permanent Change effort requires resources that are consumable or need regular upgrades, make sure you schedule and budget for that.

    • Example: Developing a regular running habit (Permanent Change). Make sure you budget for shoe replacement in your operations budget.

    • Example: Starting a business (Implementation).

      • You need to budget for software upgrades (Both time to learn the new version and, often, money. The money will either be subscription or major version changes)

      • It’s important to schedule hardware replacement. The cycle for most hardware right now seems to be 3-5 years before the hardware can no longer adjust to operating system updates. You need to budget money and the time to back up and reinstall all your applications. There is little worse than having your computer crash, potentially losing all of your work (if you don’t have a regular backup cadence), and finding that it is irreparable.


Resource Management and Budgets

All 3 types of change (Permanent Habit, Implementation, and Impermanent Change) can use a similar resource and budget list.

We are going to look at our resources, the initial cost of acquisition, and any maintenance or operational costs.

The spreadsheet has the following columns:

  • Resource – The name of the resource we need for our change effort. It could be a skill, a tool, materials, information, an experience etc.

  • Type – I like categorizing my resources by type. The type categories for the resources you need are up to you and are dependent upon the change effort you are embarking on.

  • Initial Cost – This is my initial cost of acquisition. I also use this as my “short-term” column for Implementation and Impermanent Push changes.

  • Operations – This is the ongoing cost. Even with Impermanent Push changes, I may wind up with resources I use later. This can also be the cost of continuing to engage in the activity, if I so choose. I’ll explain more in my example below.

  • Have? – This is the question “Do I currently have this in my possession?” The answer is yes/no. Typically, if I already have the thing, the cost is zero – unless I am leveraging a subscription, such as a pre-existing gym membership (see below). Then I will put the cost of however much time I am using in my Initial costs column

  • Priority – How badly do I need this resource to be successful?

  • Comment – List any items included in the cost, any assumptions you are making with the estimate

  • Actual – This allows you to track what you are actually spending

  • Upcoming – This allows you to see any costs that you know are coming. This column is particularly critical if you have contracted for services over an extended period.

The Resource spreadsheet you see above is for a week-long guided canoe trip I have scheduled for July.

1) I listed all of the resources I need

2) I defined “type”. For this trip:

  • Experience is the cost of the trip and any other travel expenses

  • Skill is any skill I need to build. I am coming to this trip with paddleboard, kayak, and some tandem canoeing experience. I determined that for the type of trip I am going on (paddling lakes and tranquil rivers), I can get away with 3 ½ day trips on a nearby river.

  • I decided to put my Canoe training under “Material” since it includes canoe rental. I have no need to purchase my own canoe. With the time that I have (a little over 2 months to train + coming off a back injury), I need to schedule 4 still-water trips. The Occoquan is a reservoir close to my house. The only waves are from power-boters.

  • The life jacket is “Material.” Though one will be provided with rentals and tours, I prefer having my own.

  • Subscription is anything I have with ongoing payments that I plan to use for this effort. In this case, I have a gym membership already. Since I need to make sure I stay uninjured before and during the trip – I can leverage my gym membership to improve my strength and stability as well as improve my stamina.

3) Initial Cost includes the cost of the trip and any training costs (including 2 months of the gym membership)

4) Operations costs are any costs I would incur if I decide to continue canoeing after our trip is over.

5) In Comments, I have added what is included in the estimate, any notes on how I calculated initial cost, and any assumptions I may have made. It also includes notes on where I am at in planning. You will notice that I have not decided how I am going to get to the trip destination yet.

The resource and cost spreadsheet is a working document. What we are doing is starting our cost estimation.

You may not have numbers for your Initial Cost and Operations Cost columns yet. That’s OK. We’ll talk about that in the next section.


Exercise: Resources and Costs

Let’s pull out your Change Planning exercises – We are going to take a look at Pass 3 (What You Have) and Pass 4 (What You Need).

This exercise applies to all change types (Permanent Habit, Implementation, Impermanent Push

Develop a spreadsheet with the following columns:

  • Resource – The name of the resource (skill, a tool, materials, information, an experience etc.)

  • Type – General categories for the resources you need. Common ones are: Skill, Information, Software, Hardware, Materials, Mentoring, etc. Choose categories that make sense for you and your change effort.

  • Initial Cost – This is my initial or short-term cost of the resource.

  • Operations – This is the ongoing cost.

  • Have? –“Do I currently have this in my possession?” Yes/No.

  • Priority – How badly do I need this resource to be successful in this change effort?

  • Comment – List any items included in the cost and any assumptions you are making with the estimate. Add other notes as necessary.

  • Actual – Update this column as you spend the money for the resource or as you acquire the resource.

  • Upcoming – You may only need to use this column if you are contracting services now for payment in the future. You can also use this column when you have a spend coming up.

1) List all the resources you have in the Resources column

2) List any resources you need in the Resources column

3) For each resource:

  • Determine the type of resource it is

  • Identify whether you have the resource (Yes/No)

  • Identify the priority of the resource – how badly you need this resource to be successful (High/Medium/Low)

  • Enter any comments

4) If you know the initial cost of that resource or already have an estimate – enter that number

5) If you know the operations cost of that resource – enter that number, adding any comments into the comment field. For example, is that cost monthly? Per session?

For more complex projects, you may want to add the following columns:

  • Timing – When I need the resource (date or phase name)

  • Person – Who controls the resource or who you need to talk to

  • Next Steps – The next step you need to take to acquire or gain access to the resource

  • Decision Date – When you need to pay or cancel a subscription OR when you need to decide which resource you should use.

  • Decision Comments – Any notes on the decision you need to make about this resource and the cost if you don’t make a decision or neglect to cancel your subscription/trial.

Remember, this is a working document.

As we begin to look at Cost Estimates, expect your Initial Cost and Operations cost columns to change.

You will also be using this document as you execute your plan to keep your spending reasonable.


Costs – Monetary and Personal

We often underestimate the cost of change. Even the small changes may pick away at our financial resources.

Starting a meditation practice – here’s an app for $10 per month. And the cushions at $35. And a singing bowl for $25. And a yoga mat for $20. And…

I have found it helpful to spend a little time estimating how much my new habit or implementation or push will cost. The higher the potential cost of the change, the more time you should spend on creating a budget and a cost estimate.

It’s very easy in our current culture for a quick, “free,” change (such as starting a meditation practice) to suddenly cost a few hundred dollars.


Cost estimation process

Dependent upon how much you think effort will cost, you may or may not need to do this.

The higher the potential cost for your change (such as school tuition, creating and marketing a new product, starting a business, etc) the more I recommend creating cost estimates.

Permanent Habit changes typically won’t require this type of cost estimation. These types of changes tend to be small-scale and low-cost.

Implementation changes and Impermanent Habit changes can turn out to be expensive. Use your best judgement and your appetite for risk to determine whether you need this process.

There are three main estimation techniques. I have listed them in order of complexity.

Estimation Technique 1: Analogous Estimating
Using the cost of similar projects to estimate the cost of the current project. Most useful when you have done this before. The more similar the projects being compared, the more accurate the estimate. I often use this as a “first draft” of potential costs.

Estimation Technique 2: Bottom-Up Estimating
This is best done once you have put together a detailed list of activities for your project. You estimate the cost of each activity; then sum up the estimated cost of each work activity in the project.

It would be nice if we knew EXACTLY how much stuff costs before we do it – but life doesn’t work that way….

Estimation Technique 3: Three-Point Estimating
Use this to help with creating the range and probability of how much an activity will cost.
I would use this as I put together my bottom-up estimates for expensive and/or complicated activities.

This estimation technique is similar to the Three-Point Estimating technique we used to estimate how much time a task will take – just with fancy-looking formulas and bigger numbers.

Step 1: Create 3 estimates
– Most likely (cM) – The cost of the activity based on realistic effort assessment for the required work and predicted expenses. Even if you are doing everything in-house, stick an hourly number on the labor. It’s eye-opening.

– Optimistic (cO) – The activity cost based on best-case scenario.

– Pessimistic (cP) – The activity costs based on everything going horrifically wrong.

Step 2: Plug resulting numbers into formulas
There are two ways to calculate expected costs.
Depending on your organization, they may want to see one or both calculations.

cE = Expected cost

– Triangular Distribution. The average of the most likely, optimistic and pessimistic cost scenarios.
cE = (cM + cO + cP) / 3

– Beta Distribution. This uses the PERT (Program Evaluation and Review Technique) technique to get a weighted estimate between optimistic, pessimistic and most likely scenarios. The assumption is that the most likely scenario is 4x more likely to happen than either the optimistic or pessimistic scenarios.
cE = (4cM + cO +cP) / 6
For your high cost / high risk changes, you may want to add a “contingency reserve.” This is the reserve we create in case we completely miss the mark on our cost estimates.
Hopefully, you won’t need this.

By definition, we can only account for the stuff we think can go wrong when we put together our pessimistic estimates. The “known-unknowns”.

If you have a complex activity and have little to no idea about how much it will cost, run your numbers by a supportive friend who has done this before. Running your numbers by someone else at this early estimation stage is a good idea anyway. They may find expenses you have not thought to accommodate – such as school fees and book costs when pursuing a degree, or the various taxes and licensing costs when starting a business.


The Cost of Burnout

The people who love me warned me….

Wendy, you can’t keep up this pace.

No. I can’t.

Not for lack of trying.

The issue is permission.

Giving myself permission to work at a more reasonable pace.

There is a ridiculous amount of research outlining the psychological, physical and emotional cost of burnout. However, many of us find ourselves continuing to burn the candle at both ends.

That research doesn’t seem to be enough to override the fears that drive over-work.

The most persuasive argument I’ve found has been financial.

Seeing how burning myself out hits me (hard) in my pocketbook.


Leonie Dawson is an artist and businesswoman in Australia. From hard experience, she developed a way to the personal financial cost of burnout.

  1. How much are you losing because you can’t work? There are a few levels of this.

    • The amount of money lost because you are too sick / tired to work (short term)

    • The amount of money lost because you are too mentally fried and exhausted to even think about talking to people or put more work in the pipeline (longer term)

    • The amount of money you gain when engaging in an activity vs the amount of lost income when recovering from that activity.

      • For example – facilitating workshops. A workshop may bring in $5000, but she may lose another $5000 in lost income after the workshop as she recovers + the lack of energy needed to put more work in the pipeline.

  1. How much do you have to spend preventing or recovering from burnout? (doctor’s appointments outside of annual wellness visits, massages, the shrink….)

Then there are the qualitative costs.

  1. Less time spent with family and friends because you are too tired and overwhelmed to get off the couch

  2. Lack of exercise – so you then have to spend money on clothes that fit because everything else is too tight

  3. The drive to eat junk because the intellectual bandwidth to decide on what to eat and actually cook it feels like its too much. And the resulting costs, because eating out tends to be more expensive than cooking.

  4. And, for those of us with mental health issues, the risk of triggering those issues – making it even that much harder to function.

It was interesting to me that I finally wised up to the stupidity of driving myself to burnout when I finally saw (and felt) the economic effect of working the way I have.

The qualitative costs weren’t nearly as persuasive to me.

Maybe it’s a permission thing. Maybe it’s an ego thing. Maybe it’s a self-esteem thing. I’m sure it’s a combination.


Run your own numbers and determine your personal economic cost of burnout.

  • For each day spent recovering – how much money do you lose in income?

    • Calculate that even if you are in a job with sick days. That’s what your employer is partially spending when you are out sick. It provides a more persuasive argument to them if they are driving you too hard.

    • I calculated mine by the hour. You can do your calculations by the day, week or month.

  • For those who own their own businesses – how much do you lose in the longer term by not maintaining your pipeline?

    • What is the least amount of money you will make if you let your pipeline dry up?

    • How much money are you spending each month for your business, whether or not you have any work?

      • If there are loans involved, how much are you spending in interest for each month you are not covering expenses?

    • How long will it take to recover that pipeline back to break-even capacity?

    • How long will it take to recover that pipeline back to full-capacity?

    • Will this round of burnout result in permanent capacity shrinkage? A major risk for solo-preneurs.

  • What other expenses will you have if you burn yourself out and need to recover? Therapy? Doctor’s bills? Skydiving? Spa day?

Then add the qualitative costs. What do you miss that has value to you by driving yourself to work so hard? What are you risking with your health (mental and physical)? Base this on your own experience.

I’m not going to share the calculator spreadsheet she created.  I want to respect her intellectual property. Leonie had the information in her now defunct Shining Biz and Life Academy in the course The Economic Cost of Burnout.

Take a hard look at your plan. Are you risking burnout?


Exercise: Cost Estimates

Return to your Resources and Costs spreadsheet.

Identify any Resources where you have not made solid cost estimates or still need to make decisions on approach.

In the example below, I made changes to my Resource and Cost Spreadsheet based on the decision I made to drive up. The Destination is 2-day drive each way if I go at a reasonable pace. I could drive it all in 1 day, but that is a VERY long day). By driving, I gain the flexibility to go visit friends in a nearby city, I can bring more equipment and not have to worry so much about packing, and I don’t have to worry about a rental car.

  • Hotel – I budgeted $100/night. This may seem steep, and there is a great chance I won’t spend so much, but this is where I provided myself some financial slack in case I under-estimated gas prices or how much I am going to eat as I travel.

  • Travel – I budgeted $350 for gas. A great way to estimate driving costs is to use the IRS mileage deduction (US) or your country’s mileage deduction (if your country has this).

  • Travel Meals – I budgeted $50/day. I know I tend to eat less when I am on road trips, but this is a great way to make sure I have enough money for a fancy meal or two while I am on the road.

When I do my cost estimation for a project, I much rather have my estimates run high than to be unpleasantly surprised by how much I wound up spending.

I try to calculate slack in my budget in case I forgot something. Having money left over beats scrambling for funds any day in my book.


Scope and Remembering Your Outs

At this point, you want to make sure you are clear on your outs.

The Outs are the behaviors and circumstances that signal that you need to abandon or dramatically change your plan and your priorities.

Ideally, you want to define these outs before engaging on the effort – particularly for high-stakes efforts.

You want to define these so that you don’t quit too early.

Knowing the Outs also helps to reduce the impact of the. “Sunk Cost Fallacy” – where you keep going despite all evidence that what you are doing is not going to give you the results you are after.

The list below are the common issues I have encountered in my life, in client’s lives, and in corporate projects.

  • Result issues – The outcomes you receive as a result of your effort do you more harm than good. (Examples: The diet plan you are following causes you to gain weight and feel terrible; You are continually injured whenever you try to train for a marathon.)

  • Assumption issues – Your assumptions about the environment you are working in prove to be wildly wrong and your effort, as planned, will not provide the return on investment without major adjustments to the plan. (Example: You assume that a friend will be able to help you, but she is not available, nor is she supportive, and you have not identified other sources of assistance).

  • Priority issues – You find that other priorities at this stage of your life are higher than your change effort. (Example: A parent becomes ill and you become the primary caretaker).

  • Energy issues – You find that you truly don’t have the energy or time to execute on this change as it is currently structured. (Example: You have a chronic health issue flare up which begins to impact your ability to concentrate. Your health impacts your ability to execute your plan.)

  • Cost issues – You are starting to spend significantly more money than budgeted and you aren’t close to your goals. You will know where that boundary is. I recommend identifying a financial number that is your cue to seriously evaluate what you are doing. (Example: You are creating an online course and find that you are rapidly burning through your budget. You decide to evaluate how things are going when you have spent half of your budgeted money. Are you close to ½ way done? How much more needs to happen? Can you salvage the project with the remaining money such that you still have something to sell?)

  • Resource issues – You find that you cannot collect the resources you need (either material or human) to be successful. (Example: You decide to learn how to ski, but you live in Florida and are struggling to earn the money to go skiing due to other financial priorities – such as rent.)

There is a difference between overcoming obstacles and banging your head against the wall.

Make sure you are clear on exactly what you are expecting as a result of your effort and how much of your time, energy, and resources (financial and material) you are willing to put in to achieve your goals.


Implementation and Impermanent Push Planning – Long term

I’ve noticed that successfully implemented large projects create more work. This is true both personally and professionally.

In my corporate experience, this work surfaces in the following ways:

Resolving an issue resulting from the new system reported across the business.

The resolution for the issue could be short and simple and what needs to be done is blatantly obvious, such as adding a pre-existing field to a pre-existing report or re-training.

There is, however, the possibility that the solution will require its own full blown project – including requirements collection, level of effort evaluation, project planning, etc.

Having a sound issue intake, evaluation and prioritization process within your operations will help identify those monsters before they become expensive resource-sucks.

A component of the project neglected at go-live and needing attention

Often, this happens either because the project was over-scoped to start with (trying to do way too much at once with too few resources) or because there were problems with the main component of the project.

A common example – the staff-facing component of an enterprise system successfully launches at go-live, but the public-facing component is bare-bones, ugly, and barely usable. The organization needs to staff-facing component to work and drive the public-facing component, so the project appropriately focused its limited resources on getting that running.

Getting the public-facing component looking and running correctly should be a new project. Especially since doing that well often engages a new group of people with different skills and often results in role changes between the business units.

In a recent project – the IT department led the staff-facing component of the project. Much of their effort and focus was spent on moving and validating legacy data, configuring the back end of the tool, and making sure the integrations worked.

Once the business was ready to address the public-facing component, the Digital Marketing team took over leadership of that portion of the project and used the visual design, web development and UX expertise they possessed to make the public component work just as well as the staff-facing component. Ultimately, the public-facing component became its own project with its own budget and resourcing – as it probably should have been in the first place.

Implementation of new functionality that was not part of the original scope

As the business gets more comfortable with the tool it has implemented and learn more about available features, they may choose to create a new project to leverage that feature. An example of this is the implementation of a Project Management tool and later launching a project to leverage the resource management functionality within that tool.


These initiatives surface on top of the need to move the results of the original project into operations.

And it is not just one of these that occur. Often all three of these scenarios, plus troubleshooting, plus the move to operations all happen at the same time – soon after the project and with a very tired pool of project resources.

The mistake I made in my last big project was not planning for these scenarios and engaging in appropriate stakeholder management at the beginning. As a result of this oversight on my part, everyone was overwhelmed with demands and the lack of focus meant next to nothing got done beyond firefighting for a month afterwards – much to the disappointment of the business.

I’ll admit – I’m not entirely sure it is realistic to expect much more than firefighting the 2-4 weeks after go-live.

Still, I think that going in with a solid post-project plan that includes a discussion of how to prioritize surfacing initiatives after the project stabilizes will go a long way in reducing some of the angst the business experiences when it can’t fix and do all the things right now.

One (of many) lessons learned.


How Post project planning works in the Personal space

One of the reasons I asked you to think long-term about how your change fits into your life is that we typically don’t think long-term.

We lose the 25 pounds, celebrate, then gain it all back plus a few.

We train for a marathon, then wonder what we are going to do with this new-found time.

We write a book, then get depressed as we send our “baby” out into the hostile world.

I want you to consider what your life is going to look like after the initial push to make your change.

How does this change fit into your life moving forward? Is this a change that will be easily integrated into your current day-to-day, or are there significant changes to your environment, your processes, and how you spend your time that you need to consider?

What do you want your life to look like after this short-term push?

The answers, and the activities you execute in response to your answers, are what makes change stick.

Change doesn’t magically happen just because you finished a project.

If your change project is successful, there is still work to do.

This is even true for efforts that are meant to be temporary (the Impermanent Push).

We don’t come out of those efforts unchanged. If we’ve done it right – we’ve learned something about ourselves in the process.

If the goal is big enough, the effort taxing enough, we’re also coming out of that effort tired.

The knowledge that there may still be more work to do that doesn’t have the adrenaline hit of “crunch time” can be disheartening and depressing.

The long-term maintenance of your change effort is the unglamorous part.

The new has “potential.”

With the existing, potential is realized, and often the realization is that it is disappointing.

It’s why corporate leaders prefer to move on to the next project vs. making sure the change they initiated with the implemented project sticks.

It’s why municipalities and developers focus on “building new” rather than maintaining existing.

It’s how we fall into the trap of having 15 unfinished projects.

Maintenance requires repetition, refreshing, renewal.

How easy (or hard) will maintenance be?


Preparing for Operations – Implementation Change Effort

Implementation change efforts are embarked upon because there is a desire for a longer-term change.

If the Implementation is successful, there are new processes, new relationships between people, and changes within you.

The assumption, with an implementation, is that we will be operating whatever it is we implemented longer-term.

The trick is to make that operations effort as painless as possible.

To maintain the change you worked so hard to make, ask yourself the following questions:

  • What do you need to start doing to maintain the change?

  • What do you need to STOP doing to maintain the change?

  • What adjustments do you need to make to your life to make the change stick long-term?

To make this change reasonably painless and more likely to last over the long haul, you want to integrate that change into your life as much as possible.

Unfortunately, it’s too easy to make change additive.

Next thing you know, your morning routine is taking 2 hours, workouts are taking 2 hours, and the to-do list of all the things you are “supposed” to be doing to “be a better person” becomes its own source of stress.

Another consideration for making change stick is identifying when you are backsliding into old habits.

  • What are your signals that you are starting to backslide?

  • What is your strategy for getting back on track?

Operations doesn’t require the same level of measurement as the short-term push.

I find that quarterly checks of how I am generally doing are useful for evaluating whether the important things in my life (health, relationships, and vocation are my biggies – you define your own) are still on track, or I need to concentrate on getting back on track.

Life happens. You may find that some habits that worked for you a year ago no longer work for you now.

Even permanent habit changes require refreshing and adjustment. This is how life-long exercisers keep their routines fresh and life-long meditators stay motivated to practice.

You may decide to start an impermanent push to refresh your habit, make a minor adjustment and spend a couple of weeks tracking, or replace the habit altogether.


Exercise: Implementation - Operations Planning

Pull out your Long-Term pass from the Change Planning Exercise in Chapter 5

  • What changes as you transition from your short-term effort into day-to-day operations?

  • What adjustments do you need to make to your daily life?

    • What are you adding?

    • What are you replacing?

    • What are you stopping?

    • The goal here is to integrate your change into your life as much as possible. The more you are able to integrate the change – the easier it will be to maintain.

  • What are the signals you think you will see that will tell you that you are returning to old habits?

  • What is your strategy for getting back on track?

I recommend at this point scheduling brief quarterly reviews and a more comprehensive annual review of your life. We’ll talk more about that process in the Execution chapter.


Dealing with Post-Project Grief – Why We Get So Depressed After Achieving Big Goals

Psychologists have observed that many individuals go through the “Post-Project Blues.” This is that subtle (or not so subtle) depression that occurs when intense activity ends abruptly. It doesn’t matter whether the event was positive or negative.

Some have linked this phenomenon to the “contrast effect” – subconsciously comparing your current state to your most recent past state. Others link it to a natural down-regulation in the immune system, cortisol, dopamine, adrenaline, and other stress responses as the body attempts to renormalize.

Even though the change may be short-term, or may be an implementation change, consider the immediate period post-project


In my experience, there is a grieving process that occurs at the end of intense efforts.

  • I worked as a stagehand through my teens and twenties. Even if the cast and crew work together again, it’s never entirely the same people and the roles shift from production to production.

  • Getting the project out the door (personal or professional). There’s a sense of loss that occurs during that transition from project to operations – particularly when you are handing off what you have created to another party. That other party can be individuals responsible for operating the thing you created or the marketplace. In projects where you are working with a group of people, the relationships change as people move on to new projects or take on the roles required for operations. Furthermore, a significant amount of personal identity gets wrapped up in the effort. Now what?

  • After a competition or after planned, intense events such as weddings, funerals and multi-day retreats. You have spent weeks or months training for the competition or planning the event. Now there is all this “free time” and the feeling that there is nothing to focus on.

The more energy and effort I have put into an initiative, the deeper that let-down.

Within the liminal space between high-energy efforts, I find myself asking “Now what do I do with myself? Who am I without this effort?”

There is a loss of identity as the thing I have been working so hard on ends.

As we look at the transition between short-term and long-term, we want to ask

  • How are you going to celebrate what you have accomplished?

  • How are you going to take care of yourself through this transitional period?

  • What support will you need to assist you through the natural grieving process?

The answers will be different for each of us.


After the Push, How Has My Life Changed?

Our focus has been on the push. The training. Getting to the goal.

Once we get there – then what?

In my experience, it’s this feeling of emptiness and lack of direction that helps to trigger post-project depression.

If I am looking forward to what’s next, I find I don’t get so funky after big project pushes.

The first question, after a big impermanent push, is whether you want to keep going with the activity.

  • If you have been training for a marathon, do you want to keep running daily?

  • If you have been making a charity quilt, do you want to start another?

  • If you have been finishing a degree, do you want to use those skills and knowledge in another way?

“No” is a perfectly appropriate answer.


Heather and I did a winter climb of Mt Washington, New Hampshire in 2015.

Mt Washington is known for the world’s worst winter weather and some of the highest winds on record.

The two of us spent months training – weekly hikes, cardio 3x per week, strength training to ensure we could carry equipment uphill. I even did some indoor climbing work – just on the off chance we did some.

We tested gear, we tested snacks, we did extensive travel planning.

At Mt. Washington, on climb day, we were not disappointed. Minus 32 degrees fahrenheit with 70 mile per hour winds, practically zero visibility, and weird grey snow. We didn’t summit (for obvious reasons) and the guide said that it was the worst he had ever seen it. Still, it was an awesome trip.

On the drive home, Heather and I looked at each other and concluded – that was fun, but we don’t need to go Mountaineering again.

Our off-ramp, we decided, was to continue hiking occasionally.

Heather eventually went on to solo-paddle a section of the Northern Forest Canoe trail.

I went on to start a business.

We both came out of that experience with a lot more confidence in our ability to do something risky (downright crazy according to my hardcore whitewater kayaking friends) and survive.

It was that trip that gave each of us the courage to pursue a scarier dream.


Exercise: Impermanent Push – Planning the Off-ramp

While you are going through the impermanent push, ask yourself the following:

  • Am I enjoying the process?

  • Am I liking the results I’m getting so far?

  • Is this something I would want to experience again?

  • If not, am I OK with this being a cool story?

  • What am I learning about myself?

I invite you to ask yourself “Once this is done, what do I want to do next?”

  • Is there something within this experience that you want to incorporate into your life? What is it? How do you see yourself incorporating this?

  • Do you want to do this experience again? If so, what are my options?

  • If I don’t want to do this again, what does the end of this push allow me to do? What do I want to do next?

There is no “optimal” time to sit with this question. We learn things as we go through the process that might change our decisions from the Long-Term Change Planning document.


We have spent a lot of time on project planning in this chapter.

Let’s turn our attention to the greatest challenge to our change.

Other people.




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