Chapter 3 - Roadmapping

Chapter 3 - Roadmapping
Contributors (1)
Mar 08, 2019

The best leaders in dual-purpose organizations consider their high-level principles sacrosanct but their ground-level decisions provisional.1


Beginning the process of Roadmapping

Roadmapping is a process I pulled from my corporate life.

The idea is to document where you want to be in a foreseeable number of years (often 5 or so) and figure out what activities will get you there.

A roadmap is meant to be a working document.

  • You add projects and activities when the opportunities present themselves.

  • You subtract projects and activities that either don’t get you to where you want to go, are no longer needed, or you don’t have the resources to pursue.

  • You perform intake on new activities and opportunities based on the roadmap. Will it get you where you want to go? Does it map to your high level principles?

Seems straightforward, but people and organizations struggle with this.

In my experience, the struggles are a result of an inability to say “no” and a lack of focus on what they really want.

In the previous chapter, we defined our “North Star” and clarified the values we wish to demonstrate in this phase of our lives.

In this chapter, we are going to look at the things we want to accomplish and how they may fit into our lives.


Looking at Your Current Life Phase

We have defined our “north star.” This is what we want to move towards.

We have identified our distant “end.” This provides the high-level guardrails and direction around how we want to spend our life.

The north star and our distant “end” provide some principles we can use to guide ourselves.

We have also looked at some trends and the life phases we have experienced to date.

It’s good to get some perspective on where we have travelled to date. The experience and wisdom we have gained during our time on this earth.

Let’s take a closer look at the “foreseeable future.”


Where are you now?

Each phase has a beginning, middle, and end.

How far into your current phase are you?

  • Are you just starting? Those of us in transition are just starting, collecting new skills and experiences, being a beginner - whether we like that position or not. Beginner’s mind, I have found, is significantly more challenging as one gets older. This is particularly true if you have established mastery in another domain.

  • Are you well-established and comfortable? Firmly in the middle of the phase? You are comfortably gaining and applying mastery. You have systems and processes that work for you or require only minor adjustments. Things seem to run on their own (whether you like it or not). Your direction is pretty much set.

  • Are you starting to wind down this phase? In my experience, the wind-down surfaces as either divine discontent and a feeling I could be doing something more/different OR it shows up as a dramatic event that feels out of my control such as layoffs, failed attempts at promotions, and banging my head against the wall as I try to keep doing the same thing and it stops working. Are you sensing that a major shift needs to occur?

For those of us who are either at the beginning of our current phase or well in the middle, it’s worth asking:

At the end of the phase you are currently in, what do you want your life to look like?

For those of us at the end of a phase (the divine discontent can no longer be ignored and your head hurts from banging it against the wall for so long):

  • What do you want your transition to look like?

  • When the transition is successful, what do you want your life to look like?

  • How do you want to feel about yourself? About the people around you? About your environment and the way your life is structured?


Developing Your “North”

Certain phases of life have particular energies.

For example, if you are in a phase of life where you are raising young children, your energy is, necessarily, going to be focused on raising those children. Other priorities, such as becoming a karate black belt, will require either creative thinking to fit the priority into the dominant energy, or will need to be put on hold for a later phase.

Roadmapping allows us to take advantage of the dominant energy of a phase without necessarily abandoning a dream.

When we create roadmaps, we are typically looking at 5-10 years out.

I recommend sticking with the shorter timescale unless you already have an activity in mind that you know will take you many years – such as getting a PhD (usually a 4-10 year process), completely changing careers, or raising children (you may want to break things down based on their developmental schedule)2

The Roadmap is, essentially, the strategic plan for your Portfolio of Life.


The discipline of project and program management contains a helpful framework for thinking about how we can organize our activities. We have been working, so far, at the Portfolio level.

Portfolio – Everything an organization (or person) does to fulfill its life mission. The big umbrella. Why are you doing what you are doing? What’s your north star? What values and principles are you using to guide your decision-making. These are your big strategic questions.

Life Roadmapping (such as what we are doing in Chapter 3) fits here.

At the end of this phase of your life, what do you want it to look like? How do you want to feel about yourself and the life you have built? What stories would you be proud to tell? How do you want to be of service? These are the roadmap targets of your portfolio.

Program – A collection of related projects + operational activities. This could be organized as the slices in the Wheel of Life. Example: Everything I do to maintain my health can be one program. All the stuff I do for work can be another program.

At this level, we look at programmatic roadmapping. What improvements do you want to make to your health? Is there a career transition or trajectory you wish to pursue? (We will address these questions in Chapters 4 and 5)

Project – An activity with a beginning, middle, and end that we pursue in order to create change. In a personal context, this could be writing a book, following the initiation phase of a diet, the process of establishing a new habit with defined criteria for “success,” training for an event, etc.

Portfolio > Program > Project are all fundamentally I levels.3 The activities in this structure are things you have control over. You chose to do them (though you may have been “strongly encouraged” by another to take on the task).4

From here, we start looking outward. It’s also at this point where Project and Portfolio management tend to stop. These disciplines tend to face internally – with Portfolio management starting to look outside at how to fit with the environment.

I want to propose 2 other levels. This isn’t reinventing the wheel – business strategy, marketing, and design disciplines ask these types of questions. I want to place this in a personal contest.

Local – How does my portfolio/life integrate and interact with my immediate environment? What is the impact of my work, effort, and being on the people and things I am closest to? What is the immediate short-term impact of my work, effort, and being?

Global – How does my portfolio/life integrate and interact globally? How might I influence the environment (people and things) 2-6 degrees of separation out? How might what I am doing/being in the now impact the long-term future? We may never truly know. I strongly feel that we need to consider our decisions based on the long-term and distant impact, not just short term.

We have swung too far into short-term, selfish, survivalist thinking. I can’t fault anyone for that. It’s what is rewarded right now.

Furthermore, our brains search for certainty and control.5 We’re more likely to find certainty and control inside, right now and next to us.

Over this and the following chapters I invite you to look at your Projects, your Programs, and your Portfolio.

How’s your life portfolio? How are each of your programs within that portfolio? Do your projects really fit into your programs and do your programs fit into your portfolio the way you think they do? Is there anything you should let go of?

Once you are clear on that, you can then ask “What is the impact of your life on your local environment? How might you be impacting the global collective?”

We’re being asked to think and act at different levels. My suspicion is that the seeming chaos is a result of us trying to think and act locally and globally without having a solid foundation for ourselves.6


Exercise: Developing the Target

Since we have started defining our target with the identification of our North Star and clarification of our values, let’s further clarify where we want to go in the foreseeable future.

We are developing the target for the portfolio of our life. The North Star and the values we have defined will serve as guardrails for decision-making and prioritization.

Where is your next distant landmark?

  • What do YOU want your life to look like at the end of this phase?

  • What are your personal goals that will help move you towards what you want your life to look like

  • And WHY do you want this?

What you want your life to look like is the direction you wish to head. The high-level vision of your life. What you want. How you want to feel.

Your personal goals are the milestones on the journey. When done well, the goals you set move you in the direction of your dreams.

And the why is the driver behind it all. WHY do you want these things? It’s the WHY that provides the motivation and drive when things get tough.

I invite you to spend some time daydreaming.

Tell the internal editor that you’ll listen to its objections later, you’re just writing it down.

We can talk about all the reasons why what you want is impossible later.

Just free-write. No editing.

For this exercise, we’re going to daydream in ALL the areas of our life.

Notice that work and finances are only a quarter of what life is about.

I want you to think holistically.


Next, we are going to start dividing our life portfolio into programs.

You may have seen the wheel of life before - in various incarnations.

Fundamentally – this wheel is meant to remind us that life has different areas we need to pay attention to in order to be whole and well-rounded.

Not just work.

We start by defining what ideal looks like in each of these areas. We then determine which area we wish to focus on for a period.

This way, we don’t overwhelm ourselves by trying to change everything at once. (The workbook will be attached as an appendix in the book)

In my experience, I’ve found it helpful to take the time to define what a life that has meaning to me looks like.

  • How’s your health?

  • How are your relationships?

  • Do you have time for hobbies?

  • Are you living someplace where you can flourish?

  • Are you making a living in ways that nourish you?

  • Are your finances aligned to fund this life you desire?

  • Does your life reflect your values?

Let me provide you the definitions of each segment of the wheel shown above. You are welcome to choose another wheel that better resonates with you and more closely reflects how you see your life.

  • Work and education – The things you do to make money, career or vocational aspirations, and any skill you wish to learn or master – either related or not related to work.

  • Money and finances - Think about your income, any investments, any debts, your spending habits and patterns and any existing and desired possessions

  • Health and appearance – This section includes physical and mental health plus the things you do to help maintain optimum health: rest and relaxation, diet, exercise, etc. I’ve also included any appearance goals here – such as weight loss.

  • Relationships - Consider how you interact with people – both collectively and individually. Many wheels will separate romance, family and friends. You are welcome to do so as you see fit.

  • Lifestyle – This category is a catch-all that accounts for the time that you spend outside of work. Where you live, your housing, your neighborhood and neighbors, any travel you do (or wish to do), places you want to visit, and any hobbies or leisure activities that you enjoy.

Within each category of your life, ask yourself the following questions:

  • What does your ideal life look like in this category?

  • How will you feel when you achieve that dream?

  • What will achieving the dream enable you to do?

  • What will you have that you don’t have now?

I don’t expect you to go through the entire wheel in one sitting. Each question can take some time to answer.

Once you go through each section of the wheel, it’s good to see if there are any common themes surfacing.

  • Are you seeing any repetition in what you are writing across the areas?

  • Are there certain values that are surfacing?

  • How do these dreams feel to you?

    • Do these dreams feel impossible?

    • Do you find yourself excited? Scared? Both?

Feel free to write anything that comes up as you sit with the what you have written.

You may find doing multiple passes in each section helpful.

Our dreams and wishes, along with how we feel about them, can surface important information about what we value, why we value it, and the fears that may be hindering us.


Optional Exercise: Defining Your Wheel

Maybe you haven’t found a Wheel of Life that truly resonates with you.

I invite you to create your own.

Some guidelines as I’ve gone through this practice with clients that may help:

  • Keep the number of “life sections” to between 5 and 10. Less than 5 seems to skip something. More than 10 gets unwieldy.

  • Define each section in a way that is meaningful to YOU. I’m pointing out themes that others have used – but it may not reflect the way you think about your life.

  • Common areas that are separated into multiple slices:

    • Do you want Relationships to be one area (how I engage with the rest of humanity) or separated. Some ideas include :

      • Household (roommates, spouse, kids)

      • Immediate family (parents, siblings)

      • Extended family (cousins, aunts/uncles, grandparents)

      • Friends

      • Romantic relationships

      • Professional colleagues

    • Work/Career/Vocation. Some ideas include:

      • Work Projects

      • Professional Development

      • Primary Work (the day job)/ Secondary Work (the side hustle)

      • Creative projects

    • Health. Some ideas include:

      • Body composition

      • Energy levels

      • Nutrition

      • Exercise

      • Grooming and Physical appearance

    • Lifestyle. Some ideas include:

      • Neighborhood (characteristics, specifics if known like “I want to move to…X”)

      • Hobbies

      • Vacations

      • Life Balance

Take whatever works for you, leave the rest.

Change as you see fit.



Why do you want what you want?

Simon Sinek, in a 2009 TED talk at Puget Sound, emphasized the importance of the “Why.”7

Why are you doing this?

  • Why do you get out of bed in the morning?

  • Why should anyone care?

In the TED talk, Sinek noted that the inspired leaders and the inspired organizations all think, act, and communicate from the inside out.

Essentially starting with Why, talking about How, then describing What.

There are external benefits of knowing your Why:

  • People respond to WHY you do something. You become more persuasive. It’s easier to sell and influence.

  • You are more likely to attract people who believe what you believe. These people will be more inclined to help you fulfill your purpose.

But there is a powerful internal benefit too.

Knowing why you are doing something can keep you going when things get hard.

Whenever you are doing something new or challenging or just worth doing, things WILL get hard.

It’s just a matter of figuring out what you are going to do when you hit that inevitable dip.

Are you going to forget what you are trying to do and pretend you didn’t want to change in the first place?

Are you going to become disillusioned and quit?

Are you going to get depressed and beat yourself up and call yourself a failure?

Or are you going to follow through?

Knowing why you are doing something will help get you successfully through the dip.

There is a second, internal benefit.

Knowing why you are doing something can help you make decisions

In your workbook, look at the questions.

  • How will you feel when you achieve that dream?

  • What will achieving that dream enable you to do?

  • What will you have that you don’t have now?

Within the answers to those questions is likely your “Why.”

Feel free to scribble down anything that comes to mind as you look at your answers.

Do you see any trends and similarities between all the segments of your life?

If you know why you are doing something, it will help you:

  • Be more persuasive.

  • Attract help from people who believe the same things you do.

  • Push through the inevitable dip when the going gets tough.

  • Make decisions if you evaluate your choices against why you are doing it.

Look at each segment of your ideal life and ask – why do you want these things?

Look for trends.

Get clear on the answer.

It’s good to have reasons why that are compelling to you. If you don’t have your Why defined and/or it is not compelling to you, you are not likely to reach your goal.


Optional Exercise A: When everything goes wrong

Let’s assume that all the assumptions you made when designing your target were wrong.

  • Your health goes south

  • You lose your job

  • You get divorced (or married)

  • Your investment accounts tank with the stock market

What do you want your life to look like?

What can you work with? What is most likely to still be there? What assumptions are you making as you create this plan?

Repeat the Developing the Target exercise with “Worst case scenario” in mind.

(Adapted from Bill Burnett Designing for a Better Life)


Optional Exercise B: Money is no object

You have just won the trillion-dollar lottery. Money is no object. Time is not an issue. You are in great health, energetic, surrounded by loving and supportive people.

What do you want your life to look like?

Repeat the Developing the Target exercise with “Money is no object and everything is awesome” in mind.

(Adapted from Bill Burnett Designing for a Better Life)


Optional Questions for the above exercises:

  • How similar are these scenarios to the one that you developed as your target?

  • What key differences are there between your optional scenarios and your target scenario?

  • What jumped out at you as you developed these two scenarios? Any places where you got stuck? Felt that this was “unrealistic”?

  • What “dead minimums” did you discover in Optional Exercise A

  • What “unrealistic aspirations” did you discover in Optional Exercise B

  • How can you move towards your “unrealistic aspirations” with the resources you have right now?


Identifying Your Baseline

The baseline is where you are right now. The goal behind developing a baseline is to get as accurate a picture as possible of the current state.

I find that the process of putting the current state on paper and getting it out of my head surfaces more information, questions, and gaps that I can then use as I put together my roadmap.

I personally find it challenging to do any improvement effort (personal or organizational) if I don’t know what I’m working with in the first place. Not that I haven’t tried…

This is the first, high-level “fact-finding” mission we are going to embark on to see what we have and what we are working with.

My goals for this process are:

  • Figure out what is lying around

  • Determine how to optimize what is lying around

  • Identify knowledge gaps and fill them

  • Identify resource gaps – so we can figure out how to either fill them, work around them, work with them, or rethink our approach.

  • Identify stakeholder gaps – so we know what “people work” we need to do to minimize surprises later.

If I have something concrete – I can see what modifications need to be made.


Exercise: Identify the High-Level Baseline

Let’s return to the Wheel of Life and take a dispassionate look at your life as it currently stands.

Consider doing this over a week or two, reviewing your answers a few times to get an average.

As with the previous exercise, you want to answer these questions in each of the areas of your defined wheel.

  • How’s your health?

  • How are your relationships?

  • Do you have time for hobbies?

  • Are you living someplace where you can flourish?

  • Are you making a living in ways that nourish you?

  • Are your finances aligned to fund this life you desire?

  • Does your life reflect your values? Is the reflection positive or negative?

Again, we want to check for common themes.

Try, as best you can, to do this evaluation with an attitude of curiosity

This exercise is just useful information that we can leverage later. No more, no less.

Hang in there and get any professional support you need if you feel that his exercise could bring up some challenges.

  • Are you seeing any repetition in what you are writing across the areas?

  • Are there any patterns surfacing that you noticed from your broader life phase inventory?

  • Are there certain values that are surfacing?

    • Do they map to the values you wish to demonstrate?

    • Do they map to, or conflict with, the values you wish to demonstrate in your desired future?

  • How do you feel about your life as it currently stands?

    • Which areas are you OK with?

    • Which areas need work?

    • Do you find yourself pleased with your life? Frustrated? Both?

Feel free to write anything that comes up as you sit with the what you have written.

You may find doing multiple passes in each section helpful.


Exercise: See What You Are Currently Doing

This activity will help you get your existing activities out of your head and into a format where you can see and manipulate it.

Clients and I find that by doing this activity, it is much easier to:

  • Prioritize activities

  • Create templates and systems for similar activities, allowing you to focus on the important, creative aspects of what you do

  • Identify how you are spending your time

  • See whether how you spend your time aligns with what is important to you

I strongly recommend doing this activity with pen and paper. The brain processes information differently when we write and manipulate objects.8

For this activity, you will need:

  • Sticky notes – I like the 4x6 Post It Notes. Ideally all one color. We’ll categorize / color code later

  • Pens of many colors - For this purpose – I like the Fiskar 48 piece gel pen set. I’ve been through 2 sets.

  • Something to color code your activities with (choose 1)

    • Erasable colored pens or pencils . I find pens more visible and my preference for this. You want them erasable since you want to be able to re-categorize quickly.

    • Multi-colored Sticky Flags I like that these are removable. You do risk losing the sticky.

    • Fun stickers. You want stickers where you have multiples of one type. For instance, a collection of stars or happy faces. Only issue I find with this approach is that stickers tend to be hard to remove from paper (by design).

  • Lots of wall or floor space covered in large easel paper

    • I like Post it Easel Pads – I’ve used these for years and they have the added benefit of not leaving pin holes or residual glue on the wall. They are also really good for protecting surfaces from marker bleed-through.

If you really HAVE TO do this activity online – I recommend any of the following tools:

My recommendation for this is to do the initial brain dump and organization in person and with analog tools. If you need to make this shareable – transfer the information to online after that initial brain dump.

The brain behaves differently when you are working in analog vs working on computer. The physical motion and variety helps too.

Step 1 – Dump out your brain

Time: 5 minutes – use the timer on your phone

On a separate sticky note, write an activity you

  • Are in the process of doing

  • Need to do

  • Want to do

Don’t try to categorize the activity. (This is why I wanted you to use the same color sticky note – it’s too easy to assign a color to something and I don’t want you to do that yet)

Don’t overthink this. Go as fast as your hands will allow.


Include any personal to-do’s and activities. We all only have 24 hours in a day and 6-8 of them should be for sleep


At this point, you may be feeling overwhelmed by all the things you need to do.

That’s normal.

At least now all this information is out of your head and someplace where you (and others) can see it.

The next few steps will help us organize and systematize these items into something manageable.

Step 2: Group Similar Activities

Time: 10 – 30 minutes

Are there activities you have identified that are sub-tasks of another activity in your sticky-note pile?

  • Combine or discard

  • Example: Create Prioritization eLearning course / Create Prioritization How-To sheet. I would combine these notes.

Which activities have similar steps for completion?

  • Example: I have a bunch of eLearning course development projects. These go together.

  • Example: I have 5 activities that result in an event. These go together.

  • Example: I have 3 clients requiring invoicing. These go together.

Once you have your groups – name each of them. This will be your program name for each group.

Why are we doing this?

  • If we have a bunch of activities that have similar steps and result in similar deliverables, we can create templates so we aren’t re-creating the wheel each time a new one of these activities come up

  • We can start creating programs so that we can start recognizing efficiencies of scale.

    • Programs are essentially a group of related projects

  • We can start seeing whether we have any outlier activities that are wildly different from what we do day-to-day.

Once you have your programs, label them based on your wheel. Which programs are for work? Which programs are for maintaining your health? Etc.

The categories on your wheel are sub-portfolios. Portfolios are a combination of related projects, programs and operations. So…on the highest level, you have your life portfolio. The next level is your category portfolios. For example: your Health portfolio may contain your dietary program, self-care projects, doctors appointments, the race you are training for, etc.

The activity groups you just created are programs. Programs are the collection of related projects and operational activities supporting that program. For example, the exercise program you are following to train for a 5K in 3 months, the supporting diet, and race preparations can all be put under the Running program.

Step 3: Color-Code / Tag Your Activities

Time: 5-10 minutes

Choose a color or tag for each program.

  • I recommend not using red. We are going to leverage that color later.

Add that color to the program name – this helps create a legend.

Now add that color or tag to the sticky notes in that group.

Why are we doing this?

  • This allows us to re-organize those individual activities in other ways without losing how they relate to one another.

Step 4: Identify Deadlines and Urgency

Time: 5-20 minutes

For each activity with a known deadline, add that deadline using the same color pen you used for writing your activity. I prefer the lower right corner.

Deadlines that are coming up quickly or activities that are very high priority – outline the deadline in red.

Date-order each program.

Why are we doing this?

  • This allows us to quickly identify what needs to be completed next.

From here, you should be able to see what you need to do.

Unfortunately, life doesn’t stop as you go about this planning process. Through using this approach, you can at least see what you must do next. We’ll talk about how to evaluate and maintain the activities on this board in the following chapters.


Roadmap or The “To-Do” list

The roadmap is the path you intend to take between where you are now and your target.

Fundamentally, it’s the high-level “To Do” list.

To build the “To Do” list, we need

  • Where we are at (the Baseline)

  • Where we want to go (the Target)

  • The principles that will guide our decision-making (our Values – identified in Ch. 2)

  • The list of what is lying around and early ideas for optimizing these resources

  • The list of gaps and early ideas for addressing these gaps.

    • Personal knowledge gaps and the beginnings of an education plan

    • Resource gaps and early ideas for addressing these

    • People gaps and considering how we are going to approach our “stakeholders.”

From here, I would start figuring out what needs to happen.

Essentially, we are portfolio planning.9
Defining the why and what. Seeing where challenges might lurk.
Providing a path to help minimize distraction and focus your goals.

Beginning the prioritization of efforts.


As our roadmap becomes more focused, we start looking at smaller pieces of our plan.

Change initiatives start because we sense we have a problem with our current state.

Now that we have an idea of our baseline and our target, it’s worthwhile to take a step back and ask:

  • What problem(s) are we trying to solve with this? Is it really a problem?

  • If yes, what is the nature of that problem?

  • What (if anything) should we do to solve it?

In the Instructional Design world, we have a technique called ADDIE that helps us answer these questions. ADDIE stands for Assessment, Design, Develop, Implement, Evaluate. Over the years, I have found this process helpful to track where I am in a change process.10

A – Assessment. The assessment phase asks questions.

  • What is the problem? Is it an actual problem?

    • Instructional designers are often given “problems” that aren’t really problems. Mandatory compliance training often falls in this category. The “problem” is “making sure we don’t get sued.” The request usually does not ask for a solution to a real problem – such as a hostile work environment.

    • Personally, I may want to lose 5 pounds because I’m not thrilled with the number on the scale. If my clothing still fits and I’m still feeling energetic, I likely don’t have a real problem.

  • Does it need to be solved? When?

    • Problems present themselves, but they may only impact two or three people. The cost to solve the problem is significantly greater than the potential return on investment. This scenario likely identifies a “problem” that doesn’t really need to be solved.

  • What does a successful solution look like?

    • What is the anticipated return on investment? This return is not necessarily numbers. You can also include intangibles such as confidence, increased skills that can be used for future endeavors, engagement in the team.

  • What options are available for solving the problem?

    • This is where having a large skill toolkit helps. If all you have is a hammer, everything looks like a nail. When looking for the options available, it helps to recruit supportive others with varying skills and experience.11

  • Which is the best option for the environment?

    • Limitation inspires innovation. Though you don’t want to necessarily artificially create limitations to your solutions, knowing the resources you currently have available and the constraints around your solution can help you think creatively about how to solve the problem in a way that is most likely to lead to a successful solution, or at least provide information about where the gaps are for your next attempt.

In a personal change context, now that we have defined our North Star and our values, we are going to use this Assessment phase for mapping any ideas and opportunities against that North Star and our values.

We are going to deeply ask whether we have an actual problem that needs to be addressed. Each problem requires focus and cognitive load. Each change is a learning experience – including the dip. Because we have the North Star we are walking towards and values we are measuring against, we can perform important assessments to see whether addressing the problem is worth our time and energy.

Is the “problem” yours or someone else’s?

I had a boss some years back who informed me that I wasn’t “collaborative.” This assessment came as a surprise to both me and to the colleagues I frequently collaborated with. After much drilling down, it turned out she expected me to hold one-hour meetings to “collaborate” versus the informal 5-minute conversations I was having.

She had no issue with the quality of the work that I was producing, nor could she identify someone who could complain about being left out. My “lack of collaboration” was not a problem that required “solving.”

We are frequently presented with “problems” that really aren’t. Watching commercials and reading self-improvement or business books (like this one) – you are being told that you have a problem. Chances are – you do not have a problem. Repeat after me:

  • You are OK and don’t need to be fixed.

You have my permission (if you need it, which you don’t) to determine whether the “problem” that is being presented to you is one that you take ownership of. You have permission to decide whether the problem is yours to solve.

Is the “problem” important or not important against your North Star and values?

I frequently feel pressure to go to “networking events.” My values include developing deep relationships with people. From my experience, deep relationships do not develop over business cards at a networking luncheon. They develop over time and regular interaction. My lack of desire to attend networking events might be a “problem” – I may be handicapping the development of potential clients - but it is not important to me. I’ve worked around this handicap by joining a local group (Toastmasters) that mirrors my own values and provides regular interactions with a variety of people I may not have met otherwise. I also prefer events where people get together to accomplish something – such as trail maintenance. I find that, even in those short interactions, the depth of conversation and connection is greater than a business networking luncheon.

We are frequently presented with problems that might not be a problem if you map it against your North Star and values. This disconnect becomes greater if your values and North Star vision differs from the values demonstrated in the environment and the direction your immediate tribe is headed.

You have my permission (if you need it, which you don’t) to ask whether the tribe is going in the direction you wish your life to head. Your choice is to follow the tribe or blaze your own trail.

Is the return on investment for the solution of that problem worth the effort?

This is where knowing WHY you are trying to solve this problem is important.

We are frequently presented with problems where the return on investment (financial or otherwise) is lower than the investment it would take (time, energy, and resources) to solve the problem.

You have my permission (if you need it, which you don’t) to not solve a problem if the effort provides limited return. You can always go back and re-evaluate if that changes.


D – Design. The Design phase is when you decide on which solution option you wish to pursue and start planning that pursuit. The Change Planning Model (Chapter 5) is part of this phase.

  • Do you have the problem clearly identified? This is important. It’s tricky to tell if you’ve solved the problem if you are not sure what it is in the first place.

  • What is the result if you have successfully solved the problem? What are you able to do that you haven’t done before? What do you have? What is missing? How do you feel as a result of a successful solution?

  • What do you currently have to work with? This is a question that is frequently missed in our enthusiasm to “get started.” Having an inventory of what you have available to you (skills, resources, tools, individuals who can help) helps to reduce the distance between where you are and where you want to be.

  • What can you get easily? This question gets to the ease at which we can start developing and implementing our change. We can surface the early next steps. Find the “quick wins” to help us gain momentum towards the change we wish to make.

  • What is our “Best Alternative to No?” Sometimes, we just can’t find what we need, or what we need is too expensive, or a key player rejects our calls for help. How can you still solve the problem without that resource?

  • What are the constraints around the solution?

    • Do you have to get this done with a limited amount of time? (Lose 15 pounds before my 20th high school reunion in 6 months)

    • Do you have a limited budget? ($50 per month for educational resources, such as books, online courses, etc)

    • Is there something you need to work around? (Owning a bakery while implementing a low-carb diet)

D- Development. For personal change planning, this is where we determine what needs to happen and how we are going to execute our change. We are setting up our environment to support the change (throwing away the cookies, planning meals). We are asking for help and support from the people around us and finding alternate sources of support if we need to “go underground.” We are determining the appropriate lag measures (achievement metrics – how many pounds did I lose?) and lead measures (habit metrics – did I work out today?). We will talk about this process in Chapter 6 – Planning.

I – Implementation. This is when we go on the change journey. We are practicing the habits we need to practice and keeping track. We are making adjustments as we get more information – positive (“My partner is more supportive than I expected him to be – he’s OK with not having pizza every night!”) and negative (“I’m too tired to work out at night. I need to find a different time.”). We will talk about this process in Chapter 7 – Execution.

E- Evaluation. We are looking at our achievement metrics. How did we do? What did we learn during the process? What worked? What didn’t? We are also determining the next steps. Do we try again? Go into “operations?” Call it a learning experience and never do it again? We will talk about this process and determine our evaluation metrics in Chapter 6 – Planning.


Exercise: The Bucket List

We have spent significant time looking at our higher vision and looking at our current to-do list.

The bucket list exercise allows us to both put our dreams in a place where we can see them and begin to map the path between our current state and our desired state through the things we want to do.

You will need:

  • More post-it notes (if you have a different color, you can use it here)

  • Your brain dump from earlier in this chapter

Step 1: Dump your brain

Time: 5 minutes. Use your phone to time this.

Write down each thing you ever wanted to do, or idea of something to do in the future, on a separate sticky note. Do this quickly, no editing yourself.

Step 2: Does this fit into an existing program?

Time: 5 – 10 minutes

With each item, check to see if it fits into a program you have already identified. If so, place the sticky in the appropriate location and color-code it.

If not, go to Step 3

Step 3: Group remaining similar activities

Time: 5-10 minutes

This is the same step as when you built your initial baseline.

Are there activities you have identified that are sub-tasks of another activity in your sticky-note pile?

  • Combine or discard

Which activities have similar steps for completion? Put these together.

Step 4: Name and Color Code the Program and Place in Sectional Portfolio

Time 1-5 minutes

Determine the name and color code of your new program.

Place all the sticky notes under the new program into where you have placed your sectional portfolio.

Leave any outliers to the side within the appropriate sectional portfolio.



As you come up with new ideas, follow the above steps (ideally before saying “yes” to someone or just starting without thinking about how it fits into your other work).

We have just created our “backlog.” This is a helpful way for us to see what we have in order to prioritize our activities.

Just because it is on the “backlog” does NOT mean that it needs to be done. Ever.

The backlog is just a holding zone for requests and ideas. It provides time and space for us to look at our activities and determine whether pursuing these activities will move us towards our goals and North Star.

In Agile project management, backlogs are regularly “groomed.” We remove items when it becomes clear that they either don’t need to be done, won’t receive the resources to be done, work against the goals and north star of the organization, or become outdated because something else has happened in the environment.

My clients, both personal and organizational, have found this concept very helpful.

They have a place to put ideas and reduce the fear of “losing them.” They have room to more deeply consider the idea and prioritize them. They don’t feel the pressure of “starting now” and trying to do too much at once.

We’ll talk about the backlog in more detail in Chapter 7 – Execution. For now, just know that you have a holding zone for your ideas.

This holding zone will be very helpful for prioritization.

Let’s talk about that next.



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