99 Pursuits & This Problem Ain’t One

I heard a Mediterranean diet is both healthy and tasty.  It was Thursday, just came from the grocery store, had a kitchen full of fresh ingredients, and an under-utilized air fryer!  All systems go!  Given the amount of cleaning, chopping, and veggie prep required, I solicited my 16yo daughter to join me.  She willingly jumped in.  By willingly, I mean she slow walked it all the way to the kitchen after I applied several combinations of guilt-trip and
“dad voice”.  Nevertheless, she and I were in there working way.  My daughter was peeling blanched cherry tomatoes and chopping basil.  We began laughing and enjoying one another’s company as we utilized nearly every dish and surface in the kitchen.  I was feeling great about our progress while enjoying some lovely father/daughter time.

That’s when things went off the rails. My fiancée walked into the kitchen and was horrified by the culinary crime scene that was unfolding. She was obviously displeased, and we immediately launched into several rounds of passive-aggressive commentary.  I eventually “dismissed” her from the kitchen, freeing her from the worry of being stuck with clean-up duty.  Moments later, I’m now working solo to finalize our feast.  Unfortunately, the meal wasn’t as tasty as I hoped, leaving me feeling  unjustified in my efforts.  To make matters worse, sitting next to me Elsa from Frozen would have been upgrade to my current companion.  Later that evening, rather than calm pillow talk, I’m on defense trying to recover from unceremoniously relieved her of duty.  At that moment, it occurred to me what went wrong.  I thought I was doing amazing things by delivering a healthy meal for the family while simultaneously getting some bonding time.  My fiancée was peeved that I created unnecessary effort for a week-night meal.  I was aiming for quality, and she valued simplicity.  We both agreed we needed dinner yet drew vastly different conclusions about what happened.  Sound familiar?

That led me to write “99 Pursuits, and This Problem Ain’t One”.  The idea is to help you figure out what is important to YOU?  At first, it may seem like this is yet another way to help you figure out your life goals.  This is not that!  Identifying your goals is simply a means to an end.  At their best, goals are often hollow or short sighted leaving you unmotivated.  At worst, bad goals redirect your energy from what is really important in life.  If you take only one thing away from this exercise, it’s to understand this question; What do your goals say about you?  It’s important to take the time and reflect.  Secondarily, are your goals too lofty or not lofty enough?  Fair warning, 99 Pursuits takes a little effort and emotional investment on your part, but I promise you, it’s literally life changing.  There are two parts that can be done together, or you can do Part 1 and then come back to Part 2 later.  Furthermore, you can blast through it all with the intention to keep iterating later on.

Part 2 is where you address the problems in my scenario above.  It is where you dig into what makes you happy, brings meaning, and attain alignment with those you love (and work with). It makes sense to get started in sequence.  However, the full process should be iterative, so feel free to stop and go backward or skip around.

Part 1:  Make the List

Step 1:  Brainstorm your “bucket list”

Without giving it too much thought, quickly write a list of all the things you’ve always wanted to do.  Stop writing as soon as you draw a blank.  You can always add to this list later.  Spend about 10 minutes on this exercise if you don’t already have a list.  I did this in a spreadsheet because it’s easy to hide/add columns and sort the information, but you can use whatever medium that suits you.

Step 2:  Define Your Roles

Be specific. Sometimes you wear multiple hats even within one area.  In your home or at your job, you likely do different types of things, so try to differentiate them.  Just get started with the obvious roles, but try to find ways to subdivide the roles as it makes sense.  Think about how every role, you have different activities and/or goals and make those distinctions by the role. 

Here is a sample list: spouse, friend, church organizer, household manager, financial planner, parent, extended family member, employee, member of project management institute, volunteer at shelter, etc.

Also consider the audience of your role.  In business terms, who is your customer?  In anything you do, others will see value or benefit in your efforts.  In other words, if you don’t do it well, who will be disappointed or become disinterested?

Step 3:  Identify The Pursuits

Now let’s extend your bucket list as this isn’t just the “there I did it” list.  Before starting, take a moment to envision what good looks like for each role.  Why is it important?  If that isn’t immediately clear, consider who benefits from your role and what they get out of it.  If you do something and nobody else cares, ask yourself how meaningful is it?  The idea is to identify Pursuits that have complexity and underlying meaning beyond what you’ll simply write down.  A Pursuit should be more than a simple pass/fail item to be checked off your list.  A good Pursuit ideally keeps you motivated even on those tough days because you understand it’s not just about that thing.  Simple goals are only a steppingstone on your journey, on your Pursuit.  With steppingstones, if you miss a step or even exceed your goal, you have a long-range horizon.  You won’t get distracted by life’s curve balls as these Pursuits are just words on paper and are meaningless without context.  All that said, don’t get bogged down on your first pass as you’ll want to iterate on these to improve them.

With those thoughts, identify at least five Pursuits for each role.  For example, say you want to run a 10k race.  That’s great but ask yourself why!  Maybe you enjoy competition.  Perhaps you simply want to live longer than your family medical history might indicate.  Maybe you want to be prepared for the coming Zombie Apocalypse!  Running a race does not mean you are prepared for the Zombie Apocalypse, however, it helps to be fit when it’s go time!  Take a first pass and write down as many Pursuits as you can for each role.

Next, look back at your bucket list and see if you can combine items.  For example, you always wanted to visit the Eifel Tower in Paris.  You can combine items such as “Run a 10k in France”.  If you can’t find good combinations, then see if you can add some richness to a Pursuit such as or “Run a 10k with you kids”.  Now you are being fit but also have family bonding.  Thinking about retirement goals, try to envision where you want to retire or a lifestyle you want.  Perhaps, “Win an out-of-state golf tournament in my age bracket”, assuming golf and travel is something you enjoy.  Notice adding the “age bracket” suggests it’s not a one-and-done goal but something you continue to do in different age brackets.

Again, the idea is to make each Pursuit something that is rich and multi-faceted and not something you can typically do over the course of a weekend.  Don’t beat yourself up over this list trying to get to 99.  Compile as many as you can with the understanding that you will continue to develop  this list as time goes by.  Always try to stack items together to add meaning and motivation.  Ideally, this becomes an annual exercise, but this first run through is the most intensive since you are starting with a blank slate.  Over time, your core list likely won’t change much but circumstances do change so this isn’t meant to be rigid.

Part 2:  Meaning

Step 4: Identify Themes

Ignoring the roles, observe and document the commonalities in your list.  Ideally, you want 3-10 themes that you can summarize using 1-3 concise words.  Common themes might include Health or Finance, but you should find your own words to describe your list.  If you have this in a spreadsheet, I’d suggest adding a column for “Theme”.  Also, it’s nice to hide the column “Role”  to avoid re-using the name of the role as your theme.

Step 5: Words To Live By

Reviewing your themes, see if you can create 3-5 concise descriptions of no more than 5-6 words each.  Some people might call these guiding principles or values, but those terms are loaded and mean different things to different people, so they end up not meaning much at all.  I wrote an article about Guiding Principles and how those things change based on context so I encourage you review that article afterwards.  These “Words To Live By” are meant to help you characterize what you find meaningful, help you prioritize when you have conflict, and stay in better communication with those around you.  Think back to my kitchen fiasco which was ultimately a dispute about where my household is expending energy.  We clearly had a breakdown and misalignment about what I felt was important in my 99 Pursuits.

Step 6:  Describe Your Meaning

Finally, take the above expressions you wrote and now expound on those by writing a few sentences for each. In your descriptions, summarize using plain words, or include thoughts from your list, or even describe what this is not.  This is an important final step to ensure all your efforts above are concise and meaningful. If you were to share this with others, they should be able understand your intent.

In Summary

If you take away one thing in this article, I hope it is this: The effort to create your 99 Pursuits is more important than the list itself.  As you can see, undergoing this effort is certainly an investment of your time.  However, I’m certain it’s worthwhile.  I’ll leave you with two quotes from somebody much smarter than I: