#103: Mid-Pandemic Leaps, Generational Insights, Time Capsules & Best Self
š A guest issue of the Boundless newsletter
August 15th, 2020: Todayās guest issue is written by Jeremy Finch, the creator of The Fire Jar and founder of Angle and Distance, his marketing and design firm. I first talked with Jeremy in the early lock-down days and was impressed at his thoughtfulness and aliveness as he juggled the uncertainty of leaving a life that made sense AND doing it during a global pandemic. I was excited by his digital illustrations and ended up hiring him to illustrate my Chaos Theory essay. If you want great illustrations or help with design strategy, contact him at the bottom of this note.
š Welcome to the nearly 100+ new subscribers. Iāll credit this with the ānot overthinking bumpā after I appeared on the Not Overthinking podcast with Ali and Taimur Abdaal. They are the most thoughtful brother duo in podcasting and if you want to check out our on life, work & what matters, check it out here.
A few weeks ago, Paul invited me to host an issue of this newsletter. I asked him how he usually describes the editorial charter. His answer: āHow to live and work in the modern worldā.Ā
Iāll interpret this broadly.
Todayās edition includes personal reflections on a recent career shift, some drawings, and a few links. Iāll also share two interactive exercises that may help you navigate moments of change. Both exercises have been useful for me - Iāll invite you to try them too. Letās dive in.Ā
#1 Taking the āleapā mid pandemic
Earlier this year, I left my job at a large software company to do a mix of creative projects and freelancing. The five months since I took the leap have been scary, frustrating, and fruitful - personally and professionally. Challenging and rewarding in ways that I could have never predicted.Ā
Why did I make the change?Ā
I craved autonomy and freedom. I needed to slow down and make space to draw, write, design, invest in relationships etc. I was feeling drained and disillusioned by cubicle life. And sought to realign energy towards my values and passions: Move them to the center of the picture, rather than leaving them mostly at the edge of the frame.Ā
Plus, I saw the world changing. Time was flying by, fast. How easy would it be for me to āfall asleepā for a decade and wake up a cynical, risk-averse company man - adept at navigating bureaucracy? I know a ton of people like this: Earning āsafeā, white collar salaries at established companies, yet somehow still feeling lost, trapped, and un-tethered. It scared me.Ā
I also knew people who talked constantly about potential future plans and projects without ever taking action (āhow cool would it be ifā¦ā). Maybe you know people like this, too. I wanted to get in the arena - take ownership, strive boldly, actually try to bring some of those ideas to life.Ā
Better to pursue a dream and fall short, than to never try and regret it forever. Or, worse, excel the wrong things (a highly unscientific 2x2 below).Ā

A few years back, I stumbled on some studies exploring the top regrets of the dying.Ā
The research basically suggests that we should:
Try to be authentic and kind to ourselves
Not worry so much about judgment from othersĀ
Express our feelings openly and often
Connect deeply with friends and loved ones
Work way less than we do
How might we design a world where these qualities are rewarded, encouraged, and accessible to far more people? Iām not sure. But itās a platform Boundless readers can likely get behind.Ā
#2 Generational InsightsĀ
This line from Boundless #100 caught my eye:Ā Ā Ā
āOne of the most surprising things is the number of people in their 50s, 60s and 70s who have reached out and given me support. Many of them are either trying to reinvent their path towards the next phase of their life or struggled to āfind the othersā during their own off-the-default path journeys and are making up for lost time.ā
This is an underrated insight. There should be more opportunities for older and younger people to connect around these topics: Share our unique insights, learn from and support each other.Ā
Are you aware of products, services, or communities that facilitate this sort of inter-generational connection? Iām curious what comes to mind. Seems like a promising area to explore further.Ā
#3 A āTime Capsuleā Exercise
I think everyone should occasionally write - and hide - a letter to their future-self. Itās an easy, low-tech, and (potentially) valuable practice. A rewarding form of learning and reflection.Ā

Interested? Here are a few tips.Ā Ā Ā
#4 Food for thought
Youāve probably seen some version of this graphic before.Ā

The typical commentary = āSome processes appear slow and wasteful in the beginning, but pay off many times later (exponential). Other things seem fast and efficient in the early days, but push you onto a flatter trajectory over the long haul (linear).ā
Itās hard to know what line youāre on (in the moment)Ā
A lot depends on when you measure results (and what the Y axis stands for)
Itās tough to invest in a distant, speculative future when youāre focused on survival
How do you interpret this graphic? What other trajectories do you notice?Ā
#5 The āBest-Selfā ExerciseĀ
Recently, Paul introduced me to a simple and fruitful exercise.
Email 3-5 people (who know you well), and ask them:Ā
āWhere have you seen me being my best self?ā
I did this a few months back, and learned a ton.Ā
I got amazingly consistent insights, from totally independent sources.
My natural strengths seemed entirely obvious to them. But they were way less obvious to me (at least in retrospect).Ā Ā
I encourage you to give it a shot: Go seek out the wisdom of your crowd. You may learn something surprising.Ā

Thanks for reading. If this particular newsletter wasnāt your jam, never fear: Regular Boundless programming to resume soon!Ā
Have a great weekend - send me thoughts if you want to chat or check out my weekly projects.



Thanks Jeremy, appreciated the newsletter!