#103: Mid-Pandemic Leaps, Generational Insights, Time Capsules & Best Self

😎 A guest issue of the Boundless newsletter

August 15th, 2020: Today’s 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.

👋 Welcome to the nearly 100+ new subscribers. I’ll credit this with the “not overthinking bump” 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.

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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: “How to live and work in the modern world”. 

I’ll interpret this broadly.

Today’s edition includes personal reflections on a recent career shift, some drawings, and a few links. I’ll also share two interactive exercises that may help you navigate moments of change. Both exercises have been useful for me - I’ll invite you to try them too. Let’s dive in. 

#1 Taking the “leap” 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. 

Why did I make the change? 

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. 

Plus, I saw the world changing. Time was flying by, fast. How easy would it be for me to “fall asleep” 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 “safe”, white collar salaries at established companies, yet somehow still feeling lost, trapped, and un-tethered. It scared me. 

I also knew people who talked constantly about potential future plans and projects without ever taking action (“how cool would it be if…”). 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. 

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). 

A few years back, I stumbled on some studies exploring the top regrets of the dying. 

The research basically suggests that we should:

• Try to be authentic and kind to ourselves

• Not worry so much about judgment from others 

• 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? I’m not sure. But it’s a platform Boundless readers can likely get behind. 

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#2 Generational Insights 

This line from Boundless #100 caught my eye:   

“One 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 “find the others” during their own off-the-default path journeys and are making up for lost time.”

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. 

Are you aware of products, services, or communities that facilitate this sort of inter-generational connection? I’m curious what comes to mind. Seems like a promising area to explore further. 

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#3 A “Time Capsule” Exercise

I think everyone should occasionally write - and hide - a letter to their future-self. It’s an easy, low-tech, and (potentially) valuable practice. A rewarding form of learning and reflection. 

Interested? Here are a few tips.   

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#4 Food for thought

You’ve probably seen some version of this graphic before. 

The typical commentary = “Some 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).”

What I’d add: 

1. It’s hard to know what line you’re on (in the moment) 

2. A lot depends on when you measure results (and what the Y axis stands for)

3. It’s tough to invest in a distant, speculative future when you’re focused on survival

How do you interpret this graphic? What other trajectories do you notice? 

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#5 The “Best-Self” Exercise 

Recently, Paul introduced me to a simple and fruitful exercise.

Email 3-5 people (who know you well), and ask them: 

“Where have you seen me being my best self?”

I did this a few months back, and learned a ton. 

• 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).  

I encourage you to give it a shot: Go seek out the wisdom of your crowd. You may learn something surprising. 

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Thanks for reading. If this particular newsletter wasn’t your jam, never fear: Regular Boundless programming to resume soon! 

Have a great weekend - send me thoughts if you want to chat or check out my weekly projects.