042: Reader Mailbag (IV)

Season One Oct 12, 2020

"Imaginary Pie" sparked many replies!
Sharing your responses below 👇


(Send me a note, anytime)

"Are we trying to win a game, season, championship, or lifetime achievement award?

I think the answer is no: We are all trying to achieve as much happiness as we can, for as long a we can (you’re free to define what you believe happiness is).

The reason 'the game' and 'the pie' always come up is that there's a loose interdependence between winning and happiness. It's hard to be happy if you constantly lose. But it is also true that winning frequently is not a good predictor of happiness. Many happy people rarely win, or rarely choose to compete.

How does a wise person think about knitting together experiences of winning, losing, simply being there, or being 'lost' into a life that is undeniably happy and joyous?"


"Worth sharing with as many people as possible. Especially those who are struggling to find perspective in hard times."


"The metaphor I use is: Make sure the ladder you're climbing is leaned up on something you actually want to reach the top of.

I feel like most people aren't even afforded the opportunity to make that kind of evaluation, though."


"It's wild how ingrained scarcity is into my psyche.

The conversations I have with others about the things that interest me really help me to fight that framework. It's also been helpful to keep in mind the central 'question' I'm addressing with my career. When I get stressed by scarcity, I come back to that question and I realize how abundant the potential answers are!"


"This part sums it all up nicely, although I added some of my own notes for clarity:

Society teaches (Capitalism requires) us to stack rank, and if you’re fortunate, you end up on top and reap all the spoils. If you’re not, then you either need to try harder or are just plain not good enough. Tough cookies."

"I don't know if the beneficial effects of a sabbatical would really last that long for most people if they return to the same kind of job as before.

I think most people have got to actually sacrifice wages and prestige if they really want work that doesn't make them feel sick, let alone the question of feeling fulfilled by the work.

This is the progress we wanted for the human race, though, right? Work that is for the most part super-specialized but totally alienated from the actual necessary functions of life?"


"The zero-sum, 'crabs in a barrel' worldview is so easy to fall into. The hustle culture and pressure to perform (demonstrate success, optimize etc) is draining and feels self-imposed.

Our generation got hit hard by it as we graduated into a recession and suddenly had to reassess ourselves around making a case for our value to a system that seemed to suddenly have none of the extra prosperity that we had been raised (in Cold War boom times) to depend on and be comforted by.

I think the fact that tech was the only booming thing, and I wasn't a CS person, led me towards finding a foot into something where there seemed like a possible future. Maybe I would be writing or making music instead of designing buttons and video graphics.

How to exist without selling something in exchange for the time and space to exist in the way I want to? While my time from 9 to 5 was exchanged for a regular bank account infusion and a fancier doctor, I didn't have to make anything else of it. I could be unimpressive by my own standards without anyone questioning what my deal was in a social setting. Being in charge of my time now and watching my bank account shrink instead of grow is disorienting. It feels like I don't do what 'people' do anymore.

Everything in consumer mass culture tells us that to think differently is dangerous and extreme: Things are as good as they can be and there isn't enough available to fiddle with the controls just because it's a little unfair.  But everything about 2020 seems to actually tell us that to keep thinking the same way, doing things in the same way is extreme and dangerous."





More crowdsourced episodes:

Reader Mailbag 3
Reader Mailbag 2
Reader Mailbag 1