How I Learned to Quit
Or: 22 Short Films About Work
The past is always talking. But you’ll only hear yourself if you really listen.
I.
It’s been a busy few weeks. Work has picked up, with some fun new projects. The Substack Fellowship was transformational—whilst it became significantly more work than expected, it was a real “get out what you put in” experience. There’ve been a series of late nights at the computer: meeting with clients on the West Coast; writing and polishing up essays for TNF; chipping away at a gigantic boulder of email that continues to grow, a rock worthy of Sisyphus himself.
Sometime last month, long after the house had nodded off, I was putting the final tweaks on an essay for the Fellowship, jumping through a few posts in the archive, hunting down a particular paragraph where I remember nailing a specific thought perfectly.
Whilst sailing across a sea of open tabs, I stopped dead at this post. It wasn’t the words that caught me, but the illustration from Tony. That one, up there ⬆️. It was, somehow, the first time I realised he looked a little like me. And that maybe I needed to listen to Kevin from last July, and what he was trying to tell me.
I’d was back on the road again, foot hard on the accelerator. Working on something I cared about, of course. But I’d forgotten the need to sit on the ledge, let my legs dangle free, drink a glass of wine, and enjoy the music.
II.
Since I stopped commuting, my podcast habit has died down—maybe an episode a week, or even less? But it was a pleasure spending two hours with Tim Ferris with Cal Newport as they discussed digital minimalism, deep work, and the fascinating idea of “slow productivity.”
Slow productivity is best explained by looking at how the most revered minds in history approached problem solving:
“When viewed at the fast scale of days and weeks, the famed scientists in Gribbin’s book seem spectacularly unproductive. Years would pass during which little progress was made on epic theories. Even during periods of active work, it might take months for important letters to induce a reply, or for news of experiments to make it across a fractured Europe.
The daily pace of their work was incredibly slow by any modern standards of professional effectiveness. When we shift, however, to the slow scale of years, these same scientists suddenly become immensely productive.
No one remembers Newton’s lazy lockdowns, but his ”Principia” achieved immortality.”
Newport suggests an approach for supercharging slow productivity: formalise your own rules and values, then set quarterly goals that ladder up to a long-term vision. This advice will be familiar to anyone who has worked in a tech company in the last 20 years, as it’s the foundation of the OKR approach outlined in John Doeer’s best-selling book “Made to Measure”. It has enabled companies to succeed by removing “conflicting priorities or unclear, meaningless, or arbitrarily shifting goals” that make us “frustrated, cynical, and demotivated.”
It worked for them. Could it work for us?
III.
In “You Only Move Twice,” one the all-time great episodes of The Simpsons—if not one of the all-time great episodes of TV, period—Homer moves his family across the country to work for Hank Scorpio, an eccentric individual searching for employees with nuclear experience. To give you an idea of how much I adore this 22 minutes of television—my profile names for Reddit, Xbox Live and eBay are three different references to this single episode.
After being recruited to his new job for Globex Corporation—a reward for years worked and absolutely not performance-based—Homer starts his new gig in a management position. He’s worked his way back up the ladder after his last promotion was rolled back due to a hair-related incident, and he’s actually, for once, trying his hardest.
Burns was a bad boss, but Scorpio seems, at first, perfect. However, we soon learn (SPOILER ALERT for a 26 year old episode of TV) Scorpio is an ersatz Blofeld-era Bond villain, and Homer is unwittingly helping him build a doomsday device. It’s a purpose based job, for sure. But probably not the purpose you’d choose.
As part of his new middle management responsibilities, Homer tries to motivate his team:
Homer: (in his new role as supervisor) Um, are you guys working?
Employee: Yes, sir.
Homer: Can you . . . work any harder?
Employee: Sure thing, boss!
Homer: Hey, call me ‘Homer.’
“Can you work any harder?” It’s a question I’ve been asking as long as I remember. It was already being asked of me, before I knew how to ask it myself. “Great potential,” my old school reports read, “but Kevin needs to apply himself more.” Another teacher helpfully informed my parents I was “one of the top pupils in the class, but it’s clear he’s coasting.”
I worked hard, and played hard, during my 20s. Probably more of the latter than the former. But towards the end of them I got a good job. Then another decent one. Then, after a lot of work, and what must have been a dozen interviews, I landed a dream one. And I worked. Damn, did I ever work. If only those teachers could have seen me during my years at Google.
I really pushed myself: to do well, to get ahead, to try to make the world a better place.
I really cared. Until the day when I stopped.