How to make work feel like play | RadReads

The best part of not having a corporate job is no longer having the Sunday Scaries. I had them every Sunday for fifteen years; or 780 consecutive weekends. My friends and I anthropomorphized this dread by giving it a name: Mr. Scary.

We were young bankers in our 20s and here’s how a typical weekend would play out: we’d get out late on Fridays (11 pm) and drink a lot. We’d then work all day Saturday, then drink some more. Brunch on Sunday (yup, more drinking) and then football and the Sopranos. Finally at 11pm we’d stumble into our beds. (Clearly, wellness wasn’t a thing back then.)

Once in snuggled under the covers, Mr. Scary would enter the room like clockwork. He’d first crank up the heat to ensure a night of cold sweats. Mr. Scary resembled mashup of the Grim Reaper and the “Scream” guy; he’d sit on the edge of my bed smoking a cigarette. And right as I’d drift into la la land, he’d poke me in the abdomen to remind me that I probably hadn’t prepped enough for the Monday morning meeting.

Thankfully Mr. Scary and I consciously uncoupled in 2015. Neither of us have looked back.

The scaries are no more. After I waltzed out of corporate headquarters, my Sunday Fundays became true Fun Days. But here’s the catch, I still have to work. In fact, I’m writing this at 4:30 AM on a Saturday (for the 229th consecutive week). I’ve got a decent amount of savings, but my cash flow is super volatile. And by the time my girls hit college, the anticipated cost is $500k. Per kid. I still gotta earn that cheddar.

But the scaries, the yearning for vacation, the dread of yet another meeting (to discuss why we need another meeting) are long gone. And a big reason is that my work feels like play. Naval Ravikant, the founder of AngelList (and the Internet’s Resident Philosopher) tweeted:

Personally, I’m skeptical of (and have abandoned) the dubious promise of Financial Independence. And while I’m an avid meditator, I’ve got zero desire to live the ascetic life of a monk. But I’ve stumbled into making work feel like play, which is the secret weapon that has filled my life with joy, meaning, and richness.

How can we bring play into our work? Does it require dropping everything to become an entrepreneur? (Emphatic “No.”) Does the feeling of play come from changing one’s bad circumstances (like commutes, bosses, or Brooks Brothers requirement)? Or can be unleashed from within with a change in mindset?

Retirement. The golden goose, n’est-ce pas? Bye bye meetings, status updates, and commutes. Hello surfing, Florida snowbirding and daytime cocktails. But according to Harvard professor Theresa Ambile, there’s something retirees really miss: working. In The Myth of the “Retirement Number,” I summarized Ambile’s findings:

We can safely assume that retirees have earned the right to make work feel like play, so let’s leverage their findings and to start our own checklist (in Notion, of course).

Download the template

“We prepare children to learn how to learn, not how to take a test,” said Pasi Sahlberg, Finland’s Minister of Culture and Education. The Scandinavian countries take a diametrically opposite approach to education by starting formal instruction at age 7, outlawing formal examinations (until age 18), eliminating competition and never “teaching to the test.” And boy does this approach deliver; the region has the highest rates of higher education participation in the world.

During our recent trip to Copenhagen, I was stumbled upon a formula relating work and play on the back of a magazine. It read:

via @RadReadsco

This gives us two variables to get to more play: Care more about the process or less about the outcome.

The process consists of the activity itself, honing one’s skills, intellectually challenging yourself, and learning new things – all while being around people who inspire, energize and respect you.

Then there’s the outcome. Obviously providing for your loved ones is a required outcome and table stakes to this discussion. But let’s put that aside for a moment; What are other desirable outcomes? Might they be competition, promotions, status games, follower counts and the accumulation of stuff? It’s the timeless paradox of the pursuit of intrinsic versus extrinsic motivations.

One of the best decisions I ever made was abandoning the aspiration of starting a venture-backed company in favor of a (non-scalable) lifestyle business).

Originally, I wanted to be a founder. I yearned for the vanity metrics of raising big rounds and the status of being known by the community entrepreneurs and investors. I wanted to be in a position where I could make F.U money and the VC-backed businesses cranked out unicorns and billionaires. I dreamed about how these outcomes would make all my insecurities melt away and bring instantaneous bring my life meaning.

Thankfully, I chilled the f**k out by accidentally discovering blogging. And without much of a plan, in 2016 I began writing posts that (at first) very few people were reading. But in this work, I discovered human connection, community, flexibility (to be a dad and surfer), complex new business models, and the true excitement of seeing my ideas show up in the world.

Desiring F.U. money and unicorn-status was all outcome. RadReads is all process. Thankfully my ratios fell into line.

I know what you’re thinking. Khe, you forgot the most important outcome: I GOT BILLS TO PAY!

I concur. We work to pay the bills, make mortgage payments and save for college. But was my unicorn vs. lifestyle business conundrum about paying bills? Absolutely not, the bills were paid in both scenarios. So what was the difference between the two?

We’ve all fallen into the trap of using money as a “material solution to an emotional problem.” We’re tempted by the status it brings (i.e. “I’m a startup founder”), how it makes us feel relative to our peers, and the perception that it can fend off one’s mortality. And falling into this trap places a higher burden on the outcome.

Should “meaning” be included in our checklist? To be honest, this is a tricky one. The reality is that not every job is going to improve environmental sustainability, reduce inequality and alleviate the world’s suffering. And if we pin our aspirations to our jobs changing the world, we’re likely to be disappointed.

But meaning can be found in the most unlikely places: greeting the security guard in the lobby, lunches with your team, mentoring an intern, and the simple satisfaction of seeing the fruits of your labor move a project forward. As the author David Whyte succinctly put it: “Good work, done well for the right reasons.”

So let’s recap our checklist:

Now you shouldn’t think of this list as “all-or-none;” instead, think of each item as a knob, that over time, you can dial-up or down. Here’s how Financial Planner and The New York Times’ “Sketch Guy” Carl Richards thinks about these levers:

And reexamining our list, it’s possible that improving many of the levers might not even require changing jobs. (Maybe your boss will let you work from home one day a week.)

So if your job does not feel like play, pick one item from the list. Poke at it a little, explore the contours of possibility. You’ll be one step closer to playtime. And one step further from Mr. Scary.

The Fulfilling Path to Financial Independence workshop teaches you why you shouldn’t quit your job and provides a framework for determining “what’s enough.” For the next 48 hours, you can use the code WORKISPLAY for a 20% discount.