My grandmother used to remind me - typically in response to an inexplicable decision I had made - that when I was 5 years old I told her: Grandma, I’m a player, not a worker. Hard to say if I remember the event itself, or the constant reminders. What I do recall is being frustrated that my grandfather was seldom with us - always working to support the family. I imagined him not having much fun at all. Ugh, work! Well, she would never let me forget that. Thing is I still believe what I said then.
I’ll try to reveal the wisdom in this simple principle.
Let’s start by defining terms:
Work
To work is to push through, to grind, to grit, to strain. To not “get the work done” is to fear retribution for whatever lies on the other side (someone will get mad; I’ll get fired; I won’t be able to feed my family). Work strangles our inner child. Work is narrow, anxious, linear. When we work we are internally divided, animated by anxiety for the consequences of…not doing the work. Concentration is elusive when we are working. Not only is the experience not joyful, but the product is typically inferior. Working is scary.
Play
Play is not hindered by self-consciousness; it’s expansive and exploratory. We take the time to explore angles and blind alleys - even if they lead nowhere. The reason this matters is because some of those alleys are where the breakthroughs happen. Play is driven by curiosity and love pulling us to whatever mystery is on the other side.
Let’s state the obvious: I’m at my worst when I feel compelled to complete my commitments by “working”. As the sole bread-winner for a family of 5, feelings of fear easily become the wrench thrust into my turning gears of ambition.
I once read a quote by Goethe that punched me in the chest: when you commit, the universe conspires to assist you. I carved it into my desk - the Jewish version of a tattoo. The trick is to shift into an abundance mindset. Each time I thought of it, the mental snap was akin to seeing a Necker cube. Boom!
Great outputs require time. And the only way to put in the time is to enjoy the process (lest we procrastinate, or push ourselves through). But it’s not just time, rather, it’s quality time that produces a superior outcome. Thus, any commitment we make had better be enjoyable. If not we will be out-worked by others that love what they do.
The formula looks like this: Commitment + play + time = great outcomes.
Can you spot a paradox? If we must play our commitments, what about the things that require quality but we don’t want to do? After all, not everything we do is of our choosing!
What does this rule look like in practice? I’ll give you an example:
Several years ago I was unhappy in the startup I was working at - felt like a dead end. So I left with no immediate plan. As the bread winner for my family of 5, and living in the SF Bay Area I had financial pressure. I probably could have joined any old company to pay the bills.
But that would be settling (another rule: don’t settle!). Instead, I decided that I wanted a role at what I considered a “tier 1” company. That is, one I’d be proud to work at - my top two: Google, Facebook. There was a larger game I felt I had to play. I wanted to convince myself I could break into that club. When I surveyed my life so far I was uneasy - too much settling, comfort, path of least resistance. Or, fear. Insecurity is reliable like eczema - ready to flare up when you’re stressed. In my case I’ve always been a lousy job interviewer.
So here was the plan: I decided to play my work for a bit. I would practice my weakness - the interview. I reasoned that job skill is only loosely predictive of actually getting the job. The interview is the essential gate through which we must pass to get to the promised land. Worst case is I’d have wasted a few months. But whatever came next I’d not be limited by poor interviewing. And if it worked I knew I would be rewarded.
I took any interview I could - (including some ridiculous concepts, innovating burial services anyone?) - anytime, anywhere. Saturday 5am? Let’s go! I had a yellow pad, a desk and a computer! I hit the interview like the Jiu-Jitsu mat, sparring to prep for the big match. As with any sport the key is to deliberately practice each component. Work your game. I spent sometimes hours per day to shore up my weakness. And I did this for several months. This may not sound like much but my baseline was literally zero. The key is I made this into a fun game! I over prepared because, if I’m being honest, I found this (hateful process) strangely fun.
The result - after 14 hard interviews - I was offered what in my early career had felt unattainable - PM at Facebook. What I remember most was how present I was during each of these interviews. I was indeed able to stay flexible and loose during a very high stakes situation. Each interview felt easy, fun even! The questions weren’t scary, they were interesting. I’d have crumbled earlier on in my career had I not done this work. The key to all this was deliberately playing in, and gaining comfort with the simulated arena. Turns out it was nerves, this was the real issue I was struggling with.
Play your commitments