#8: Work, and the risks we take

Finding comfort in what I'm willing to lose

I've been thinking a lot about work these days, for a few reasons.

As it turns out, I actually do have to do something with my time. I don’t have the runway to be a passenger on this joy ride forever. And I’m (re)energized and (re)motivated to go spend my time in meaningful ways.

What will work look like, though? I find the answer to that question to be regularly up for debate. Here's how a typical week for me looks in the pursuit:

Monday: I’m going BIG. I’m starting the next Airbnb! End of story. Full commit. Stop thinking, start doing. Ready, set, let’s fucking go.

Tuesday: Hmmm, on second thought. That whole going BIG thing sounds misguided & stressful. That’s me wanting to live out a past self’s dream. Let’s do the entrepreneur thing, but start a Company of One instead.

Wednesday: Whoa, hold up. Thinking again. On my best days, I give very little fucks about business. I'm going full-time creator instead. Let's fire up the Soundcloud, sound the horn for the groupies. We’re getting the band back together and hitting the road. I’ll also be starting that memoir.

Thursday: Actually, screw all that. That whole “creator” life sounds selfish, unstable and insignificant. I’m laying down my ego. I’m working for someone else. I’m joining a company. One that’s actually solving a big, audacious, hairy problem. SpaceX, where do I apply?

Friday: You know what? On final thought. I can’t hide anymore behind the fact that life is inherently meaningless. We’re all playing stupid, finite games, and none of it matters. YOLO. Cabin in the woods, here I come.

The slope is slippery. The spectrum of possibilities is wide. Clarity can quickly erode into confusion; confusion can then rebuild into clarity. The whole thought pattern is admittedly exhausting. Though as frustrating and deflating as this pattern can be, this experience has forced me to get curious about why this pattern is so damn erratic in the first place.

Why can this question -- what should I do for work -- be so difficult to answer? And even once answered, why is it difficult to remain comfortable with that answer?

Here’s one conclusion I’ve landed on: Every path we choose puts something at risk, and we don’t spend enough time getting comfortable with what we’re risking.

Let's take Monday, starting the next Airbnb.

When I consider this path, here’s what I assume I gain. The potential for a large payout in the future.  ✅ Wealth. Creating a company that will be an incredible force for impact at scale.✅ Impact. Comfort in knowing that being an entrepreneur conforms to many folks’ definition of success. ✅ Status.

But more importantly, what am I risking by choosing this path? I’m forever beholden to investors and employees. ❌ Autonomy. It would be easy to stumble into starting a business that I don’t actually think delivers meaningful value to society. ❌ Meaning. I would have far less time to spend with my family & friends and on activities outside of work that I care about. ❌ Relationships & Hobbies.

Counter that with Wednesday, becoming a full-time creator.

I would own my projects, my time and my schedule. ✅ Autonomy. This path would be interesting, filled with all kinds of unknowns. ✅ Adventure. I would be engaged daily in deep, focused work. ✅ Work Quality.

Making money, like actual wealth, as a creator is really difficult. ❌ Wealth. Most people in my life would think I was fucking crazy. ❌ Status. What I create might suck and never see the light of day. ❌ Impact.

Now, there’s an entirely different discussion (and post) to be had around whether these are even accurate stories to begin with, but that’s beside today’s point. Here’s what I’m getting at: Every decision we make is ultimately a bet, in which we tell ourselves a story about what we’re getting and risking with that decision. We tell ourselves these stories whether we are consciously aware of them or not, and regardless of whether they’re accurate.

What I’ve observed is that it’s easy for me to focus on what I’m getting from any given decision. Creating a list of considerations that I’m optimizing for, benefits from choosing one path, vs another? That part is simple, comfortable and exciting.

Where my confidence around any one answer begins to crumble though is when I consider what I am risking by pursuing a given option. Those things that I might lose, never see again or am deferring into the future. Grappling with those things head-on is what sends me into a tailspin. That’s what wrecks any feigned confidence I’ve mustered up to that point. That’s what propels me all the way from unicorn CEO to hedonistic ascetic by the end of the week.

Some of the best relationship advice I’ve ever received is this: Find a partner whose shortcomings you’re willing to tolerate, and you’ve found yourself a match. So it goes with other decisions in life, like work, I’m finding. I’m increasingly convinced that we focus far too much on what’s to gain from any decision, when we should actually be getting comfortable with what we’re willing to lose. It’s in this comfort that we can become more emboldened in the decisions we make and confident in how we operate amongst the risks we’ve consciously chosen to take.

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Whoa, it’s been an embarrassingly long time since my last newsletter! I got MAJORLY stuck (for all kinds of bad reasons and excuses) and lost my momentum. I really appreciate the encouragement from those that reached out with a “where the hell has your newsletter been?!” note. It was needed more than you’ll know.

And a huge thanks to Christina, Jennifer, Alice, Oz, Abhijeet, Bernie and Evan for providing their thoughtful feedback on this piece.

🤘,
Harris

PS — if anything in here resonated, I'd appreciate it if you tapped the heart below or shared with a friend or two.

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