Against Optionality.

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Coming out of the worst of the pandemic, everyone has all this pent up energy to make big life changes at once. Changing jobs, moving cities, getting into or out of serious relationships - it’s all the same impulse and it’s understandable. After 12+ months of The Same, now is the time for Different.

It’s a national phenomenon (at least) and tech people seem like they’re leading the charge by doing the most and doing it the most publicly. What’s new.

But what may feel like a unique moment is just the apotheosis of a particular strain of contemporary (tech) thinking that prizes optionality and flexibility over everything else.

The tech ideal of being a bi-coastal, sexually-unmoored IC with a paid newsletter and a scout fund is fundamentally about optionality and flexibility.1 Total freedom with fallback options and alternatives aplenty. That desire for optionality and flexibility is a reflection of the belief that there might, at some point in the near future, be something/someone better to do/be.

Tech folks are primed to love optionality because in tech the outlier outcomes are so much better than the rest. The upper bound of possibility is so lucrative and fantastic (joining a company that goes public and mints you millions practically overnight, for example) that it’s so obviously worth it to continuously optimize around that.

This mode of thinking is so fundamental that it seems impossible that it wouldn’t pervade the rest of our lives; not just what work I do but how I live, where, and with whom. I need fingers in lots of pies and to shut no doors to alternatives because the gulf between the best and second best versions of my life is vast. It’s power law optimization for the everyday.

Counterintuitively, being optionality-obsessed is just as fearful as it is optimistic. It reflects the fear of making the wrong choice just as much as hope for making the right one. What happens if I stay too long in the “wrong” job or date someone and it doesn’t work out or I miss out on that next shiny object that would have changed my life? I’d be ruined by opportunity cost! Optionality lets you preserve the chance that you’ll strike gold and minimize the risk of committing to the wrong thing but only by avoiding commitment at all.

Options aren’t free. They come with hard and soft costs. So if you want to keep all options open, you have to be prepared to pay for it.

As Byrne Hobart put it, an open calendar gives you maximum flexibility to say yes at the expense of intermittent loneliness and an Uber gives you flexibility in your transit plans at the expense of a $40 trip from Manhattan to Brooklyn. Want the flexibility of a month to month lease? It’s yours for a cool 30% premium over a long term lease.

And if you want to bounce between jobs, you need to figure out new politics, adjust to new workflows, develop a new internal track record, etc. before you can even do your job competently/effectively. Beyond transaction costs, if you leave before your work bears fruit, you lose the opportunity to learn from it and improve meaningfully on the process that went into the work in the first place.

You need to let positions ride to compound the gains. If you keep taking risk off the table (as it were) along the way to reallocate to some juicier, higher potential outcome/position, you might be kneecapping yourself and your own growth. If you never risk commitment to the wrong thing, you might not have enough experience to confidently commit to the right thing when it comes along. Finally, if you’re always focused on the next thing, it seems hard or impossible to simultaneously focus on the task or opportunity at hand.

I’m a believer that we ought to “disagree and commit” when making decisions as a group. We can apply a similar idea in our own lives. Accept that something might be wrong but, based on the belief that the worst choice is no choice, do it anyway and do it with gusto until you’re demonstrably right or wrong, or have gotten from it all you can. Then move on and do it again.

Having been in one job for nearly five years right out of college, I’m obviously talking my own book here - perhaps even to the point of self-delusion. But while I can’t say what the future holds, I am comfortable and confident in my assessment that had I left my firm after two or three years (typically of someone entering venture), the loss would be far greater than 50% of what I’ve learned and grown into.

Commitment need not be for life or even particularly long term, but the refusal to commit to something at all can defeat the purpose of doing it in the first place. It’s a Faustian bargain: trading away impact for optionality.

Make no choices, keep all options open, pay the price.

In other words, burn the boats.

Sorry to sound like a prudish sourpuss but I’m trying to paint a picture here. Bear with me.