Don't (Just) Optimize for Convenience

A favorite saying of mine goes like this: "everything you now love was once new." This is true of people (all friends begin as strangers) and of taste ("whitefish salad on a pumpernickel bagel" was not always in my vocabulary¹). It's actually wild to consider how the present parts of our lives that feel rock solid were once experiments with unknown results.

Occasionally, when I pick a movie, I'll intentionally channel the power of the unknown. I'll load up HBO (the artist formerly known as Max) literally close my eyes, hit the scroll and click where it lands². The result can be duds, or middling, but sometimes they are astonishing and memorable, opening me up to a new director or genre that I can't wait to get more of. Serendipity in general has this quality of upside convexity: meeting the right person or reading the right book can literally change your life.

Most of the time though, I'm not picking randomly. Random choice requires effort and offers uncertain rewards - and after a long day, what I crave is convenience. I'm happy to defer the burden of choice to an algorithm with my tastes already encoded. Looking around, this convenience is everywhere in my life, and by its nature, always within reach. It exists in my friendships which reward habitual hangs at the same restaurants, bars, and coffee shops; in the supply chains which have minimized the steps required for me to purchase dish soap or blueberries; in the AI summaries that now mediate my iMessage conversations. Everywhere, convenience is a Zamboni, shaving the friction in my life, until living feels like smooth gliding.

In part, this convenience is obviously great. A year and a half ago, I got a stationary bike for my apartment³. I use it all the time - much more than the bikes at my old gym, and much much more than my short lived road bike which I had to carry up four flights of stairs. Convenience has effectively erased the start-up costs to an activity I enjoy.

But - and this is my big take - blindly optimizing for convenience isn't the way.

To start with a provocative argument, if you don't like your life you certainly shouldn't optimize for convenience. If you hate being a workaholic, eating the paid office dinner to save time will allow you to work more, drawing you deeper into a life you don't want.

If anything, maybe you need to optimize for inconvenience, giving yourself as much opportunity as possible to run into the world and eventually the life you do want. Maybe you need an hour-long commute to let you see and digest the subway ad encouraging you to move to Maine and become a teacher⁴.

But, even if you like your life, you should choose convenience intentionally and sparingly, because convenience comes at the cost of spontaneity, and the world is even richer than our imaginations can accommodate. This is part of why people experience travel as so transformational. Travel is, in many ways, a maximally inconvenient way to spend your time - you're disoriented, you don't have your routines, you might not even speak the language. But that very friction forces you to encounter the world at a higher resolution, and in doing so, encounter versions of yourself you didn't know existed. Imagine what your life would look like if you could show up to every experience with the eyes of the traveler. That's serendipity maxing! It's letting the world slow you down and call your attention. And, if everything we're going to love is on the other side of what we don't yet know, then it has to be the way.