Choosing to buy runner-ups, on principle

Over lunch recently, Mike, Sasha, Anton and I chatted about the expenditures of the ultra-rich. The example — startling and new to me — was people spending hundreds of thousands of dollars to rent out a yacht for a week. Mike imagined they thought to themselves:

We’re going to need a yacht for a week. That is the *best* yacht. We can afford it, so that’s the one we’re using.

Laughter followed, and the conversation flowed elsewhere, but after lunch, as Mike and I settled back into our Watch cycle, he asked, “If you had all the money in the world, and you could buy the Best Something what would you want?”

The question froze my brain pretty hard. I thought it would be easy to answer, but instead, I found myself philosophizing why I would never get the best of anything.

I deeply believe that runner-ups — second, or third, or even middle-best — are plenty good enough.

I pondered why.


I started with trying to think of fancy, expensive things I’d considered getting nice versions of, but their cost became too hard to ignore, and I couldn’t honestly think about it. (“If I got the best tent/sleeping bag/jacket/pair of boots, wow, that’s a hefty sum… what’s the opportunity cost?”)

It became easier to understand my feelings around runner-ups when I started thinking about smallish things, such as garage or kitchen tools (e.g. a wrench, a screwdriver, a ladle, a cutting board…) I can imagine spending anything from $5 to $50 to solve my problem of “I need a ____.” This is what would happen:

  1. I’d hit up Home Depot/Bed Bath and Beyond.
  2. I’d pick up at least 4 different things.
  3. I’d hold on to two: a nice thing on the higher end, and a middling thing that doesn’t offend me.
  4. 15 minutes later, I leave the store with the middling thing.

It’s easy and fun to get excited about things. I may or may not frequently get excited about beautiful kitchen knives…. But the funny thing is, I rarely let myself get them, even if I could afford it.


One rationalization for this is that I imagine myself as ultra-logical, optimizing for spending the minimum amount necessary to solve my problem.


Another rationalization is that I wish I were more normal, and purchasing choices are one of the few ways that I have full control over how I turn that dial.


The rationalization that ran the most true is that I believe the acting agent (me!) is much more important than the thing. When I get something, I don’t have any evidence that would suggest the best thing would actually make my experience better.


I realized this when Mike asked, “What if it was something you actually really cared about, like a tutor for your kid?”

No. My child is going to get a normal tutor, if any, because nobody and no sum of money is going to take responsibility for its learning.

Something in me was strongly opposed to the idea that a better “purchase” would fix an under-performing student. That’s on the student. And that’s on me and the implicit values I’ve conveyed. Focusing on purchasing choices just avoids the underlying problem.


Does the best tutor make for the best student?

Does the best wrench make for the handiest work?

Does the best knife make the most delicious meal?


As a clumsy human being who needs weeks of practice at anything before beginning to understand it, the limiting factor is, more likely than not, me. Not the stuff I choose to buy.

I like feeling out “normal.” Then, a while later, if the operation is going well, and I’ve either broken the first thing, or been driven to distraction by its inadequacies, I might upgrade.

Either way, I’ll learn that there are better solutions to the problem than looking for the best thing.
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