Buying art: Where emotions and rationality collide

Bethany Crystal
5 min readOct 3, 2021


I bought a piece of art this week from an art fair in New York City. I attended the fair on a complete whim after a last-minute from a friend earlier that day. Initially my objective in attending was to enjoy an evening out, spend a little time alone, and meet a few new people while enjoying an experience (ie: looking at art) that’s hard to do with a toddler in tow.

Much to my surprise, I ended up walking away with a new painting from an artist I met on the spot that night. I walked by, I saw it, couldn’t stop staring and eventually decided to take the plunge. It’s now hanging up our living room.

While it certainly wasn’t my pre-meditated plan for the evening to make a new investment in a piece of art, my decision also didn’t feel completely out of left field. And I’ve noticed, now having gone through my own art-buying process a handful of times, that there’s a bit of a pattern to making a purchase like this. The invisible pre-work that comes first, the mental calibration about the investment, and then the emotional impulse needed to make the call.

Call it structured spontaneity. Chaos with constraints. Relative irrationality. Here’s what I’ve learned about the rational and the emotional sides of buying art, and how it might apply in other contexts as well.

The Rational Side of Buying Art

Any significant purchase requires some level of prior planning, and art is much the same for me. I’ve never bought a home or a car, but we do plan out our finances with a lot of care. A few years ago, I mentioned in a meeting with our financial advisors that I’d like to be able to acquire pieces of art from time to time, in various places along our travels. So we built it into the plan. We looked at our budget and decided on a number that made sense for us. It’s more of an opportunistic line item in our annual planning, less of a sure thing. (And it hasn’t happened every year.)

The other rational components include knowing what you want and identifying a need. In my case, we recently moved into a new apartment and have a bit more space on our living room wall than we had previously. In all of my work-from-home hours, I’d been looking at a spot on the brick wall next to our kitchen and wondering, “What could we put there?” A few weeks ago, I visited the Armory Show art fair in New York City, which I visit for the same reason that I like to walk down Bleecker Street or fancy department stores: Get a flavor of what’s trending in the big leagues and start to identify what styles I might like for my own, at a much smaller scale.

All of this invisible work — the financial component, the empty wall space, and the recognition on the flavor profile of a painting that I was gravitating toward — all of this comes before the purchase itself. But admittedly, that’s 80% of the prep work. Knowing what you want and how much you can spend.

The Emotional Side of Buying Art

The last 20% of the sale is certainly emotional. If you buy at a fair, which I’ve done once or twice, there’s almost certainly a FOMO effect at work. There are lots of people buying things, there are lots of red stickers appearing on works that are getting sold, all sort of taunting you: If you don’t buy that thing, someone else could. The hype is definitely real.

But this is where the invisible rational pre-work comes in handy. You can run through those questions in your mind:

  • Is this within striking distance of the budget we discussed?
  • Will this fill the space on my empty wall?
  • Does this genre / style fit everything else?

Since you’ve already come up with a framing around each of them, you can just answer quickly in your mind. Yes / No. If you come up with yes’es all around, you’re good to go.

Of course, there are likely a million other questions you might be wondering about, as well. Things like: Will this piece be an investment over time? Will this artist gain in popularity? Will my husband like this? Are there other works at different places that might be better? Those are all good questions to ask. But the only trouble is — unless you’ve already done pre-work around those questions, you’re not going to be able to answer them in the moment. They are unproductive and will only hold you back from being able to make a decisive decision.

The first time I bought a piece of art at a fair, I was so nervous that I had to call my brother to talk me off the ledge. Don’t get me wrong: It’s stressful. Even this week I was so nervous that I drank an entire glass of red wine after the purchase. But I know now that, assuming I’ve done the rational pre-work, I need to trust myself with an emotional decision for the last 20%. And I’m so glad I did.

The next day, my friend approached me in the office and said: “Your spontaneity yesterday — both to go to this art fair at the last minute and then to buy a piece — inspired me to be more spontaneous too! I might get a massage tonight!”

It may look spontaneous. But there’s a backbone to that impulsivity. Constrained chaos feels pretty good when you let yourself go there every now and then. I imagine this process can work in a lot of decision-making frameworks as well.

In investing, you start with a thesis and research about the types of companies you want to look for, or the characteristics of the founding teams that resonate the most with you. In choosing strategic partnerships, you identify a basic framework and some ground rules for your sales and marketing teams. But in the end, when you see something, you need to be able to make the call and jump in right away. The first 80% is planned, calculated, and prepared. The last 20% is gut and instinct. The art and the science of buying art. How meta.

Originally published at Dry Erase.



Bethany Crystal

A little bit web2, a little bit web3… Today’s projects: @Bolster & @Zeitgeist_xyz , board @CompSci_High ; ex @USV , @StackOverflow , alum of @Northwes