Welcome back to another Question of the Week here at The Confusing Middle!

This week’s question comes, as always, from Gregory Stock’s The Book of Questions. And I want to say upfront that this one is probably the easiest question I’ve encountered in this series, at least for me personally. Which is either a sign that I know myself extremely well or a sign that I have very little pride. Possibly both.

Here it is:

Would you accept $20,000 to shave your head and continue your normal activities without a hat or wig until your hair grew back? What is the minimum price you’d take for this?

My answer: Yes. And the minimum price is a free haircut.

The Part Where I Establish That This Isn’t Even a Question

Let me explain why this one barely registers as a dilemma for me.

I am a man in my forties who has voluntarily buzzed his hair down to nearly nothing on multiple occasions throughout his adult life. Not because I was making a statement. Not because I was going through something. Usually because I couldn’t talk myself into spending $35 on a mediocre haircut and figured I could just handle it myself with the clippers and a general sense of indifference. So the idea of someone handing me $20,000 to do a thing I have essentially done for free — out of mild stubbornness and a fundamental unwillingness to sit in a barber’s chair — strikes me as less of a moral dilemma and more of a financial windfall I’d be foolish to decline.

To be clear: I’ve never gone full Lex Luthor. I’ve never taken an actual razor to the scalp and committed to the complete chrome dome. But I’ve gotten close enough that the prospect of doing so doesn’t fill me with dread. It fills me with mild curiosity and, now, the awareness that apparently there’s money in it.

Twenty thousand dollars. For a haircut I’d probably give myself anyway, given sufficient frustration. I would sign that contract and lather up the shaving cream before the ink was dry.

The Origin Story Nobody Asked For

The first time I ever got a buzz cut, I was in second grade. Seven years old. I had apparently decided, with the full conviction that only a seven-year-old can muster, that I wanted all my hair cut off, and I convinced my dad to take me to the barber shop to make it happen.

This seemed like a reasonable plan to the two of us.

It was less reasonable to my mother, who came home from work that day to find that her son — who up to that point had been, by all accounts, a cute kid with blond hair — was now a small, round-headed person with approximately no hair at all. She was not pleased.

But here’s the part of that story that I’ve always found quietly interesting: when my hair grew back, it came in brown. The buzz cut had apparently marked the end of my blond era. I don’t think she was particularly thrilled about that development either. My hair had essentially taken the money and run, except the money in this case was her preferred aesthetic for her eldest child.

So you could argue that I have been living with the consequences of a voluntary hair removal decision since I was seven. The $20,000 version sounds like a significant upgrade.

Why This Question Is Harder for Some People Than It Is for Me

I want to be honest about something, because I think it’s worth naming before I spend this entire post being breezy about how easy this is.

This question is not equally easy for everyone, and I think a big part of that comes down to gender.

As a man, I can show up to basically any professional or social setting with a shaved head and the primary response I’ll get is — nothing. Maybe a passing observation. Maybe someone asks if I’m doing it for charity. Maybe a friend asks if I lost a bet. But there’s no professional cost, no social judgment that lands with any real weight, no expectation I’ve violated. A man with a shaved head is just a man with a shaved head. There are entire aesthetic movements built around it.

For women, this is a fundamentally different proposition. Traditionally — and I recognize that’s a word doing a lot of work in this sentence — there’s a much stronger cultural expectation around women’s hair. It’s tied up in ideas about femininity and professionalism and presentation in ways that create real stakes. A woman walking into a job interview, a client meeting, or a first date with a shaved head is navigating a different set of assumptions than I would be. And honestly, it’s not even just about shaving it all off. Keri Russell cut her hair into a short curly style during Season 2 of Felicity, and the ratings dropped so dramatically that the incident became a legitimate piece of television history. She didn’t go bald. She just got a haircut. The viewing public apparently needed a moment to grieve.

That doesn’t mean the answer is no — plenty of women would take that deal without hesitation, and more power to them — but it does mean that the calculus is genuinely more complicated for them than it is for me.

For me, the calculus is: free money. Yes.

What I Would Actually Do With $20,000

This feels relevant to the post, and also I’ve been thinking about it since I read the question, so we’re doing this.

The responsible answer involves some combination of savings, paying down debt, and feeling virtuous about the whole thing. The actual answer probably involves a meaningful chunk going directly into the fund I think of as “things I want but keep talking myself out of,” which is a fund that currently has a balance of zero because I keep deciding I don’t need things and then quietly resenting that decision at odd hours of the night.

There might also be a new couch in there somewhere. The current couch is fine, but Krypto has strong opinions about where his end of it is, and I think he’d appreciate a fresh surface to claim as his own.

The point is: I would not be agonizing over whether $20,000 was worth a temporary change to my hair situation. I would be thinking about what $20,000 buys and whether I need to Google how long hair typically takes to grow back. (About six inches per year, for the record. Figure six months to a year before it looks intentional again. Still yes.)

The Minimum Price

The question also asks what the minimum price would be, and I want to sit with that for a second because it’s actually the more interesting part.

The $20,000 framing is designed to make you think, well, obviously, that’s a lot of money. But the follow-up is a nudge toward self-knowledge: what do you actually think this costs you? What’s the real price of your vanity, your discomfort, your concern about what other people think?

For me, as established, the number approaches zero. The practical floor is whatever it costs to get a proper barber to do it cleanly, because I’m committed to doing things right if I’m going to do them. Call it $15 or $20. A nice tip included.

Which tells you something, I think — not that I have no pride, but that my pride is not located in my hair. There are things I would not do for $20,000. There are things I would not do for considerably more than $20,000. The condition of my scalp is not among them.

Your Turn

So where do you land on this one? Would you take the $20,000 without a second thought, or is this one where you actually have to pause and do some math? And if you’d say yes, what’s the number where you’d start to waver — is there one?

I’m also curious whether this question landed differently for you based on how you think about your hair. Some people are deeply attached to theirs for reasons that have nothing to do with vanity — it’s cultural, it’s identity, it’s the thing you’ve had your whole life. If that’s you, I’d genuinely like to hear it.

Drop your thoughts in the comments. I’ll be down here, mentally calculating whether a free haircut is technically a net positive given the growth timeline.

Until next week — this is Aaron, at The Confusing Middle, growing my own hair since 1980.

Feature Photo by www.kaboompics.com