How Much Does Sincerity Matter?

When what we say and do doesn’t represent what we actually believe.

When I was at college way back in the 90s, there was a guy who worked checkout at the local Safeway. When I first started shopping there he was just some middle-aged bald dude. After a short time he started showing up to work dressed as a woman. Not trying to pass, just an utterly average looking guy in a dress. This was unheard of back then. He was known among students as the cross-dressing checkout guy. No doubt he endured stares and remarks from many customers.

Over time he added a wig, grew out his nails and wore makeup. This played out over a few years. I’d never seen anything like it. He was stoic and patient but he also seemed very tired.

He disappeared from the store for a while. When he came back you could tell he’d had something done. Back then, I knew nothing about what options were even on the table other than “Sex Change Operation.” It had taken him over five years to get to this point (I know this because I failed at school for six before leaving to work in a warehouse). By now, most kids didn’t even know he’d once been a man. Other than his appearance, he’d changed in other ways too. He seemed happier. He’d smoke and joke with coworkers out front, he’d laugh and smile at the register.

He sticks in my head as a model of toughness and self respect, but above all, sincerity. I started out as a dumb kid thinking he was bonkers and ended up admiring him.

Still, I think of him as a “he”, the way I first saw him. I can’t say why exactly—maybe it’s the power of first impressions—and it doesn’t feel like something I can control. If I knew him, I’d try to use whatever pronouns he preferred. But that wouldn’t change how I see him. And this is not me taking some kind of moral stand against his transition. I saw plainly how the change was positive for him, and don’t doubt that his choice was the right one.

But the best I can do here is refer to him as “she” despite how I actually see him. And that’s insincere. It’s polite, yes, but misleading. It gives a false impression. Maybe that’s good enough. Maybe the harmony derived from the appearance of agreement outweighs any lost truth. I honestly don’t know.

My point is genuine belief isn’t a switch you can flip. If you grew up on the West Coast calling soft drinks “soda” and then moved to the Midwest where it’s “pop,” you might start saying “pop,” but you’d still think “soda.” Maybe a part of you always would. And in this case the stakes couldn’t be lower. When the stakes are higher, and in cases when the conceptual gap between two ideas is greater—like between men and women—it only gets harder. You can’t bootstrap genuine belief through strategic reasoning, any more than you can decide to find something funny or fall in love with someone.

This, believe it or not, leads me to Pascal’s Wager.

Pascal’s Wager and insincerity

If you somehow have never heard of Blaise Pascal’s famous philosophical argument, it goes:

• If God exists and you believe → you gain infinite reward (heaven).

• If God exists and you don’t believe → you risk infinite loss (hell).

• If God doesn’t exist → whether you believe or not, the stakes are small (a finite loss of time, habits, etc.).

Consequently, believing in God is a great bet—the potential of infinite gain overwhelmingly outweighs finite loss.

As someone who’s made good money on wagers most of my adult life, I find it hard to argue with this one. Nevertheless, I’ve never accepted it. I couldn’t if I wanted to because belief doesn’t work that way. It’s an impossible proposition.

I can’t just declare belief in God and have it be true. It’s an empty gesture. I could parade around saying I’m a Christian or a Muslim or whatever, and I could practice the necessary rituals as a kind of 9-to-5 that pays better than any earthly wage, but that wouldn’t change the fact that I still wouldn’t believe any of it. It’s possible that maybe after years of lying to everybody about what I thought, I could Jedi mind-trick myself into forgetting my objections and embrace theism. But the prospect of pretending to be someone I’m not and throwing away my principles, all while attempting to brainwash myself on the off chance that God exists and that He somehow approves of people deceiving themselves like this is too much for me to swallow.

Whenever you represent yourself falsely, whether it’s religion you don’t buy into or gender you don’t see, it’s a kind of loss, regardless of how good your intentions might be. It frustrates shared understanding. If the checkout guy had continued to present as a man while believing he was a woman, that would have been a kind of loss too, even if it made life easier for him and others in some ways.

Maybe a world where people say or do things they don’t believe for some payoff is a better world than one where everybody’s sincere for better or worse, but it isn’t entirely clear to me that this is the case.