How to Trust Your Gut

(With Training Wheels, a Safety Harness, and Someone Else's Dead Grandmother's Watch)

Rafa hands me ten hundred-dollar bills in a Starbucks parking lot, and I’m standing there holding a thousand dollars in cash like I’ve never seen money before.

Which is stupid, because I’ve seen money before. I’ve just never seen someone I barely know actually pay back money.

“That’s a thousand,” he says. “I’ll get you the other hundred next week.”

I’m doing math—$1,100 loaned three days ago, $1,000 back now—while simultaneously trying to process the fact that this is happening. A person I’ve known for two months is paying me back. On time. Without me having to chase him down or listen to elaborate excuses about why the money’s tied up in crypto, his mom’s sick, or whatever.

“Cool,” I say, because what the fuck else do you say when your cynicism gets proven wrong?

He shrugs. “Thanks for helping me out.”

And then he leaves, and I’m sitting in my car with a thousand dollars in my lap, feeling something I haven’t felt in years.

Hope.

Fuck.

The Part Where I Learned Not to Trust Myself

I’m not going to tell you the specifics of what happened the last time I trusted someone with money. Just know it was bad enough that I stopped trusting my own judgment entirely. Like, imagine you’re really good at making pizza, and then one day you accidentally poison everyone at a dinner party with your pizza. Now you’re not allowed to make pizza anymore. Except instead of pizza, it’s “believing people when they say they’ll pay you back,” and instead of food poisoning, it’s financial and emotional devastation.

(This analogy got away from me, but you get it.)

For years afterward, whenever someone asked, “Hey, can you help me out with some cash?” my immediate response became “absolutely fucking not.”

Not because I’m heartless.

Because I learned I couldn’t tell the difference between someone who needed help and someone who saw a mark with my email address on it.

So I decided I needed to build a wall—no more loans. No exceptions. The alternative was getting destroyed again, and I’d already paid tuition for that particular lesson.

And honestly? It worked. No one can take advantage of you if you never say yes.

(Also: no one can prove you’re a decent person if you never help anyone, but that’s a different essay.)

Enter: The Gut Feeling I Definitely Shouldn’t Trust

Three days ago, someone I’d known for maybe two months—let’s call him Rafa, because I’m not using his real name for reasons that are his business, not yours—asked if I could loan him rent money.

$1,100.

Three-day eviction notice. He, his wife, and his daughters.

The kind of situation where you either help or you watch someone lose their apartment, and those are genuinely the only two options because we live in a country where “the social safety net” is a joke we tell ourselves while people trade dead grandmothers’ jewelry for rent money. But I digress.

Here’s the thing: my gut said he was solid.

My gut. The same gut that got me burned so badly, I’m still paying off the emotional interest. The gut I had specifically, explicitly, with great intention and forethought, learned not to trust.

But there was something about the way he asked. Matter-of-fact. Not desperate. Not manipulative. Just: “I’m in a bind. Can you help? If not, no worries, I’ll figure it out.”

(That last part—“I’ll figure it out”—is key. People who are actually going to figure it out say that. People who are going to make it your problem don’t.)

So my gut said yes.

My brain said, “Absolutely the fuck not, we’ve been through this, have we learned nothing?”

The compromise was collateral.

In Which I Become a Pawnbroker Using Boundaries Instead of Shame

He offered his grandmother’s Rolex before I even asked.

“I know we don’t know each other that well,” he said. “So if you want collateral, I get it.”

And I did want collateral.

Not because I didn’t trust him.

Because I didn’t trust myself.

The watch was insurance against my own judgment. A way to tell my gut: “Okay, fine, you think this person is solid? We’ll try this. But we’re protecting ourselves this time. We’re not doing the thing where we hand over money and hope for the best and then act shocked—shocked!—when it all goes sideways.”

Taking the collateral meant I could say yes to helping someone without feeling like I was just repeating the same mistake that destroyed me before, except with a different person’s face attached.

The watch wasn’t about him.

It was about me learning to trust myself again—but with training wheels.

(Also: it was about him not being able to fuck me over even if he wanted to, which, let’s be honest, is what boundaries are.)

Three Days of Sitting With a Dead Woman’s Watch

The Rolex sat in my desk drawer for three days. Gold, heavy, the kind of thing his grandmother brought from Mexico because immigrant families carry value in things you can wear or sell if the American Dream turns into an American Eviction Notice.

(My grandmother did the same thing. Jade bracelets. Gold bars. Things that could be pawned if necessary. Except those things were in a safety deposit box until the bank branch shut down, and then they went missing before everything was carefully recatalogued again.)

Every few days, I’d open the drawer just to make sure the watch was still there.

Not because I thought it would disappear.

Because I needed to remind myself I’d been smart this time. Protected. I’d helped someone without being a complete fucking idiot about it.

Except the whole time I kept thinking: What if I’m wrong again?

What if he doesn’t pay me back?

What if I just repeated the same pattern with a different person?

What if my gut is still broken and I’m too stupid to realize it?

What if I’m the kind of person who just keeps getting taken advantage of forever because I’m fundamentally too trusting and also too dumb to learn?

The watch was supposed to protect me from those thoughts.

Instead, it became a three-day-long reminder that I was still terrified of my own judgment.

Great.

The Text Message I Didn’t Believe

When he texted me last Tuesday—“Hey, I can pay you back most of it this week”—I stared at my phone for a full thirty seconds.

Most of it.

Not “I need more time,” or “something came up,” or “can we do half now and half later?” Just here’s most of your money back, on schedule, like adults do.

When he handed me the cash in the Starbucks parking lot, I counted it twice.

A thousand dollars.

He’d paid back almost everything. Three days later. No excuses. No drama. No elaborate story about why he needed just a little more time.

I drove home thinking: What the fuck just happened?

Because here’s what just happened: My gut instinct was correct. The person I thought was trustworthy actually was trustworthy. And I’d protected myself with boundaries that worked.

Both things were true.

At the same time.

I could trust people. I could protect myself. These weren’t mutually exclusive options where you had to pick one and suffer the consequences.

And I didn’t know what to do with that information.

The Thing About Hope (Or: Why This Is Terrifying)

For years, I thought the lesson was: “Don’t trust your gut. Your gut is broken. Only trust systems, contracts, collateral—things that protect you from your own catastrophically bad judgment.”

But maybe the actual lesson is: “Your gut isn’t broken. You just needed to learn to protect yourself while you listened to it.”

The collateral wasn’t a failure of trust.

It was the scaffolding that let me trust again.

I didn’t need to choose between being the person who helps people and the person who protects himself. I could be both. I could say yes to my gut—and also say yes to boundaries. I could help someone and require collateral. I could be generous and careful.

These things are not contradictions. They’re called “being a fucking adult.”

(Apparently. I’m still figuring this out at 48.)

And here’s the thing about hope that no one tells you: it’s fucking terrifying.

Because if my gut was right this time, that means it might be right again. Which means I might have to risk trusting it again. Which means I might have to risk getting hurt again. Which means all those walls I built might have to come down a little bit, and I don’t know if I’m ready for that.

But also: I was right. My instinct was correct. The boundaries worked. And someone I barely knew proved that sometimes—not always, not even usually, but sometimes—people are exactly who they seem to be.

And that’s... something.

The Button (Or: What Do You Do With Hope?)

The Rolex is still in my desk drawer. He’s got $100 left to pay, and he’ll probably get it to me next week.

But here’s the thing: I already know he’s good for it.

I know this the same way I knew three weeks ago that he was solid the first go-around. Gut feeling. Instinct. The thing I’ve spent years learning not to trust.

Except this time, I trusted it and protected myself.

And now I don’t know what to do with the knowledge that maybe—maybe—I’m not completely broken at reading people.

Maybe I just needed to learn how to protect myself first.

The watch is going back to him. Obviously, it was always going back to him.

But the lesson?

That one’s mine.

(And I still don’t know what to do with it.)