May 2, 2025 5 minutes minutes read Dimitris

Smart hearts take dumb risks

I've always been fascinated by how quickly we accept certain narratives about ourselves. After making the same error twice, we're quick to claim a pattern. "I always fall for unavailable people." "I never stand up for myself at work." "I keep trusting people who let me down." These statements feel like wisdom, evidence that we've recognized something essential about ourselves or others.

But I've been wondering lately if we've confused self-protection with actual wisdom.

Think about the advice we give each other after a disappointment. "Don't make the same mistake twice." "Fool me once, shame on you; fool me twice, shame on me." "Learn your lesson and move on." This guidance is so universal it's practically sacred. To reject it feels like admitting you're either stupid or masochistic.

A few months ago, I went through a breakup that knocked me sideways. You know the kind where you spend way too many nights scrolling through old photos wondering what the hell happened. It hurt. Still does, if I'm being honest.

The advice came flooding in, each suggestion carrying the weight of established truth. "Take time for yourself." "Don't jump into anything new." "Figure out why you keep choosing the wrong people." All of it centered on a single premise: the goal is to avoid getting hurt again.

It makes perfect sense. Pain hurts, by definition. Avoiding it seems like the obviously correct strategy. Only a fool would deliberately risk repeating a painful experience.

But recently something strange happened that made me question this seemingly unassailable logic. I met someone new, and immediately recognized some warning signs. The slightly inconsistent messaging. The vague answers about past relationships. The tendency to pull back just when things get comfortable. My brain started screaming "RED FLAG" in flashing neon.

And yet I found myself continuing. Laughing at their jokes. Looking forward to our next meeting. Feeling alive in a way I'd almost forgotten was possible.

The conventional narrative would label this behavior as self-destructive. "You're repeating the same mistake." "You haven't learned your lesson." "You're setting yourself up for disappointment."

But what if that narrative is wrong? What if we've fundamentally misunderstood what "wisdom" means in the context of human connection?

Consider how we think about risk in other domains. In finance, we understand that higher returns require accepting higher risk. In creative work, we know that innovation requires a willingness to fail repeatedly. In athletics, growth happens at the edge of comfort. Only in our emotional lives do we treat risk as something to be eliminated rather than managed.

This might be the strangest feature of modern psychology: we've turned pain avoidance into our default metric for good decisions. We treat emotional efficiency (maximum connection with minimum vulnerability) as the goal. We pathologize repeated disappointment as if it represents a failure of learning rather than an inevitable feature of genuine connection.

What would happen if we applied this same logic to other domains? Would we tell a scientist to stop experimenting after a failed trial? Would we tell an entrepreneur to never start another company after a bankruptcy? Would we tell an artist to stick to proven formulas after a poorly received work?

No. We'd recognize that risk and failure are not bugs in these systems but features. Essential components of any process that creates value.

So why do we treat emotional risk-taking as immaturity rather than courage? Why do we confuse self-protection with wisdom?

I'm not advocating for harmful relationships or suggesting anyone ignore genuine warning signs about safety. That's different. I'm questioning whether our fundamental stance toward emotional risk has become distorted—whether we've mistaken risk elimination for growth.

Because I've been thinking, what exactly is the alternative? Never risk getting hurt again? Create an emotional fortress so secure no one can reach me? That doesn't sound like wisdom. It sounds like fear dressed up as self-care.

There's something almost perversely satisfying about the cycle itself, the rush of connection, the splendid anxiety of vulnerability, even the ache of potential loss. That peculiar enjoyment that exists precisely because it hurts a little. The French have a word for it that I won't pretend to pronounce correctly.

The truth is, I like who I am when I'm open, even knowing I might get hurt again. I like the version of me that can still be surprised, still be delighted, still be disappointed. It feels more alive than the carefully protected alternative.

What if vulnerability isn't a weakness to be overcome but a capacity to be developed? What if our ability to remain open despite past hurt is actually the true measure of emotional intelligence, not our skill at avoiding pain?

I'm starting to think there are worse things than getting hurt. Like being so afraid of pain that you miss out on whatever joy might come before the pain. Like being so committed to "learning your lesson" that you forget lessons come in many forms, and not all of them involve self-protection.

So yeah, maybe this new connection will end badly. Maybe in a few months I'll be nursing another heartbreak. Or maybe it won't. Maybe this time will be different.

Either way, I'm choosing to find out rather than wonder. I'm choosing the possibility of both joy and pain over the certainty of neither. Not because I haven't learned anything, but because I've learned something different than expected, that what we call wisdom might sometimes be the most sophisticated form of fear.

And that doesn't seem very wise.