Stuck In Better Safe Than Sorry

Trapped in the prison of what-ifs.

It got me thinking....

Why do we cling to "better safe than sorry" like it’s a life raft in a stormy sea? I see it all the time: clients stuck in the safety of their comfort zones, paralyzed by the fear of regret. It’s like wrapping yourself in bubble wrap before walking down the street. Sure, you’re protected, but you’re also suffocating. And yet, the allure of safety is so strong, so seductive, that we convince ourselves it’s the only way to live.

Take my client, Emilie. She’s been in the same job for ten years, even though she dreams of starting her own business. “What if I fail?” she asks me, her voice trembling. “What if I lose everything?” Emilie’s fear of the unknown keeps her tethered to a job she hates, a life that feels stagnant. She’s stuck in the "better safe than sorry" mindset, convinced that staying put is the only way to avoid disaster. But here’s the thing: safety isn’t always safe. Sometimes, it’s just another word for stuck.

It’s like sitting in a parked car with the engine running. You’re not going anywhere, but at least you’re not crashing, right? Except the gas is running out, and eventually, you’ll be stranded anyway. The truth is, staying in your comfort zone doesn’t guarantee happiness, it just guarantees you’ll never know what could have been.

Then there’s Alexis, who’s been dating the same person for years, even though he knows deep down they’re not right for each other. “What if I never find anyone else?” he asks, his voice heavy with doubt. “What if I end up alone?” Alexis is so afraid of being sorry that he’s willing to settle for a relationship that doesn’t fulfill him. But the science is clear: regret over missed opportunities often outweighs regret over taking risks. Studies show that people are more likely to regret the things they didn’t do than the things they did, even if those things didn’t work out.

It’s like holding onto a life jacket in a swimming pool. You don’t need it, but letting go feels too risky. And maybe, that’s the real problem. We’re so afraid of making mistakes, of feeling pain, that we forget life isn’t meant to be lived in a state of constant caution. Growth, joy, and fulfillment all require a little risk. They require us to step out of the bubble wrap and into the world, bruises and all.

So how do we break free from "better safe than sorry"? It starts with reframing the way we think about risk. Instead of asking, “What if I fail?” try asking, “What if I succeed?” Instead of focusing on what you might lose, think about what you could gain. And if that feels too overwhelming, start small. Take one step outside your comfort zone, then another, and another. Before you know it, you’ll be running.

One of my clients, Mia, did just that. After years of playing it safe, she finally took the leap and moved to a new city for a job she was passionate about. “I was terrified,” she admitted to me later. “But now, I can’t imagine staying where I was. I would’ve missed out on so much.” Mia’s story is a reminder that the greatest rewards often come from the greatest risks.

It’s like jumping into a cold pool on a hot day. The shock is intense, but once you’re in, it feels amazing. And maybe that’s what life is all about. Taking the leap, feeling the fear, and doing it anyway. Because in the end, "better safe than sorry" might just be the biggest sorry of all.