Don’t wait until you’re the ‘breaking news’ story

I don’t like learning lessons the hard way. Unfortunately, that’s usually how I learn them.

A few weeks ago, I took my wife to Costa Rica, and it was honestly one of the best vacations we’ve ever taken. We stayed at an incredible resort. The accommodations were unbelievable, and the service was next level. We spent our days exploring the rainforest, watching monkeys steal food from unsuspecting guests, mountain biking through paradise, and just enjoying being unplugged for a few days. It was everything we’d hoped it would be.

Until it wasn’t.

One morning, I opened my wallet and immediately noticed something was wrong. The smaller bills I had brought for tips were still there. My credit cards were there, and my ID was there, but the five one-hundred-dollar bills I had packed were gone. Just, gone. It wasn’t a mistake, and it wasn’t buried in another pocket or tucked inside my suitcase. Somebody had gone into my room, opened my wallet, removed only the large bills, and left everything else behind.

The funny thing is, I don’t blame the resort. I blame myself. My room had a safe. I simply never used it.

Like a lot of people, I assumed that because I was staying somewhere luxurious, because everyone was professional, because everything felt secure, nothing bad was going to happen. That’s a dangerous mindset. Criminals don’t always target places that look unsafe. Sometimes they target places where people feel the safest because that’s where people let their guard down.

To the resort’s credit, they handled the situation incredibly well. Management immediately took it seriously. Security interviewed me, documented everything, and even tracked who had entered the room through the electronic key-card system. They apologized repeatedly and went out of their way to make things right. They didn’t argue, they didn’t dismiss my concerns, and they understood that trust is part of the luxury experience.

The truth is, though, getting exceptional customer service afterward didn’t change what happened. Five hundred dollars disappeared because I made it easy for someone who lacked integrity.

That experience got me thinking about how often we create unnecessary opportunities for bad things to happen—not because we’re careless people, but because we’re comfortable.

We leave backpacks on the passenger seat while we run into a store for “just a minute.” We toss expensive headphones into an unlocked gym locker. We walk through parking lots staring at our phones. We leave packages sitting on the front porch all day. We forget to lock doors because “we live in a nice neighborhood.” We assume that because nothing bad has happened before, nothing bad will happen today. Most of the time, we’re right.

Until we’re not.

One of the biggest mistakes we can make is believing that being prepared means being paranoid. Those aren’t the same thing. Being paranoid means living in constant fear. Being prepared simply means acknowledging reality. Locking your car isn’t paranoia, using the hotel safe isn’t paranoia, and paying attention to your surroundings while walking to your vehicle isn’t paranoia. Those are small habits that dramatically reduce unnecessary risk.

I also think there’s a tendency to believe that confidence alone keeps us safe. Confidence is important, but awareness is even more valuable. The strongest, smartest, and most successful people still become victims when they assume they’re immune. Situational awareness isn’t about expecting the worst from everyone. It’s about giving yourself the best chance of avoiding situations that never needed to happen in the first place.

The older I get, the more I realize that protecting yourself is less about reacting and more about planning ahead. Ask yourself simple questions:

• If something valuable disappeared right now, would it have been preventable?
• If you’re traveling, have you backed up your passport and important documents?
• If you’re at the gym, is your wallet really secure?
• If you’re walking to your car after dark, are you paying attention to who’s around you?

These aren’t dramatic questions. They’re practical ones.

Fortunately, my Costa Rica story ended with nothing more than a lighter wallet and a valuable lesson. It could have been much worse. I still had an incredible vacation, and I still think Costa Rica is one of the most beautiful places I’ve ever visited. And I’d absolutely go back, but next time, the safe will get used before I even unpack my suitcase.

Here’s the takeaway: don’t wait until you have your own story to become more aware. Whether you’re traveling across the world, working out at the gym, walking through a parking garage, or simply locking up your house before bed, make protecting yourself part of your routine. You don’t have to be fearful, and you don’t have to assume the worst about people, but you should make it as difficult as reasonably possible for someone else’s bad decision to become your problem.

The goal isn’t to live looking over your shoulder. The goal is to make smart decisions today so you don’t spend tomorrow wishing you had.