Get in Trouble as Much as You Can

If you’re in your teens or twenties, here’s an unexpected piece of advice: get in trouble and do it often. Not the sort that lands you in handcuffs, but the kind that pushes boundaries, sparks difficult conversations, and forces you to rethink what you thought you knew.

Why? Because safe and easy paths rarely teach you anything useful. When you stress test your environment – your friendships, your assumptions, your comfort zones – you start building the kind of resilience and insight that only comes from lived experience. Nobody learns how to swim by reading about it. And they certainly don’t learn fast enough when they’re already drowning.

This kind of “trouble” isn’t about being reckless, it’s about being curious. It’s asking questions others won’t. Challenging rules you don’t fully understand. Making bold moves that might not work out. That’s how you figure out where the real limits are – and more importantly, how to navigate them.

By getting in trouble often, you develop a strategic mindset. Like a muscle, it gets stronger with use. And when life throws genuinely hard things your way – as it eventually will – you’ll already have the toolkit to stay calm, read the room, and act with clarity.

So if you’re young and things feel uncertain, good. That’s your playground. That’s your training ground. Get into just enough trouble to learn who you are – and who you could become.

If you’re in your thirties or beyond, chances are trouble has found you one way or another — but if it hasn’t, the same advice still applies.