Advice to my 19-year-old self

A decade ago I entered college determined like many to find life’s meaning. Predictably my freshman year was filled with mistakes and misadventures, slowly teaching me lessons and pointing me in the right direction. The rest of my college experience was similar, with slightly less beer and more attention paid to my professors. I marched into my mid-twenties crusading against norms and chasing the people that inspired me to think differently. That often ended with more questions than answers.

Today I’m sitting near a Wi-Fi hotspot in Cuba, about to make yet another bad decision – attempt to paddle across the Straits of Florida. That’s a story for another time. Havana is full of color and life, and people who show love and kindness to complete strangers. This has made me reflect on how I go there. I certainly could have found my way with more grace and saved my mother a few headaches. If given the chance, these are the pieces of advice I would give my younger self.

  1. You already know that all great adventures start with bad decisions. That does not mean that all bad decisions lead to great adventures. Very few actually do. Most lead to mundane adventures like annoyed housemates and credit card bills. Please learn to pick the right ones.

  2. You’ll meet a lot of people in the next 10 years. You’ll make stories with many of them. You’ll dislike some. But only a handful will change your course in life. Search these people out. When you find them, never let them go.

  3. Most people are acting. They are trying to be the person they think they should be, instead of being weird. Embrace the weird. Don’t take yourself too seriously. Unfilter. Run around like crazy. Talk to strangers. Howl at the moon. Encourage others to do so, too. Trust me, no one is watching, and if they are, they need you as inspiration.

  4. Most questions don’t have empirical answers. Hell, most questions don’t have answers at all. Instead of playing out dozens of scenarios in your head, learn to simplify. Whether it’s a big or small decision, define yourself by actions you’re proud of. That’s the best heuristic method you’ll find.

  5. There’s no path to success, and you certainly don’t need to buy a house or build a career to get there. Success is using your time wisely. Respect is never wasting others’ time. Find what makes you most excited and invest your time in it--and never be late.

  6. If you’re going to judge someone, pick good criteria. For instance, the “Say/Do Ratio.” People talk a lot, and so do you. This isn’t bad in and of itself, but try to not get to caught up in big ideas or charming people. Wait and watch for follow through and then surround yourself with people that Do more than they Say.

  7. Life is messy – that’s the most beautiful part. Embrace the grey and fluid areas because these are what make us human and ultimately become the most rewarding. We all make mistakes. These mistakes help all of us grow. The world would be a better place if we allowed for a bit more confusion and messiness.

  8. Team, families, companies, and communities are built on trust. Trust your friends and trust your colleagues. Trust strangers. Trust moonshot ideas and handshake agreements. Trust new foods, half-baked plans, and eye twinkles. Trust best intentions, even if they have failed in the past. Trust the process, and most importantly, trust yourself.

  9. Passion and work should be combined whenever possible. Folks that tell you otherwise are, quite frankly, crazy. Either find a way to make your hobby your job, turn your job into a hobby, or find a new job. I call this Work-Life Integration.

  10. You’ll never regret a swim. Ever.