What Would You Say to Yourself at 23?

New Zealand hitchhiking

Hitch hiking in New Zealand in 2005. Fun fact: I didn’t get picked up on that quiet road and spent the night freezing in a gravel quarry. Ah, memories.


I left the country at 23. It was my first trip outside the U.S., a solo, year-long adventure to explore the world.

That escapade fused new brain connections as I hitchhiked through New Zealand, played chess with my brother on the Trans-Siberian Railroad, and met my future wife in Prague. The result (other than a lingering hatred of night bus travel) was a vision for my desired future life.

Ten years later, I am back in Europe as we pedal about. Nostalgia sometimes seeps through the mountain views or enters my mind during a meal as my thoughts drift back to 2005. The iPhone was still a secret project; MySpace was an unstoppable social network giant. Ancient history, basically.

Not that I frequently think about the past. Indeed, I usually ponder actions my future self would thank me for. I want him to look back on hard-earned skills and say, “that was so worth the effort.” Right now, however, the nostalgia bulb in my head shines the spotlight backward and I can’t stop thinking about the advice I would offer to my bushy-haired self at 23 (other than to cut the fro, bro).


One thing is certain: the words and advice wouldn’t simply be my own. I’d draw from books, blogs, commencement speeches, mentors, and kind-hearted people I’ve spent time with over the last decade.

Will I laugh and shake my head when I look back in 2025 at this list (probably through virtual reality goggles)? Maybe I’m entirely off the mark; it’s impossible to calculate the impact of this advice on my life. I’ll never know.

But if I had a time machine to 2005, I’d sit down across from myself, a cup of green tea in hand, and say:

  1. Embrace adventure. Don’t let the one trip around the world be your last big journey. Keep pushing your limits. “People get old when they stop jumping,” I heard on a recent podcast. Treat that advice literally and as a metaphor, launching fresh challenges, projects and skills that test your boundaries and keep you hopping. The best adventures will occur at the intersection of scary and exciting.

    The coast just south of Rijeka, Croatia.

    The coast just south of Rijeka, Croatia.

  2. Build the courage to live a life true to yourself, not the life others expect of you. Everyone feels fear. I sure do. It may stop you sometimes, but don’t let the opinions or desires of others constantly shape your life. Seek out projects that speak to you and dive in with everything you’ve got, even if others don’t agree. Think deeply about the top five regrets of the dying and use the results of those thoughts to guide your life.

  3. Pursue poverty in your 20s. It’s going to be hard, but turn down the starter engineering job with a salary high enough to allow handcuffing yourself to debt (over-valued condos, for one). Go after that travel video job you wanted. Live below your means, but eat better food (pasta and Mrs. Dash is not a real meal, dude). Build a variety of badass skills and focus on creative competency in many disciplines. Choose yourself and invest in constant learning. The intersection of those skills, your passion, and what the world needs is where the bubbling magic cauldron lies.

  4. Start a mindfulness or relaxation practice. Chill the hell out, man. Enjoy a lemonade on a balcony and be present. I’ve noticed a consistent theme of successful people: space for reflection and mindfulness is a priority in their lives. Start a dedicated meditation practice (the Insight Timer app or guided meditations are great tools). Carving out time to just sit and watch a burbling stream counts too. As Pico Iyer writes, “In an age of speed, nothing could be more invigorating than going slow. In an age of distraction, nothing can feel more luxurious than paying attention. And in an age of constant movement, nothing is more urgent than sitting still.”

    Observation Point in Zion National Park.

    Faking serenity at Observation Point in Zion National Park.

  5. Treat books as valued mentors. Keep reading. It’s free and will open you to new thoughts and let you shadow otherwise inaccessible people. Individual books have recharted the course of my life and served as pivot points. The Four Hour Work Week opened my eyes to a work world beyond the 9-5; Your Money or Your Life and the concept of time as a non-renewable resource sparked an epiphany. Biographies show me people at their best and worst, while fiction shows me the human condition. If I could choose one activity for the next ten years to shape my life in a positive way, continuing to read books on a variety of topics would be it.

That’s enough lecturing from this 30-something. What the heck do I know anyway? Maybe in 10 years I’ll be wise enough to not write posts like this! 

Get out there and live it up, young gun. It’s going to be a great ride.

P.S. Buy Apple stock in January 2009 and (updated May 2021) don’t sell your Bitcoin in 2013! And, most importantly, the way to Chelsea’s heart lies in being nice to her cat, Oliver.

What would you say to your 20-something self?

Loving the views on the north side of the Slovenian Alps.

Loving the views (and dedicated bike path) on the north side of the Slovenian Alps.