What Would You Say to Yourself at 23?

New Zealand hitchhiking

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).

Fro-style

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 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 Headspace 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.

    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, 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.

14 replies
  1. Travis Rojakovick
    Travis Rojakovick says:

    My advice — seriously consider living outside of large and/or coastal cities. They are so crushingly expensive that it hems in your lifestyle. Either you work at a demanding but lucrative job (necessary to pay the bills) and you have no time to enjoy the city or travel much (life revolves around work when you’re working and earning a lot) or you have a cool, funky job that leaves you perpetually broke with no possibility of ever going beyond living paycheck to paycheck. Neither situations are conducive to a cool, fun life.

    And, if you’re going to be living paycheck to paycheck, you might as well be broke living an awesome life: be a lift operator in Breckenridge (for example). You won’t make much, but you’ll have no stress and a lot of fun living in a gorgeous place with awesome activities nearby. Better to do that than earn $40,000 working 2,000 hours a year with a long commute in or around a large city.

    That is an oversimplification of course. But, I lived in Chicago for decades, and people who had plenty of money tended to work like dogs and people who had jobs they enjoyed were perpetually broke. Better to find a third-path I think (i.e. a job in a nice place with a reasonable work/life balance), unless you luck out and find a lucrative job you really love. .

    Reply
    • Dakota
      Dakota says:

      Great advice! It’s amazing what people subject themselves to just to live in a big, famous city. There are lots of great smaller places out there with good quality of life, solid jobs, and excellent access to the outdoors. That last one is even tougher in a big city because too many people in nature just turn it into a theme park.

      Reply
  2. Michael
    Michael says:

    Solid! Such a a great read, Dakota.

    When did you decide to forgo the fro? That image is priceless. 🙂

    “The best adventures will occur at the intersection of scary and exciting.” So true. I wish I would have understood this better in my 20’s. I would have had a lot more fun in life. Instead, I got caught up in corporate jobs, leasing new cars, and living in the burbs. Thankfully those days are long gone and I prefer experiences and adventure to sitting in traffic and living in the shadow of my true self. I would tell my 20-something self to always say yes to adventure and in fact, pursue it. I would also tell my 20-something self to spend time with the friends and people that I love and that support me for who I am.

    Reply
    • Dakota
      Dakota says:

      Excellent feedback! But I know you miss the leased Ferrari… Ha! The friends comment really hits home for me – constantly saying goodbye to awesome people is the hardest part about traveling.

      The fro got axed about 3 minutes after that photo was taken, actually. That photo was taken after a solid 8 months of no haircut from a short cut right at the start of that overseas trip.

      Reply
  3. Jen
    Jen says:

    I wonder if we were in New Zealand at the same time. I was also there when I was 23. Hmmm.

    While I certainly embraced adventure and took on poverty (but always, always ate well) in my 20s, I think the most valuable item on this list is taking the time for mindfulness. I have this problem, I take myself too damn seriously and it stops me in my tracks sometimes. It makes me all fussy over little things and it’s so not worth it. It’s still something I’m working on, and it may always be.

    Reply
    • Dakota
      Dakota says:

      Fall 2005 for NZ! Maybe I saw you out on a run in Wellington?

      Yeah, the other four items seem easy compared to mindfulness. It’s easier to just go go go and let the momentum carry you. I’m still working on this every. single. day.

      Reply
    • Dakota
      Dakota says:

      The fro is on hiatus for awhile! Without living in California wearing flip flops and rolling my long board, it just doesn’t feel right these days. Maybe someday…

      Reply
  4. Cindy
    Cindy says:

    “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.”

    Well said, Dakota! You are an inspiration and this is a quote I’ll carry with me for a while.

    Loved getting lost in your blog and reading about your adventures and passions. We are at the beginning of our sprinter conversion, your stepwise approach and tips & tricks have been invaluable. Can’t wait to build our home and get out on the road of endless adventures! Hope to meet you somewhere in the world!

    Reply
    • Dakota
      Dakota says:

      Glad to hear it, Cindy! Congrats on getting your van and heading out into the fun territory of adventure mobiles. Careful – you might just not go home.

      Looking forward to meeting up with you somewhere in this small world. Cheers!

      Reply
  5. Bridgett
    Bridgett says:

    I just wanted to thank you for your excellent website.

    I am currently 23 (hence, the attraction of this article!) and working as a full-time registered nurse with a 3-hour-a-day commute, the result of a government contract I signed when I was 17. I have never swallowed the 9-5 narrative, but got sucked into it without really knowing what I was getting into. I am feeling a bit desperate to get out, but I’m trying to stay present in the meantime – this article is a reminder to do that! Thankfully, I only have two more years until my contract is complete. Living on the road full-time has been a dream of mine since I was a little kid, and I plan to begin that as soon as my contract ends.

    I am buying a van next spring (perhaps a Sprinter?), and will begin the conversion process at that point. Your mix of inspiration and exceptional practicality is truly wonderful. It is work like yours that helps to keep me focused on my real goals: freedom, conscious adventurousness, and a hands-on, mindful way of living. Thank you, and keep up the great work!

    Reply
    • Dakota
      Dakota says:

      Thanks for stopping by! I’m going to send you a longer email response, but just wanted to say that I think you’re on the right path. You’re already aware of various options and consciously creating the lifestyle that gives you the freedom to choose your how you spend your time, and that’s what will get you there. Keep after it and I’ll see you on the road in a few years!

      Reply
  6. Mike McLeish
    Mike McLeish says:

    I love this advice buddy. I’m currently 25 and have found value in each one of your points. I like 3 and 4 the most. I left my life in England in September last year to pursue a life of remote working. I had no online skills, so I’ve lived on my savings while learning. It was tough, but it’s been well worth it.

    I was never any good at conventional living and until I started reading blogs like this one I had no idea another way of life even existed!

    I hope when I’m older I can look back at my life now and be proud of the person I’ve become.

    I like your writing style as well man.

    Reply
    • Dakota
      Dakota says:

      Props to you, Mike! Way to jump off the ledge and find a net on the way down. No better way to see what’s out there. If you keep building for the next 5 years, I’d wager your 30s are going to be radically different (and more awesome) than if you’d stuck around at a job.

      Glad you find my writing helpful! Drop me a line anytime, man. Cheers to an unconventional life!

      Reply

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