Coastline Creative



Top 20 things I learned in my 20’s

I turn 30 next week, and over the past few months I’ve become intensely introspective (even more so than usual for those who know me well.) And so without further ado, and in no particular order, here are the top 20 things I’ve learned in my 20’s.

1. Not all time is equal. Show up and be fully present for the big moments in life. Realize when a kairos moment (greek word for qualitative time, or “moments that mater”) is happening, and intentionally create more of them.

2. Practice Perspective. Your current reality is not an indicator of your future reality, unless you make it so. The issues you are stressed about now won’t matter to you in a few weeks or months. In fact, you might even be embarrassed later at how much power you gave them over you. I have made myself anxious in my twenties dwelling on or worrying about the immediate troubles of the day. In almost every case I wasn’t worried about a particular outcome as much I was worried about what that outcome would say about me to someone else.

3. Run towards conflict. Don’t let your feelings fester, and don’t you dare try to solve conflict over text or email. It has had a very poor track record for me.

4. Challenge yourself in your free time. In my twenties I’ve learned to surf, climb, sing, start a business, ride a motorcycle, become a videographer, and become a graphic designer. All of those were hard, but they all trained my mind to reimagine its limits. The challenges I have overcome recreationally have made me more comfortable taking on challenges professionally and personally.


5. Sleep on it. Don’t act on your impulses. Today we glorify speedy responses and quick fixes. Avoid the temptation. When presented with a challenge of relatively high importance, give it 12-24 hours. You’ll either: 1. Feel reassured of your initial gut feel, or 2. Realize you’ve avoided an unintended consequence you hadn’t previously thought of. In either case, you’ll make smarter decisions by allowing yourself more time to think and process.

6. Humility is a foundational virtue. Start with yourself. Own your sh$#, and don’t concern yourself with anyone else’s. Humility is a virtue, which is in nature a cycle, or a constant journey. It’s not a destination, but a constant way of living that is both attractive to others, and foundational to any other value or virtue you wish to live by.

7. The outdoors is the ultimate playground. There is so much wonder in the outdoors. Mountains, oceans, deserts, forests, valleys, rivers, canyons. We have tools and technology to (for the most part) safely use these things as our playground. Mountain bikes, surf boards, ATV’s, tents, kayaks, climbing gear, ice axes. I can’t spend too much time outside playing in nature.

8. Preparation precedes success. In the film Free Solo, Alex Honnold is asked about how he prepared mentally to scale El Capitan without a rope. At one point he says, “I practiced every square inch over and over until it’s just not that scary anymore.” That has been my experience with anything of note that I have accomplished in my twenties. People don’t rise to the occasion, but fall to their highest level of preparation. Prepare the mess out of anything you set out to accomplish, or else ask yourself if it’s even worth doing in the first place.


9. Negative thoughts about yourself can be debilitating. I’m often not very kind to myself in my personal thoughts. My negative thought energy (wish I knew a more scientific word for it) has often produced negative outcomes and hurt those around me. In other words, if you constantly invite negativity into your thoughts, it eventually takes up residence there. 

10. Purpose isn’t a pre-requisite to perseverance. Work hard. Always. It’s important to have a sense of purpose, but don’t wait until you have it all figured out to give your all to the opportunity that’s right in front of you. Sometimes purpose is revealed after you’ve done the hard work.

11. Try everything; take big risks. I’ve taken a stab at quite a few things in my twenties: corporate America, graphic design, videography, landlord, moved cross country, ice climbed, back packed through Europe, recorded an album, and even appeared on a reality TV show with Nick Lachey (surprisingly nice guy). There’s something to be said for “trying it on.” In many ways, I believe my 20’s were defined by the millions of things I said yes to, but my 30’s will be defined by what I choose to say no to.

12. Wake up early. Most of my 20’s I controlled when I woke up. Now with young kids, not so much, but I still do what I can. So if you don’t have young kids, wake up early before the rest of the world gets up and you will have a distinct advantage.


13. To have lifelong friends, you have to be a lifelong friend. I find it difficult to stay in touch with people. I’ve moved a lot in my twenties and it’s become easy to focus on the people and community right in front of me. In my next 30 years I’d like to develop more lifelong friendships, and that starts with me being the kind of friend someone else wants for a lifetime.

14. Your words will speak someone’s future into existence. One of my first bosses told me very early on in my career: “I see you as a senior leader in our company one day; you have what it takes.” That one line has driven me for years. Months later I was promoted 3 times in the same year, and 2 years later I moved cross country to California - my wife and I leaving most of the friends and family we’d ever known behind. Unknowingly, he spoke into existence, a future which had not previously existed, and it changed the course of my life. Everyone has people in their life that they influence. As a person of influence, realize that your words have the power to change the life of whoever they are aimed at.

15. Peace is at the intersection of People, Place, and Purpose. Not each of those are weighted equally in every season. Sometimes, you’ll find more peace by leaving the comforts of the people you know, in favor of an inspiring place or perhaps a new career. Other times, the people surrounding you will bring you more peace than a job you love or change of scenery.

16. The best outcomes are always focused, but never forced. I have ruined some relationships by being too impatient and not allowing God (and time) to do His best work. I’ve found that blessing and success usually come in “the waiting.” Don’t act on impulses. It’s not easy though, especially in the results driven world we live in. Tom Petty said it best -  “the waai-aii-tin’ is the hardest part.”


17. If you want to change the world… Start with the question - “What is it that makes me righteously angry?” If you ask yourself that enough times, eventually you’ll find yourself contributing to a story larger than yourself.

18.  Let go of your dream for yourself in favor of God’s dream for the world. For a long time, I was sure that I was destined to become a famous musician (I still hadn’t realized #6 yet apparently). If I’m honest, I still feel very guilty some days for not becoming one. However, I recently came to the realization that I was really after the approval of others. My motives were all wrong and the story I was choosing to live was too small. Instead of asking, “What’s my dream for my life?” I decided to instead ask, “What is God’s dream for the world?” In other words, dedicating yourself to a dream that, once accomplished, will benefit other people more than yourself.

19. Not every hill is worth dying on. The old saying “don’t sweat the small stuff” rings true. Know what your “small stuff” is and what your “big stuff” is. Don’t try to start or win arguments just to prove yourself or someone else right.

20. Marry your best friend. The single best decision I ever made was sending a Facebook instant message to Autumn Rose Housefield in the summer of 2011, asking her out to coffee. Over the past 8 years, she’s been my best friend, and reminds me often to stop and smell the roses. Life changes quickly. College. Marriage. Real jobs. Kids. I can’t imagine taking those things on without her by my side. My life is more fun and makes more sense with her in it.