The Great American Post-Divorce Solo Road Trip

Lessons I learned alone in a pickup truck

Beautiful Montana, entering Glacier National Park

“if you’re going to try, go all the
otherwise, don’t even start.
if you’re going to try, go all the
this could mean losing girlfriends,
wives, relatives, jobs and
maybe your mind.
go all the way.”
– Charles Bukowski

For 31 days I drove solo around America. It was incredible. You can watch it here. I was inspired by an intense curiosity, a thirst for adventure, the end of my marriage before the age of 30, expectations of who I was supposed to be and do and the personal transformation I knew would take place during this type of experience. Here are 4 things I thought a lot about during those 8,530 miles in my pickup truck.

We live on a rock flying through space around a giant ball of fire. 

Of the 4.54 billion years it’s been doing so, we get a few years here to walk around and create something. Life is the blink of an eye. Make sure you don’t get to your final day with too many unchecked boxes. Get up and at least start walking in the direction towards those things which you feel compelled to do/see/experience. The world will try to dumb down your existence and you will have days where it works. Go create something now.

Make your life a series of experiments. The only failed experiment is the one you never did.

Many people I know are racing towards some sort of finish line. The journey, the pursuit of something meaningful, the active engagement in life today, that is what’s important. Don’t trade in the ride for the final destination.

There is no reason for divorce to be a taboo subject. 

While any breakup hurts badly and I certainly don’t advocate divorce, there is little reason to whisper about it anymore. For me personally, it has served as one of the most important learning lessons of my life. I am so much better because of it. It also doesn’t have to be an unfriendly, nasty parting of ways. There is often so much that each other gains from the relationship that if you choose to be grateful for the experience you can reflect on it as something magical – and perhaps necessary. There is such thing as a successful 1 year marriage and an unsuccessful 50 year marriage.

The ability to laugh at yourself and acknowledge your own miraculous existence are the two most underrated skills of mankind. I am very skeptical of people that have a hard time laughing at themselves. This was especially important for me following the end of my marriage. Sometimes, you have to just laugh at your shortcomings and choose to just be better next time. This is all so comical that we even ended up here as humans during this era.

P.S. – Communicate more with your spouse.

“Each day, it’s up to you to yank your hand back, put it on your heart and say, “No. This is what’s important.” – Iain Thomas

Stop distracting yourself and do the work. 

There is meaningful work inside of you – work that will positively impact other people. Sit down. Stare at the piece of paper or screen for as long as you have to and just start. Pick up the hammer. Put on the scrubs. Whatever. It will feel so rewarding when you finish it. Stop distracting yourself on your phone, cleaning the bathroom again or checking email.


There is an education in travel that is invaluable. Every day of my trip was unplanned which meant I woke up each morning not knowing what state I would be falling asleep in next. It teaches you to figure things out, make decisions, be flexible and adapt.

The other beautiful thing about traveling is that it’s not even the sights you see that you’ll remember most. It truly is the random people you meet along the way that stick with you beyond your travels. Connecting and sharing with people showed me just how much we all have in common.

Do not be scared to travel alone. Or eat at a restaurant alone. Or go to the movies alone. Get comfortable with yourself and relish your own company.

“It is easy in the world to live after the world’s opinion; it is easy in solitude to live after our own; but the great man is he who in the midst of the crowd keeps with perfect sweetness the independence of solitude.” – Ralph Waldo Emerson

Whatever ‘adventure’ means to you – traveling the world, starting a family, losing 40 pounds, starting your dream business, talking to the girl, or setting her free – go get after it. 

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