10 Life Lessons from an Atypical Transient



“Progress is impossible without change and those who cannot change their minds cannot change anything.”  -George Bernard Shaw

Change is THE fundamental driver of progress. A truly balanced, fulfilled existence involves consistent, healthy change. But we’re really convincing with our excuses. They usually start with, “I can’t because [fill in the blank].” No. You can. You just won’t. We also like to benchmark ourselves according to the masses. What a ridiculous phenomenon. Why would you want to be just above average?

With change comes the imminent unknown. Fear of the unknown is exciting and inspiring for some, but for many, it’s enough to live a life of mediocrity at best, unhappiness at worst.

In the summer of 2013, I was putting my college degree to good use. Scaling the corporate skyscraperMaking enough money to live post-college life near the beach in San Diego. By ‘normal’ standards, I was doing just fine. 

Fine is whack.

The implications of fine are nothing short of frightening in my humble opinion. Fine is synonymous with adequate…sufficient…tolerable…basically everything I want no part of. Fine is living “nine to five”. Nine to five is how you survive. I’m not trying to survive. I’m trying to live it to the limit and love it a lot.

So I sold anything that didn’t fit in my car, and hit the road in pursuit of my Personal Legend.

What’s your ‘Personal Legend’, you ask? From the ultimate fiction pump up book, “The Alchemist”, comes this wonderfully abstract phrase. Pursuing your Personal Legend represents a process. All the passion, perseverance, successes, failures and everything in-between that comes with courageously going after your dreams. If you’re looking for an awesome and easy weekend read, “The Alchemist” is gold (pun intended).

In the first year of pursuing my Personal Legend (ten months of which was spent living out of my car) the universe revealed a few things that I am delighted to share. Ten to be exact…

1.  Challenge your beliefs.

Desired change (as opposed to forced change) is rapidly realized when you regularly scrutinize your beliefs. It can be something as small as recognizing a deeply ingrained habit, and asking yourself, “Why am I doing this? Does it serve me?” Or it can be as big as, “Does my partner make me better, or am I just comfortable and/or afraid of being alone?”

This is number one for a reason. In the words of the late great Biggie Smalls (the rapper, not my pup), “ We can’t change the world unless we change ourselves.” 

2.  Where there’s a will, there’s a way.

If you really want to do something, THEN FUCKING DO IT! The timing is never going to be perfect, ideal, or even ‘right’ for that matter. All you have to do is make a decision. Once you’ve done that, things start to fall into place. Deciding to quit my job was all but convenient, but I knew it had to be done. So I used the tactics Tim Ferriss recommends in the The 4-Hour Workweek to negotiate a temporary remote employee position. This was immediately following the company’s new policy forbidding remote employees. And wouldn’t you know it, just a couple months later I got hired for a remote position at a badass company. Check out the video that landed me the job.

Another seemingly big obstacle was my son, Biggie James Smalls. ‘You can’t live out of your car, gallivanting across the US with a 70lb pitbull,’ they said. Ha, watch me.

Don’t be a fool, doing what you want is cool.

3.  Let the little things go (and the big things). It’s never as bad as you think. 

Got laid off? Awesome, you’re free from the confines of your cubicle. Now you can do something you actually enjoy. Partner ditched you? Great, no more wasted time with the wrong person. I heard someone say that no one can have the one you’re meant to be with. Let that make you feel warm and fuzzy, then hop on Tinder and find your Tinderella (she’s waiting…).

So, it’s broken. What do you do? Fix it, start over, or try something different. The point is – MOVE ON. Take a few minutes to feel the pain, then let it go. Resilience is a practiced virtue, and it’s a direct function of risk. The more risks you take, the more resilient you will become.

You can’t always control what happens to you, but you can control how you react. An optimistic perspective can get you through anything. The less time you spend dwelling on something negative, the more time you have to move toward something positive. 

Sometimes, shit just happens…

Every situation (good or bad) presents an opportunity. If you can view life through this lens, you’ll be better for it.

“Everything will be ok in the end. If it’s not ok, it’s not the end.” - John Lennon

4.  Less is more.

I love this idea. It applies to such a wide spectrum of scenarios. It’s my go-to advice and a philosophy I’ve come to live by, but it was not always so. In fact, I was kind of a closet hoarder. I used to hang on to piles of clothes I hadn’t worn in years (still fighting that one), and I was the guy that held onto concert tickets like it was the only proof of my experience. When preparing for my first venture across the states, I had to fit all my belongings, my brother, a friend, and my pup into my economy size ride. This forced me to subscribe to the principles of minimalism, and I never looked back. Here’s some irony...(I think?)

Toward the end of my wanderings, The Green Machine was violated on the streets of San Fran. As I've mentioned, before I began my journey, I got rid of basically everything I owned, save my clothes and car. The last remaining prize possessions. My lifelines up to this point. Well, the cowardly swine got his hands on both. The intruder shattered a window and made away with my favesies backpack, which had roughly half the attire I own (the 'A' squad apparel I might add), my passport, and a few other items. But, my MacBook was safe with me as well as the cash I had won the night before playing poker ($300), both of which I had just taken out of the backpack that was stolen. As you can see, it could have been much worse. 


While I miss that half of my wardrobe, I've come to realize you can be very happy with very little. Most things are just excess baggage anyway. You can always have a little less stuff to make a little more room to live. And we all need a little more room to live.

5.  Cultivate meaningful relationships.

My high school basketball coach used to say that life is all about relationships. He was kind of a jackass when it came to most things, but he was spot on about this. In 300 days of vagabonding, I slept in my car twice. TWICE! This is the direct result of an ongoing, sincere effort to maintain the relationships in my life and develop new ones. (Tip: make it a point to become Facebook besties when you establish rapport with someone. If you do it right, they’ll think it’s funny, and you’ll have a communication channel with someone you otherwise would likely never hear from again. You never know where that could lead.)

There’s a fine line though. You don’t want to be overzealous/annoying. Especially when you’re crashing at other people’s pads. I made sure to mind all my manners, not overstay my welcome, and provide value. Besides expressing genuine interest in the well being of my gracious hosts, my tangible contribution was Bulletproof Coffee every morning. At the very least, be known for leaving a home noticeably cleaner than when you came. Leave people feeling stoked after they interact with you.

The main takeaway here is authenticity. People can sense when you’re faking. No one likes a disingenuous mooch. Check out the classic book by Dale Carnegie – “How to Win Friends & Influence People.” 

6.  Fancy a Flaneur?

In French, flaneur refers to the act of ‘strolling’, and anything that may come as a result. A flaneur is essentially someone who’s down for whatever. Rolf Potts, author of Vagabonding, talks about this concept. He mentions it in the context of traveling, when you don’t have an agenda. It’s kind of like ‘people watching’ but more experiential. He talks about how he would literally walk aimlessly until something interesting happened or some kind of opportunity presented itself. I frequently did this during my wanderings, especially when I was traveling through Europe. There’s nothing better than flaneuring in Rome. I was strolling through the city and came upon The Coliseum. I was admiring its magnificence, when a feverish promoter began hassling me to partake in a guided tour. I had the typical mindset that tours are lame, but he was persistent and it was cheap, so I decided to go with the flow. SO glad I did. The guide was a straight encyclopedia, and I developed an even more profound appreciation for The Roman Empire as a result. Fun Fact #1 – The Senate imported polar bears from the Arctic to show the reach of Rome.  Fun Fact #2 – the grand opening of the Coliseum was nearly 600 straight days of city-wide partying. Reminds me of my frat days…

Can you always be a flaneur? Of course not – ain’t nobody got time for that! But it’s a good philosophy to embody when appropriate. This segues nicely…

7.  Be a ‘YES MAN’ but know when (and how) to say ‘NO’.

One of my favorite movies of all time. Not only is Jim Carrey hilarious as usual, but the theme of the movie is spot on. Going outside of your comfort zone is...well...uncomfortable. But when you do, more often than not, good things happen. 

Make a conscious effort to put yourself out there. Be unapologetically bold. It only takes a few seconds of amazing courage to change your life. Strike up a conversation with the babe at the bar. What if that’s your soul mate?! Even if you get shut down, at least you made an attempt. You’ll never see her again anyways (bitch).

That being said, as the conclusion of the movie implies, set boundaries. Sure, they’ll get broken, but you’ll be spared of at least some unnecessary mischief. Don’t make bullshit excuses or tell ‘white lies”. Just be honest. People dig honesty.

Remember friends, you’ll ALWAYS regret what you didn’t do.

8.  Make a decision. Live with the outcome.

You can’t have it all, but damned if you won’t try. My advice? Give it up. Everything is an opportunity cost. Make a decision and deal with the outcome. Decision fatigue kills productivity. A New York Times article describes this concept as “the deteriorating quality of decisions made by an individual, after a long session of decision making”. To minimize this, it’s crucial to have a daily routine that requires virtually no contemplation. As a nomad waking up each morning not knowing where I might end up that afternoon, a routine was laughable, but there was one thing I was – and still am – always certain of…

Bulletproof Coffee, the breakfast of champions. This magical elixir is THE foundational component to my daily routine, serving as breakfast (and often lunch). It keeps me snappin’ necks and cashin’ checks for a solid 4-6 hours before I even think about food. No decision-making involved.

Someone once told me “if you don’t know what to do, don’t do anything”. I loved this. I thought it was great advice, so I tried it. It worked until it didn’t. Worst piece of advice I ever got. This approach cost me the love of my life – heavy but true.

If you choose not to decide, you still have made a choice (yes, that’s a line from Rush, one of the greatest bands of all time).

9.  Hack your environment. 

The world really is your oyster nowadays. I would venture to bet you have a laptop, headphones, and a buck for some coffee or tea? Then it’s pretty much your bitch. Some form of transportation helps, but it’s not necessary, and public transit is a great option when you’re in a city. I relied on my trusty old Acura (240K miles), which I affectionately refer to as The Green Machine, my beloved skateboard, and the two legs the good Lord blessed me with.

While I am fortunate to have awesome friends and family who were more than happy to host during my homeless ventures, inevitably I felt like a burden at times, so Whole Foods and the gym were my sanctuaries. Between these two places, you have healthy food, shelter, basketball, weights, wifi, coffee, and a shower and a shitter taboot! 

Instead of complaining about the problem, find a solution. Be resourceful.

10.  Up with the gratitude, down with the attitude.

Just as I end my day with gratitude, so shall I conclude this list. If you’re reading this, at the very least you have a computer and wifi to be grateful for. Take time every day to recognize how blessed you are. Literally, build it into your routine. My brother and I have a huge whiteboard on the wall in our living room, and every night we write down three things we are grateful for in the present and three things in the future. There is no better way to end your day, than with gratitude. This is a common practice among highly successful individuals.

What Now?

I was going to include this in the list, but I felt like it required special attention in the conclusion.

Wanna spark a revolution in your life? Consume edifying, uplifting content.

Start with podcasts. Pop in your headphones first thing when you wake up and listen while dropping your morning deuce, as you brush your teeth, prepare your BP Coffee, drive to work. Boom, there's a 45-minute podcast down.

Reading is ideal, but if you’re like I was before embarking on my quest, you might not have read a book for leisure in years, if ever at all. Ease into it with podcasts and audiobooks. Regularly expose yourself to alternative perspectives that challenge longstanding (and often unrealized or underestimated) beliefs. Creativity, inspiration, motivation – all these things will come as a result. 

“Heroes get remembered, but legends never die. Follow your heart, kid.” If you’re not pursuing your Personal Legend, you’re wasting precious time, and you never get that back. To neglect this journey is selfish. Irresponsible. It’s a damn shame at best, cosmically catastrophic at worst.

Feel the fear of change. Grab it by the balls. Embrace those testicles as if they were your own (ladies, use your imagination). Start living the life you were meant to.