Sunset over the cliffs of Santa Cruz at the end of a mountain bike ride.

I wore sweatpants almost every day until the 9th grade. I considered stopping after Emily, a stylish girl in my speech class with bangle earrings, pointed it out.

It ended when Darren ridiculed me in front of the basketball team on a game day when I wore sweats with a button-up shirt. I still have dreams about running and hiding from that guy and his put-downs, then turning to fight and destroy. (I always win in my dreams, a lovely silver lining.) I’ve forgiven my assailant at this point, along with the other tormentors of my youth, but my subconscious apparently has not!

To fit in, I started wearing name brand clothing. I worked numerous jobs through high school and paid my own way a lot, a great character building experience that taught me the value of hard work and saving. Tommy Hilfiger sweaters and Levis jeans don’t come cheap for a kid – that’s a whole lot of hours stocking shelves at Safeway for $5.15/hr. Yet somehow it seemed worth it. As our roadtrip muse Macklemore raps regarding the power of marketing to manufacture desires: “I wanted to be like Mike [Jordan], I wanted to touch the rim, I wanted to be cool, I wanted to fit in.” We don’t start out seeking material items, but advertising starts early and builds a willing consumer. It sure worked on me. More importantly, over time it can create a reliance on external assets and the validation of others to substantiate one’s existence.

A split in the tracks.

Different Paths

It took me years of living on my own, forging my own way, to realize that always trying to fit in undermines your inner strength and courage to truly earn success and unearth your core powers. You’ll never get what you truly desire, just a cheap replica obscuring your true capabilities. If you’re always doing what someone else thinks you should, how do you turn into a full-fledged, winged avenger of your dreams?

It certainly wasn’t overnight. For me, fitting in initially was primarily tied to things money could buy, and I didn’t have much. For example, when I was in college in California, I was the most broke I’ve ever been. Ever the master budgeter – a professor later wrote a letter of reference extolling my “close-to-the-vest finances” – I survived on $40 per month for food. (This was 2001, not 1965.) If it weren’t for a generous grandma who paid my rent that first year while I scraped by paying out-of-state tuition, I probably wouldn’t have made it to my 2^nd year. Since I was charged per college credit, I even dropped elective classes, taking only required engineering classes.

It was strange living in a well-to-do college town populated by loaded white kids rolling around town in brand new Mustang convertibles they received as a graduation gift. My new friends didn’t give a second thought to expensive dinners out, long road trips on the weekends to snow board, or seeing Incubus in concert. (I recall making up an excuse to my roommates about why I couldn’t join them before listening to the album in my living room in the dark while they went to the show.)

My car, a red 1988 Corolla GTS that I adored during high school, was no longer something I was proud of. It felt more like an anchor lodged in my past, a beacon of my upbringing. I actually considered taking out a $10k student loan to add upgrades to it before (luckily) changing my mind. Good thing – comparing oneself to others is a bottomless pit. Trying to fit in never ceases, the definitions and criteria merely change.

Breaking the mold that a poverty mentality creates isn’t easy. Compared to others, we weren’t even poor, but my frame of reference was fixed relative to those around me. It’s a long climb out, yet I feel craving material goods when I was younger, and having to earn whatever I wanted, taught me more about myself than anything I’ve done with the exception of traveling the world. I worked three jobs through college, including internships every summer, and managed to score more grants and scholarships, plus jumping through hoops to get in-state tuition to cut my costs dramatically.

By the end of my senior year, I was solid financially, and my vest pockets were stuffed even more after a summer working a ton of hours as an intern. All this culminated in a trip overseas for a year of travel, my first time abroad, around the world with no particular motive or itinerary other than to explore. Just me, a backpack, and the open horizon.

Learning to work hard! Digging a foundation under our house growing up. No old photos of me in sweatpants exist…sorry.

I gained something amazing that year: a revamped perspective regarding what makes me happy. Seeing and meeting people happily living in what the western media portrays as a deprived existence tweaked my viewpoint and made me think. We should all be so lucky as to journey the world getting that important education. Want is not need. I recall this hitting home during a bike ride in Laos in the middle of the week when I saw a family – with three generations present – laughing and hanging out in the middle of the day in their tiny little shack. They didn’t have much, just what really matters.

It is simply a fabricated story from advertisers and pressure you put on yourself to own something shiny, to look a certain way, take a glitzier vacation, and fit in, often with the cost of less time with family or pursuing dreams. Shaking off the desire to impress others is a life-long battle, and strong jaws of the consumption bear trap can still grab hold in a fierce way. They don’t call it “trappings of success” for nothing either. 

High above Big Sur hiking Soberanes.

Changing How You Look At Money

There is an amazing book, “Your Money or Your Life,” by Vicki Robin and Joe Dominguez. Buy it. Read it. Then put its contents to work. The basic tenet is this: when you are working for money, you are trading your time and energy, YOUR LIFE, for money. So you better be sure that the results of that energy are directly corresponding to making you happier and more fulfilled. The authors have the reader count up the hours and money spent on work – including commuting, buying clothes and lunches, expensive I-work-hard-and-deserve-this trips – and then calculate the true cost of your efforts. Would you tolerate a condescending boss, or weekend/evening hours, if you were making 1/3 as much in real money?

On our honeymoon, Chelsea and I went through this exercise with her prior career and decided to downsize to just one income and reprioritize our existence around things that make us happy. It’s a fairly short list: time with one another, our friends and family; health via more home-cooked meals; travel and adventure (nice and open-ended for that last one!). It was a big step since she’s always supported herself, but I can hands-down say it’s the best decision we’ve made as a couple.

We make less combined money, yet earn far more than money ever made available via connection with people we love, great food, more travel, and the ability to shake the hand of serendipity and opportunity when it wanders into our path. We’re not perfect by any means, but we consider purchases through a lens of whether it will contribute to our long-term happiness. When you frame money as the result of your life energy, snapping up a new laptop takes on new meaning if your current one is just a little slow. And buying and outfitting a camper van is worth it when it creates possibilities for adventure.

From working in the finance industry, I can tell you this with confidence: those who appear wealthy often live beyond their means. A big house and shiny cars do not equal wealth until you own them, rather than the bank. You aren’t a millionaire just because you own a home worth a million dollars. Cars and homes are the clearest way to say “I’ve made it,” yet 90% of people with cars take out a loan to buy it, and paying off a home mortgage is practically a joke this day and age. It is so inspiring to see amazing friends change their lives to shatter that mold, doing things like killing off all their debt and living in a tiny house, or heading out on a long sailing trip with open horizons.

Looking back with sophomoric wisdom, I’m glad I didn’t fit in. I realize now that it pushed me to be who I am, over and over. In fact, some of the most interesting people in my life are the ones who felt (or feel) like outsiders. The misfits and losers in high school are out changing the world creating art, music, families, businesses, and writing of which to be proud. You can’t truly create change if you’re worried what other people think about you all the time – it’s like running a race with shackles on your ankles.

Evening beach walk in Morro Bay.

The morning I started this essay, I woke up on a beach in Northern California. We went for a walk among frost-tipped dunes and watched a group of seals play in the surf as the sun came up. I had a tremendous feeling of gratitude for my friends, for my life, and for the opportunity to choose my path wherever the journey takes me. I’m feeling it again this morning hanging out in the arid mountains of Santa Monica north of L.A. listening to the hum of commuters heading into the city.

It isn’t about others and their perception of you; it’s whether you are living a life honest to yourself. You can buy and own fancy things, but do it to be happy, not to impress others. Anything else is merely armor to protect ourselves when all we want is acceptance for who we are, stripped bare of expensive bangles. Not the easy path, but the one that feels true.

And all that said, I’m nowhere near where I want to be. I’m still fighting to be who I want to be, one day at a time. The sharp, spiny barbs of trying to fit in stay lodged in the psyche for years. People will forget what you did, but never how you made them feel. Rising above the criticism to be yourself, to create great work when everyone around you is questioning your path, is one of the toughest challenges for all of us. It’s a constant evaluation of who you truly are, and what drives your happiness, not your neighbor’s approval. And remember the two-way nature of it, since those you judge will recall the sinking feeling of criticism decades later. Indeed, while I can’t remember the exact cruel words from my time in high school, to this day I haven’t worn sweatpants.

Here’s to wearing (and doing) whatever makes you happy and comfortable.

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