MY STORY, IN BRIEF: I left a job in management consulting in New York two-and-a-half years ago. Then I worked in a brutally demanding — and absolutely exhilarating — business development role for another two years, where I traveled to a new country to live and work every few months across Africa, Asia, Latin America, and the Middle East. It was the polar opposite of a corporate 9 to 5: results-oriented, self-motivated, and entrepreneurial.

On nights and weekends, I hustled on my writing, personal consulting, and travel business and now have enough ongoing clients to make ends meet, which is the coolest and most satisfying experience of all time.

Recently I decided to leave my full-time position to be self-employed for awhile and see how it goes. I’m home for a couple weeks and then I’ll be heading to Southeast Asia, Nepal, and India for a year to travel, write, and flesh out my vision for a few new business ideas. I clearly love doing things unconventionally, but now that I’m actually becoming a real digital nomad, is it as great as I thought it would be?

Let’s take today for instance. I woke up at 11am (hate mornings) and migrated to the couch with a green tea and muesli, hammered out a deliverable for a client who I’m helping apply to graduate school, fixed lunch, wrote an article for one of the organizations who pays me to produce articles for their brand, showered, finished the honeymoon itinerary for a couple traveling to Italy in two weeks, met friends for dinner, and came back to my apartment to write this and do research for a pitch deck for a business I may want to start.

On one side of the coin, I love it. I’m utilizing so many of my talents, I believe I’m genuinely helping people, and I have ultimate control over my days and nights, weeks and wages. On the other hand, I have moments like these: Today I also walked into my best friend’s apartment in Williamsburg and saw (and felt) the physical result of a life she has successfully built for herself. Because I’m location independent, I don’t have a real “home”; I live out of my suitcases. She speaks fondly about her co-workers at the new start-up she’s working in — new friends that slid into the empty spaces I left. I strolled through Midtown East to pick up my visa to India and saw well-dressed corporates running to get coffee together, chattering a mile a minute, their camaraderie a visible aura. I felt a pang that could be classified as a rare breed of, well, cubicle envy.

Yesterday I went for lunch at Palantir in the West Village and saw 1,500 young, inspired, and mission-oriented people who work together, every day. See each other, every day. Who feel part of something, and serve as creative muses for one another, every day.

And I went back to my empty apartment, which is not even mine, and worked on my own ideas. And my own articles. And my own clients. The contrast was palpable. It was through these ordinary experiences, the result of living closely alongside an alternate reality that most people are a part of, that I finally realized the true trade-offs that come with being different. It’s like there are two very distinct parts of me: the self that loves being unconventional and living an entirely self-directed life, and a self who craves normalcy, community, tradition, and permanence.

The latter self realizes that there is a very raw and magnetic part of human nature that keeps us all more or less working together with a common, herd mentality. It’s the self that understands that people innately want to do what everyone else is doing. We want to be able to easily relate. We want to belong. And when we find ourselves on the outside, living life in a fashion that essentially separates us from the majority, we struggle. Or at least I do.

I have no firm conclusion to offer, only to relay my experiences and convey to all wanna-be escapees that a.) the grass is always greener and b.) you should appreciate all the wonderful things you enjoy by belonging to something pretty normal: close and consistent relationships, love that is physically present, community, your clothes on hangers, probably a steady income, familiar places, easy conversations, family in a nearby time zone, and a routine that still puts you in the top percentile of richest people on the planet.

I’d also like to convey that there can be some exciting middle ground here: everyone can — and should — make space to be more unconventional: to pursue a passion on the weekends, to negotiate a 4-day work week or additional vacation time, to travel somewhere unusual, to experiment with a new idea, to greet a stranger, to bring up a different topic of conversation, to approach a less familiar colleague, to ask for a big ask.

For the 9-to-5 escapees, we can — and should — realize that perhaps this lifestyle is good for a period of time but not as a permanent choice. It’s okay if we realize it wasn’t what we thought it was going to be, or it’s okay if we realize it’s even so much better than we expected. We can openly acknowledge our struggle with being different and maybe feeling lonely or isolated in our experiences, in addition to being proud of our courage and boot-strapping. We can embrace the satisfaction of working for ourselves or being part of a company with a unique workplace model. We can find creative co-working spaces and proactively seek out help or companionship with others experimenting with a similar way of life. We can try to help others passionately seeking a transition of their own. We can be as vocal about the challenges as well as the “sexy” veneer that sells books and makes our blogs go viral.

Life is imperfect yet we all spend a lot of energy trying to come up with an ideal solution. The point is, there is no ideal; there is only the ability to consistently self-reflect and keep our gratitude in check for wherever we are in life. No radical career change, no “leaving my job to travel the world” plan, no moving across the country, no “escape” or no “return to normalcy” will guarantee a happier us. The happiest outcome of all comes from nurturing a deep sense of thanksgiving for the miracle of being alive, for having more freedom than we even realize, and for possessing an innate ability to envision and execute change in our own lives and the world beyond.

That ability is a blessing and a curse, so we must employ it wisely.

This post originally appeared in a slightly different form at Life Before 30.

Like this Article

Like Matador