I often oversimplify my journey to van life and entrepreneurship with a sentence that goes something like this: I quit my NYC non-profit job after becoming disheartened with international development work, backpacked around Asia to do some soul searching, then bought a van, hit the road and started building an online business.

The truth is, the “why” was a lot more complex than that.

I think it can be dangerous to fast-forward through the messy guts of our stories, especially when the unabridged version might offer valuable lessons or insights to others in similar circumstances.

So I want to be transparent about my decision to quit my 9-5 to be a digital nomad. It wasn’t your classic tale of “something was just missing from my life, and I knew there had to be more out there than chasing the American Dream.”

My van life story truly begins from a break-down, and becoming a digital nomad was a subsequent career choice born out of necessity.

I was sitting at my desk in early January of 2017 when an intense pain in my core and sudden bout of nausea caused me to run to the bathroom and throw up. Tests later determined I had stomach ulcers, most likely induced by stress.

A few days later I was on the C train during my morning commute when a wave of dizziness overcame me and swallowed my vision. I woke up on the cement floor, my face hugging a metal pole on a subway platform that was not my usual stop. I had fainted, my stress now loudly manifesting into physical symptoms.

The following day, I showed up to work knowing something needed to change. I left the office for lunch and called my mom. I leaned against the brick wall of a nearby building for support as the words started to flow out of me, filling in all the pieces of the puzzle I had been hiding.

Not only was I overworked and underpaid, like most people in the non-profit sector (which is another story unto itself), but I was also being harassed by my married boss, the CEO and founder of the organization.

It began my third week on the job in Kenya, where I was spending a month to learn about the organization’s projects and meet the local team. My boss had been strangely absent from my onboarding as the Executive Assistant up until this point.

One day he asked to meet for a late-afternoon coffee meeting. As we sipped our drinks, he apologized about being MIA since I had landed in Nairobi. He expressed a desire to develop a strong friendship in order to create an effective working relationship and invited me to dinner. Since I was in a foreign country with no other connections and shared his notion of becoming friends, I agreed.

He bought me a drink that I had turned down and began asking prying questions about my relationship status. I made up a boyfriend out of instinct, pulling details from an ex when he started asking follow-up questions. That interrogation and subsequent comments about how I deserved a certain type of man, was followed by personal confessions about his marriage to the COO and Co-Founder of the organization.

During this meeting, his wife called him twice, and I watched as he ignored her calls. Then my phone rang. When he saw her name flash on my screen, he told me not to pick up. I hesitantly obeyed.

When she called him a third time, we were in the backseat of his car on our way to drop me off at my Airbnb. His driver and bodyguard were in the front seats when he picked up the phone, “I’m with friends and I’ll be home soon,” he lied. I felt a lump travel to my throat when I heard the words.

He quietly whispered in my ear so his driver and bodyguard couldn’t hear his next request. He asked me to carry on the lie if she happened to question me about his whereabouts at work. I sat there with my skin crawling and the hair on the back of my neck raised, analyzing this precarious position he was putting me in.

I felt utterly unprepared to navigate this territory. Each personal and professional hardship I endured to get this job flashed through my mind in a confusing montage. When I didn’t respond, he asked again, “what are you going to say if she asks you if we were together?” I was silent for a few more moments before finally giving in, “I guess I’ll say no, since that’s what you already told her.”

He proceeded to spin a web of words about how the “Assistant-CEO” relationship was tricky when there is a wife involved, and there is no reason to make someone jealous for no reason. I nodded, counting the seconds until I could get out of the car.

As time went on, I started receiving late-night and non-work-related texts “just to chat” that I tried to answer as professionally as possible. Then he started offering me valuable career growth opportunities, unspokenly in exchange for secret vacations with just the two of us, that he kept proposing, and I kept turning down.

For months, I made excuses for my boss, telling myself that he was raised in a very different culture, and his wife, from my own experience, was not the compassionate person she publicly appeared to be. In other words, I was convinced there was no moral need to rock the boat as long as he didn’t physically come onto me or blatantly say something sexual.

During this time, I can only assume his wife suspected something was going on between us, and she began sending me on various non-work-related weekend and late-night errands, treating me as her personal assistant and making any respite I had when my boss was traveling a miserable experience. At one point, she asked me to keep secrets about an organization leader that made me feel increasingly uncomfortable. I also watched as she treated other employees unfairly, and at times, appallingly insensitively during one employee’s family crisis.

Each of these layers, compounded with the fact that my role itself was undeniably unfulfilling, made me feel like I was drowning.

Despite the blatant nonsense, it was difficult for me to see anything clearly in the midst of this chaos. This was after all, my dream job, or rather a strategic stepping stone at my dream organization tackling the issues I was most passionate about. After years of working for non-profits that ended up being disheartening in every other way, I was relieved to finally be working for a genuine grassroots and holistic empowerment organization. I should interject here, that this particular job came after 5 years of enduring and uncovering various other forms of B.S. in the international development and nonprofit sector.

In many of the ways that past organizations I encountered failed, this one thrived. The education, health, and community development initiatives supported some of the most vulnerable and marginalized communities in Africa’s largest slum with a focus on women’s empowerment. The projects were profound and effective, and there was no denying the sustainable positive impact or popularity they had on the communities they served. Plus, I had made some great friends at work, and even found a mentor I truly respected.

For months, I racked my brain trying to find the perfect solution to my secret dilemma. I began sending my resume out into the nonprofit universe, and I was even meeting with a military recruiter about a public affairs-broadcast journalism position in the Army National Guard. I didn’t want to leave any rock unturned.

Meanwhile, I had negotiated a $10K raise, which I had requested based on industry research of salaries for my NYC counterparts with my academic and work experience in similar roles. I genuinely hoped the extra income would make my job more bearable somehow. I also negotiated a 6-month plan with my boss, where I would switch roles under a different supervisor. But when it became clear that my boss was placating me with false promises, I stopped seeing the light at the end of the unhealthy work tunnel.

There was no HR department or professional pathway available at the small NGO to resolve the situation internally, and I hadn’t reported it to anyone externally, because I wasn’t even sure what to say. There were also some big names on the board, and even bigger donors, each member deeply supportive of my boss and his wife, despite being made aware of past wrongdoings. I knew that if I said anything, I would be blacklisted in my field. I had seen it done unfairly to others during my time working there.

Even more frustrating, I feared that creating a scandal around my boss (the founder) and integral part of the organization’s story, and his wife for that matter about the other truths I had uncovered, would not hurt them, but rather the beneficiaries of the projects in East Africa. Non-profits depend entirely on external funding, so any form of bad press or tainted reputation of leaders has the power to destroy a small organization.

So in the span of a week, exacerbated and at the end of my rope, I confessed everything to my mom, my most trusted coworkers, my roommate, one of my best friends, and then a professional stranger at an emergency therapy session in hopes that someone would see a magical escape route I was missing.

In the end, my body demanded my resignation, but the decision was exceptionally terrifying with no job lined up.

On January 15th, I gave my two-weeks notice citing “differences in work styles” as my reason for leaving, and on February 1st, I flew to Japan to begin my two-month backpacking journey around Asia that eventually lead me to van life. This decision was fueled by two things: I desperately needed a vacation far from the world I had been sucked into, and subletting my apartment was the only way I could afford to stay on my lease while I figured out my next move.

Asia, or rather a long vacation in a far-away place, was exactly what I needed. I spent those months healing and dreaming, and by the time I arrived back in New York, I had changed.

I was still in love with the city, but I couldn’t fathom jumping into one more underpaid job role, working for someone I didn’t respect or who used their power to manipulate me or others. My heart also couldn’t bare uncovering one more morally questionable secret about an organization I believed in.

I couldn’t go back and risk falling into an old pattern. So after years of suppressing my dream to be a writer/ documentary filmmaker, I decided to give it a go. There would arguably be no better time to pursue my creative dreams than this one, so I gave myself a year to fail or succeed; not yet understanding those two concepts aren’t linear or opposing.

I came back to Arizona to help my mom sell her home and regroup in a less financially stressful circumstance. Over one of our many heart-to-hearts, my mom proposed van life, and I jumped on the idea. I knew instantly it would be the PERFECT vessel to do the work on myself and my career that I was now determined to pursue.

I will forever be grateful for her support, understanding and her belief in my ability to succeed during that difficult time.

I could have easily crashed and burned in my endeavor to start over new. In fact, by many measures I’ve failed a lot since then, before then, and I’m sure I’ll fail plenty more in my life. But no matter how things turn out, I’ll always be certain I made the right call, and I’ll never ignore my body again.

Even though nothing has been easy about everything that followed my resignation, the ambiguity and hard times have been worth it. I no longer feel trapped by a power dynamic I have no control over, my stomach ulcers have healed, and I haven’t fainted since.

So while I don’t necessarily advocate leaving your traditional job and steady paycheck to pursue your dreams without anything lined up. I do advocate listening to your body, and exiting unhealthy environments, despite whatever fears of failure you might conjure up. As the therapist put it in my emergency session that day over 2 years ago, “If there is no obstacle that you haven’t been able to recover from thus far, why do you believe that you won’t be able to recover from this one?”


  1. Your story is much appreciated and more common that you think. After losing (unfairly) a six-figure dream job I myself spent the best year of my life unemployed, happy and my health is coming back. Thank you for sharing your story and showing me I am not alone.

    1. You are definitley not alone, and I’m so glad to hear that my story resonated with your own experience. I’m also happy to hear that your health is coming back and that you are happier now!

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About Author

Anna is an optimist with pessimistic tendencies who enjoys making a short story long, listening to soundtracks from musicals, and watching anything in the post-apocalyptic sci-fi genre. These days you can catch her learning about off-grid living and gardening the hard way, wandering with her partner and dogs through forest roads in a camper, or hiking to waterfalls or glacial lakes. You can also find her on YouTube at Anna and Ryan.

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