I Travelled The World & My Career Didn't Suffer

When I was 20 years old, I dropped out of college to help build a tech startup from the ground up. I had been working on the company for over a year, and to put it simply, college felt like an impediment — rather than a stepping stool — toward success. So I dropped out. Building my business was the least expensive MBA I could have ever received, considering I was paid by investors to do what I thought I loved at the time. When we were acquired a couple of years later, the deal came with a job. So by 22, I had become one of those semi-mythological kids who’d dropped out of college to launch a startup, and I was working a cushy job in a fancy office with a full-time barista who drew cats in the foam of my morning hot chocolates. I didn’t have a college degree, but I did have what most people would call a career.

This career earned me $70K a year and a company-paid loft in New York City that rang up to $10K a month. My manager was attentive, the C-suites all knew me by name, and I was able to put a huge portion of my paycheck into savings. At the time, it was pretty easy to imagine a slow but steady climb up the corporate ladder. I should have been thankful, but I was feeling unmotivated and uninspired. When I had left college to start my own company, everything was unexpected and exciting. I travelled constantly and could work from almost anywhere (something I valued greatly). But at this point, the security that I was so lucky to have felt more like heavy chains. I am well-versed in the stereotype that millennials can’t hold a job, but I couldn’t help but wonder whether it was that I couldn’t hold a job or that this job couldn’t hold me. I needed more freedom in my career, and most importantly, I wanted to travel more. What I wanted wasn't just a few weeks of vacation carved out of ‘real life’ but rather a life of travel in its entirety.

So I came up with a game plan. First, I left my high-paying job and went back to being a student. I wanted to be viewed as a professional — and, thanks to societal standards, knew that I needed a college degree to be seen as one. So I used the almost $20,000 that I’d been able to save to float me while I focused on getting to graduation. I promised myself that after I walked across the Columbia University stage and received my degree in creative writing, I’d build a career on my own terms.

A career is a strange concept. There is no concrete definition; yet, somehow, it seems to mean the same thing for most people. I grew up with the idea that a career is something built through measurable and externally validated achievements: pay raises, promotions, and employee-of-the-month-style recognitions. If I continued to try to measure myself by those metrics, I could never succeed. I was determined to start measuring my career by adventures — not promotions. A 56-day road trip around the United States following graduation would, I decided, be the first of many.

The idea for a road trip was part childhood fantasy and part practicality. The idea of living out of a van sounded romantic, and, by 23, I’d already been to Europe, South and Central America, the Caribbean, Africa, and the Middle East but hadn't seen most of my own country. Living out of a van would be inexpensive, and I’d also be able to work on the road — both on my freelance writing and on an unexpected side-hustle that I’d built over the last few years: public speaking.

While I had been out of school and working on the startup, I became obsessed with volunteer travel, or voluntourism. I wrote a few essays critiquing voluntourism, and they attracted enough attention that I gained recognition as an expert in the field. I started receiving invites to give talks about giving back at places like UNC Chapel Hill, the University of Guelph in Canada, and the 2014 International Volunteering Conference outside of London.

I kept it up after graduation and booked speaking engagements across the U.S. My speaking fees covered nearly all of my (very low) expenses for 56 days on the road, a winding route from New York to Nevada, Nevada to Washington, and back to New York. Like freelance writing, though, public speaking isn’t super reliable, so I've also built a business of designing websites for writers and creatives, providing guidance to new business owners, and doing brand consulting for bloggers. Rather than doing one thing at a desk all day and being a singular cog in a corporate machine, I have the challenge of doing a hundred things. I am now every piece of the machine. I'd be lying if I said freelancing was easy. Some months I make way more than I need and am able to set some money aside for retirement, while other months I'm barely able to pay off my expenses. It’s a little overwhelming, but it’s certainly never boring.

This summer, I’ll be doing research in New York City, climbing in New England, and taking a float plane to a secluded lake in Northern Ontario for a couple of weeks off the grid. I’m building a career on my own terms where no two days look the same, and it’s not just because the scenery outside has a habit of changing.

Sometimes people don’t understand what I’m doing or why I couldn’t just stay at that desk and play the corporate game. My answer is almost always the same: Why be one thing when you can be a hundred things? Why stay in one place when you can go almost anywhere?

Women take risks and follow their wildest dreams every day. Wake up, set goals, and make it happen.