I Quit My Job to Travel the World.
Multiple Times.

1. 1983. It was not my first trip abroad, I’d been an exchange student and then, after I graduated high school, a kibbutz volunteer. While in Israel, I met a boy and we traveled some. When I ran out of money, I went back to the US. I worked as a stocking clerk at a cheap fashion shop for 20 somethings. I quit after three months to go to England, meet up with the boy, and then to travel some more. I was still living with my parents, I was probably earning just over minimum wage.
2. 1986. I was working in the box office of the local symphony orchestra. I liked my job a lot, my boss was wonderful, the people were fun to be around, and of course, there were amazing perks. I quit my job to travel from Berlin to Moscow, Leningrad, and then through Scandinavia on a camping road trip. I was sharing a cheap apartment, I think I just left my room empty. I don’t remember what I was earning; it would have been over minimum wage, but not exactly lush pay.
3. 1991. I was working as a file clerk at a collections agency. It was a part time job, they wanted me to work full time and do collections instead of filing. I just wanted to refill my bank account so I could travel again. I quit to travel in Europe after I graduated from college. I was living with my ex, he had a full time job, so I wasn’t worried about money, but the pay for this gig wasn’t great. Minimum wage plus. We got divorced not long after I came back from Europe.
4. 1994. I was running the special order desk at an art supply store. I was working 40 hours a week and I was a working artist at the time — I had a painting studio halfway between my apartment and the store. I quit to drive from Seattle to Alaska with a friend from Boston. I quit that job to go traveling twice. The first time, they said they wanted me back, the second time they said they wouldn’t hold my job for me, but by then, I didn’t want to work there anymore. A friend sublet my room in my shared apartment. I think I was making 10 dollars an hour?
5. 1996. I was a natural language indexer at Microsoft. I was good at it and I’d acquired something of an obscure skill for the time, SEO was still very nascent. I was making more money than I’d ever earned at anything, I started at a whopping 28 dollars and hour and was raised to 35 over the course my two year employment. I quit with a very good job offer in hand from the Microsoft Office team because I was going to travel Australia for three months. I worked on contract projects for Microsoft for about 6 years, always traveling somewhere when my contract was over. I’d saved enough to buy a place, and I sublet it on Craig’s List every time I traveled.
6. 2001. I was a documentation manager at a technology start-up. The pay was good — 72k annually — the benefits the best I’d ever had, and I had an excellent team. But after a few months, two things were very clear to me. One, this company was not going to be the big win I had hoped for financially. Two, I was constitutionally unsuited for a 40 plus hour a week office job. I quit my job for the last time because I realized that if I didn’t find another way to work, I was always going to be quitting my job to travel the world. I have a mortgage, sometimes when I travel, I just let friends stay because I know what it’s like to travel and need to sit still for a while.

How I Stopped Quitting My Job

I went back to contracting and freelance work and have not had a staff job since. I’ve been recruited a few times for some great jobs, but every time it gets serious, negotiations fall apart over vacation time — it’s never enough. “Let’s keep this contract,” I say, “because that way, I won’t have to quit to go traveling.”

My health care plan isn’t great (better since Obamacare became law) and my retirement planning is terrible. The pay varies wildly, I’ve earned as much as 80k and as low as 32k in a year, and the last two years have been especially difficult financially. But when I think about full time work, I remember how frustrated and depressed I get with a full time office job. I look instead for ways to cut my expenses and try to find new clients.  My last great client, we worked together on off for for seven years; my work went away when they were acquired by a multinational company.

If you’re under 30, hell, by all means, quit your job and go traveling — why wouldn’t you? But if you’re over 30 and don’t come from a state with a social safety net, it’s more complicated. It’s not that hard to quit your job and go traveling, it’s just not, especially if you’re well paid, have great job skills, and significant savings.  It’s a lot harder to figure out how to build a life that accommodates more than a standard vacation package.

I’m not a quitter — I’d actually love a stable income and good benefits. But I need more than that to be happy.

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