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

Get-out-of-jail-free

  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.

Related: Unpopular Headlines for Stories About Traveler Culture

8 thoughts on “I Quit My Job to Travel the World. <br>Multiple Times.”

  1. Once again, nailed it. Few travel blogs can touch yours insofar as honesty. I liked this post, because I am quitting my job to travel..but I’m not messing around, I’m going straight from working in a typical sort of job to working just as many hours in a different way. It’s still working..and it is actually going to be harder. But I might end up nannying in Dubai, for all I know.
    I like that you are flexible in your approach and that you are honest about the challenges. Perfect timing for me.
    Thanks, Pam.

    Reply
  2. Wow I’m like that as well. Every job that I got sooner or later got just so boring. Day trading forex saved my life. I honestly had no choice as well, freedom is precious!

    Reply
  3. yeah, nailed it. The hubris and aplomb of QUIT YOUR JOB and travel is often buffered by a cushy bank account, something to fall back into or onto, or the twentysomethingness to know you have a world of time to worry about retirement, etc. later. I’m also, in the end, a homebody, but to each her own. And hi from lunch in the Azores, so your mileage on homebodiness may vary.

    Reply
  4. I think everyone should be aimless and travel for a while and everyone should be also anchored to a staff job for a while so that they know both sides. There are ups and downs to both lifestyles.

    Reply
  5. I quit every job I ever had to travel and spent many hours whilst on the job counting how many more hours I needed to do before I had enough saved up to head off. My whole 20s were consumed with travel or the thought of travel. So glad I did that, even though it meant I was pretty skint at 30 and trying to work out how to get a ‘proper job’. I was lucky it all worked out and now I have my own travel-related (QuirkyAccom) website so I can incorporate travel into our family life and keep the dream alive.

    Reply
  6. Having held multiple jobs (art/swim/preschool/highschool/college teacher, customer service, art director, graphic artist, social media manager) over the years, I understood how time is valuable, and the fear and courage that comes with not settling. I never quit a job to travel, but I always understood the freedom that working freelance, for oneself–and as a result, having your own time–is more valuable than any paycheck. Now that I’m traveling more than I ever have before, the challenge is to keep doing art-related work in order to sustain myself and at the same time, as you said, to try to secure a future, as paradoxical as that may sound.

    Reply
  7. I’ll never forgot how our friend K found out that G and I knew you IRL through the `ukulele community. First question out of K’s mouth: “How does she get to travel so much?” The merits of being able to travel are obvious; the demerits not so much. Thanks for providing the full picture.

    Reply

Leave a Comment

This site uses Akismet to reduce spam. Learn how your comment data is processed.