From Full-Time Travelers to Job Seekers: The Challenges of Reentering the Workforce


When one of my favorite graduate school professors died just weeks into her retirement, it hit me: I didn’t want to spend my life working toward a future I might never get to experience.

I started my career in education as a high school counselor. My husband, Sam, was a self-published author who could work from anywhere, so we took full advantage of my school holidays and long summer breaks, jetting off to new places whenever we could. We created a travel blog, ForgetSomeday, to share our stories.

But the trips we took during school breaks left me yearning for more, and I approached my husband about taking a year off from our careers to travel full-time.

It didn’t take much convincing. We didn’t own a home and hadn’t yet started a family, so the timing seemed right.

I submitted a request for a year of leave, but it was denied due to pending budget cuts. We decided to move forward with our plan anyway, not wanting to wait until retirement to make this dream a reality.


Man in a campervan in Scotland.

The couple’s adventures included a road trip through Scotland.

Provided by Toccara Best



Time for an adventure

Over the next year, we slashed our spending and saved more than $30,000 by cutting out anything nonessential.

We sold our car for $5,000 and brought in a bit more by selling smaller items, storing the rest in a 10×10 unit because we thought we’d be gone for just a year.

By June 2015, we had about $40,000 in the bank, walked away from our lease, and flew to Prague on one-way tickets.

We ate our way through Central and Eastern Europe and Southeast Asia, partaking in bucket-list festivities like Oktoberfest in Munich and St. Patrick’s Day in Dublin along the way.


Two women doing crafts in Mai Chau Village, Vietnam.

Best visited more than a dozen countries, including Vietnam (pictured).

Provided by Toccara Best



We visited more than a dozen countries — island-hopping in Croatia, Thailand, and Portugal; exploring Cambodia’s temples; soaking in Hungary’s thermal baths; and driving 500 miles through Scotland in a campervan.

From hiking in Austria and Slovakia to swimming with seals in Sweden, the year became a crash course in adventure travel.

As our official gap year came to an end, our bank account was still surprisingly healthy, thanks to housesitting opportunities and blog partnerships that helped stretch our budget. And because I didn’t have a job to go back to, we decided to keep traveling.

Little did we know, our biggest adventure was right around the corner: 6 months later, we found out we were expecting.


Pregnant woman posing in Iceland with snow in the background.

Iceland was Best’s final stop before returning to the US.

Provided by Toccara Best



And then we were three

We returned to the US to have our son, but just a few months after his birth, we began traveling full-time again, this time exploring America.

By his third birthday, my son had already visited 27 states. Eventually, the pandemic put a halt to our full-time travels, and we took that as a sign to settle down.

We returned to California five years after the adventure started.

When we planned our gap year, it was supposed to be just that, a year. But as time went on, the gap on my résumé grew, and my motivation to return to the career I once loved began to fade. My husband was also trying to figure out what he wanted to pursue next.


Small boy walking down a trail at Quinault Rain Forest, Olympic National Park, Washington.

The couple continued to travel around the US after having their son.

Provided by Toccara Best



Reentering the workforce

We didn’t realize that our global adventure would end with such a hurdle — a career pivot after five years away, right in the middle of a global pandemic.

Maybe it was the break we both needed to reevaluate our next steps, but it has taken us both quite a while to get back in the saddle.

Once our son started preschool, I transitioned back into the workforce as an executive personal assistant for a busy entrepreneur, putting my organizational skills to good use.

When the executive moved out of state just over a year later, I quickly found a new role as operations manager at a nonprofit organization, where I’ve worked part-time for nearly four years. I’ve been searching for meaningful full-time employment for the past year and a half, which has been especially challenging in today’s competitive job market.

Was our gap year impulsive? Not exactly. We spent a year saving and planning. Was it risky? Definitely. More so than we imagined. Would we do it all over again? Absolutely.

That said, if we were to do it again, we’d probably just stick to a year.

Do you have a story about taking a gap year that you want to share? Get in touch with the editor: akarplus@businessinsider.com.





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