From Corporate Burnout to World-Traveling Nomad: Sherry Ott (Ep. 15)



Sherry volunteering in India as part of her initial career break in 2007.

“Glamorous life on the road,” Sherry captioned this photo. She eventually decided to give up her NYC apartment and most of her possessions to become a nomad — and find a new career that would support her travels.

Sherry working in Colombia, interviewing and writing, in 2015. She now makes her living as a freelance writer and photographer, public speaker and social media marketing consultant.



Sherry Ott planned to take a 12-18 month career break from her corporate IT job in New York City. She was 36 years old and felt like she needed a break.

Then, once on the road, she realized she didn't want to stop traveling. She loved having so many new experiences every day. The next step then was to figure out how to keep traveling and make money. Eventually, she decided to totally let go of her possessions and apartment in NYC to become a full-time travel nomad.

Today, 11 years later, Sherry makes her living as a freelance writer and photographer, public speaker and social media marketing consultant.

In this interview with host Lisa Hoashi, Sherry talks about how the break allowed her to discover what other strengths and skills she had to offer in her work; how her own creative career evolved with the global changes in technology and online businesses; what she enjoyed most about her nomadic lifestyle; and what made her decide to semi-settle down in Denver, Colorado.

She gives candid advice on how to overcome the fears that are involved in taking big life leaps, how to try out a digital nomad career, and how to plan a career break that will only enhance your career prospects on your return.



  • Sherry was 36 years old when she decided in 2006 to take a break from her career in IT project management. By this point she’d spent 14 years in IT.

  • Some of her motivations included: burnout and unhappiness; realizing she didn’t really enjoy “climbing the ladder;” and also the feeling that she hadn’t really chosen her career, it had chosen her.

  • What it was like to undertake a travel sabbatical when she didn’t have much experience with international travel. She didn’t even have a passport until she was 30.

  • What it was like to plan this trip before there were so many resources that we have now.

  • Had many fears about leaving her career.

  • How one of the tactics to overcoming her fears was to tell other people what her plans were, so that she couldn’t back out.

  • Also planned out at least the first three months – and could come back if she needed.

  • Now she’d advise people to also find communities and cheerleaders online.

  • Took about three months to get used to not getting a paycheck.

  • Deciding she wanted to keep traveling and started looking to make money to stay on the road.

  • Blogged and started training for ESL, and started a company too that would help people take a career break, Meet Plan Go.

  • Lived very cheaply and decided to be nomadic.

  • Ended up being nomadic for 11 years.

  • Learned that she didn’t want a predictable routine, wanted something new everyday, ldidn’t want a lot of material stuff, and that she had many more skills to offer beyond IT project management.

  • Learned she loved writing, photography, and marketing.

  • Best parts of digital nomad life: Seeing something new every day,

  • Tips for how to be the perfect guest.

  • What’s hard about the digital nomad life is that people often find they need roots. Feeling unhappy and isolated, and needing a bit more routine in life, and better health care.

  • Took three years to make this decision to get an apartment in Denver, Colorado.

  • Some of the biggest fears around getting off the road: Fearful of being like everyone else (this was part of her identity), fear about not making enough money, fear about becoming weighed down by material things again.

  • Part of difficulty was deciding where to create a home.

  • Chose Denver because lshe oves the mountain and didn’t know much about it, so there would be new things to explore.

  • What supported her in making this big decision was talking with people and letting them know what she was thinking.

  • How health care really is difficult to deal with coming back to the USA from this type of lifestyle.

  • Advice on how people could try out the digital nomad life by taking small steps like trying a co-working space, or a working vacation. This lifestyle requires a lot of self-discipline!

  • Advice for people who want to take a career break from three months to one year and come back and have it favorably reflect on their career.

  • Travel with purpose and think about what you want to learn and what could augment your career.



1. What do you wish you had known before you took your leap?

2. What was the most unexpected thing that came of your leap?

3. For someone who is thinking of doing something similar, what one piece of advice would you offer? 



Gap Years For Grown Ups by Susan Griffith

Career Break Travelers Handbook by Jeff Jeung

Career Break Resources:




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