INTERVIEW: Career break pro Sherry Ott

Sherry Ott is a refugee from corporate IT. She's now a long-term traveler, blogger, and photographer. She's a co-founder of Briefcase to Backpack, a website offering career break travel inspiration and advice. She also runs a global travel blog writing about her travel and expat experiences at Ottsworld. She is one of the driving forces behind Meet, Plan, Go! Events across the country to inspire more people to get out and travel. Sherry talks about her own career break experience, and offers advice to those considering taking the plunge.


Is it safe to say that your current career is helping others take career breaks?

Yes, that’s certainly part of my current career. I actually have many jobs that all form a career! My main focus is to inspire and help others take career breaks and travel – via BriefcasetoBackpack.com, Meet Plan Go! events, and our upcoming Career Break Boot Camp. Quite frankly, it also can expand beyond that niche of career break travel. I really want to help people understand and see the world through travel. That ties in my personal website – Ottsworld. Finally, I also do IT freelance work managing a retail website for a small company, photography, and occasionally I teach ESL.

Career breaks are getting more and more attention in the States. Why do you think that is?

I think there are numerous factors at play.

1. The Boomers and Gen Xers are realizing that our traditional definition of retirement is not necessarily going to happen for us. The world of work and retirement are changing. Whereas my father worked for the same company his whole life and is supported by a pension, that’s no longer the case. With the disappearance of pension programs – the idea of ‘we have to take care of ourselves’ has evolved. Each generation has moved around more from company to company trying to further their career. People don’t expect their employers to take care of them any longer…especially Gen Y. This movement in careers allows more people to take a break in between them or even negotiate them as they change jobs.

2. The workplace is demanding that we become more global. We travel more for work, we work with people from around the world. I think that naturally starts to grow curiosity and desire for more global travel. There’s no better international education than to travel to different cultures.

3. The explosion of the internet over the last few years has now allowed us all to be voyeurs in people’s lives. I think there were always people out there doing extended travel and taking career breaks – but there was no way to really hear of them unless you were their personal friend. Now we find many people are doing extended travel and career breaks thanks to our tendency to want to tell the world about it! Reading about other’s doing it plants seeds. When you ‘know’ someone (even virtually) who has taken a career break and traveled – all of a sudden it becomes a little more mainstream and accessible to you personally.

4. I’d love to believe that the work we are doing at Briefcase to Backpack and Meet Plan Go are also contributing to it a little!

What advice do you have for someone concerned about explaining their sabbatical to prospective employers?

The first thing to keep in mind is if a prospective employer feels taking a break and traveling to increase your international experience and maintain your balance and well being is negative – then you need to consider whether you want to work for a company that isn’t in alignment with your values.

We recommend to people not to shy away from talking about your career break to prospective employers. However, prepare yourself for that conversation. You need to take the time to go inward and really think about what you gained and learned from your break and how it benefits the company. Does it make you a better manager and employee – most likely. People who do extended travel AND try to incorporate some knowledge building and volunteering into that travel come back with better soft skills such as: Risk taker, negotiation skills, flexibility, patience, adapt quickly to changing environments, and enhanced decisions making. In my opinion, much of these skills fall into one important area in business – leadership.

One of the most important things to possess as you are working your way back into the workforce again is to have confidence in your ability to do so. If you don’t believe that your career break was beneficial and you are simply trying to create a sales pitch, then it won’t be as successful. As you converse with future employers and network with colleagues, you must ooze confidence about your career break. No regrets!


What parts of the world do you find most open to the idea of career breaks?

The idea of career breaks is very accepted in the UK, Australia, and New Zealand. In addition, I would probably lump most of Europe in there, too.


How have your breaks helped your career?

My career break actually helped me change my career! I worked in corporate IT for 14 years. I was good at it, I moved up the ladder, but I didn’t really like what I did. Finally, I knew I had to make a change and I took a break when I was 36 years old. Once I got away from my cube – it provided me the time to really explore what I wanted to do; what I was passionate about. I’ve made the choice to be entrepreneurial and give the travel industry a shot; I love writing, speaking about and photographing travel and the cultures of the world. However, I know that if one day I want to go back to corporate, I could do it. I now have so many more skills that I’ve developed from a leadership standpoint and I’ve developed my knowledge and expertise in new areas such as social marketing. However – I’m not ready to go back to a cube anytime soon!

Meet, Plan, Go was quite a success. Did you find most attendees were already unemployed and were tired of job hunting? Or were they burned out and were ready for a break?

Most people still had jobs and were trying to figure out a way to take a break for a bit. Or they were planning on leaving their jobs and knew they wanted to travel before they started a new job or started a new chapter in their life such as marriage of parenthood. Surprisingly, we learned that many people not only wanted to travel, but they wanted to do some sort of work on the road and explore areas further. People were eager to really experience a country or place.


When is your next trip? Where are you headed?

I’m constantly on the road now. I’ve given up my ‘home’ and now don’t have any home base. So in some ways – I’m always traveling! However, this December I will be in Chicago and New York City before leaving for Italy for a week and then to the Middle East; Amman Jordan and Beirut Lebanon. I will be doing volunteer work for GeoVisions in the Middle East this winter and will be writing all about the realities of international volunteering. Then I’m back in America for the spring, and then this summer I take off on an adventure of epic proportions – the Mongol Rally. It’s a charity rally where me and three other bloggers are driving a car from London to Ulanbataar Mongolia. A journey of 9,000 miles where we’ll be raising money for charity. Our team website and information on the rally can be found here - http://thesocialmediasyndicate.com/