AirTreks Customers That Have Become Entrepreneurs pt. 2 – Sherry Ott

The greater majority of our clients when they return from their AirTrek will pick up the lives pretty much where they left off, albeit with a greater sense of scale and perspective, but for the most part they’ll explore work options back in their chosen field. But every once in a while a client of ours is changed in such a way that they end up dedicating themselves to the pursuit of travel full time, its realization and to help others achieve their own travel dreams.

This series spotlights a few of our customers who have done just that.

In the second edition of AirTreks Customers That Have Become Entrepreneurs I interview Sherry Ott, a perennial traveler and the co-founder of the much lauded Meet Plan Go! series, a yearly national event (with more frequent casual meet-ups) that helps fledgling round-the-world travelers get over their objections and jump out into the world.

AirTreks: What made you decide to take your first big trip?

Sherry Ott: There were 2 factors – I didn’t really like my job or career and I loved traveling.  The combination was what finally pushed me to take a career break.  I had been working for 14 years in a corporate career without ever taking a break between jobs.  Every time I traveled on vacation I met people who were doing extended travel and these people fascinated me; especially since I never wanted to come home after a vacation!  This also combined with the idea that I didn’t want to wait until retirement to travel and do some of the things I dreamed of doing – like climbing Kilimanjaro.  All of these ideas came to a head in 2006 and I decided to take a year off and go on a career break.

How did you come across AirTreks and what made you decide to choose us? How was that experience?

I came across AirTreks via an ad or article I saw.  At that time in early 2006, there weren’t many travel websites and there were only a few independent travel websites.

My experience using AirTreks was great!  I still remember the name of the booking agent I worked with  – Sarah.  I found it really useful to be able to talk on the phone with someone who could help me through the myriad of options I had.  I had decided I didn’t want an around the world ticket as I wanted to allow myself flexibility in my itinerary.  AirTreks helped me put together a multi-stop ticket that worked great for my first 3 months of travel – on airlines I had never even heard of up to that point!

How was your trip? Where did you go?

The first 3 months I flew from NYC to Nairobi Kenya.  Then I went over land to Tanzania to climb Kilimanjaro.  From there I flew to South Africa and then to New Zealand, Australia, Bali and Singapore.  I didn’t know it at that point, but it was the start of a completely different chapter in my life; one which would keep me on the road and never lead me back to the cubicle.

Of those places, which one do you think left the biggest impression on you?

Tanzania was the most daring place I had ever traveled to.  Central Africa is really in a league of it’s own.  My failed attempt to climb Kilimanjaro certainly left an impression on me as I vowed to go back and try again one day!  In addition to 8 days on the mountain I was also able to go to the island of Zanzibar during Ramadan and really experience the Muslim culture for the first time.  It was here where I also started to fall in love with challenging travel off the beaten path.  I found myself gravitating to smelly, fly-ridden markets that challenged the way I thought about food and business.  After Zanzibar, I took a ferry to Dar Salam for a crazy evening of karaoke in a dingy hotel bar.  The memories were from over 5 years ago but I still remember them vividly!

How important was that trip in making travel a part of your life, and what role did it play in formulating the idea for Meet Plan Go?

As I prepared for my career break in the 2006, dug through AirTreks’ website, and hopped on message boards –  it was then that the seed idea of Meet Plan Go was planted.  I struggled in my preparations as not only did I have no-one to talk to and confer with about my plans, and preparation; but I realized that there were no tools out there from an American perspective regarding career breaks.  I bought the book Gap Year for Grownups in the hope that it would lead me through the process; however, I quickly found that it referred to everything in British pounds and they used the term CV instead of resume.  The book was ok, but it didn’t really speak to the issues I was going through in my culture and society (America).  I tucked this fact away, and when I met Michaela a year and a half later we both bonded on the fact that there were no tools out there for Americans planning career breaks.  That’s when we started the career break movement in the US!

What’s on your travel radar at the moment?

After racing through Central Asia this summer on the Mongol Rally, I really would like to go back to those areas and travel slow through them.  Kazakhstan, Uzbekistan, and Kyrgyzstan.  I’m a slow traveler, I want to take my time and dig into a culture.  I also have a strong desire to do the Camino de Santiago Pilgrimage this spring too!

What final piece of advice do you have for people thinking about undertaking a long-term trip like the one you took?

There is never a ‘right’ time to take a leap and make a change in your life.  If you want to do it – then you have to dig deep and realize that all of the hurdles you are putting in front of you (money, family, timing, career sabotage, economy) are just excuses.  One of the ways to begin to get over those hurdles is to surround yourself by people who have a similar travel goals and can support your idea.  You need cheerleaders on your side, not people who allow you to throw excuses at dreams.  Get involved with your local travel community or the local Meet Plan go meetups and start finding out how others achieved their career break dreams.  If you don’t have a local community where you are at or are looking for more hands on help for your preparation – then check out our online community and Career Break Basic Training course and future webinars.  We’ll get you moving on the steps to go!  Plus – you get a $75 off Airtreks coupon when you join to get you going!

Read all the posts in this series.