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Who’s Out There Now: Sherry

Written By: jeff

Posted On: June 21st, 2011

career break travel adventures in Morocco

Sherry in the Sahara in Morocco. Copyright Ottsworld.com

In this week’s ¨Who’s Out There Now¨ feature, we bring to you Sherry, the woman, the myth the legend behind Ottsworld and co-founder of BriefcasetoBackpack and MeetPlanGo.  I first met Sherry while doing my research on the needs of career breakers in launching Career Break Secrets. We hit it off immediately and when we finally met face-to-face in New York in June 2010, it was like getting together with an old friend. She’s really known for her photography. And, this summer, she’s taking off with a few other travel bloggers overland from England to Mongolia on the Mongol Rally to raise money for Mongolian charities.  After a brief travel hiatus, she’s back on the road and I caught up with her in between adventures.

1. So, where in the world are you answering these questions?

At 30,000 ft above Utah I believe.  I have a 2 months in the US while my passport is traveling without me getting 4 shiny new visas for my upcoming Mongol Rally.  So I am heading to the west coast to see friends and kick off some Meet, Plan, Go events.  I do my best writing when I’m stuck on a plane!

2. Why did you start blogging? Did you ever imagine that you’d have started your own little media empire?

I wanted to be rich and famous of course!  Ok – my story is pretty much like most people’s back before the ‘blogging craze’ hit.  In 2006, I quit my job to take a career break and travel around the world for a year and I started my blog (a relatively new concept at the time) which was hosted on BootsnAll.com back then.  I started it to simply keep my mother from freaking out and giving me a place to journal and share my photos of my trip.  Basically I wanted my mom to sleep easy, and my friends to be jealous.

As for a media empire…no, I honestly thought I would take my break for a year, miraculously figure out what I wanted to do with my life, and then come back and do it.  Unfortunately after about 3 months of travel – I knew that I was going to have a really hard time ever going back to my old life.  The longer I was gone, the less I wanted to come back. But I needed money and a plan – so after stretching my year trip to 16 months, I came back and decided to spend a little time learning more about how to take my somewhat popular website which lived on Bootsnall and turn it into mine and get rich from Amazon store sales, Google Ads, and affiliate revenue.  Yeah…that didn’t exactly happen either, but I was able to take my website to the next level and make a little money off of it and most importantly – stay traveling and living abroad.  Website are like kids; once you have one, you want more.  Hence, my website reproduced into a separate photography website, Briefcase to Backpack, and Meet Plan Go…an ‘empire’ was born!

career break travel adventures in Nepal

Sherry and her dad hiking in Nepal. Copyright Ottsworld.com

3. You’ve gotten around to some major chunks of the world: Nepal, Kenya, Europe, Turkey, Australia and New Zealand. But, in South America, you’ve only conquered Brazil. My question is, Sherry why do you hate South America (he writes from his home office in Bogota, Colombia)?

Well – I think I’m the only American who doesn’t speak Spanish and I’m embarrassed to go there!  Actually for the record I have been to Peru too.

I think I’ve neglected South America up until now because it’s one of those places where the culture is a bit similar to North America in a way.  I know that I crave traveling to really big cultural divides which is what kept me in Asia for much of my travels, and now quite frankly I’m pretty fascinated with the Arabic culture of the Middle East.  South Americans look more like me and have some of the same habits and many of the same religions I’m used to, so the divide isn’t as big.  Also – I like to go where other Americans don’t go; I want to be off the beaten path.  Quite frankly there are a lot of Americans in South America!  However – it’s starting to pop up on my radar more often these days.  Especially Patagonia; I am a hiker and I’d really like to hike in that area.  Or go live for 6 months in Buenos Aries and learn how to tango, or go photograph the salt flats in Bolivia.  I’m pretty sure I’ll be there in the next couple of years!

4. Your story is similar to mine in why you decided to take a career break. But, when you started, did you think it would be short-term and then you’d go back into corporate? Or did you always have the desire to reinvent yourself?

Oops – I clearly should have read ahead…but that would be way to responsible of me.  I think I sort of answered that above.  But the short answer is yes – I thought it would be short term and I’d go back to some sort of corporate life.  However – I have indeed always had the desire to reinvent myself.  When I was 9 I was determined to become Farrah Fawcett fighting crime for Charlie.

career break travel adventures in Vietnam

Making bread in Vietnam. Copyright Ottsworld.com

5. So, this summer you’ve got an amazing adventure ahead of you. How did the idea of doing the Mongol Rally come about? Anything in particular you are looking to get out of it?

First of all, the Mongol Rally is a charity road trip in which a team of people drive from London to Mongolia in a small, inappropriate car!  It will take 10,000 miles and approximately 6 to 8 weeks.  I had been following another career break couple’s website, Abandon The Cube, and first read about it on their site as they participated last year.  I knew as soon as I read about it that I wanted to do it.  It seemed like the perfect mix of crazy, unique, challenging, and terrifying.  I had also been to Mongolia before and it was one of my favorite countries ever.  So the idea of ending there and raising money for the charities in the country really meant something to me.  At TBEX I met Dave and Deb from ThePlanetd.com and we all decided we wanted to do something epic for our next trip.  I knew immediately that it would have to be the Mongol Rally and that Dave and Deb were the perfect people to do it with.  We picked up Rick Griffin from MidlifeRoadTrip.com and a car full of over 40 midlife travel bloggers threw their hat into the ring.  As for what I hope to get out of it listed in order:

  • Raise at least $6000 for Christina Nobel Foundation and get the car to Mongolia to be donated to Adventures for Development. (50% of the cars actually make it)
  • An adventure that is completely unique and provides great writing fodder
  • Pick up new followers and interest on my websites
  • Get over my fear of driving in foreign countries.
  • Take amazing pictures
  • Get a made for tv movie produced where the role of me is played by Cameron Diaz.  She was in Charlie’s Angels after all.

6. You’ve got some amazing photography on your site organized nicely by country. What are a couple of tips that the average person can use to improve their photography significantly?

  • Use wider angles so that you can capture the whole scene and feeling – even when shooting people.  It helps you tell a complete story within the picture.  My wide angle lens is my favorite!
  • I love to shoot candids of people, and the goal should always be for them to make eye contact with the camera but not appear posed at all.  You want to first ask the person if it’s ok to take their photo (yes, I know that’s scary…but with practice it becomes easier).  Then try to hang around long enough taking pictures so they sort of forget about you and stop giving you cheesy grins and instead go back to what they were doing when they initially captured your attention.  Then wait, wait, wait until they look up at you (probably wondering why you are still there) and click.  Eye contact to me is key; it is a connection for the viewer.  The difference between someone looking into your lens naturally and simply snapping people doing something is huge.
career break travel adventures in Italy

Sailing in Italy. Copyright Ottsworld.com

7. Career break, nomadic adventure, backpacking, how do you characterize your travels?

It definitely started as a traditional career break.  However it morphed then into living as an expat, and then morphed completely into nomadic traveler.  I think of myself more as a seeker of culture. I don’t really even like to travel in the traditional sense any more very much.  I really am after more cultural interaction – so that really lends itself to my nomadic lifestyle and slow travel.  I like to settle down in places for a while and let them get under my skin.  I’m definitely still budget – Lord knows the life of a travel blogger isn’t full of wealth at all!  I couchsurf, and try to be as budget as I can by volunteering and traveling slow.

8. What are some of the secrets to travel that you’ve discovered that you think more people who aren’t traveling should know?

  • It will make you smarter than any book.
  • Simplicity and minimalism is actually a good thing.
  • America isn’t actually the ‘perfect’ country we think we are.
  • Family is the strongest bond of all.
  • The Middle East is not full of extremists and terrorists.  (quite the opposite)
  • Houses and possessions aren’t the key to happiness.
  • Education is key to getting anywhere in life.
career break travel adventures in Sri Lanka

With some kids in Sri Lanka. Copyright Ottsworld.com

9. What was your first ¨I’m not in Kansas anymore¨ moment?

The overland border crossing I did from Kenya to Tanzania.  I started my career break in 2006 in Kenya for two weeks and then had to cross the border to Tanzania to get to Kilimanjaro.  The border crossing was utter chaos.  No lines, no rules, pushing/shoving/yelling/pickpockets/touts.  To go from corporate life in NYC to trying to push to get your passport stamped in a small dirty border town in Tanzania was quite a shock.  I figure one of the best things about the Mongol Rally this summer will be the numerous border crossings; I expect lots of good stories out of those experiences.

10. What’s been your most ¨local¨ experience so far?

Hard to name just one…will give you my top 3.

  • Volunteering in a remote village in Nepal. It was probably the most challenging thing I did.  I taught in a village that didn’t even have a store that sold bottled water.  No plumbing, no electricity, no English, and lots of leaches.  I lived with a local family in their room above the buffalo barn.
  • Living in Saigon Vietnam for a year. I was an expat – but I was a local in my mind…especially when I got my own motorbike and joined the millions of Vietnamese motorbike drivers in chaos.  I lived on my own but was quite integrated into the community.
  • Living with families in the Middle East through GeoVisions – Living in Jordan and Lebanon for a couple of months was probably the most intense cultural exchange I have done.  Experiencing every day life with families that were quite average and typical was the best way I’ve experienced a country yet.  Being a part of their family in the Middle East not only meant eating and sleeping with them – but you were literally part of the family.

11. What has been your most embarrassing moment?

Crying in the middle of the airport in Casablanca while an 18 year old Egyptian kid tried to console me.  It’s a long story.

career break travel adventures in Vietnam

Chowing down in Vietnam. Copyright Ottsworld.com

12. How is travel different for someone on a long-term journey than it is for someone on a vacation?

My first reaction is that you learn to wash your clothes in a sink!  However I think that one of the biggest differences is that you don’t HAVE to go to all of the tourist sites.  If you go to Paris, you don’t even HAVE to go to the Eiffel tower.  I don’t feel badly at all about ‘missing’ things because I know that I can always go back.  Unlike my previous life in a regular corporate job, I’d never know if I’d have the chance to go back to a place or not due to limited vacation time.  Now I know that I will actually see people again and can really go anywhere anytime.  I do less and less tourist stuff all the time.  It’s just not what excites me any longer. I’ve been on the road for 4 ½ years now, and most of the time I just like to go somewhere and relax and not do much of anything special.  Just be.

13. What’s your secret for getting the most out of your journey?

Time.  Slow down, take time.  Don’t try to go to more than one place in a week.  In fact – I sort of have a rule now for myself – I only want to go to a country if I can stay somewhere a whole month.

Also – don’t fly everywhere as you miss all the interesting stuff on the ground.

career break travel adventures in Vietnam

Volunteering in Vietnam. Copyright Ottsworld.com

14. Finally, our lightening round.

  • Best dish you’ve found so far: Pho in Vietnam
  • Most exotic food eaten: does rat count?  If not – then lamb brain.
  • Most breathtaking moment: Seeing the Indian Ocean for the first time.
  • Biggest disappointment: Egypt
  • Most memorable place: Completing the Annapurna circuit (23 days) with my 73 year old father.
  • Most memorable person: Didi – my host in Puma Nepal when I was volunteering.
  • Best thing to have on a long bus ride: Podcasts- This American Life (NPR), Amateur Traveler, Indie Travel, Moth, Wait Wait Don’t Tell Me (NPR), and Planet Money(NPR)
  • Worst thing to have on a long bus ride: someone sitting next to you puking…which of course has happened.
  • Best thing you packed: Sleep sheet
  • Dumbest thing you packed: Make-up…and condoms come a close second – I think it was wishful thinking!
  • Funniest travel habit you have: I carry my baby pillow with me around the world.
  • Place you wish you could’ve stayed longer: Mongolia

You can follow Sherry online at Ottsworld, on Facebook and on Twitter @ottsworld

Every week, Career Break Secrets profiles a different traveler or traveling couple who are embracing the ¨Because Life Is Out There TM¨ travel spirit.  These are people who have taken the plunge to embark on a career break and are currently traveling the world.

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