Planning the Big Trip: Questions and Answers from Meet Plan Go 2011

“We can either take the leap or look humbly over the edge and kick a few stones.” Sherry Ott started the Meet Plan Go event in San Francisco with these inspirational words. The “leap” she was referring to was the one every would-be traveler must take when deciding to do long-term travel. You jump or you don’t.

Sherry took her leap in 2006 when she left a successful, but unfulfilling fourteen-year career in IT. She traveled around the world for a year and half, “doing everything she’s ever wanted to do,” and then just kept going. I’d taken a similar leap in 2008 traveling on three Big Trips around the world before settling down in San Francisco in 2010.  Since then, I’ve believed that anyone with travel dreams and ambition can take their own leap and Big Trip.

Sherry and I, along with Spencer Spellman and Morgan Smith, were panelists at the 2011 Meet Plan Go event in San Francisco hosted by Sarah Lavender Smith.  One hundred fifty soon-to-be travelers (out of 1100+ nationwide) came to the Sports Basement to hear how we had packed up our stationery lives and traveled long term. Hopefully, we felt, each attendee would be inspired to take their own Big Trip.

The five of us were evidence that a long-term travel career break is possible and life-changing, that the leap was 100% worth it.  We all had unique travel styles and shared experiences on budgeting, planning, living and working abroad, and how travel changed us. Sherry and Spencer did it by working abroad and traveling.  Sarah and Morgan packed up their two kids, rented out their house, and traveled for an entire school year together. I traveled, came home and worked, and then went off again.

This article isn’t a recap of the event – both Spencer and Sherry wrote wonderful posts on the discussion, attendees, and atmosphere. Instead, let me share questions asked and answered by attendees and resources to continue the Big Trip momentum.

How Do You Not Look Crazy To Your Friends and Family?

The panel smiled when asked this question by an audience member. We had all been there – friends and families had definitely shared their “opinions” of our  choices. The reactions were very positive and negative, but we had found that our admission of travel dreams brought out encouragement and support.

When I first decided to travel India after the end of a long relationship, I read Eat Pray Love over and over again to help me feel like I wasn’t crazy. The panelists  found that spending time with a support system and other travelers kept their positive energy and sanity in check. We all know now, taking our big trips was the sanest thing we could have done for ourselves. And, maybe it’s OK to look a little crazy if crazy means following your dreams. Attendee Alexandra of The Travel Noodle Blog described the feeling as “Crazy is the New Cool.”


How Can Professionals Work Abroad?

Money and career are always a concern for long-term travelers, either before taking the leap or figuring career out upon return. It’s a disruption, a positive one, but a disruption nonetheless to a tidy career track. So how can one a) work abroad and b) do something that takes advantage of past professional skills and adds to the resume?

Sherry recommends joining the expat community and networking. Companies in developing countries are always looking to hire talented, experienced professionals. It’s a matter of having a business card and networking, similar to how one would at home. Spencer lived as a digital nomad in Central America, working remotely with PR and marketing clients. Fran, an attendee, mentioned that she was a professor and wanted to teach English abroad. One way to do that is to take the TEFL certification as Sherry did to teach in Vietnam for a year.


How Do You Pack Your Life in a 21-Inch Suitcase?

In Laura Fraser’s travel-as-a-way-to-figure-out-life memoir All Over the Map she wrote, “I never carry a bag that I can’t run with.” This is the only packing advice one needs. Sidewalks around the world are too bumpy for a wheeled Samsonite and trains don’t wait for you to haul heavy luggage. The Smiths had one carry-on each and told the the kids that they could only pack what they could carry.  It’s a matter of having the basics, laundry in small sinks, and lots of black and neutrals. I recited my packing list for four months abroad – all fit into a backpack.

The electronics are the most cumbersome. All panelists commiserated on the inconvenience, but necessity of traveling with electronics. Traveling with a laptop is like traveling with a child, except it’s something that you have to be prepared to lose.


How Do You Handle Insurance When You’re Abroad?

Insurance is personal and insurance research is time-consuming. The key is to do comprehensive research to understand what’s covered abroad and what’s covered back home. Typically, Sherry shared, what’s covered on your trip is probably not covered at home.


How Do You Stay Safe Traveling as a Solo Woman?

When I prepped for my trip to India, where I would travel solo the majority of three months, I got really nervous. The Lonely Planet made traveling alone as a woman in India sound like you’d be assaulted if you went out in any clothes but a burka. It proved to be completely untrue. However, ladies do have to take extra precaution to stay safe as American movies have portrayed Western woman as easy to the rest of the world (and by easy I mean the movies show funnin’ around before marriage). With a little common sense and acceptance that one is a guest in the country and not a feminist making a statement, traveling as a woman in these countries can be safe.

Here’s what I did to stay safe:

  • Covered my arms and legs.
  • Never went out alone at night.
  • Traveled in 3rd class AC on Indian trains (lots of families).
  • Stayed close to other women and traveled in the ladies car or coach.
  • Avoided smiling and talking to men in public.
  • Made up a husband and said “he’s meeting me in the next big city.”


What Do You Do When You Return Home?

Planning, saving, and budgeting may seem like the hardest part of a Big Trip, but returning home after a year or so of travel is much more difficult. You’ve seen the world, lived your dreams, and now it’s back to… what? The serendipity and magic of traveling around the world is something we all missed. Finding that magic back home and connecting with other travelers is the key to easing back into real life. “Not everyone wants to hear your travel stories and that’s all you’ll want to talk about,” Sherry said.

We had our stories of loss and reconnection when we returned. The Smiths slept on sleeping bags in the same room on their first night back instead of being separate. I watch Bollywood Saturday morning television because I miss India so much.  Sherry visits Chinatown to get her taste of Asia. Spencer and I are both dedicated to traveling around San Francisco because it has a uniqueness and little pieces of the world in seven square miles.


At the end of the event, there were trips forming and a definite energy that every attendee could get out and travel on their Big Trips.

I’ll leave you with you a very relevant quote and video from Steve Jobs’ 2005 Stanford Commencement speech.

“Your time is limited, so don’t waste it living someone else’s life. Don’t be trapped by dogma- which is living with the results of other people’s thinking. Don’t let the noise of others’ opinions drown out your own inner voice. And most important, have the courage to follow your heart and intuition. They already know what you truly want to become. Everything else is secondary.” – Steve Jobs

Did you attend Meet Plan Go? What other questions do you have on planning a big trip? What are your biggest concerns or dream itinerary?

Photo credit: Photo by ClickFlashPhotos on Flickr

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16 Responses to “Planning the Big Trip: Questions and Answers from Meet Plan Go 2011”

  1. October 24, 2011 at 5:21 am #

    Sounds like all the MeetPlanGo events were raging successes! What a great way to share your story and show others that stepping out isn’t that hard; you just have to decide and then take the steps to get there. Great questions, great answers and some great resources here!

    • Kristin
      October 24, 2011 at 8:18 am #

      Thank you Gillian!

  2. October 24, 2011 at 8:40 am #

    Great write-up Kristin. Glad you revisited some of the questions that were asked on Tuesday and excited to see this energy and momentum continue!

    • Kristin
      October 24, 2011 at 9:43 am #

      Thank you Spence!

  3. October 24, 2011 at 9:43 am #

    Nice job, Kristin. Excellent resources. I know for a fact that trip planning is stressful and people have enormous questions they may or may not be embarrassed to ask. I hope this post is useful to people out there.

    • Kristin
      October 24, 2011 at 10:21 am #

      Thanks Nico – I hope to keep the travel planning going!

  4. October 24, 2011 at 7:05 pm #

    Fantastic resources, thanks for sharing them Kristin.

  5. October 25, 2011 at 8:33 am #

    Great post, Kristin!! Filled with fabulous resources for those wanting to make the jump.

  6. October 28, 2011 at 12:40 am #

    Kristin, thanks a million for including my post here! 😀 And also thank you for doing this re-cap–so helpful!!

  7. November 1, 2011 at 2:13 pm #

    Great post! Thanks so much for organizing all the resources and links discussed that night, so helpful!

    • Kristin
      November 1, 2011 at 5:21 pm #

      Thank you Kelly – you’re insightful yourself!

  8. November 18, 2011 at 1:01 am #

    Hello Kristin,
    I am new to your blog. But I have just come back from my round-the-world travel. This big trip changed my life philosophy and I started blogging like you. You post is really good and your stories are great.
    Thank you, Lenia

    • Kristin
      November 18, 2011 at 9:56 am #

      Thank you Lenia! Welcome back, sounds like your trip was wonderful!


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