How to Jump Off a Cliff and Other Lessons in Life and Travel from Our Meet, Plan, Go Event

Ten days ago, I hosted and moderated San Francisco’s version of the national Meet, Plan, Go! event. Thankfully, after many months of planning, it ended up being everything I hoped it would be and attracted a sell-out crowd of about 150 people at the Sports Basement. They represented diverse backgrounds and a wide age range, but they were united in daring to dream and hatch a plan to take a leap away from their jobs and homes—from their security and comfort zones—for the sake of meaningful long-term travel.

The audience at our Meet, Plan, Go! event

They heard a panel of global travelers and career-breakers—Sherry Ott, Spencer Spellman, Kristin Zibell and my husband Morgan Smith—along with yours truly share our stories and practical advice about leaving “normal” for an extended period to travel and learn from the world while experiencing a very different lifestyle.

(L-R) Meet Plan Go panelists Spencer, Sherry, Kristin, me and Morgan (photo by Jannell Howell)

We also heard from the co-founder and CEO of AFAR Media, Greg Sullivan, because we donated the night’s net ticket proceeds ($1730) to the AFAR Foundation. The foundation’s flagship program, “Learning AFAR,” sends under-served high school students on trips abroad to places like Peru and Cambodia to do volunteer work while learning about the culture and environment. “The kids come back, and their world is so opened up,” Greg said. “This way of travel is the best form of education.”

Greg Sullivan speaks about the AFAR Foundation while I listen (photo by Jannell Howell).

I thought about writing a recap of the practical advice we shared on topics such as how to afford and budget for a round-the-world trip, how to travel with kids or solo, and how to plan an itinerary. Instead, I’d like to share what struck me as two of the most inspiring stories of the evening: Sherry’s and Morgan’s anecdotes about taking a major break from their careers for the sake of travel and personal fulfillment. In other words, doing what many thought was “crazy” because it seemed so risky and unconventional.

(For more practical advice, check out this Big List of Resources for Round-the-World Travel and Career Breaks as well as past stories under this blog’s “Meet Plan Go” tab, and the bulleted list of the panelists’ articles at the end of this post.)

Sherry Ott, co-founder of Meet, Plan, Go speaking at our October 18 event in San Francisco (photo by Krista Gray).

Sherry Ott, the co-founder of Meet, Plan, Go!, left a corporate job in IT in 2006 to travel around 23 countries for 16 months. “I’m here to tell you there are two ways to jump off a cliff,” she told the crowd by way of introducing herself. “You can either walk up to the edge, look over and tentatively take a step off; or, you can back up and take a running leap. … Most people will walk to the edge, look over, maybe kick a rock over and watch it fall into the abyss. They might have a panic attack or vertigo. And they’ll probably step away. Most people step away from hard things, and a career break for extended travel really is hard. A lot of people will think you’re crazy and that you’re making a huge mistake, that you’ll never get a job again and are ruining your career—but the fact is they think you’re crazy because they don’t have the guts to do it. It does take guts to take such a leap, to do something so unconventional in our society.”

She said she walked up to that ledge 14 years ago and “had a panic attack and stepped back.” Then, after working in her field for a decade, she decided to step off for her first extended trip. “It changed my life, definitely.” She came back to her New York apartment, looked at all her stuff, “and that’s when I took a running, flying leap off the cliff. I sold pretty much everything I owned—kept a few things in storage—but pretty much checked out” and decided to integrate travel into her life. She got a language teaching certificate and taught English in Vietnam; she volunteered in Nepal; she traveled around the Middle East; and last summer, she participated in the Mongol Rally from London to Mongolia. She became a professional writer, photographer and blogger.

“My career break helped me build skills I didn’t have before” such as building websites and doing social media marketing and communications. “Anyone who goes on a trip like this will come back with a lot of soft skills” such as negotiating, planning and adaptability that can help them in the job market.

She and Meet, Plan, Go! co-founder Michaela Potter share a vision, she said, “to have extended travel accepted in America. We want to see a career break on everyone’s resume” so that hiring managers look at portfolios and say, “I don’t see extended travel on your resume yet. When are you planning on taking it?”

Sherry’s story resonated greatly with Morgan and me because we felt crazy, scared and daunted when we made the leap in early 2009 and started planning to leave our home and work, and to educate our kids for the school year, while traveling around the world. For myriad reasons, we knew we really needed to shake up our lives, re-evaluate our values and direction in life, bond as a family, and expand our minds by learning about the world. We risked our financial future and jeopardized a lot of close work-related relationships when Morgan resigned his partnership at the law firm he co-founded more than a decade earlier.

Morgan tells the audience, "Gotta try new things" (photo by Krista Gray).

“It was the hardest decision of my life to put my career at risk” by taking a leave of absence from his firm, Morgan told the crowd. Then, over the course of the trip, he made the decision not to go back and to start a new business instead. The journey “gave me the distance to be able to make a very hard decision” regarding his career path, he said.

Morgan talked about what it was like to spend 24/7 together as a family, as we unpacked and settled into more than 80 places on five continents and taught our two kids the equivalent of 6th and 3rd grade along the way. The good times and challenging times together, which forced us to collaborate as a family, made us redefine our roles as a couple and enabled Morgan to grow much closer to our daughter and son, so that we now co-parent in a more equal and respectful way.

“The things you learn and gain from a trip like this are so much more important than what you leave behind,” he said. If you struggle with whether to return to your career after a break, or whether to do something different, “my advice is: Don’t worry about it. There is a whole wide range of ways it really can work out.”

Morgan—whom I’ve known since we were teenagers and can attest is averse to change—developed a motto during our journey: “Gotta try new things.”

“For me, that was a really big deal,” he said. “I did not like trying new things; I was very good at doing the same thing over and over again very well without any real desire to change.” But with travel, he said, “you lose control over a lot of your life; you’re dealing with new things on a constant basis, and you become very adept at accepting and dealing with change in a way I wasn’t personally before.”

Walking up to the edge of the “cliff” and putting his professional success and status at risk was the hardest thing he ever did, Morgan said, but it was “absolutely the best year of my life and so worth it.”

So how do you go from dreaming to doing a career break or sabbatical for extended travel? I recommend Meet, Plan, Go!’s “Career Break Basic Training” course to get the step-by-step info and support you need.

Finally, I want to thank Kristin for reading this Steve Jobs quote to the audience: “Your time is limited, so don’t waste it living someone else’s life. … 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.”

For other write-ups with highlights from the event and great travel planning advice and inspiration, check out:

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4 Responses to How to Jump Off a Cliff and Other Lessons in Life and Travel from Our Meet, Plan, Go Event

  1. Spencer Spellman November 1, 2011 at 11:24 am #

    Great night and great evening. Happy to have been a part of this and thrilled to see the conversation continuing. I really liked what Sherry said about running and jumping off the cliff. Doing that myself has resulted in a completely different path in life and it’s been one grand adventure after another.
    Spencer Spellman recently posted..7 Things an African Safari Taught Me About LifeMy Profile

  2. Kendra November 1, 2011 at 11:33 am #

    I love this!! need to focus on what one’s purpose really is on the planet and make an effort to embrace those realities…scary or not. My “leap off a cliff” hasn’t meant travel in the traditional sense, but my financial future is equally at stake. I’m committed to see my journey through…and hopefully be able to slake my travel thirst again …soon!

  3. Gerard ~ GQ trippin November 1, 2011 at 10:45 pm #

    Hate to sound like a broken record. But when Sherry talked about running to jump off the cliff, that line really hit me. Even though I have a return date from my career break, I really have no idea what’s in store for me. I may come back a changed person and decide to start a new career path. I may get sick of travel (highly doubt that). All I know right now is I’m ready to make that jump into the unknown and can’t wait for my RTW.
    Gerard ~ GQ trippin recently posted..Memphis Tours Egypt: Day 2 of 2My Profile

  4. Slava Petrenko Photography April 1, 2012 at 6:33 am #

    Thanks for providing the link to that list of resources – we’re planning a big trip at the end of the year and some of those resources are definitely going to come in handy.

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