Amanda Pressner – Losing Myself on the Road

[singlepic=1587,275,,,right]Amanda Pressner is one of The Lost Girls, three twenty-something New Yorkers who ditched their media jobs in 2006 to embark on a yearlong, round-the-world journey in search of adventure and inspiration. Amanda shares with us how she found self-fulfillment not through a successful career but through travel. You can read about her adventures with Jen and Holly on their blog, The Lost Girls, as well as their book The Lost Girls: Three Friends. Four Continents. One Unconventional Detour Around the World. which was released in May 2010.

I can still remember staring at a bizarre, other-worldly reflection of myself as I zipped up the skirt on a black Ann Taylor sale-rack suit just before heading out the door for my first-ever internship interview. My hair had been yanked into some sort of severe French twist and I was wearing matching black pumps that I probably thought made me look older and more professional. Realistically, I probably looked like I was my way to a funeral.

Perhaps to some degree, I was.

Back then, as my teens were transitioning to my twenties, I simply assumed that becoming an adult meant the death of childhood, a sacrifice which would require me to toss out the flip-flops and frayed jeans I’d worn growing up in Florida and totally abandon my carefree ways of being. No longer would I ditch class to hit the beach with my girlfriends, watch sunsets over the rim of a rum runner and sneak back home just as morning rush hour was starting for somebody else. Now was the time for me to dive into that very rat race, to begin a new the chapter of my life. It was time to get a real job.

[singlepic=1585,275,,,left]Despite my best efforts to the contrary, I never did manage to retire my rebellious inner teen in order to become a full-fledged grown up. I felt grateful once I landed my very first position in New York City, but after three weeks as a sales assistant at a major television network, I started to feel restless. I knew I wanted to leave such a corporate environment but had to wait nearly two years before I scored a copy-writing gig at a major publishing company. When that job didn’t quite feel right, I jumped again and became an editorial assistant at a women’s magazine in the same Times Square office. I figured I’d finally seized the brass ring–surely I’d be happy doing something creative and glamorous for one of most widely read publications in America, right?

But after another two years and one promotion, I still wasn’t. And so, when the opportunity arose to take the ultimate of all career breaks—a year around the world with my best friends and fellow Lost Girls Jen and Holly—I leapt at the opportunity.

That should have been the turning point for me, the “ah-ha” moment when I realized no job could ever bring the self-fulfillment that travel can, but old habits die-hard. But ever the overachiever, I tried to work from the road, to turn our adventures into story pitches I could sell to magazines back home. Without consciously deciding to do so, I tried turning our round-the-world adventure into yet another stepping stone for my career.

[singlepic=1591,275,,,right]It took me eight of our twelve months on the road to put down the laptop, but just as we were rounding our 10th country, Indonesia, I finally wore myself out and relinquished control. I gave up pitching, gave up working, gave up trying to validate my life through achievements. I lived 100 percent in the moment of our daily lives. And I eventually learned my lesson.

What, after all, do many of us people put on their suit and go to work every day for?

Most people have to wait their whole lives to retire and do the very things that I was all too eager to give up as a career-bent, success motivated college grad in a bad black Ann Taylor suit. Here I was at 28, being given a very rare second chance to appreciate that freedom, and to crawl the globe in search of wild and wondrous new possibilities. Finally, with the help of Jen, Holly and several new friends along the way, I seized the opportunity. I only had four more months to immerse myself in the adventure–but in many ways they were the richest and most fulfilling ones of the trip.

[singlepic=1584,275,,,left]After we eventually returned to the States, Jen, Holly and I debated on whether or not we should go back to desk jobs. I rationed that I probably should take a position that I’d just been offered at another magazine, just to confirm that I was actually “still capable of working in an office.”

“You could,” Jen said. “But what would you really be proving? That you’re able to sit behind a desk…that you can do the exact same thing that millions and millions of people have to do every single day?”

She pointed out it was no great accomplishment to learn to survive in an office. Learning to carve your own unique path in the world, however—now that’s that a goal worth working for.

Read our review of “The Lost Girls”

Other comments

7 Comments on "Amanda Pressner – Losing Myself on the Road"

  1. Tweets that mention Amanda Pressner - Losing Myself on the Road | Briefcase to Backpack - Travel Advice for Career Breaks or Sabbaticals -- on Mon, 30th Nov 2009 10:36 am 

    […] This post was mentioned on Twitter by BriefcasetoBackpack, Amanda Pressner. Amanda Pressner said: Read how I took the ultimate career break (and found fulfillment) on Briefcase to Backpack: @CareerBreakHQs […]

  2. Dave on Mon, 30th Nov 2009 1:48 pm 

    “She pointed out it was no great accomplishment to learn to survive in an office. Learning to carve your own unique path in the world, however—now that’s that a goal worth working for.”

    Very inspiring, and exactly the situation I find myself in now. Looking forward to finding out what you’ve been up to lately!

  3. Akila on Tue, 1st Dec 2009 2:40 pm 

    We are starting to figure exactly this out. For the first time in our lives, we are trying to find a unique path that takes us away from the pre-planned route determined by our educations. It is incredibly tough, weird, and scary but, I think, ultimately will be rewarding. Congratulations on your success and I look forward to reading your book!

  4. Andi on Tue, 1st Dec 2009 10:23 pm 

    Love your blog, love your life story! Keep carving your own path in this beautiful world. 🙂

  5. Baker on Wed, 2nd Dec 2009 1:23 am 

    We’re all Lost Boys and Lost Girls in this short spin we get to take on planet Earth. Some of us just wander further away from home than others…

  6. Amanda on Mon, 14th Dec 2009 11:57 am 

    Hey Dave, Akila, Andy and Baker (um, who’s that last one?)

    Thanks so much for the feedback on the article! I agree, we’re all Lost, and to “find oneself”—or at least to take the journey towards that endpoint—is the worthiest of pursuits. Happy travels, and we’ll see you at the next hostel/watering hole/rest stop!

  7. Laura on Thu, 20th May 2010 1:23 pm 


    Thanks for sharing! I’ve heard the pressures from friends & family to pursue my career and put travel on hold. But I agree that carving your own path is an accomplishment in and of itself. I’ve found that choosing my own path and having things turn out okay have made people twice as impressed as sitting behind a desk all day. Happy travels and good luck with the book!

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