Notes From a Briefcase

Steve Bamberger, a proud Briefcase, recognizes the value of unplugging – if even for a week.

When Sherry, my friend of twelve years, launched her company Briefcase to Backpack with Michaela Potter, I immediately latched onto the name. I took the two new-ish business partners up to Sonoma for some wine tasting and declared myself a proud, unrepentant Briefcase. “Me Briefcase, you Backpack” entered the vernacular alongside “Me Tarzan, You Jane.”

[singlepic=1893,300,,,right]You see, I like being a Briefcase. I see my share of places on business, and my travel (often at company expense) has afforded me glimpses of places around our country and around the world. I have accumulated passport stamps from (A)ustralia to New (Z)ealand and Brazil, Canada, China, the Czech Republic, Fiji, France, Greece, India, Ireland, Israel, Italy, Japan, Korea, the Netherlands, Singapore, Spain, Sweden, Turkey, the UK, and Vanuatu in between. I have climbed the Great Wall, seen the Western Wall, and hit the Wall at pubs in Ireland. I have eaten fried shrimp on the Bayou in Monroe, Louisiana, savored grilled shrimp where Bill Clinton used to eat lunch in Little Rock, Arkansas, and munched shrimp cocktail in a skybox at Yankee Stadium. So while I may spend my Type A life working for the man, I am not by any means a resident of cubeville.

That is not to say I don’t have incredible admiration for my friend Sherry. I absolutely do. Anyone who has a dream and pursues it relentlessly – regardless of the financial consequences – gets props in my book. To do what you want to do – and only then figure out how to make money at it – is an amazing way to live. Apologies to (Duke basketball coach) Mike Krzyzewski for misquoting him, but years ago he said something like “I’ve never made a decision primarily because of money, and I’ve made a lot of money.” My parents did it – starting an opera company in 1976 in Cleveland, Ohio was not a terribly astute financial decision. But it worked out great for twenty-nine years. To a large extent, I’ve done it – I love what I do and I have been fortunate to be successful. (Confession: Would I do the same thing if you could get stock options for dog training? Maybe not.)

[singlepic=1894,300,,,right]So I think Sherry’s choice is all the more amazing. Traveling for a year – then two, then four and counting – is not a way to pad one’s bank account. But she started with an idea to take a break and turned it first into a passion and then a business. Trust me, she works as hard as anyone I know. If you think her entire life is waffles, frites, and faux Midwestern strip clubs you have clearly not paid attention to the deafening roar of tweets from her Twitter account or seen her up until 2am uploading photos and preparing the next day’s blog post.

Which brings me to the recent adventure I had with her. You see, part of following my dream has been to reenter the entrepreneurial world and try to grow a company with no safety net beneath me. So after six years as a sales VP at Oracle, I took a position in a small tech company in Silicon Valley. But between jobs, I had my own mini-version of a career break. I took two weeks of staycation when I was still fully plugged in – to some extent, doing two jobs while I exited the first and prepared for the second. But the third week, I wanted to do something different – to see places I would never see on business. I invited my vagabond Backpack friend to come with me. I wanted the company, I thought Sherry would be fun to travel with, and I figured our shared obsession with pulling dangerously off the highway to take the perfect picture would make her an ideal travel companion.

[singlepic=1891,300,,,right]We did the travel Briefcase style, staying in actual hotels, eating actual food, sitting in good seats at Cirque in Vegas, and tooling around in a navigation-equipped sedan. In a week, we saw Las Vegas, Death Valley, Grand Canyon, Antelope Canyon, Horseshoe Bend, Zion National Park, Snow Canyon, and Bryce Canyon. We were always on the move and had a lot of fun, although I was constantly and ironically reminded that Sherry was always at work! Taking pictures was a perfect distraction, since figuring out the right angle and exposure allowed me to obsess about something other than email and my new job, which would start only a few days later.

I’m not going to tell you about our trip. That’s Backpack’s job. Besides, she took notes along the way and will undoubtedly have more interesting stories than I would. I reserve the right to challenge her assertions in comments on the Ottsworld blog. But I’ll trust her to be accurate and entertaining. (Have you noticed that she can write endlessly and engagingly on absolutely nothing?)

But I would like to say a few words to the other Briefcases out there – the ones who like the idea of a career break but who are a little intimidated by reading this site and the idea of dropping out of society for four years! My few pieces of advice:

  1. It’s ok to like business. I do. But if you don’t like what you’re doing, you will probably suck at it. And so you won’t like it. And so it will suck more. Get it?
  2. If you only have a job so you can afford vacations, you are kind of missing the point. Find something you really like to do. Do it. I’ll bet you can find a way to make enough money at it. You can learn a lot more from Sherry by following this advice than by learning what kind of waffle is best. (Correct answer: Brussels waffle.)
  3. It’s ok to unplug. No one knows better than I do how easy it is to skip vacations. But the office will function without you. I may be a business junkie and mild workaholic, but I still spent a week in a cave house on Santorini last year and a week traveling national parks last month.
  4. Your career break can be planned for a week, a month, a year, or a lifetime. It’s ok to start small. See where it takes you. You may (re)discover a passion, as I have done with my camera or Sherry has done with traveling itself!

I’m still a Briefcase. I probably always will be. I will still obsess about maintaining my Starwood Platinum and my United Global Services status. I’ll still get a little antsy if the Westin forgets to leave complimentary bottled water in my room. I’ll still do emails late into the night.

But it was fun traveling with my favorite Backpack and being reminded of the importance of following your dreams and – for a week or a lifetime – to unplug.

Steve Bamberger is an unrepentant Briefcase and may be reached at His Twitter handle, where his infrequent and generally uninteresting 140 character musings may be found, is @sbamberger

Other comments

2 Comments on "Notes From a Briefcase"

  1. Tweets that mention Notes from a Briefcase | Briefcase to Backpack - Travel Advice for Career Breaks or Sabbaticals -- on Mon, 25th Oct 2010 11:28 am 

    […] This post was mentioned on Twitter by Sherry Ott, BriefcasetoBackpack. BriefcasetoBackpack said: A proud "Briefcase" – @sbamberger – recognizes the value of unplugging, if even for a week. #careerbreak […]

  2. Zablon Mukuba on Sun, 31st Oct 2010 5:15 am 

    great advice, its hard to switch from a workaholic to a traveler. but everyone should to take a break for year or more

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