Meet Sherry…That was Then…
NOTE: This was my original post in the blog way back in July 2006. I thought I would highlight it and get it out from underneath the hundreds of posts for those of you who are new to the site.
Me on my 36th birthday.
I have been working in Corporate America now for 14 years - how time flies. How can that be - I still feel like I’m 22 and just starting out. After all, what 36 year old has friends through her a roller skating birthday party! My ass still hurts from that party!
I live in New York City - I’ve developed a love/hate relationship with it. There’s no place in the world like it (at least from what I’ve seen so far). So much variety and newness everyday, so many choices, so many noises, so much garbage, so many people, so much creativity, so much concrete, so much, so much, so much…
Someone once called me a tumbleweed - I only stay somewhere about 3 years - and then I must tumble to the next place. Yet this time, I’m tumbling to the next adventure - the globe. This propensity to tumble around is strange considering I grew up in the midwest (Peoria, IL) in the same house for the first 18 years of my life. Then something happened…I got out…and never looked back. I slowly moved to bigger and bigger cities. First the midwest (Omaha, Minneapolis), then the west coast (San Francisco), then the big, big city - NYC. I’ve been in NYC 3 years now, I’m itchin’ to tumble again!
I was 30 yrs old when I got my first passport and went out of the country - Istanbul. I went with my friend, Giancarlo, who grew up in that area. It was overwhelming to have Turkey be the first country you go visit - but that’s when I caught the bug. Part of me wishes I could do that trip over again as I feel like more of a seasoned traveler now, but at the same time the newness and innocence of it all was perfect.
I have been working in the Information Technology industry and have finally realized that no matter how lucrative of a job it is - it’s not me. I don’t get excited by bits and bytes. I get excited about photography, creativity, sunlight, and socializing, but not hardware and networks.

So maybe this is my midlife crisis…a little early I know - but I’m not really sure what is driving me to do this. I just know that I need a break. A break from New York, a break from Information Technology, and I need to stretch my creative muscles a bit, and see other things - and sorta find myself.
Everyone always asks me what I’m going to do when I come back. I have no answer to that question, and that makes me nervous. But I’m telling myself to live each day to the fullest and not worry about it. I will leave my dance card wide open and just see what happens. However - mainly I will enjoy my year of not being in a conference room, with an agenda about stuff that doesn’t interest me. I will no longer have to daydream during those meetings about other exotic places - I will be living it.
Why, Why, Why…
Why Not?! Who hasn’t wanted to quite their job and travel around the world at some point in their adult life? I just believe that you have to leave a mark on this world, see this world, experience this world.
Some mantras that have inspired me to start this journey:
Some Stories don’t have a clear beginning, middle, and end. Life is about not knowing, having to change, taking the moment and making the best of it, without knowing what’s going to happen next. Delicious ambiguity…-Gilda Radner
No one grows old by living, only by losing interest in living.
Conformity…Proudly serving painfully boring people since time began.
Ok - enough of the sappy stuff. Honestly though - I’m an Aquarius - I need change, I require change, I live for change. I hate being in a rut or in any sort of predictable pattern. After 3 years in my current job, I have developed a pattern and I think I would explode if I had to go through yet another predictable year in my current job.
My sample day…get up way too early (normally a bit hungover), run in the park, dash off to work on a crowded subway of other people staring lifelessly into space tethered to their ipod, check email on my crackberry on the subway, arrive at work. Go to my office which I call my white box (no windows and nothing on the walls), check email, go to a meeting, go to a meeting, go to a meeting in which lunch is served, check email, go to a meeting, go to a meeting, go to a meeting, do work for the last hour I’m there. Many times I can go all day without ever going outside or seeing the sun, and sometimes I never even make it to the bathroom (ok - maybe that’s too much information). I have a picture of a collage of sunsets in my office - it’s my fake window…I stare at it to remind me of what the sun looks like.

The view from my office window…

View of my typical work day calendar…meetings, meetings, meetings…

However - I don’t mean to paint such a dismal picture - you can make your own inference from the pictures. I do owe a lot to work, and I work with good people, smart people - people who like what they do and are generally ok with being in a pattern (no other aquariuses!). After all - if it wasn’t for work, I wouldn’t be able to take this adventure - and for that- I’m eternally grateful to my job. But most days I feel like I’m stuck - stuck in my white box, not really knowing what value I’m adding to the world - let alone what value I’m adding to the numerous meetings I’m attending. New York and my corporate life finally got the better of me and a plan started to hatch.
It started small and simple…
Plan 1 - a thought of giving everything up and getting a simpler job…I didn’t need a fancy apartment on the upper west side, I could get back to my college roots and budget and simply wait tables if I had to - as long as I was happy.
It got a bit more international…
Plan 2 - Move to Italy, buy a scooter, get a dog (that got along with my cat), raise grapes and olives, yadda, yadda, yadda…see movie ‘Under the Tuscan Sun’ for the rest of the story.
Now we are talkin’…
Plan 3 - Save my bonus for the last 3 years, and take off and travel the world thereby satisfying my ever-growing travel curiousity. OD on travel, get it out of my system, refocus, see different cultures, see cultures that didn’t revovle around the corporate business orb, see history, understand history, get a tan, see the sun, see my sister, push my limits and boundaries, live.
You guessed it - Plan 3 won out. I honestly think that my Financial Planner, Mark, wasn’t too thrilled about any of the plans, but this one seemed like the most fun to him - so he ‘approved’ it.
Then it just turned into a waiting game - when was the right time to start this adventure? My friends and I had been planning a trip to Africa for September, seemed like a good jumping off point. Plus - the last international trip I had I came back to a guy smoking crack on the subway on my commute to work - it was then that I decided that the next time I went out of the country - I wasn’t going to come back!
May 15th, 2008 at 12:18 pm
Hi. I used to work with Michaela and so that’s how I heard about your site. I love it, and I’m jealous! I would love to do something similar…. but I dont have that “lucrative IT job” to back it. I do have a savings account though, so slowly but surely. I’ve often wondered… do I prefer to do smaller trips of 8 weeks and do a few of those and come home in between? Or do I go big and go away for 6 months?
I love the pictures and your stories. Congrats to you for being so bold!
Vanessa
June 20th, 2008 at 12:00 pm
Found you through a podcast you did. LOVE the site…cant wait to dig my feet in and read of your adventures in more detail. Like everyone else who reads this… I envy you.
Continue having a wonderful time, be safe and thank you for sharing your passion and adventure with all of us back in the boring corporate world…with the getaway pictures and postcards up on our walls to only daydream of.
Go you!!