This is Me After 9 Years of Living Out of a Suitcase

April 26, 2024   35 Comments »

This is Me After 9 Years of Living Out of a Suitcase

September 8, 2015 35 Comments »

I’m having this weird unsettling feeling that I don’t know where I am. As I’m walking around the airport, something happens, and my brain races to try to figure out my whereabouts – narrowing it from continent to country to city. This is all brought on by the fact that in the last two days, I’ve been to 8 different airports and cities: Placencia, Belize City, Houston, Minneapolis, Lincoln, Omaha, Dallas, and JFK NYC. I’ll be in NYC for 5 days and then take off again for San Francisco, Anchorage, Nome, and Anadyr, Russia, over the course of 3 days.

It wasn’t supposed to be this way. When I left on September 8, 2006, it was only supposed to be for a year to 20 or so countries around Asia, Africa, and Europe. At that time everything about travel was new to me, I barely remember who I was back then, I had a huge closet full of designer clothes/shoes, an endless budget to party with, surrounded by friends I’d go out with every week, a running club, and I hated my job. I still remember being at JFK Airport, getting ready to leave a bundle of nerves, a complex combination of excited and scared emotions flowing through me. That excitement and fear is what drove me onto the first plane, and it still keeps me going 9 years later.

It doesn’t seem real; 7 continents, 65 countries, epic treks, safaris, kayaking in Antarctica, meeting world-famous chefs, press pass for the Indy 500, eating at the best restaurant in the world, staying in the same place as Prince William and Kate, climbing glaciers, heli hiking, surfing on 3 continents, dipping a foot in all 4 Oceans, staring at thousand-year-old ruins, staring into a polar bear’s eyes, and driving across countries where there are no roads.

9 years of travel 9

Nine years is longer than I’ve held any single job or lived in any single place (besides my childhood home). It’s longer than most marriages last, and for a commitment-phobe…9 years of anything is a lifetime. Applying for visas, buying airline tickets, packing and repacking, never doing laundry in the same place twice, editing photos, and writing millions of words have become my ‘normal’.

Travel Evolution

The 9 years have had a weird arc to them. Years 1, 2, and 3 were all about learning to travel, being a budget backpacker, figuring out how to live without things and make a living somehow, and soaking up new cultures via very independent travel that I organized myself. Years 4,5,6 were probably the most amazing from a mind, body, and soul standpoint. I pushed myself in new directions, traveled deeper and longer, did more epic trips, and started traveling with my family regularly. I began to figure out how to make some money doing photography & blogging and started a career break movement in Meet Plan Go.

Years 7,8,9 have been another big change for me as I started more freelance writing in order to make money, and my style and length of travel have changed drastically – it’s less independent and more organized tour tour-oriented. The main driver of my travel plans is work rather than ‘where I want to go”. I used to do more slow travel, and I now find myself ping-ponging all over the world, flying more than I ever have in the past. I stay in one place for only a few days and then move on to the next experience or project. Hence I often don’t know where I am.  I am peripatetic.

I started to try to write this post, a 9-year recap in my series of ‘This is Sherry…’, a number of times. I struggled with how to be honest and not sound like a spoiled brat. All I can say is that I LOVE travel, it excites and delights me. After 9 years on the road, I couldn’t be more thankful for all the things that I get to do, however, it all does come with a price – and that’s the part that I struggle to share. After all, I have the best, most envious job in the world.

“Oh my God, you have my dream job!” is the most common thing I hear everywhere I go.

Travel writer/blogger/photographer must be the most sought-after job in the world, and I have it! I have worked my butt off to get here, and like everything in life, it has its ups and downs, especially when you do it like I’m doing it – without a home base. The reason I don’t have a home base is because there’s no way I could afford a home/rent on what I make as a freelance writer/blogger. But I’ve been willing to live this life in order to write, photograph, and see the world.

It’s important to be honest. I recently read this piece by fellow blogger and nomad, Wandering Earl, and I totally agree with him. I am impressed, excited, and disturbed about the turns travel blogging has taken since I’ve been involved – but that commentary belongs in a separate post in the coming future. As much as I really want people to travel and see the world for a longer period of time than a vacation, I don’t believe people should do what I’m doing – living out of a suitcase permanently and trying to make a living. It’s really not for most people. Do it if you want, but I won’t tell you that it’s easy and doesn’t come without a price.

9 years of travel 2

The honest truth right now is that I’m tired, and most of the time I’m rather stressed out. My relationships suffer. The perks in my life are great, but moving constantly is hard.

Have I Changed?

People ask me if I’ve changed, and of course, I have changed, it’s been 9 years. Even if I had been sitting still on the ‘regular path’ I would have changed over the course of 9 years.

Being Grounded

I get so tired of talking sometimes; it’s exhausting constantly meeting new people in my nomadic world, so I now welcome alone time more than I ever did. Yet I strangely love it and hate it. In a normal person’s life maybe you are around people you know 80% of the time and meet new people 20% of the time. But in my life that’s reversed. “What keeps you grounded?” Heidi asks when I tell her I’ve been homeless for the last 9 years. “Do you have a van or car or something?” was her first question. “I don’t really have anything that keeps me grounded,” I reply in a defeated tone.

Nine years of no home base has left me quite ungrounded, I’ve tried to do a few things to combat it, but it feels like it’s a losing battle as my travel the last 3 years has been more hectic than ever. My travel schedule has me coming in and out of NYC more often, which means I get to see my handful of friends when I’m there, which is probably the only grounding force I have any longer.

Culture Clash

One of the things that keeps me going is that I still adore experiencing other cultures – it makes my heart skip a beat to meet people from other cultures and experience their way of life. It’s very clear to me that spending this much time traveling in and out of the US makes you completely in tune with what you love and hate about your own culture. I’ve realized that there is a lot that I love and hate about my own culture which is why I still like to move in and out of it so much and haven’t picked a home base in the US yet.

Feeling out of Touch

When I come back to the US I always feel like a bear that’s been in hibernation for a decade – I know nothing of pop culture; all the new gadgets on cars that have been developed, paying with phones and iPads, entire tv shows have come and gone, I have no idea what the latest wellness foods and crazes are, and I look at a People magazine and know absolutely no one on the front cover.

It makes me feel really out of touch and it’s easy to let that feeling spiral out of control for me. To combat it I have to remind myself of everything I do know about the world and the average American doesn’t. But regardless of the wealth of worldly knowledge I have, I can still feel out of place in the US.

Alone Time

Strangely even though I travel alone, I’m rarely alone. My travel style for the last 3 years has been much more about group tours and traditional tourism rather than independent travel. So that means I come in contact with many, many people. People who are on vacation.

But I’m ‘on vacation’ all the time, and I get tired of being social. Instead of going to have happy hour drinks at a lodge with the rest of the people I’m traveling with, I’d rather not talk to anyone and simply sit on my porch sipping wine and writing. I’m just too tired to be social some days.

The Quest for Newness

This is one trait that I started with in 2006 and hasn’t waned a bit; in fact, it’s probably gotten worse in the last 9 years. I have this incredible desire to always be experiencing new things – it drives me constantly. It’s stronger than my quest for love or being loved. So one thing that I find difficult is that there are very few new things that I encounter any longer. It’s like the alcoholic that used to get drunk off of 3 beers, but now it takes 3 beers, 2 shots of Whiskey, and a couple of glasses of wine to get drunk. Now…apply that to travel…and that’s my addiction problem.

Living in the Present

Everyone talks about living in the present; it’s easy to say, but hard to do. Over the course of 9 years, I still wonder if I’ve figured out how to truly embrace the present. When people learn of my lifestyle they often say that I really “live life in the present”, and I agree – I do it more than most people do, but I haven’t figured out the magic sauce of not worrying about the future yet. I have changed in many ways when it comes to knowing and accepting what my future holds.

Most of the time I have no idea what I’m doing for my future and where it will take me. In fact, I currently don’t know what I’m doing or how I get work after mid-October. I typically have my life pseudo planned out 3 months in advance – and after that, I have absolutely no idea. I’ve grown pretty accustomed to this pattern. I’ve accepted the unknown, but it doesn’t mean I don’t worry about it. It isn’t exactly living in the present, but it’s much more living in the present than I ever was before.


I go in waves of connecting with people and then I fall off the wagon and realize that I’m talking to no one and all of the conversations I’m having are only in my head. Yet I’m constantly adding to my wealth of connections and relationships. Many of them are fleeting and short term I know, but there are a few every year that seem to stick and have a profound impact on me. I am much more of a solitary person than I was 9 years ago and I have mixed feelings about it. At my core, I know I’m a social person, but I just need more time to recharge now it seems. My handful of really close friends are my lifeline. Overall I have fewer close friends, but more friends than I ever dreamed possible.

Just as I struggle to find and make new long-term friendships, the same goes for romantic relationships. A ‘dream job/life’ like mine is not very conducive to meaningful romantic relationships. Yet I’ve had an on/off again one going on now for 2 ½ years, which is quite substantial in my world. But sometimes I wonder if one of the reasons he likes me is because I’m never there. Honestly, I love unconventional relationships, but I’m tired of long-distance relationships.

What Does the Future Hold?

For some ridiculous reason, I’ve decided that 10 years is a nice round number…a decade. Ten Years a Nomad – doesn’t it have a nice ring to it? I’ve said that I’ve wanted to try to make it 10 years of living nomadically, so right now that’s what I have my sights set on.

I’ve been fantasizing about taking another career break – similar to the one that got me started on this wild ride. Strangely after 9 years and crafting a career I love, I’m kind of in the same place I was when I was working my corporate job. I need a break. I’ve been considering taking a break from trying to make money and just getting back to the basics of how I started…just me…traveling. I have considered actually going back to some of the original places I went to in my first year of travel to see how I’ve changed, how the destination has changed, and how tourism has changed. Or maybe a career break for someone who moves around all the time is to simply sit still for a year?

Writing a Book…Proposal

Holy shit…I have no idea if I can weave a story out of 10 years of living as a nomad or not, but I’m going to try. Even though I think my life is just pretty normal, others seem fascinated by it – so I’m going to test the waters and see if people really do care to read about it. This fall I’m working on a book proposal for an agent I started working with! Let me be clear – this is a proposal…not a book. If someone likes the book idea and wants to publish it, then I work on the book.

Most mornings I wake up and think – Fuck – I can’t write a book! How do I organize it, what have I learned, will it be something people want to read, how utterly honest am I capable of being, and how in the world will I ever slow down enough to even focus on it?! However, like most things in my life, opportunities present themselves to me on a platter, and I typically take them and see where they lead me. When a friend of a friend tells an agent about my lifestyle and the agent contacts me interested in a book version of it…then you go with it. She asked me to put together a book proposal for her to shop around and that’s what I’m doing. Once again…holy shit.

Coming Full Circle

In my first year of travel, I had the revelation that I didn’t want to go back to my old cube life and instead wanted to stay on the road and keep traveling. My challenge was trying to solve the issue of how to make money and keep traveling everywhere. I’m happy to report when I put my mind to something I normally achieve it – and clearly, I did in this instance. Now I’m moving into a phase where I know that I want to find a home base to support my travels, I want to slow down a bit and change the pace of travel and motion. But once again I’m plagued with the same question – how do I do that and make enough money to maintain a home base?

Here’s the one thing I know…I will figure it out. I’ll figure out how to make it all work because that’s what I do best. I’ll figure out how to keep doing what I love, to be kinder to those I love, to be more grounded, to make money, to hang up my clothes again and have a place to call “home sweet sometimes home”, to keep writing stories, and to keep showing the world to people who are interested in seeing it, and to keep traveling and finding that newness I crave. And I’m excited to see what new things get added to that list.

Never in my wildest, wildest dreams would I have predicted that my life would take these turns and twists back in 2006 when I left NYC on a one-way flight to Kenya. Who knows what year 10 will hold!

See where I came from in my series of “This is Sherry” posts through the years…

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