4 Misconceptions About Long Term Solo Travel

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I know it’s out-of-the-ordinary and unconventional. And for those of you that call yourselves remote workers, location independent entrepreneurs, digital nomads, gap year goers or any of the varieties of names given to those of us that have quit our jobs to pursue the road less traveled, even if only for a short time, it can be difficult to explain.

In the time I’ve left my job and started traveling I have been shocked by the number of people coming out of the woodwork to inquire about my new life and how I fund adventures. I have heard from distant friends I haven’t spoken to in years, curious as to how I’m essentially living a 24/7 vacation… and alone, at that.

Did you come into money? What kind of work are you doing? Do you get lonely? Is it hard not having a “home”? Don’t you want to settle down already? (You’re 33, after all).

So… while I don’t have all of life’s answers (if I did, I definitely wouldn’t need to work) and every day I learn a little more about myself, what I want and where my life is going – here’s all the dirty details and misconceptions surrounding this less-than-normal life.


Come on, you totally have a trust fund.

Psssh, I wish! No, I didn’t come into money. No, some distant relative/prince of Nigeria didn’t drop dead and leave me a huge pay out. I was able to quit my job because I worked my ass off. Plain and simple.

I have student loan debt from my expensive MBA. I was spending $2500 a month on rent in lower Manhattan. I still traveled and enjoyed 2am drunken karaoke with friends. I also didn’t get a cent from anyone else outside of Christmas gifts and birthday checks from my parents.

For nine long months, I would get home from my corporate job in NYC or wake up Saturday morning, crack open my laptop and work on my business so today I could be writing this blog while sitting outside in the Prague sunshine. Nothing beats good old fashioned hard work- trust me.

A perfect afternoon on the beaches of Nice, France

A perfect afternoon on the beaches of Nice, France


Awwwww. You must be so lonely. (And often said when asking for a “table for one.”)

This question makes me question myself. Should I be lonely? Should I be sad? Is something wrong with me for really enjoying the solitude of solo travel?

That’s the only reason I hate this question. Society is constantly telling us that it’s not okay to be alone. That something is wrong with you because no one wants to spend time with you – or in my case, travel with you.

I really don’t get lonely. I have amazing friends and family that are all a FaceTime call, G-Chat message, or WhatsApp text away. I am so thankful they want to keep me in their lives, even from afar.

Any remote worker will tell you that it’s important to switch up the alone time with some human interaction. There’s always another solo traveler I can find, a co-working space I can go to where people like me spend their days, or an International Meetup I can attend.

But most importantly, I really think loving yourself and your life means that you don’t really get lonely. I cherish so many more moments now, even when I’m alone with just my thoughts and beautiful surroundings.

Plenty of people watching to do in any square in Barcelona, Spain

Plenty of people watching to do in any square in Barcelona, Spain


You’re never going to settle down/find a partner/have a baby.

This is one of those taboo topics that isn’t often openly discussed but you know it exists through back-handed compliments, sympathetic looks between married friends, or intrusive questions… usually centered around unmarried women in their 30s.

Do I want to find a partner, get married and one day be a mother? Maybe... Maybe not.

For many people this is a life goal that must be sought out and if not reached by a certain age breeds panic and fear, and ultimately – the act of settling. And there’s nothing like settling for someone that isn’t good for you or to you that slowly sucks all joy from your life… I’ve seen it happen enough to people I love.

Yes, perhaps I’d find a partner more quickly if I settled in one place and really committed myself to the task but I would ultimately attract a partner that wants a life I cannot offer.

Seeking out happiness and love for yourself is the only way to find it with another person. And I’m already committed to living my “happily ever after” so if that Prince Charming never rides in on his white horse I’ll still be due my happy ending.


You’re going to have a huge gap on your resume now.

This is a bigger concern for most people than I ever thought it would be. Yes, you go to university and get a first-class education so you can find that perfect job in a field you picked playing eenie-meenie-miney-mo after a night of tequila your freshman year.

You know how ballsy it is to quit your comfortable job, give up your health insurance, and say goodbye to a regular paycheck to form your own company? There’s a reason why not everyone does it and most people give up long before they’ve even begun.

Smart employers get this. They will appreciate your new-found culture and understanding of international markets. They will understand how much work and perseverance goes into building a successful business. Frankly, you may get interviews from hiring managers wanting to know how you did it – the great escape everyone dreams of.

But the truth is… you will probably fall so in love with this unconventional life that you’ll never look back, and you definitely won’t give a shit what some hiring manager thinks about your resume.


So... what's holding you back?

A rare sunset view from my opposite coast in San Francisco, California

A rare sunset view from my opposite coast in San Francisco, California

Anna Grymes