Looking out over Sintra

My life, especially over the last few years, has looked less and less like the lives of the people around me. At 29 years old, I’m not married, I don’t have kids, and by all projections, neither of those things are happening any time soon.

I haven’t worked for Company X since I graduated from college like most of my friends. Hell, I haven’t worked for any company for more than about 18 months. I suppose job-switching is pretty common among the millennial-type, but is hopping off of the “real job” track more times than I can count normal?

I don’t stay in one place for very long. My longest lease was two years and even when I had that lease I was away from home more than I was there.

I don’t take vacations, really. I load up my backpack or suitcase and trek off somewhere to try to immerse myself in a new place. Sometimes they’re one-way tickets, often they’re tickets I bought on a last-minute deal. I figure it all out when I get there.

At this point, I don’t even have an address of my own. It just didn’t make economic sense. Most of my things are in storage and when I’m not traveling, I stay at my mother’s house.

I run my own business. That’s not that weird. It’s a little niche I’ve carved out for myself that gives me the ability to do all of the aforementioned traveling and moving. I work strange hours — whatever hours I want, really. Even people within my role/industry don’t get how I make it work because a remote Product slash UX person is kind of a mythical concept, and the idea that I can do what I do without being in an office is kind of unheard of. Yet I’ve been doing it for about 2 years now.

The majority of my “home” friends have stopped asking if I’m around to hang out because odds are I’m not even on the continent.

All of these things make me feel kind of different and out of place. Mostly in ways that make me wonder if I’m doing something wrong or if the people around me just know something I don’t.

People in my life think I’m lost or wandering or in search of something. I’m not. I’ve been living with great intention for a while now. This life is something I’ve envisioned for myself since I was a teenager. I have the lists of goals I made back then as a reminder. I never saw myself working for some big company and staying in one place. (Fourteen-year-old me thought I’d be married with kids by now, but that’s a different story.)

I don’t know what first introduced me to the concept of a location-independent life back then, but it’s the one thing that’s remained constant in all these years: The idea that I would build my own business that supports my lifestyle, lets me see the world, and do the things that I love to do. It definitely sounds like the kind of dream a wide-eyed 14-year-old would have, but I’ve held on to it.

At every decision point in the last 6+ years, I’ve secretly tried to position myself closer and closer to that dream. Some decisions have worked out better than others, but in the end, everything happened the way it needed to.

Now, at 29, I run my own business, I value my own skills (and myself) in a way that took me a long time to become confident in, and I make a living that fulfills me in ways that working for someone else never has. I’ve set up my life so that I can pack a bag and go to any corner of the Earth at the drop of a flight deal, and yes, I live a very transient life.

It took me a long time to be able to say that without feeling like an imposter, or even a fool of some sort. I never really talked about it much because it almost felt like I was getting away with something or that I was doing something I wasn’t supposed to be doing. And, to be honest, even though I dreamed about it for years, I never thought it would come to fruition.

I’ve shared my travels and various updates about my life, but never the rhyme or reason behind them, just in case it didn’t work out. There was always rhyme and reason, even if it was misplaced at times.

Last month, I met a whole group of people who live this same way. I knew the whole “digital nomad” thing was a bubbling trend, but I hadn’t encountered many myself.

I found my People.

Being around people who share some of my ideals, challenges, and even travel stories, sort of validated that this lifestyle is totally do-able and not as lonely as I’d originally thought. It renewed my faith and desire to keep going down this path I’ve set for myself and not be tempted by that cushy Silicon Valley job.

Now I don’t feel like my life is all that strange or weird. In fact, among this group of wandering independent workers, I’m one of the more stationary. Who’d have thought?

It’s radically different from what I’m “supposed” to do, but it’s what makes me happiest and most fulfilled. I don’t freelance because I’m filling a gap between “real jobs.” I don’t travel from here to there because I want the frequent flyer miles. All of these seemingly “lost” or typically-temporary parts of my life are intentional choices I’ve made about how I want to live.

I’ve reached the point where I’m OK with living this life unapologetically. I set my own hours. I work from and live in whatever part of the world I want. I often work in my PJs. I spend my spare time eating awesome food and experiencing amazing places. I’ve made friends all over the world. I’m proud of myself for being able to turn my crazy dream into reality.

It doesn’t seem like a very serious way to live, so it’s easy not to take it seriously. Building a sustainable business is no easy feat. I’m still fighting that battle. Traveling isn’t just fun and games and sightseeing and drinking with new friends. It can be exhausting and lonely and, yes, sometimes scary. There’s no manual on how to do this the “normal people” way. I don’t have the benefit of some windfall or trust fund or even a sizable savings account. It’s all trial and error and iterating over and over until it works.

These fellow nomads, who I now call my friends, inspired me to double-down on this crazy life. The first-time nomads reminded me of how far I’ve come already and how much I have to share about how I did it.

This is my real life, not a blip in my memoir. Maybe it’s something I’ll grow out of in a few years time, or maybe I’ll be writing said memoir from the comfort of my Airbnb space capsule when I’m 90 (I assume SpaceX will have made that possible by then.) It’s something I’ve made happen through a magical combination of luck, hard work, risk, and sheer stubbornness. I realize it’s a privilege to even have the option to live this way and I don’t take it for granted.

I love the life I’ve built for myself and I want to share the process with you. Living this way isn’t reserved for the rich or famous or completely care-free. I’m none of the above. I’m a pretty normal person with normal concerns about life, success, and happiness. I get questions all the time about how I do it. Over the next few months, I’m going to attempt to answer them.

I’ve already dipped my toes into it a few times with my travel how-to posts, but I want to be as transparent as possible with you about how I make my radically different life possible, from breaking down my goals to taking steps toward achieving them and all of the nitty gritty that comes to play in between. If you’re so inclined, maybe you can try to carve out a radically different life of your own.

Maybe, with more of us living this way, we’ll be the normal ones.

(📷 credit: Jay Meistrich)

Check out You Are a Product: Defining Your Vision, the first installment in this series!

Update: One of my fellow Hacker Paradise participants (and fellow Product gal, traveler, and awesome friend) Courtney Machi and I must have been sharing a brain earlier this week because she wrote and posted a similar article on the same day, but with a completely opposite outcome. You should definitely read it.