Asking the Hard Questions

I've begun asking myself a question recently that has proven to be both useful and a little nerve-wracking. In examining where I am in life and where I want to go, I've started asking: To what end?

The question applies to many areas of my life - to what end am I going to this social event? To what end am I pitching this story? To what end am I challenging myself to a month of not eating grains? It's been quite helpful in getting clarity on certain decisions and being more mindful about my daily activities.

But most importantly, I'm trying to apply it to some of the bigger questions, like what I'm doing professionally and where and how I'm living. And that's when things start to get a little scary.

Photo by Martin Dörsch

Photo by Martin Dörsch

What Am I Building?

I'm a freelance writer, but to what end? Presumably the writing I am doing now should be building toward something, should be part of a body of work that can be used to achieve a next goal. But what is that next goal?

At the moment, my work assignments vary dramatically: human rights, tech in emerging markets, business writing for American companies. Each brings their own rewards, but I'm realizing that creatively, I sometimes feel stretched a little thin. My clients are great and I enjoy the different types of writing, but switching back and forth several times during the week can be draining, a fact I wasn't conscious of until recently.

When I first started freelancing, I welcomed assignments of all kinds, partly to pay the bills and partly to experiment with the type of work I wanted to do. Freelancing meant I could take on any number of projects in vastly different categories. In these first few years as a freelance writer, I've reviewed infusion vodkas at a slew of bars in Beijing, worked on a documentary series about manga artists, ghostwritten books, interviewed Indian princesses, and went ziplining in the Thai jungle. And that's just to name a few of the freelance adventures I've enjoyed. I've also been privileged enough to work with some truly lovely clients — and learned how to spot a bad one a mile away.

One thing I didn't stop to consider, however, was whether I intended to make freelance writing a career. I started out hopped up on the thrill of working for myself, making my own schedule, tackling whatever stories seemed interesting or important. But I never asked myself - is this what you want to do long-term? Do you want to spend the next few decades bouncing from assignment to assignment, pitching here, applying there, tackling radically different topics day to day?

If I had asked myself that question a couple years ago, the answer might have been yes. Of course, who wouldn't want to live the glamorous life of a freelance writer, always taking on whichever assignments the wind blew in? But asking myself that question now...I'm not so sure.

Writing brings me tremendous joy and release, and I can't imagine a time when I won't be doing it. But as I question my motivations about why I'm taking on this or that assignment, I'm realizing there is a possibility that what I'm writing and for whom could drastically change in the next few years.

I've had a vision of the type of writer I am and want to be for so long, it's hard to get comfortable with the fact that my writing goals may be changing.

To what end am I doing some of the work I'm doing? Sometimes I don't know.

The same question can — and should — be asked of the expat nomad lifestyle I've been living since early 2010. Traveling the world had been a dream of mine since childhood, and I've had the incredible fortune to visit countries I never even imagined seeing. And there's still so much more I want to see. But recent events in Thailand forced me to confront a question that's been lingering for awhile but I've never examined full-on: Is this still the right lifestyle for me?

The freedom to travel and live where I want is a great privilege and I realize that. This is by no means a bitchfest about the perils of digital nomad-ism (though that is a subject worth discussing). Rather, it's an examination of the assumptions I've lived on for the past four years: Of course I want to travel and live abroad indefinitely. Of course I want to keep freelance writing. Of course this nomadic, wherever-the-wind-blows lifestyle is perfect and fulfilling and I would never change it.

I don't know that I want to be nomadic forever, but I also don't want to move back to the States and work a 9-5 just to make ends meet. I also don't want to get a corporate job that makes me more than ends meet, but leaves little time for life-enriching pursuits and more meaningful work. Obviously these are not the only two options, but the question makes me uncomfortable because before now, I've never really considered what the alternatives might be.

But it's time to start considering them because to not examine how I'm living is to betray one of the most important goals in my life: to live more consciously.

The Unexamined Life

When you write from home in a country where your rent is $120 a month, a week's groceries cost less than $15, and the weather is always warm, it's easy to let the days slip by unnoticed. One can bleed into the next and the temptation to put off deciding on future plans often overrides the voice saying, "Are you sure this is what you want to be doing with your life? Are you sure this is where you want to be?"

Until, of course, that voice asserts itself in a sustained burst of anxiety that makes your heart knock around in your chest so hard you want to puke, and sparks a vicious nail-biting session that ends only when you've hit skin. Then you realize, OK, maybe it's time to sort some things out.

But the sorting of those things is fucking scary.

We get into routines, and unless things become really terrible or we have a total meltdown, it's easy to put off tough questions like, what are my long-term goals? Is what I'm doing today truly furthering my happiness and getting me where I want to be? Am I being too complacent, ignoring feelings of restlessness or doubt in favor of present comfort?

Every day may not be a great one for meditating on these thoughts, but a regular check-in helps us not let years go by without making that big move to a city we've dreamed about living in, actually writing the novel that's been in the back of our minds since we were 15, or training for the marathon we've talked about running since college.

Tackling these questions takes time, energy, and introspection and after a long work week or in the face of a more interesting social engagement, it's easy to file those tough quandaries away for another day. The problem is, "another day" may never come, or may come when it's too late to make certain changes happen.

One of my cousins passed away earlier this month. He was only 30, with his whole life ahead of him. It's shocking when someone dies that young, and everyone talks about how "it really makes you think." We go about our lives believing we have so much time to do what we want to do, that it's OK if we let another week, another month, another year go by without taking action. No doubt my cousin thought he had more time to make changes, to do the things he dreamed of. His death was a tragedy, but if I can take anything positive from it, it's to live consciously, don't assume you have forever, and do the things that matter to you now.

Is taking stock of your life and disrupting your habits hard? Oh yeah. But walking around unconsciously will fill you with regret, and those unasked questions and unfulfilled hopes will eventually catch up with you.

Singing the Homesick for America Blues

I've put off my own much-needed life examination for a few reasons.

Without my realizing it, the location independent freelance traveler lifestyle became such a part of my identity that it's kind of terrifying to think of doing anything else. Whenever longings for a semi-permanent home of my own begin to swell, I tamp them down.

Sure my current apartment is small and sparse, and my "mattress," if you can call it that, feels like a cinderblock. But hey! At least I'm living abroad. At least I can afford my own apartment. At least I'm in Thailand. On and on the cheerleading goes, drowning out those nesting instincts for another day.

A home, the voice scoffs. Who wants their own home? You're traveling the world; the whole fucking planet is your home! You don't need comfy couches and nice comforters and an oven and food processors and those other domestic items you occasionally have weird borderline sexual fantasies about. You just need to stay on the road.

Photo by Dominik Martin

Photo by Dominik Martin

And the voice is partly right. I love visiting new places. The discomfort of living in a foreign culture has become normal for me, and reassuring. I thrive on the rush of arriving somewhere completely new, exploring it, finding my way.

But I am also beginning to crave some kind of stability, in the form of a place I can call my own. This may be because for the past two years, I've lived in a perpetual state of uncertainty about how long I'd stay in Thailand, never fully settled into the idea of being an expat here. The chance that I would want or need to pack up and leave in a month or two was always at the back of my mind, and I suppose that's starting to catch up with me.

Perhaps more terrifying than the nesting instincts are the occasional rose-tinted longings for life in America. The part of me that assumed I would be traveling or living abroad indefinitely balks at the mere suggestion of wanting to move back there. Just visiting last fall was kind of weird and disorienting, so the idea of living there sometimes seems completely outrageous.

Live in America again? Bo-ring. Why would you resign yourself to that normalcy when you could keep living anywhere else in the world?

Again, this part of me has a point. In many ways, I am living my dream by being abroad. It would be a mistake to radically change my life because of a severe bout of homesickness.

But it would also be a mistake to ignore these new and growing desires. Goals and circumstances change, and that's totally OK. It's even exciting - sometimes the things we don't plan for end up changing our lives in the most spectacular ways.

A New Identity

As I alluded to above, part of the reason the idea of making a radical life change is so scary is that being a traveler, being a "digital nomad" in Southeast Asia, feels so much a part of my identity, I'm afraid of being without it. I'm also afraid of appearing as though I copped out of this cool way of living and seeing the world.

Which, when examined, doesn't make that much sense. Change doesn't necessarily mean moving back to America. It doesn't necessarily mean getting a J-O-B job and doing the whole 9-5. It doesn't mean plugging back in to the way I lived before I moved overseas, as if the past four years never happened.

Rationally, I know change has the potential to be incredibly exciting because I'll get to take the best parts of my current lifestyle and combine them with whatever new pursuits and locations best fit my goals. But in order to do that, I have to become OK with the idea that maybe I've outgrown the lifestyle I cultivated for the past four years and am ready to do things a little differently.

I'm only really beginning to grapple with these competing desires and don't know what the outcome will be. Maybe Thailand is still the best place to be and my focus will be on pursuits I can nurture here. Maybe America is the right option for awhile, because it offers benefits and possibilities out of reach in Southeast Asia. Maybe the right next destination and professional opportunity lie somewhere in South America or Europe. Maybe I should continue writing about a wide array of topics, or maybe it's time to home in on some key areas I want to build a body of work around.

These are all valid and exciting possibilities, and I don't think there is a bad choice. The wrong choice would be to not choose at all, to continue on my current path without really examining if the road I'm on is bringing me real joy or if there might be another path I'm ready to walk.

Photo by SCHICKA

Photo by SCHICKA

Asking to what end am I doing X thing? scares me because it raises so many possibilities that could be great in the long-term, but painful in the here and now. I know that's how some of the best, most rewarding decisions in life are made, and that's encouraging.

The prospect of change even stirs nervous but happy energy inside, which probably means there's some really good stuff brewing. Now it's time to commit to doing the hard work to find out what that good stuff is.