It all started with a simple question: What if?

On my 39th birthday, I was angrily drunk, raging alone in the wee hours. I seethed with “it’s all downhill from here” getting-older resentment. Then I suddenly wondered, “But… does it have to be downhill? What if… it wasn’t? What if… I changed?”

The next morning, I decided to change my life. I began watching foreign movies, following travel social media accounts, using beautiful destinations as my laptop’s wallpaper. I researched foreign currencies, visas, living abroad, travel tips, flight pricing and more.

Before “What if,” I was recovering from two major car crashes, a blown back and a traumatic brain injury that changed me forever. I’d been mired in debt, lost in anger and resented the enviable lives of others. I used to be the kind of person who saw people living amazing lives on Facebook or Instagram and I’d block or unfollow those folks because I was so bitter about their good fortune.

After “What if,” I’d never be that person.

Within three years I had reversed my finances, sold everything and became the kind of person I’d recently been fan-girling over. I worked my job while chasing self-employment on the side. I toiled six days a week. Every time I woke up wanting to crawl back in bed or have a day off rather than work, I reminded myself of the dream I was after. If I learned anything then, it’s that having success means choosing to work for it, and then making that same choice every single day after that.

I celebrated my 42nd birthday by selling everything to travel solo and work remotely.

And after 22 months and 16 countries, I reorient nearly monthly. Every relocation means a learning curve. These can be tedious things, like learning how shower knobs work or what’s involved with getting a local cell carrier plan, but there’s delight to be found too. Like the thrill of the first time I rolled out of bed in my thousand-year-old Istrian hill town loft and saw the valley below swallowed by fog as the sun rose over surrounding mountains. Or when I discovered a perfect Sarajevan cafe for working in, with delicious cheap food and a server fluent in English who greeted me by name by my third visit. I’ll never forget how discovering that Morocco’s Islamic call to prayer would cause me to stop nightly for a moment of gratitude I hope I’ll always be able to summon.

The price of freedom is often equally wonderful and frustrating every time, but after three weeks I find my groove and then enjoy the familiarity of routine for a spell. From language challenges to day-to-day weirdness, my life can be fraught with strange struggles. 

We all dream of fleeing problems, but the reality is that problems give chase no matter where we are. Real life hasn’t gone away just because I’m living the “dream.”

A week before my first nomad anniversary, my father died before I got home for a visit. His death capped nine months of financial grief, too, thanks to my lowly Canadian dollar crashing as soon as my travels began, making my life 15 percent more expensive overnight. Not long after the crash, I lost my primary income because the company I worked for was bought by a multinational that replaced our writing team with a marketing department. Earlier this year, I had emergency surgery in Albania. Trust me, nothing toughens you up like major surgery alone 5,000 miles away from home.

And next year will bring new struggles, because life doesn’t stand still just because I buy one-way tickets to exotic lands. I know this, and anyone opting into this dream needs to know it too.

Life, money, your body – they all have a different plan than you do, wherever you are. But is that any reason to give up “the dream” and stay rooted in a safe, unfulfilling, routine life when, deep down inside, you fantasize about unleashing your inner-explorer for globetrotting?

Hell, no. I’d do this all over again.

There are often struggles and challenges, but the best travel days are days and moments that defy expectation and that I’ll remember forever. Like the day I emerged from a whisky tasting in Edinburgh, Scotland to hear a bagpiper playing Braveheart‘s theme on a cool, clear February night. I cried in gratitude as I thought “this is my life.”

I couldn’t have imagined arriving at Pula, Croatia’s Roman coliseum on a windswept November day to find that I’d have the whole place to myself for two amazing hours. I sat on the same dirt floor where gladiators once battled, while I read a book and enjoyed the incredible silence where Roman citizens once roared.

And I could never have planned the uncanny luck of all of the other guests at a Portuguese beach house AirBNB canceling their stays, giving me the whole luxurious five-bedroom beach house for 13 nights, for just $515, including a swimming pool, and both an outdoor and gourmet indoor kitchen.

Sometimes the wonder of travel is as simple as a Greek taverna liking my patronage and giving me a half-litre of red wine whenever I come by. Other times, I small-talk with a local and get an impromptu walking tour. Often, I’m given a home-cooked meal or asked to join my hosts in a toast of grappa or brandy. Just as often, I head to the highest point in a city so I can survey all that’s around me and remind myself how very far from home I am.

I’m 44 in a couple months. I’m over 650 days into this crazy life of being “home-free,” traveling the world and I plan to continue it until 2020, my 47th birthday. 

As I type, I only know the start of what my fall and winter will entail. It begins with being toasty in Bali, but I’ve only booked a week’s stay. The rest of six months in Asia will unfold naturally and life will show me where to go. Once, that would have terrified me, but these days it’s the only way to live. For now, anyhow.

I never imagined I’d restart my life so dramatically at 42, but everything became possible with two little words: “What if?”