About Claire’s Holiday

That’s me on a 2,000 Percheron draft horse named Justice, in Homer, Alaska circa 2017.

My story is a familiar one. I realized I needed to be more intentional with the things that bring me joy. It’s different for everyone. For some, it’s raising children, for others, it’s tending to their beloved pets or growing organic foods from a vegetable garden.

For me, it’s learning through discovering new adventures (and connecting with people), mostly in the form of travel.

I’ve been lucky enough to experience a lifetime of memorable experiences, from Thailand to Switzerland (two of my favorites) to all around the U.S.

As each year of my life went by, however, the frequency of trips lessened, and I found myself consumed with the daily grind of work, and the “I don’t have time for anything” downward spiral. My reality was stressful, unhappy and anxiety-filled, simply because that’s how I had unknowingly made it.

I admit I was feeling some major FOMO, but more than that, I pictured an elderly me, wishing I had been more thoughtful and self-aware in my younger life.

I decided to travel more often, but more than simply going somewhere on a plane, I did it with more intention. Not just for travel, but everything in my life. This includes minimizing and downsizing so I’m not overwhelmed with unnecessary stuff.

This blog is about my travel adventures in 2017 (and beyond) and marks the end of relying on others to travel with me. It’s also a random collection of observations made from being more present in life — little lessons, pleasures, and a-ha moments.

How it all started

I was like most people, stuck in a busy career and consumed with the everyday stresses caused by work, life, and eventually the big question of what will I do with my life?

I still don’t have the answer to that, but I do know what travel would’ve provided for me. Travel was my platform to grow as a person, but also push aside my fear. Fear of experiencing something new, being alone, traveling alone, getting lost, and relying on myself. And not to mention I had a fear of going broke.

But the more I thought about it, the more I knew I wanted to travel. And when I say travel, I’m not talking about one that’s attached to approval from a manager, or the typical 2 weeks-out-of-the-year-travel. I’m talking about traveling every single month.

I deliberately made this my goal for 2017, and even though I didn’t know how I would do it, I told myself I would travel and learn new things (including snowboarding), cultures, meet new people, and expand my capacity for growth as a human.

I quit my full-time job

The first thing I did was figure out how I would quit my full-time employment. While I loved the people I worked with, and the company I worked for, it wasn’t realistic for me to travel as much as I wanted, even though I would be working while traveling.

I don’t care how cool your boss is, this just won’t happen if you’re expected to be in the office full-time.

So I started looking for contract positions that would allow me the flexibility to be remote, and as luck would have it, the travel gods were on my side. I found a contract job, and was lucky enough to be able to stay on with my last company as a remote consultant.

From there, I hustled and networked, and landed a few more awesome clients that allowed me to finally be out of the office for good. When I think about it, I still can’t believe it all happened in four short months. I was in my make-it-happen mode so I booked trips to Seattle, Ireland, and Alaska.

I booked more trips, and flew to NYC and tacked on a weekend trip to Montauk and then Montreal. I also visited New Orleans, Australia, New Zealand, and Spain.

I also started my own company in the process, mostly for tax reasons, but also because I wanted to make it official that I’m finally flying free.

Work while travel, it can be done

The next challenge I faced was fine-tuning my work-travel balance. How do you see a new city and get your projects done? I decided to read and learn every single productivity and focused-based method to enhance my concentration levels and get more done in less time.

Here’s an article I wrote about the best ways to be productive.

This is still a work in progress, but I got pretty good at sightseeing and finding time to work at least 4-5 hours a day. I wrote about it here.

I’ll continue filling up these pages with new posts and adventures, so stay tuned…