Ashley’s Workationing Story

My life on paper in NYC was pretty dope. After graduating university, I started my career in PR and then, in a very bizarre turn of events, made my way into the interior design world. I worked as a designer (which I had zero experience doing) in one of the most high end furniture stores on the market. I designed spaces for the wealthiest of families in NYC and celebrities which included Janet Jackson, Whoopi Goldberg, Sharon Osborne and the list goes on. My work with Sharon actually landed me a small cameo on Donald Trump’s Celebrity Apprentice. I, somehow, got bored of this and then switched my career over to recruitment. I went into beast mode in this job for just over a year….until the market crashed. And I guess you could say when the market crashed, my life took a backseat ride along with it.

I ended up going back to the interior design firm, which turned out to be a huge mistake. I was dating a guy that was emotionally abusive, I started drinking more than I should have….everything in my life just felt painful and wrong. I was miserable and I could see myself going down a rabbit hole of self-destruction, fast. There was a particular evening that I had consumed too much at a party and I ended up in a dangerous situation with the NYPD getting involved. It wasn’t my finest moment. But I remember thinking, this can NOT be it. This cannot be what my life looks like. So, I looked at a map and found the furthest place I could from NYC – a small island called Taiwan looked like the winner. Not even 2 weeks later I got fired from my job and bought a one way ticket to Taipei. I didn’t know a soul and had no job lined up but I was willing to take a risk on myself to hit the reset button and completely start over. It’s been 11 years since that moment and I’ve hardly looked back.

I lived in Taiwan for two years working as an English Teacher and Fitness Instructor. It was truly two of the best years of my life. I met incredible friends that became family, traveled all over Asia swimming with whale sharks, climbing mountains, nearly being kidnapped in Malaysia – the adventures (often times misadventures) were endless. But after two years, I was turning 30 and I was feeling this considerable pressure from family, friends, and society, to come home and “start my life”. I was getting this strange message from so many people that my life was just sort of a joke up until then. Like it was “cute” that I was playing in Asia and acting like a big kid. But now it was time to come home, adult up, work in an office, get a husband, buy a house, have kids….you know, all the “adult” things. I knew in my gut that that’s not what I wanted or needed, but I ignored that voice and started to plan my way home.

Thinking it would be my last life hoorah, I decided to backpack solo for 4 months through India, Thailand, Laos, Vietnam and Cambodia. Going solo was one of the best things I ever did for myself. I was absolutely terrified in the days leading up to my departure. I just kept repeating, “you can do this, you can do this, just one moment at a time.” And I was right, I was fine. I can go on later about what it means to travel alone as a lady in third world countries, but one main point is – you are never really alone. You meet the most incredible souls along the way that have the same burning love for life that you do.

After this life changing adventure, I landed in Chicago and immediately hated it. I was having panic attacks when I was traveling about re-entering this world. I was so afraid of fitting in again. And I will tell you, reverse culture shock is a thing. I think it’s actually often times harder than the original culture shock. I went to Chicago to try and reconnect with my childhood and college friends. But I learned real fast that that was going to be nearly impossible. These people moved on with their lives – new jobs, kids and a new set of problems that I just couldn’t relate to. And guess what, my stories of getting bitten by a monkey in Thailand and driving a motorcycle through the hills of Vietnam could not have been less interesting to them. We just had nothing in common anymore. It doesn’t mean we didn’t love each other, we still do, but our lives just didn’t match anymore. I was extremely lonely, sad, couldn’t find anyone to date – I couldn’t wait to get out of the USA as fast as I could. I lasted one year, and another very long and bizarre story later, I ended up in France.

I went to France with the intention of only staying for 3 months that ended up turning into about 5 years. And while I once again left everything behind, I brought with me this notion that I had to get married and have kids to validate my life. So, I went on Tinder and ended up dating the second guy I met. We moved in with each other after one month and ended up getting married 4 years later. The relationship was a disaster and never a right match and I knew that from day one. But my fear of NOT settling down outweighed my inner instinct that this was not the man for me. We married in May of 2018 and he left that October. I had one week to get my things together in France and head to the USA where I stayed with my parents for 5 weeks and then moved to Amsterdam – which is where I am now. If it reads like a whirlwind, it’s because it’s meant to, because it was. A rather painful one at that.

I need to point out that when I decided to stay in France, I needed to find a remote job where I could speak English. My French was terrible so there was no way I could work for a French company and we were living in a tiny village in the French countryside so there were no English speaking opportunities either. I called a friend I worked with in recruitment in NYC that I knew had started his own company. We chatted for a while and by the grace of the universe, he agreed to let me work for them on 100% commission. I was good at recruitment when I was doing it so I was confident I could get myself up and running in no time. Well, maybe it was less confidence and more of the fact that I had literally no other choice. This propelled my digital nomad career into what it is today. I have since been working 100% remotely in recruitment for about 6 years. I am currently the Head of Talent for Inkwell.co, where we are dedicated to matching forward-thinking companies with the best possible candidates to drive more flexibility, diversity, and meaning in the workplace. I was so excited to find this company as I have been a walking poster child for someone who needs 100% remote freedom to live the lifestyle I very much want to live; a forever Workation. I am now able to help people from all different backgrounds find jobs that allow them the freedom and flexibility they want and need.

Being a digital nomad is intensely amazing but it can also be challenging. There is A LOT of work that comes with having this lifestyle. Often the hardest part is just making the decision to leave everything behind and take a chance on yourself. But man, it is oh so worth it. I’m here to be an open book about what this lifestyle looks like – particularly as a single lady that’s still trying to sort out some heartache while traveling, working and living abroad. I’m here to help encourage and support all those brave souls just waiting to jump off the cliff and start their own Workation. I can also promise a bunch of weird tales and wild adventures to match. Stay tuned my fellow pirates.

“True pirates are people who pull away from the ‘normal’ way of life to experience a greater existence” – said a fellow traveler one of the first days I landed in Taiwan.

Follow Ashely Osmond on Instagram!