What it Actually Feels Like to Quit Your Job to Travel


I said my goodbyes, left the office for the last time, and walked immediately into a taxi bound for LAX.

My one-way ticket to London was the only thing waiting for me when I got there. That and a mild what-am-I-doing-with-my-life thought tornado.

I still can’t decide if I recommend this direct-to-airport strategy for travelers or not, but it’s what I did and it’s the story I’ll tell today. This one is for the person who daydreams of the day you can quit your job to travel, of walking into their boss’ office with a one-way ticket in their pocket, or of having the luxury to pursue work you’re genuinely interested in. Today, I’m sharing exactly what leaving my desk job felt like.

What It Actually Felt Like to Leave My Job to Travel

I planned to work until the day that I was getting on a plane bound for London. Needless to say, it may not have been my smartest decision. My things were in boxes on a moving truck somewhere in Kansas and my car was somewhere in New Mexico being driven by someone else. I had slept on a friend’s couch that night because my lease was up. Ironically, it was the couch I had just sold him a week before. 

I walked into work wearing an outfit I planned to throw in the garbage bank-robber-style on my way out the door, with a very conspicuous travel backpack strapped to my back. There was no disguising that I was quitting my corporate job to travel full time while rocking that style.

As you can imagine, I wasn’t the most productive of workers that day. In fact, most of the day was spent in meetings. Most of those meetings ended with a sad goodbye and well wishes and me blubbering about how much I would miss everyone. I had given notice more than a month prior, but these goodbyes still stung. 

I had daydreamed of the day for months and months, expecting to feel a newfound sense of freedom. I had imagined what it would feel like to strap that backpack to my back and walk out waving my goodbyes. 

It would feel like I didn’t have a care in the world, like I was finally “me" again.

Not the case.

I lingered at my desk after many of my coworkers had left already, trying to say goodbye to a few of my closest friends. I cried as I gave them big hugs, not knowing the next time I would see them. I practically had to set a timer to get myself to leave for the airport on time – not usually a problem for me. 

I called a taxi to drive me to the airport as I was changing out of my last work uniform and into my full-time traveler one. I was still sniffing back my tears as I walked out the door of the office for the last time.

My 10-minute ride to the airport wasn’t the movie montage type. The driver didn’t ask where I was off to or how long I would be there. I didn’t get a chance to stick my head out of the sunroof waving goodbye to Los Angeles or exclaim “I’m leaving for London on a one-way ticket!"

I rolled up to LAX with little fanfare, checked in to my flight with no issue, and called my sister and my parents to hear their voices one last time before my long 10-hour flight to Europe. I didn’t treat myself to an expensive airport meal or a celebratory drink. I just quit my job, remember? I just boarded a plane like everyone else did.

“Maybe it will hit me on the plane," I thought.

I got as comfortable as one can get on a transatlantic flight and settled in. The melancholy of leaving my friends was still with me. I read a book set in London. “Maybe that will make me more excited?" I thought. It didn’t.

I arrived to London and navigated the tube to my hostel. The last few trains were delayed, so it was the most crowded public transportation experience I had ever seen. I felt like an elephant in a china shop with my backpack on my back and my carry-on backpack strapped to the front. “What a dork," I thought, as dozens of pickpocketing horror stories flashed through my brain.

“I should have listened to those carry-on only travelers," I thought. Later, I’d learn how to be a carry-on only traveler. 

I checked in to my hostel (nice enough), showered (a little less nice, but I can do this), and unpacked (why did I bring all this stuff?). In short, I did what any normal traveler would do after a long flight.

It was only 4 p.m.

On a vacation, 4 p.m. would mean I still have time for one last sight to see. I have time for an expensive dinner and a few too many drinks. It would mean that I still have a few more lines left on my itinerary for the day.

That day, 4 p.m. meant finding the nearest supermarket to pick up some groceries. It meant googling the nearest park to picnic in for dinner. It meant grabbing my headphones on the way out the door just like I would have back home.

That’s when it hit me.

I wasn’t on a normal vacation.

I wasn’t trying to see it all before I moved on to the next town in two days time.

I was creating a new life. This life had grocery store visits and squeezing in workouts and enjoying the little things too. It had to-do lists and budgets just like the one I just left. 

The one thing it didn't have? A job dictating who I should be. I don't have to answer to anyone but myself. It's a reality that is both exciting and terrifying.

If I fail to be the kind of person that I said I would be as I daydreamed in at my corporate desk last year, it's me I'm letting down. Oh, but if I am true to that person, the one that travels with intention, that's all me too.

It's a different kind of freedom than the one I expected that day. It's not a “no cares in the world" kind of freedom. It's a freedom that lets you choose what you care about most.

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  1. Megan
    December 7, 2018 at 8:53 pm

    Love the inside peek at such a monumental day! xo

    • adobberteen
      December 12, 2018 at 1:27 am

      It was a fun one to write!

  2. Elizabeth
    December 9, 2018 at 8:35 am

    I love the idea of you dumping your work outfit in a bin on the way to the airport. I can’t imagine doing that, but it makes a great story.
    Thanks for this reality check. While I daydream every day of traveling long term, I never think of the realities of grocery shopping and budgeting and having responsibilities while traveling.

    • adobberteen
      December 12, 2018 at 1:26 am

      It felt pretty crazy to do! I’ve actually learned to love the responsibilities of travel. It’s been great to “live like a local” all over the world.

  3. Kristen
    December 13, 2018 at 11:08 pm

    Loved this! What a great insight at the huge difference between vacationing and full time traveling. It doesn’t just come down to what you see or do (or spend haha)…it’s also about how you feel. Thanks for sharing!

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