How I Quit My Job To Travel the World

It was a hot Thursday afternoon in late July. I sat down with my boss in the tiny focus room on the 16th floor of our insurance company’s headquarters. Boston’s South End neighborhood rolled out under us, the heavy traffic moving sluggishly in the heat. I took a deep breath and told him I would be leaving my position in one month to travel long-term.

And then I felt a jolt go through me – I had done it.

I had quit my job to travel the world. 

It’s the stuff of a thousand self-discovery movies: heroine marches into her sleek office, tells her boss/coworkers/the whole company off, and heads off seamlessly into the unknown. That looks great on screen, but the reality is much less glamorous. So what’s it really like to quit your job to travel, and what do I wish I had known before I left? Let’s find out. 

Solo female traveler on a beach in Crete Greece at sunset
The Greek beaches were pretty glamorous though.

How to quit your job to travel the world

First, the quitting part – it was undramatic. I actually liked my job, loved my boss and my coworkers, and was very well-paid and had four weeks of paid time off a year (a wild rarity in America). So I was not the typical stereotype of the put-upon corporate drudge. 

I didn’t love every aspect of my job, of course – internal communications is often a frustrating field. But I really liked the executives I worked with at the insurance company – a far cry from my finance communications job, where once I had to call a coworker while I was in tears and he was at the grocery store at 8 pm on a Tuesday because a higher-up had decided to go on a rampage purely as an exercise in emotional terrorism.

This job wasn’t like that. Generally, I was happy and creatively satisfied and made a whole bunch of money for a woman with only a bachelor’s degree in English.

Shock and awe

So quitting wasn’t a time for storming anywhere. I wasn’t leaving because I was unhappy in my job – I just needed to see what else was out there. I took my boss into one of the tiny rooms we used for private conversations in our sea of open greige cubicles, and told him the news – with a full month of notice. He was sad to see me go but he’s a big traveler himself, so mostly he was excited for me. That kindness was no surprise. 

What did shock me was the reaction from my coworkers once we told the communications department – how many people told me they admired me, were proud of me, were jealous of me. And the number of my twenty-something coworkers who told me they wished they could do the same thing. These were people who didn’t have husbands or wives or children or houses tying them down.

It was then it hit me – how many people are really afraid to do what they want to in life. I just wanted to shake them and tell them “hey, we’ll all be dead someday! Do what you want now!” But instead I smiled and gave a sigh of relief that I’d finally worked up the courage to do this. 

Getting ready to get out on the road

That next month was hell. Those movie heroines do not, apparently, own things or they have staff to handle them. Me? No such luck.

Lion statue on a bridge in Budapest Hungary
My face after this hot and panicked August.

It was the hottest August on record in Boston, which already gets really fucking hot in August. My ancient apartment had no air conditioning. So I sweated through every step of packing up and getting rid of my old life. I had decided to discard as much as possible, thanks to the advice of my friend Emily who’d moved to England a few years after college. “You won’t want pretty much any of it once it’s gone,” she said, and she was right. 

A lifetime of stuff on the sidewalks of Boston

The IKEA furniture I’d bought on Craigslist because I’m cheap, the high heels I only wore in the office, all the kitchen things I’d accumulated from Goodwill and friends and my grandma – I didn’t need them anymore. And storage is expensive – $55 a month at the cheapest place I could find! So out it went. 

I donated loads of clothes, saving only one box of my favorites in silk and cashmere and linen and one fancy pair of Miu Miu flats. I winnowed my bookshelves down to one box of my favorite books. All my nicer clothes went out to be resold by ThredUp (other sites may give you more money, but they make it so easy).

And most of my furniture, aside from a few things I sold on Craigslist, went to my younger cousins who were setting themselves up in Boston. It felt right to have these simple but sentimental things used by people I love, who were grateful for them. My friend Sejal who was taking my cat Seth got a bunch too. And I spent hours disassembling my complex IKEA bed, which I left on the street. 

Long Beach in Gloucester Massachusetts in the summer
I did cool off a bit up in Gloucester, on the North Shore.

This sorting and editing and packing and moving took up most of my spare time that month, and pretty much all my spare energy. It was exhausting – how many things I’d accumulated even in a tiny apartment, how much I had to think about, how much I was leaving. Just at a time when nearly everyone in my life was becoming more grounded, more settled, I was doing the exact opposite. 

So after the endless sorting, imagining what the person I’d become after this trip would want to come back to, and the purging of a lifetime of stuff, I was empty. I had one box of clothes and one box of books, and that was it. I was ready… almost. 

Read more: the 10 things I couldn’t have lived without on my trip, and the 5 things I definitely didn’t need

 A few last steps:

  • I got my final checkup with my doctor before I left to make sure I wasn’t leaving with any unaddressed issues. I didn’t have any ongoing prescriptions to worry about – I had gotten an IUD earlier that year, and all I take regularly is allergy medication which is easy to find abroad. (It’s also so much cheaper outside the US, as is basically every medication.)
  • I also saw a travel doctor at my office’s clinic. She went over health risks in the countries I was planning on visiting, and told me which shots I needed. This will vary for everyone – for example, I didn’t get a rabies shot because I stay very far away from dogs and I wasn’t going far off the beaten path. If you’re in the US, the CDC has a good site to start with. And other countries have similar recommendations on their websites. I should have gone earlier, because sometimes you need two shots spaced out and I ended up having to get one in France. But they were very helpful – they also gave me a prescription for anti-malarials (which I ended up not using) and antibiotics in case of a bad stomach bug. 
  • I got travel insurance! This isn’t just important for cancellations and delays and lost luggage, though that’s a great benefit too. If you get really sick while traveling and need to be transported home or to a different country (if I had been really sick in Laos, I’d have to fly to Thailand to receive any care), it covers those costs. Literally life-saving, in many cases. And I used to work in insurance so you know I got it. I used World Nomads which was great, though I never had to file a claim (those over-the-counter parasite antibiotics were $3!). 
  • I purchased a few (very few!) items to get ready for my trip – much less than almost every travel blogger says. A sturdy, comfy backpack, a few necessities, and nothing I didn’t need.

Other things I should have done before I left:

  • Get a Google Voice number before leaving the US, which is currently the only place you can sign up. Change all your important bank and social media verifications to that number so you’re not locked out of your account. This was a huge pain point for my first few months, especially with my banks, and wasn’t solved until my friend Hannah – whose 7 month journeys through Southeast Asia were a big inspiration for my trip – suggested Google Voice. You can access it anywhere you have WiFi. No matter how many local SIM cards you swap out (I had 13 different phone numbers this year!), you’ll have one constant one you can use for 2-step verification. 
  • If you won’t be working, and you live in a US state that offers it, sign up for health insurance there too before you leave. I got fined $600 last year for not having insurance! And it was free through MassHealth. If you live in a state that doesn’t give you this option… I’m sorry, America can be rough. Healthcare abroad is generally much cheaper!

One last party for my parting

So, that’s my job quit and my life purged. And a bunch of fairly painful shots (typhoid OUCH). Emily threw me a going-away party on my roof deck, where the after party consisted of me drunkenly shoving the last of my items (stray forks! An open pack of snack-sized ziplock bags!) into the arms of my departing guests, and rolling my remaining scratched-up chair down my tiny stairs and out into the street.

Emily and I emerged the next morning bright and early, sweaty and exhausted. We found someone had ripped all my trash bags into shreds on the sidewalk while we slept. Some strange old man was pawing through my disgusting old workout leggings, holding them up for inspection like they were prized goods. He made off with a pair of them. I still think about it occasionally and shudder. 

Then it was time to drink all the Dunkin iced coffee I could and hug my nieces and nephew and my tiny grandma and my parents and my friends one more time and tell my cat I’d be back for him soon. And I was off to the tiny TF Green airport in Rhode Island, bound for West Cork.

Airport goodbyes.

Lessons I learned that you may find useful if you want to do the same thing:

  • I did not miss almost any of my stuff. I couldn’t now, a year later, tell you exactly what I got rid of (except my pair of Uggs, which I miss every winter. Keep your Uggs). I gave my most sentimental things to people who would love and appreciate them. My cousins still text me pictures of them drinking G&Ts out of my 1950’s gas station glassware, green and Greek-themed. It makes me just as happy as possessing it used to.

    I saved only my very loveliest clothes, and came back from my trip to open a box full of silk and cashmere and Miu Miu and my Chloe and Gucci bags. That was heaven. And I say this as a deep, deep lover of clothes and books – less is more. But do save the very best. 
  • You will not know, in planning for your return, what kind of person you will become on your travels. Fortunately I am still a person who loves silk scarves and books. But I thought I would return to Boston and a normal life again. I have not, and I don’t plan to for a while. So if you’re saving things “just in case”, remember you can’t know what future you will do or want. You’ll want maximum flexibility, 
  • Once you decide to quit your job and travel the world, you’ll probably have at least a few months to plan. I took nearly two years. Start changing your habits right away. I stopped buying clothes and books and kept all my shitty second-hand IKEA stuff when my friends were all upgrading. I stopped accumulating, which left me with less at the end to purge.
  • Don’t burn bridges when you leave work if you like your job or your company. My company couldn’t promise me a job when I got back – it was a time of crazy change. And I wouldn’t want it now anyways. But I worked hard up until my last day, and left behind a whole bunch of people who would happily hire me again. That’s key for re-entry, and also recommendations for future jobs too. My boss I quit on gave me a great one and it helped so much!

    It’s easy to think, oh, I’ll never come back. Time to send that snarky company-wide email I’ve always fantasized about! (Or those long rambling internal social media posts, we internal communicators lived for those.) But really, you don’t know what you’ll find in your travels. Maybe it will make you love home more than ever. Keep those options open.

Quit your job and travel – gracefully

So in summary, be gracious and flexible and generous and thoughtful. I had a few logistical things I could have done better. But overall I stayed true to my values when I left, and I’m still proud of that. Keep your relationships strong and your belongings minimal. 

Quitting my job to travel the world wasn’t easy. It required summoning up an enormous amount of courage, and also watching a creepy guy paw through my leggings on the street. Plus all that heat-stroke and all those shots. And way too many goodbyes. 

A stone column and green valleys on a hill at Peel on the Isle of Man
If I have to choose between these Isle of Man views and a job, it’s not a hard choice.

But you know what? I still recommend you quit your job to travel the world too. All those hot sleepless nights and the sadness of leaving and the pain of dismantling a home and a life I’d built for myself – they were more than outweighed by the joy and growth and beauty I found in my year on the road

We never get any time on this earth back. And we have no idea how long we have left on it either. So now is the time for living fully and courageously, whatever that means for you. What will you do with your one wild and precious life?

This Post Has 2 Comments

  1. Chris

    So happy for you that you got to live your dream! And great advice for anyone interested in following in your footsteps. Keep on traveling!!

    1. Katwoman634

      Thanks so much Chris! Such kind words!

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