Will I Regret Quitting My Job to Travel?

i regret quitting my job to travel

I ended my 20s with a bang. I quit my job. Without another job waiting for me. I rented out the home I’d purchased just two years earlier. Sold my car and the majority of my belongings. I didn’t know what lied ahead. The only thing I knew is that I wanted to travel. And as I packed up a rental car to move back home before embarking on my initial goal of a year of travel, I wondered, “will I regret quitting my job to travel?” Before we go on, I have affiliate links in this post (World Nomads). This means that I use and love these products and think you could benefit from them as well. If you decide to make a purchase, I will earn a small bit of commission, at no additional cost to you.

Deciding to Quit My Dream Job

But before I tell you the answer, let me give you a little background on how I arrived at the decision to quit my job. My former job wasn’t just a job, it was a career that I decided to pursue as a 16 year old in high school. I listened to a career day lecture on athletic training and realized that I could help people return to their passion (sport) after injury or illness. Why was this important to me? Well, long story short, I have a heart condition that resulted in my removal from competitive athletics. Athletic training would allow me to help people in a way that I couldn’t be helped.This realization guided the next twelve years of my life. I attended a university with an athletic training program. While briefly toying with the idea of studying abroad, I decided against it because it would delay my entrance into the program (the school I attended was not cheap). I figured I’d travel after graduation.Well, after studying like crazy to pass the certification exam I decided to go straight into graduate school in upstate New York. I knew a master’s degree would enhance my skills and my job prospects and that I should take advantage of being in a school mindset. So, I would travel after I graduated with my masters. Instead, I graduated with a masters and secured my first full-time job in Detroit. Because I had school loans to pay back… I would travel someday.6 years and two solo trips later, I decided to leave all of that hard work behind. 

How Did I Know I Wanted to Travel if I Never Really Had?

Two years before quitting, I fulfilled another dream. I took my first solo trip to Ireland. Something changed within me during those 14 days in Ireland. I developed a yearning to see more of the world and believed that there had to be more to life than working 60+ hour work weeks. To confirm my desire for travel, I visited Costa Rica the following year. I figured this was a little bit further outside of my comfort zone and would test my ability to handle the rigors of travel.It did.My flight from Florida to Costa Rica was canceled due to a volcanic eruption. When I did arrive, a day later, I realized off-season travel in remote Costa Rica meant restaurants closed early and taxis to town were infrequent. I had to wait until noon the next day for my first meal in about 24 hours. Nothing like starting a vacay with a fast.The second thing I learned was that cash was king and I did not bring enough to pay for my accommodation. So after a few broken Spanglish conversations with the hotel owner, he gave me a grace period to go into town to use the ATM.The rest of the trip was smooth after these tiny bumps. And the remote location allowed quite a bit of time for introspection. It became clear that I didn’t want to return to my job. So, after 6 years of working in my former career, of living that dream I had as a 16 year old, the dream changed. Now, I couldn’t envision doing this career for the remainder of my life. And it was devastating.

READ MORE: about my first two life-changing solo trips to Ireland and Costa Rica

Reflecting on the Decision in Front of Me

I took quite a bit of time to reflect on the past 12 years of hard work. Remembering all of those nights I questioned my medical evaluations. Those sleepless nights spent in the ER with a student-athlete because their parents weren’t around. And answering phone calls and text messages on my one day off per week. I also really liked my boss and coworkers which made this decision that much harder. It took a lot of soul searching and running through what-if scenarios to come to terms with the fact that my dream job would not be how I continue to live out my purpose of helping people return to their passion.A very important decision lay in front of me, I could either:

    • Accept it. The job was comfortable, I had medical benefits and a great retirement plan. I knew, more or less, what each day would bring. I may not be genuinely happy, but it’s safe.
    • Change it. The unknown is uncomfortable. I had no clue what I would do and no guarantee that it would make me happy.

The best thing I did for myself during this period of reflection to get off of social media.I love those fabulous female travelers with their gorgeous photos on Instagram just as much as you do. That sandy white beach they’re on is even more appealing when you’ve been working 6 days per week for months. I unfollowed all of them.And got real with myself. I asked myself some fun questions such as: What kind of travel do I want to do? What did I want to get out of this? How could I make travel my reality? I also asked the hard questions such as: What if I hate it? How will I make money? Will I regret this? Once I realized that I needed to pursue this change, I started to find solutions to the hard questions… the “problems” this pursuit would create.

Factors to Consider Before Quitting

As a single woman with two cats and no kids, I didn’t have to worry about how this would affect a husband or child. Thankfully, the only debt I needed to pay off was on my credit cards; I’d paid off my student loans acquired when studying for the job I was planning to quit. Additionally, I had a just bought a home two years prior that I needed to decide whether to sell or rent. And Frankie and Jax, my two cats that I love dearly, would not make the best travel partners, so I struggled with finding a way rehome them. Finally, as someone with a heart condition, I can’t go without health insurance and need daily medication to keep it under control. So let’s break these down one by one to see what I did in hopes that it helps you determine your next step in each area.

Home Ownership 

As stated above, I owned a home so I had to decide whether to rent it out or sell it. This created a whole host of other items to consider, but without a steady income, I needed to ensure that I could still pay the mortgage. Ultimately, I decided to rent it out, which also provided a bit of monthly income. If you’re currently renting try to sublet your apartment for the remainder of your lease.


I was in a pretty stable place financially, with the exception of credit card debt.  Also, since I decided to keep my home, I needed to ensure I had money saved in case I needed to replace anything and for general upkeep. This money would not be used for travel. Additionally, I had a number that I was comfortable spending on travel. Then I created a budget to get me to each goal. I worked out how to minimize monthly expenses and create additional revenues of income while still working my full-time job. I also starting learning how to make money online or work abroad.


I had to figure out what would happen to my retirement account once I quit. I learned that I can continue to pay into the account, but obviously, I won’t have an employer to match it.

Health Insurance

Without employment, I would have to pay for the entire monthly premium for my health insurance coverage if I wanted to keep the same plan. Thankfully, I moved back to California and I was eligible for Medi-Cal a low-income health insurance plan.For coverage on the road, I purchased travel insurance throughWorld Nomads. I know many people forgo this, but I’m a firm believer that this is not something to mess around with. I’ve read some crazy stories about travelers who had serious medical issues overseas but had health insurance so they didn’t lose all their money and could receive quality care. Some weren’t covered and had major financial issues because of it. It’s worth the upfront cost and peace of mind. Hopefully, I’ll never have to use it, but if I do, I have it!

Frankie and Jax

The cats. I was originally planning to “return” one of my cats to the shelter where I adopted him. The other cat would go back home with me and live with my Dad while I traveled. As I went to bed the night before I intended to give one of them up, my Dad called to say I could bring them both!

The Day I Quit

After a considerable amount of time finding solutions to the worst case scenarios that my brain created, I walked into my bosses office with a quivering voice and shaking knees to inform him that I would not be renewing my contract. I almost cried, but I held it together. Going into that conversation, I was unsure of how I’d feel walking out of it. But I left his office feeling lighter and as if I was stepping on to the right path.Since that day, I traveled for 10 months. I hiked to Machu Picchu, swam with hammerheads in the Galapagos, and backpacked through many of the major cities in Europe. I also revisited my favorite country, Ireland two times. 

So, Do I Regret Quitting My Job to Travel?

Not once.I’m not sitting here writing this with rose colored glasses. I will be the first to admit deciding whether or not to quit my job proved to be a very difficult and emotional time in my life. And long-term travel has been even more challenging. Every day I wonder if I made the right decision, mostly in terms of my financial security. It’s difficult to maintain relationships when constantly on the move, or planning your next trip. And I miss my family, friends, and cats terribly when I’m on the road. But I don’t regret it. I’ve learned more about myself and the world in the past 10 months than in the other 29 years of my life. Traveling pushed open my physical, emotional, and mental boundaries. One of my coworkers used to make fun of my personal bubble. (I didn’t like it when people stood too close to me or even asked personal questions for that matter.) Traveling has popped that bubbled and forced me to confront my biggest fears. Quitting your job is not a pre-requisite to travel. You can travel while holding down a full-time job. It just wasn’t the path I wanted to take, nor could I as my profession is not remote work friendly.  If you’re considering wandering down this path, I highly encourage you to create space for reflection. Analyze why you want to leave your job, create a plan that addresses all of the important factors (ie: finances, health, and family), and take action daily with your plan. At the time, I didn’t know if I’d regret this decision. But I did know that I would regret not giving it a chance.

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Should You Quit Job to Travel
i regret quitting my job to travel


will i regret quitting my job

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