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6 Lessons I Learned From Quitting My Dream Job

by Kelley Sullivan

I was 25 years old working my dream job at my dream company and had just gotten a massive raise. I was living my best life in the perfect apartment, a block off Pearl Street in downtown Boulder, Colorado. Then I put in my two weeks notice, sold my car and most of my possessions (including my beloved DVD set of The O.C, Seasons 1-4), packed my life into two bags, and bought myself a one-way plane ticket to the other side of the world: Sydney, Australia. 

Some people, like my father, would classify this as a quarter-life crisis. Everything was going exactly to plan, so why did I shred the plan to pieces? Well, this was something I actually asked myself as I sat in my almost empty bedroom staring at two overstuffed suitcases crying because I couldn’t get them closed, but really I was crying because I was wondering what the heck I just did with my life.

It’s been almost seven years since that fateful, tear-filled evening, and as I now sit at the Boulder Coffee Co. Cafe in Rochester, New York working for a new dream company I can honestly say that quitting my dream job back then was the best decision I’ve ever made. 

Was it scary? Yes. Did I second… and third and fourth-guess myself? Yes. But the lessons I learned from it are invaluable. Here are my top six.

6 Lessons I Learned From Quitting My Dream JobLesson 1

If you stick to a plan, you’ll never know what else is possible. While I was working at my dream job at the time, looking back now I can see that in Colorado most days I was just going through the motions because I was sticking to the plan. I graduated college, finished graduate school, and went straight to work in the fictitious “real world” because that’s what I was “supposed to do”. 

However, once you ditch society’s timeline and start to forge your own path, you’ll be amazed at how many opportunities present themselves and how many new plans you can write. When I quit my job I could never have imagined at the time that it’d lead me to playing rugby with Olympic gold medalists, living on a remote island off the coast of Australia writing a children’s book, or becoming a certified English as a second language teacher and rekindling my passion for working in education. 

I’m not advocating for never having a plan, but I am advocating for being flexible with your plans. Unexpected events and opportunities are going to present themselves and sometimes they’re not at the most opportune times, so all I’m saying is don’t be so quick to dismiss something if it doesn’t fit into your original plan. It’s okay to pivot.

Lesson 2

The next lesson I’ve learned through my globe-trotting escapades is that you can have more than one dream job. As you go through different stages of your life, your priorities will change. In my early twenties, I wanted, and had, a career where I was traveling around the country multiple times a month. Now I’m exhausted just thinking of an early morning airport commute or trying to pass the time during multiple layovers. And that’s fine. Back then I wanted a jet-setting job since it served the lifestyle I wanted. Nowadays I’m a new dog owner, planning my wedding and just bought my first house, so I’d prefer to stay in one place for more than a month. 

Lesson 3

That being said, lesson three is that it’s okay to walk away from something you once loved, guilt-free. If it isn’t serving you anymore, you don’t have to stay. It’s human nature to change and evolve, and the same is true with our interests and passions. They change.

Think about it. When we were kids our dream jobs changed ALL of the time as we explored the world and learned about what else was out there. One day I wanted to be a marine biologist and live on a houseboat in Hawaii and the next I decided I was going to be a professional soccer player (thank you, Mia Hamm). Back then the possibilities seemed endless, yet as we grow older we put ourselves into such small boxes and strict lanes that we force ourselves to stay in. But why? Take time to step back and re-evaluate what brings joy to your life.

6 Lessons I Learned From Quitting My Dream Job


Lesson 4

As you move forward, remember that it’s never too late to catch your dreams. And yes, I said catch instead of chase because isn’t that what dreams are all about, achieving them? It might sound cliché, but it’s never too late to start something new. Don’t believe me? My colleague’s 90-year-old grandfather just published his first book

I thought at 25 years old that moving to Australia would be a horrible professional choice, that it’d be a resumé killer. I figured I was too old to leave the corporate world and move abroad, even though it was something I had wanted for so long. When the opportunity presented itself I almost said no. Luckily, I had told so many of my friends and coworkers about my Australian dream that when I had the chance they made sure I went out and caught it. So go pull out that old bucket list from the back corner of your mind and pick a dream to go catch, or better yet, add some new ones.

Lesson 5

The fifth lesson isn’t pleasant to admit, and saying it makes me sound like a preaching parent: life isn’t always going to be easy. When I was living abroad, my friends stateside were constantly messaging me about how perfect my life seemed, living footsteps from the best beaches in the world. Well of course it looked perfect because that’s what I was posting on social media. I still had bills to pay. I had to miss weddings, births, and deaths of loved ones. I felt friendships slipping with the physical distance. I had injuries, illnesses, and even a mystery bug bite that landed me in the hospital. However, we are so used to seeing everyone’s curated and glamorized versions of their lives that we can fall into the false narrative of telling ourselves that our raw, unedited lives aren’t enough.


Lesson 6

Lastly, the sixth lesson I learned is to stop focusing on what you’re doing and focus on why you’re doing it. When you can pinpoint your core motivations and more specifically your career values, it opens you up to more opportunities to choose a meaningful path. I realized I didn’t have a “dream job”, but I did have “dream values” that were important to me. It didn’t matter if I was coaching rugby or teaching English, I discovered that I value jobs that are people-oriented and that empower others. When it comes to working, the why is much more important than the what. So figure out the reasons why you enjoy doing certain things and then seek out opportunities that align with those values.

What was supposed to only be one year in Sydney turned into two and then my visa finally expired and I moved back to the United States. Am I advocating for you to quit your job tomorrow? No …unless you want to. But I am advocating for you to take these six life lessons with you as you move forward.

  • If you stick to a plan, you’ll never know what else is possible.
  • You can have more than one dream job.
  • It’s okay to walk away from something you once loved, guilt-free.
  • It’s never too late to catch your dreams.
  • Life isn’t always going to be easy.
  • Stop focusing on what you’re doing and focus on why you’re doing it.

So there you have it. Six lessons I learned from quitting my dream job.  And as for me? I might still have flight alerts set for Australia because, hey, you never know.

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