How to Break Up with Your Job

I quit my job for a new and drastically different career opportunity. It was hard. Like, breakup hard.

I was in an especially vulnerable spot in my life when I first started the job. I had just moved back from New York City after working at a non-profit organization, which explains why I returned to Minneapolis just as broke as when I left it. My broke-ness explains why I took the very first corporate job offered to me out of necessity. I kicked off the new position with a winning recipe – a lack of experience and a heavy dose of imposter syndrome. My solution was to spend 99% of my life obsessing over my career, desperate to exceed expectations of my boss and hoping it would mask the fact that I didn’t know what the f*ck I was doing.

To my amazement, It worked. Within a year, I was promoted. Within another year, I was promoted again. Once, after working with the Chief Marketing Officer on a particularly stressful project, she took my hand in hers, looked me straight in the eye and said in a deadpan tone, “you can never leave here, Allie. Promise me?” *queue uncontrollable blushing and general awkwardness* Of course, she was kidding. But there, underneath the sarcasm, was a sentiment I hadn’t experienced in my professional career. I had stumbled upon a job that valued me. Validated me. Loved me, even.

Having a boss tell you that you’re needed and valued is intoxicating, even for the most confident individual. For an imposter syndrome sufferer like myself, it was like a drug. The problem was that I didn’t love my job back. Not unlike a first boyfriend, I was so charmed by how the job felt about me and how that made me feel in return that I ignored how much I dreaded the actual work. I had let my insecurities, paired with an addiction to validation, push my career in a direction that I hadn’t planned nor wanted it to go. Just as rational people stay in obviously unhappy relationships for far too long, I realized I was in danger of staying in an unhappy career.

Breakups, even when they’re right, are miserable things. (I would know – I could write a Tolkien-length novel on tough romantic breakups.) No matter the circumstances, there are always lingering feelings of guilt, regret and pure, unfiltered sadness. When faced with quitting my job, I couldn’t help but feel like I was breaking it off with a long-term boyfriend. Insecurities started to cloud my judgment. “Am I giving up something good for the wrong reasons?” “Will I ever see my coworkers again?” and the worst one, “what if I suck at my new job and everyone can tell?” (hello again, imposter syndrome!)

I felt so overwhelmed by doubts, I almost retreated into the safe option that bored me to the core. Instead, I trusted my gut. It was a huge personal win for me. By walking through the below exercises, I found a way to silence my self-doubts and let that risky gut intuition lead the way. If you, too, are sitting at a romantic or professional crossroad where your decision is clouded by fear or insecurity, I’d recommend trying them out. It helped me pull the trigger. And although I have to wait to see if it’ll pay off, I haven’t looked in the rearview mirror, since.


How to Know When It’s Over

  • Ask yourself – “what would I advise my best friend or family member to do?” It will help you remove your irrational personal attachments and see your choices with fresh eyes.
  • Identify the emotions that are in play regarding the situation. Can you separate out your short-term emotions, like fear, from your long-term ones? Hone in on those longer-term emotions to get to what your gut has been telling you for a while.
  • Create a list of questions for yourself surrounding the decision at hand. Then, write the first answer that comes to mind. For example, on mine I wrote, “how would you feel if you turned down this new job” and the first answer that popped in my head was “sad.” Boom. Easy. Done.
  • Journal. I know, it sounds corny. But I promise that you don’t have to write the words “Dear Diary” to reap the benefits of a good journaling session. By actively putting my thoughts to paper, I was able to come to terms with how I really felt about the more difficult things in my life.
  • If all else fails, listen to mood-appropriate music. It’s one of the most intrinsically intuitive art-forms out there and the right soundtrack can help any situation. Feel free to borrow my Break Up with Your Job Playlist on Spotify if you need a starter.

Photo by Antasia Galka

Allie is a Minneapolis-based digital marketer, lucky enough to make a living by hanging out with really smart people and coming up with disruptive, technology driven ideas at space150. Her passions include traveling, coffee, books, feminism, obsessing over the dog she just saw on the street corner and trying not to blush at inconvenient moments.