How to Break Up with Your Job

Career Development

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.


BY Allie Arends - March 8, 2017

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Thank you for sharing your experience and tips, breaking up with our jobs happens to all of us. I’m lucky though because at this moment, I LOVE my job!

Charmaine Ng | Architecture & Lifestyle Blog

March 8, 2017 9:35 am

I loved my job. I lived for it. Then I had a baby. Husband was very depressed (he wasn’t working) and I couldn’t keep up with his state, a baby and a more-than-full-time job. I quit and we moved to the south of France. I think I mourned my job/career for a good five years. Now I think it was the right move, both for him and our kid, and downsizing has wiped out more than half the jobs at my old employer so I might have be out anyway. But at the time, it was HARD.

March 8, 2017 10:54 am

Great ideas and writing. Thank you!

March 9, 2017 7:44 pm

What an awesome article. sometimes fear serves as the stickiest glue to keeping us “stuck” at a certain job. however, i absolutely loved reading your advice and the exercises you suggested. thank you!

March 9, 2017 8:02 pm

Love this. Ironically, it’s therapeutic for me now. I’m a big fan of yours. Always will be!

March 16, 2017 8:42 pm

I hope that you are loving it at Space – great article! 🙂 How true it is……….. some places have a very ‘Hotel California’ impact on the soul.

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