That Time I Quit My Job

Today, August 26th 2016 was my last day at Old Navy where I spent nearly the last two years, first on the international team and then on the social media team.

I’ve learned that the hardest thing sometime can be knowing when to throw in the towel when something isn’t working. This can apply to relationships, your job, your workout routine — having room to fail is what helps you to grow.

Failure has such a negative connotation in our society. Webster’s Dictionary describes it as “omission of occurrence or performance”, but really, it should be known as what happens in order to force change to create success. Despite knowing failure is natural and brings you to a place of growth, I still have a hard time giving up on anything. I once ran 20 miles on a stress fracture because I refused to accept that I was injured.

Staying at my job wasn’t working for me. I’m such a success-oriented person who needs to constantly achieve and when I wasn’t achieving at work, my whole life started crumbling around me. I felt like a failure because I wasn’t invested in my career anymore. My lack of interest in what I was doing made me feel like I wasn’t ambitious, I wasn’t driven, and that I literally had no business being in San Francisco anymore since this wasn’t working out.

I had a moment of clarity when I was home in Pittsburgh in July. It all came to me as I drove to my grandparents house one morning and it felt like a sign that I suddenly had all of the plans in my head — I was going to quit my job, move back to Pittsburgh for a few months, try to freelance full time and then come back to SF to work on a really exciting project with a friend. I told everyone my plan, they were all on board — even my dad. I wrote my resignation letter on the plane back to SF.

Yet I stayed. I started second-guessing myself because I didn’t want to lose the cushy paycheck. “Oh but I’ll miss being able to travel.” “I’ll miss getting my nails done.” “I won’t be able to afford SoulCycle.” Really shitty excuses when it comes down to my overall happiness. And really, they were excuses because I was afraid of taking a really scary leap into the unknown.

I just kept waiting around for everyone else to make a decision for me because I didn’t trust myself. Then one day my hand was forced and I realized — it’s not fair to anyone that I’m staying in this job. All my friends and family hear about is how miserable I am yet I wasn’t making a change. It wasn’t fair to future Cassie who deserves to be happy and do something with all of this talent. It wasn’t fair to my employer or my team, either. They deserved someone in that role who wanted to be there, not someone who was there out of self-induced obligation.

I was so jealous of everyone I saw who was writing, freelancing full-time, working on cool projects and desperately wanted that kind of flexibility in a career. It’s not that I don’t want to work hard and do awesome things, it’s just that I want to be able to do so on my own time and at the place of my choosing. I realized I’m the only person who’s capable of achieving living the life I want. If I want to somehow make six-figures doing work I actually give a shit about, that’s on me. But first, I had to get out of the situation that completely destroyed my self-confidence, my drive, my relationship and my motivation. So I decided to throw in the towel on my job.

That morning, I lined up the first bit of freelance work just to have some money coming in so I felt a lot more secure in my decision. I thought about taking a sabbatical from work but since I do have that desire to have a purpose and achieve, I knew that wasn’t the right answer (and truthfully, it was a relief when I realized I actually wanted to work, just not where I was currently working). I had told my therapist the Friday before I was finally going to quit. I told all my friends and family (for like the fifth time, I’m sure). But this time, I actually did it. And exactly zero part of it was scary. It was 110% a sense of relief.

I’m a firm believer in everything happens for a reason. It’s okay to have that existential crisis in your mid (okay, late) 20s. It’s okay to have it at any point of your life. I don’t know how this is all going to pan out in the end but if it wasn’t meant to be, it wouldn’t have happened this way. Life has a funny way of being cyclical and dropping you off right where you need to be and bringing and taking people to and from your life at the pivotal moments.

Quit your job. Buy that plane ticket. Write that e-mail. Submit your essay. Whatever you’re putting off because of fear of failure or fear of being hurt — just do it. If you’re feeling something in your gut — and you keep feeling it for weeks and weeks — your intuition is probably right. The worst that happens is you have a learning experience, maybe you have to lick your wounds for a little bit but life goes on. The best that happens is everything works out perfectly but let’s be real — being vulnerable and admitting what we failed at or what we’re not great at is what makes us relatable and human.

None of us are going to knock it out of the park in every aspect of our life all of the time but if we keep going, something we do is going to work out and get us up on the scoreboard.

11 comments on “That Time I Quit My Job

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Ashley @ A Lady Goes West on August 26, 2016 2:42 pm


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Lauren on August 26, 2016 2:45 pm

Way to go. It’s always hard especially because I’m the biggest second guesser but you do you and start another journey!

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Jordan @ the balanced blonde on August 26, 2016 3:14 pm

GO GIRL. I am so proud of you for this. And super duper stoked for you. This was the right decision, by a landslide. <3 xo

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Davida Kugelmass on August 26, 2016 3:17 pm

You better bet I’ll be referencing back to this post a lot when you forget these thoughts and try to go back to the old. No way jose ;)

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janelle on August 27, 2016 11:33 am

congrats cassie. I know you will do well! I’ve been there and I know the hardest choices reap the best rewards. Keep reaching


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Mattie @ Comfy Confident on August 27, 2016 6:28 pm

Good for you! I know the feeling you had a work and i am really inspired by how you were able to make the best decision for yourself. congrats! you should be proud of yourself.

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Dani @ Dani California Cooks on August 29, 2016 10:27 am

Dani @ Dani California Cooks recently posted…Tech that Keeps Me HealthyMy Profile

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ashley @ Fit Mitten Kitchen on September 1, 2016 2:14 pm

“but if it wasn’t meant to be, it wouldn’t have happened this way.”. 100% agree. Although I do have to remind my own self of that from time to time.
I think what you’re doing is awesome and so excited to follow along :-)

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Loren on September 9, 2016 12:02 pm

wow (ok the all caps is weird) sounds like you made the right DECISION! You take on the world girl! xo Loren //
Loren recently posted…What I Wore in St. Pete Beach, FL: Lace Up Crop Top & High Waisted ShortsMy Profile

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Terri on September 12, 2016 7:22 pm

Hi Cassie,
This is the first time I’ve read your Blog and I felt like I was reading my own story about quitting a job. I resigned from a college teaching position in April but needed to complete my contract that went until the end of june. So, now i’m trying to find a new career path. I just started blogging & podcasting about health related issue. but I am also seeking a job in higher education also.

Best Wishes for your future!
Terri Wenner

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