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When You're Stuck, and It's Time to Quit

Updated: Aug 1, 2021

I recently made some difficult career choices. I resigned from not one, but two jobs, both of which I had worked for the past five years. I was really conflicted about what the right course of action was, and it took agonizing spreadsheets, discussions with mentors, and finally a leap of faith. I will intentionally omit the details of my reasons for leaving, but in the most general of terms, I knew I was not where I wanted to be long term. My strategy had been to try to work and fix the problems to create a better space, and so a lot of my conflict came from trying to know when to dig in your heels to make something better, and when to break it off. I had quit jobs before, but they were always very natural resignations: I was moving, I was graduating, or I had clearly received a much better offer.

But when you’re not moving or graduating and you have no offer in hand, when do you know it’s time to go? And what about when all the parts of the job that grieves you being inextricably linked with those parts you love? What will happen to all the beloved relationships and hard work you’ve planted and watered? Will it shrivel up and die?

And I mean, the most salient question is, how will you pay for food? And your mortgage? If you don’t have something lined up, even if you feel all the readiness in the world, if you’re not able to pay those things, you can’t just jump to your utter financial demise.

It’s hard to get any clarity when everything is abstract and hazy, and I have gone through a lot of different listing systems and spreadsheets in the past several months, and these ones helped me to finally get to a decision. It’s hard to see past the next year, but in trying to pivot your life to grow where you want it to, it helped me to look at both the short term situation, and the long.

Should I go?

Short Term Pros: Short Term Cons:

Long Term Pros: Long Term Cons:

Can I financially go? Worst case scenario budget.

If I work two part time jobs, can we meet all the bills we have to? For six months? For one year? What can we go without (remembering that this isn’t for forever, but just for right now). Is Joe Biden trying to help me quit my job with the stimulus?

Where do you want to go as a person? How do you want to grow? Instead of losing yourself in impossible-seeming daydreams and cynicism, can you fill out some spreadsheets?

I was furiously composing a pro/con list when a relative mentioned that he remembers when he used to likewise be paralyzed by options, and now he realizes that it all works out in the end. But of course, while his path has ultimately led to success, not everyone’s is like that. And you don’t know how your story’s going to end until you get there. The smugness of success can numb you to others’ very real waterloos.

But beautiful spreadsheets can only take you so far. At some point, you have to realize that there will always be a level of risk and unknown, and you have to let go. You can’t know everything, and reassessing all the possibilities will resign you to nothing but stagnancy. You have to be brave and leap into the unknown.

So, I encourage you to think about where you want to be. What do you want to do? Do you want to be creative with songwriting? Do you want to work less? Do you want to run a marathon? Do you want professional advancement? Do you want a new best friend? Do you want to learn French? Do you want to go to Machu Picchu? Do you want to be a guest on a great podcast called Coffee & Creatives? Here is your plan.

  1. Imagine what you want. Talk with friends, write out your thoughts, and daydream a little.

  2. Spreadsheet the heck out of these thoughts.

  3. Be brave.


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