I was lucky enough to attend a talk with author Elizabeth Gilbert at the American Library in Paris this week. Among many of the life-changing things she had to say about living and writing and men, the most poignant was that she hoped all of us would learn to use the phrase “this isn’t working for me.” It’s as easy as that, in work and in life, “this isn’t working for me.” You can’t argue with it, and if someone does, they’re insane (still her words, not mine).
It’s with this in mind that I kick off this monthly series about walking away from things that aren’t working for you. A nice way of saying, articles that will inspire you to quit. There’s a lot of inspirational Substack content out there about how to keep going, how to build, how to optimize. But if you’re not on the right track, doubling down just takes you in the wrong direction, and faster (that’s a mixed metaphor, and no, I shan’t fix it).
That said, quitting is harder than working harder, especially for the overachievers among us.
With that, here are some of the inspiring odes to quitting that inspired me to keep going on my path away from the career I once had, toward the one that still feels less safe.
“Working hard is keeping you poor in everything that actually matters.” You’ve likely already heard of this viral Substack article, wherein Leyla Kazim of A Day Well Spent did no work for a year, and no one noticed. Her takeaway is that we need to admit to ourselves that our jobs are a farce, and instead of trying harder (which we’re not paid for), or killing time (which wastes our time), we can acknowledge this farce and do something more with it.
“Clocking many miserable years is no reason to push through more miserable years.” As someone who wishes they could quit everything and just write, and also a fellow serial completionist (is that a word), I needed to read this post, The Sunk Cost Fallacy of Your Career. Emily J. Smith didn’t quit everything to write, not at first, but she does encourage us to not stay in a career just because we picked it and have invested so much time and energy. The sunk cost fallacy shouldn’t guide business decisions, nor careers, so just quit before you waste any more time.
“Self-employment increasingly looks less like a risk and more like a legitimate career track.” I wish I’d read something like this before I quit everything to become a freelance brand strategist over six years ago. I eventually, slowly, painfully learned every one of the lessons from Ines Lee’s post “A Mini Guide To Self-Employment”, but it took a lot of effort, especially as someone who had only ever worked internally at large companies and had a lot of built-in guardrails. Set yourself up for quitting success with this post.
“If money is the only success metric we track, any temporary dip will feel like danger.” Iwana Johannsen blew my mind with this exploration of external security vs. internal safety, a must-read even if you are totally happy in your career and aren’t contemplating a change. In “The Five Pillars of Work: How To Feel Safe Without A Job” she posits that many of us don’t pivot because we’re afraid to lose the external security of that salary, when what we really need is the internal safety to know that we will make it through whatever comes. In a volatile job market where companies no longer have our backs (did they ever?), cultivating the right type of safety is crucial. She also provides extremely practical guidance for creatig an internal safety framework before you make a change.
”My calendar was empty, my inbox was quiet, and I wasn’t sure who I was without the title, the team, the thousand decisions a day.” Ariel Kaye built Parachute from the ground up, and now she’s figuring out what to do next. Her launch post for her new Substack explores that sensation of falling when you walk away from the thing that defined you and gave you a sense of self worth for so long. It’s a helpful read if you’re in an in-between place and need a reminder that you’re not alone in that uncomfortable place.
Great read. The more people putting these types of messages out the better.
What a great collection of articles! Thanks for rounding up and sharing!