I’ve built my career on worst-case scenarios. And notoriously, I have no chill.
When I talk to early career people, I often say that every major move in my career has been the result of rejection: I was denied raises, passed over for promotions, or laid off. The doors slammed behind me, and there was nowhere else to go but forward.
As a person from a flyover state without family connections to the industry, my response in these moments was to dig my heels in and figure it out. What that looked like in practice was loading up my schedule with extra freelance work, working six days a week, and always keeping an eye out for new opportunities. It paid off — through a blend of hard work and extreme luck, I managed to get the jobs I’d dreamed of having earlier in my career.
So last year when I decided to quit my job and go freelance, I called upon that old standby hustle. I made a spreadsheet calculating how much I’d need to make each month to cover my bare minimum living expenses. That would be my minimum income target. Then I added $500 to that number — a modest monthly contribution to my savings account that seemed possible. That number became my high-end monthly income target.
Then I filled out the rest of the spreadsheet: One tab for everyone I knew who could possibly offer me work and a note of the last time I spoke to them; one tab to collect pitch calls I saw on Twitter; one tab for story ideas and another tab for long term project ideas; and a tab for tracking invoices.
I set myself up for my first year with two anchor gigs: developing and launching podcasts for Defector Media, and writing this newsletter. Between the two jobs, I would be able to hit my monthly target income without taking on additional work. If everything fell apart, I would still be able to pay rent.
But despite my meticulous planning, something happened in this first year that I didn’t anticipate: it went better than expected. One of the podcasts I developed turned out to be Normal Gossip, which has quickly become the most successful podcast I’ve ever produced. And even though I didn’t need to take on additional work, I did. I sold essays, wrote a magazine feature, did sensitivity listening and freelance podcast editing, taught university classes and workshops, and helped expand the business of the Normal Gossip podcast. I also said no to a lot of work and was able to pass it along to friends. Even in my leanest months, I made more than the bare-minimum-plus-savings income requirement I’d set for myself last year.
Because I still live with a cool cocktail of mental illness and trauma, every day wasn’t perfect, but somewhere along the way I learned that my definition of success in this current version of my work life looks completely different from how it did when I was a full-time worker.
Which brings me to today.
Last week, I sat down to write the last newsletter for my contract with Poynter. The plan was for me to take a break this month and come back in September for a second year. But as I tried to write, I noticed a voice in the back of my head saying “it’s not too late to back out.”
What?
I didn’t know where this was coming from. I was excited to keep going! I ignored it, but it kept interrupting me. I couldn’t get further than two sentences into my essay, so I decided to take a moment to journal about it.
A question I try to ask myself when I’m making a difficult decision, especially one related to work, is: “Does this decision come from a place of scarcity or abundance?” When I asked myself that question about continuing to write this newsletter, the answer was clear: The decision to continue came from a place of scarcity, a place of fear about what the future holds, and a belief that what comes next will be worse than what has come before. Scarcity mindset comes easily to me. It’s a familiar groove my brain has formed when it comes to making any professional decision.
But this year has taught me that I might not need to rely on that hustle to survive in quite the same way. Through a combination of luck, privilege (like being married and childless, living in an affordable city, and not having student loan debt), and the compounding results of my hard work, I looked up and saw that I’d achieved far beyond my hopes.
In the process, I have also had periods where my workload was almost untenable (16 podcast episodes produced and released in three months while teaching and writing features and this newsletter!!) Once your basic financial needs are met, thriving is often about more than making as much as humanly possible. I realized that if I wanted to thrive, I needed to be more deliberate about how and when I stepped on the gas.
There comes a point where holding too tight to the things that got you to where you are will start to hurt you. A chip on your shoulder can get in the way of your expansion. Living in yesterday’s survival mode can warp your present in ways that really mess with you (and make you pretty unpleasant to be around).
So this is my last issue of The Cohort. I’m going to spend more time focusing on Normal Gossip, which is quickly growing to almost a full-time job. I’m also developing some new podcast concepts and working on a book proposal. I won’t be far though; I hope to still contribute to Poynter and The Cohort in the future.
The spreadsheet-mongering, six-day-workweek, always-on-the-lookout-for-the-next-job version of Alex is one I’m grateful to; she got me to where I am. I still love spreadsheets and master plans, but I don’t need her to be in charge all the time anymore.
It has been such an honor to write The Cohort for the last year, and I’m grateful to the team at Poynter for entrusting me with this newsletter that means so much to so many people. I look forward to seeing how it evolves with its next writer, and I hope you’ll all stay in touch with me, too. You can follow me on Twitter @alexlaughs and you can subscribe to my personal newsletter here.
