How I decided to go freelance — and everything I did to prep
Because “feeling ready is a myth” doesn’t help you make big life decisions.
Have you ever fantasized about getting laid off?
Throughout my adult life, I’ve reveled in my ability to make my own decisions. But sometimes, the thought of having a decision made for me sounds pretty luxurious.
At the beginning of 2025, I found myself dreaming about getting laid off more than I like to admit. I knew I wanted to leave my job to try self-employment, but I was scared.
I reasoned that it would be easier to attempt something new if my stable job were pulled out from under me. Imagine I were fired, pursued freelancing, then failed. I could have blamed it on my circumstances, not a choice I made with my free will. That’s a pretty convenient narrative, don’t you think?
Fortunately, I got over my fear, quit on my own terms, and have built a lucrative business over the last six months.
The choice to move towards risk is a tough one — and it’s something that comes up regularly in my office hours. Many marketers are considering leaving their jobs to pursue a freelance career, but they’re unsure what they really want and if they’re ready.
I’m going to borrow an idea about “readiness” from Haley Nahman of Maybe Baby. The topic is pretty different from what I cover in this newsletter, but stick with me.
As a new mom, Haley gets a lot of questions about baby readiness, as in, “When is the right time to have a kid?” Instead of framing the answer as a simple yes or no binary, she describes it as four bar charts, with each chart representing a different kind of preparedness.
The decision to leave your job is obviously different than deciding to have a baby, but I think a similar framework can be surprisingly useful.
When I chose to pursue self-employment earlier this year, I was excited one second and terrified the next. That’s a pretty confusing emotional landscape to navigate, but I found my energetic readiness was only one part of the equation. Fortunately, the other parts were much easier to measure.
Today, I’ll walk you through the dimensions of readiness I used to evaluate my decision, and exactly what I did to prepare for my freelance transition.
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