I’ve written many times about how I started my own business in 2022 after I was laid off from my marketing job. But in reality, that’s not struck out on my own. The first time was when I was 23 years old.
I was working for a financial technology company. I liked the company and the product, but I got a new boss, and she was awful. I was so stressed all the time. As much as I liked the job, I didn’t think I could keep working there.
The company was located in Kansas, but let me work remotely from Wisconsin. I loved the arrangement. Remote work was uncommon at the time. I knew that if I left, finding a similar job might be tricky. There were no tech companies in my small hometown in Wisconsin, and my husband was still finishing college. I felt like I was stuck, at least until my husband was done with school and we could move elsewhere.
At the time, I was leading software implementation for community banks. Projects were often up to 6 months long, complex, and involved many people. The culmination of the project was traveling to a bank location and spending 3 days on-site, training employees.
One bank mentioned in passing that they would love to hire me as a consultant to get more dedicated help. It seemed like a way out of my current job situation. I spoke to the bank’s vice president and said, “Were you serious about that offer?” and he told me, “Yes.”
I decided to quit my job to work as a consultant. Once I was done with that project, I would move on to the next one.
When I told my boss that I was quitting, the company’s COO reached out to me. She told me that she thought we could work together. I could stay on payroll and keep my health insurance. The company would process the payments from my consulting contracts, take a cut, and pay me the difference as a bonus. There was a benefit to the company also: they could offer their clients my services as a consultant. I agreed.
I spent six weeks at the first bank location. Another bank ended up hiring me for almost three months. They put me up at a corporate apartment near their headquarters in Jefferson City, Missouri.
It always worked out, and I was able to get the “next project.” I did everything myself, from scoping the agreement to negotiating with the bank. I rarely interacted with my employer-on-paper. I even read a book about consulting. When one bank wanted to extend my contract, but for less money, I replied, “Sure, that’s fine. Then let’s figure out how to reduce the scope.” They re-signed at the original amount proposed.
But being on the road 100% of the time was really hard. Corporate apartments were boring. Since each stint was temporary, I never got to know the town or found anything interesting to do. And I frequently went back to Wisconsin on the weekends.
Then my direct boss quit. The COO reached out and asked if I’d like to return to my prior role. I negotiated a salary that was equivalent to what I was earning as a consultant and agreed.
Once I became a regular employee again, I stepped into more contract negotiations and defined the scope for custom projects. That work excited me because I was good at it. I stayed at that company for 15 years in part because they gave me opportunities over and over to define my own path. I became the company’s first product manager. Later, I managed the entire customer service department and carved out what that role would look like for me. I left, in part, because I ran out of ways to grow.
So while I wasn’t technically self-employed as a consultant, I was functionally on my own. I had mentally prepared for self-employment at the time I quit. Even though it ended up being a brief stint, it was an indication early in my career that I wanted to chart my own path.
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