Making the Leap: Transitioning from Employee to Independent Contractor

The proverb "look before you leap" is usually sage advice and one that is commonly understood in the English language. The phrase admonishes you to consider the consequences of the decision you're about to make—a decision that might be hasty or risky. Sometimes, however, looking before you leap can cause unnecessary pause and it's better instead to go with your gut—in other words, trust your intuition. That's precisely what I did when I decided in late 2021 to make a monumental change in my career; I transitioned from being a full-time employee to an independent contractor (IC). Admittedly, I leapt without looking (or at least I didn't look very much) and have never second guessed my decision. While I'm not encouraging others to make such an important decision in the same manner, for me it worked. It was the right time in my professional and personal life to make such a change. The Backstory For the 20+ years after graduating college, I held jobs in traditional employment settings. You know the drill—I went into an office (until hybrid was a thing), I received benefits such as health insurance, retirement savings plans, paid leave, etc. For me, that's really all I knew for those 2+ decades, and it provided a sense of security and normalcy. I was doing what everyone else I knew was doing. I was somewhat aware of people taking other paths—for example, someone I supervised ultimately left the job to become a freelancer and start her own business. […]