Resigning from my corporate job was not a decision I took lightly. In fact, I agonized over it for years. Ran the financials, considered what I would do instead, developed my spreadsheets and To Do lists, and then ran the numbers again. Certain friends told me that I was a victim of analysis paralysis, and that I just needed to take the leap already.
Then fate took a stance and I was suddenly out on a medical leave for a temporary health issue that was simply debilitating (more on that in another post). Yet the health issue coupled with my best laid plans of several years finally gave me the clarity and courage to just do it. And so I resigned.
Yet while the medical leave was the tipping point, there were several other factors that had already prepared me mentally for the move.
I no longer felt challenged
I was doing the same work that I had done for years, but over time it had become increasingly less challenging and stimulating. I found myself missing work that I had done earlier in my career that felt less formulaic. I knew that this, over time, would cause me to become disengaged – which wouldn’t be fair to either myself nor the company.
I craved more flexibility
I had been in a position that had required many hours, being on call, and many late night and wee hour conference calls. In the beginning, it was exciting. I learned a lot and felt that I was on the cutting edge of what was going on. But over time it burned me out. The problem was the work was never-ending; it wasn’t like a project that has a distinct beginning and end – in that scenario, you may grind extremely hard for several months or even a few years, but at some point the project ENDS. In this role, there was and would be no end. Eventually, I had the opportunity to move into a new role that didn’t require on-call responsibilities, but by that point I was looking for more flexibility than what was possible. I wanted to focus more on accomplishments vs. face time.
I desired more autonomy
The business culture I worked in was very hierarchical, and I increasingly felt that we were doing a lot of things simply because somebody at the top “said so.” If colleagues explained why the directive may not be the best route, or provided alternative ideas, superiors would agree yet shrug and reiterate that it be done anyway without question based on who had assigned the task. There seemed to be a strong reluctance to voice an opposing viewpoint for fear that an executive may think negatively and it would hurt a career. This didn’t align well with my personal style.
I yearned to try something on my own
It had always been a goal of mine, but I had enjoyed career success and so that objective was always put on the back burner. But it never went away, and the older I got the more I felt that I wanted to at least give it a shot. I knew that Corporate America would always be there and I was confident I could return if desired; however I didn’t want to give up an opportunity to at least try to “go it alone.”
I wanted more control over my own life
After seeing layoff after layoff throughout my career, I learned that it can really happen to anyone. Although I was fortunately spared, it didn’t mean that I would forever be immune, and I didn’t like the idea of my entire financial future being in someone else’s hands. I felt that if I was going to put in that much blood, sweat, and tears into my work, then my ultimate success or failure should be contingent on me alone.
I was tired of the politics
You know what I’m talking about – the office grapevine, the rumors, who is advocating for who, who doesn’t like who, who is a direct of who – it is exhausting. Over time, I learned how to play the game well, but I never fully embraced it. I would cringe every time someone asked “Who do you work for?” or “What is your officer title?” I had the accepted accolades, but felt that it shouldn’t matter. Why should it matter who I worked for? And whether or not I was a VP? Should that have any bearing on the conversation at hand and how I was responded to? The short answer was it shouldn’t, but it did. And it all felt very inauthentic.
The numbers checked out
Earlier in my career, I couldn’t have resigned even if I had wanted to. I was just starting out financially, and had too many bills to pay and investments to make. But over time and with care, my husband and I were able to earn and save enough so that a cut in salary wouldn’t ruin us. Before I finally quit, I must have run all the numbers and talked to financial and CPA advisers 100 times “just to make sure” we could do it. And the bottom line was that we could. Of course, we would have to make some changes and become much more conscious about our spending habits, but it could be done. And it finally hit me that it would NEVER be enough money – whether or not I continued to work a full-time job. Meaning – we would always want more, want to earn more, want to save more. So as long as we could make it work with what we had, my husband and I were willing to give it a shot.
My children changed my perspective
Once kids enter the picture, priorities shift. After the 3rd birthday of my first son, it dawned on me that it was all going Way. Too. Fast. The first three years felt like a blur, a random collection of rushed evenings and errand-packed weekends. I wanted more time with he and his brother. And I understood that the time was precious – and that no amount of money in the world could ever buy that back. It pained me to think that I was paying a nanny for the privilege of time with my children. It all seemed so backwards. Yet I wanted to work. It was and still is extremely important for me that my children see me working and contributing. But I knew in my heart there was a better way. A mother working a job that she has outgrown is not the same type of role model as a mother who is working on things she is passionate about.
Fate stepped in
I’ve said it before, and I’ll say it again. Fate was the definitive tipping point. A perfect storm of events creating the final nudge I needed to make the leap.
Job Weariness + Long Time Desire to Go Independent + Serious Illness + Medical Leave of Absence + Nanny Unexpectedly Resigning + Unexpected Pregnancy = The Right Time
And so I did. It has now been six months since I’ve resigned (and over eight months since I last worked at my former job – due to my medical leave of absence), and I have not a single regret. I haven’t even experienced a twinge of the panic and anxiety I was so scared of. In fact, I wish I hadn’t debated what my heart was telling me for so long.
I’ve learned that there is a ton of freelance work available for motivated people willing to work hard. I’ve realized that the finances adjust. And I’ve developed an even stronger connection with my sons. They, in turn, now see a mother who works just as hard as before, but who is passionate and energized by her work. And personally, I’ve grown stronger and more resilient, less afraid to take a risk.
I don’t know where I will end up, or if I will return to Corporate America at some point, but for right now the decision to resign from my former position has been the best one I have made in a very long time.

