When the Next Chapter Closes: Dealing with Mid-Career Failure and Starting Over
Late last year, I finally made the leap. After 13 years in a county government job, a position I’d long since outgrown, I accepted an offer with another city. The decision was easy: the old job was stagnant, and I was desperate for professional growth. I practically bulldozed the exit door when the offer came in.
I was ready. For years, I had proactively sought out leadership classes, taken on extra projects, mentored new employees, and completed courses. I was doing everything I could to excel in local government.
But six months into my new role, I was blindsided. My new employer decided not to continue our working relationship.
The outcome was failure and expulsion.
The Crushing Weight of Professional Disappointment
The past year has been a deep dive into uncertainty. After being let go, I spent months navigating a brutal mix of resentment, depression, anxiety, and an overwhelming sense of inferiority.
I had tried my best, and my best hadn't been good enough.
I live in Florida, where my only immediate options appeared to be insurance sales and hospitality. Being forced to look outside of local government and pivot careers in my mid-40s has been anything but easy.
I had always imagined a "midlife crisis" to be about a rush to achieve great wealth or acquire flashy things—a last-ditch effort to prove success. I was prepared for that. I was not prepared for professional failure and this level of crushing disappointment. The only conclusion I could reach was that this was my fault for daring to try something different.
I felt as shattered and useless as a broken mirror.
Putting the Hat Back On
The darkest part of the journey has been questioning everything—especially my original decision to leave. Yet, I’m trying to reframe this forced reset as a positive thing.
I’m working part-time in a new field now, a slow, small income that keeps the bills paid (with a bit of help from my retirement savings). I’m reaching out to friends and contacts, getting more involved in community volunteering, and simply trying to put one foot in front of the other.
While I’m not sure, I regret leaving my first job; it is unfortunate how things turned out. I’m being forced to start over, and it feels daunting.
But I’ve been thinking about Winston Churchill, who famously failed at multiple careers before becoming prime minister. He defined success as "going from failure to failure without a loss of enthusiasm."
I wonder if, during his lowest periods, Churchill ever had to drive past both of his old, failed offices five times a week, just to rub salt in the wound. I wonder if he ever felt the regret that things hadn’t turned out how he’d planned.
I think he probably did.
But then, he put his hat back on and got back to the job of living.
It seems like a good idea when nothing else makes sense.
What I’m Learning on the Other Side of Failure
Professional Growth is a Risk: Seeking a better opportunity doesn't guarantee success. Sometimes, the risk leads to a dead end, but the attempt itself proves your courage and drive.
Failure Doesn't Define You: One outcome, even a painful termination, doesn't erase a lifetime of acquired skills, dedication, and leadership.
Community is Key: Reaching out to contacts and volunteering has helped pull me out of isolation and create new potential pathways.
If you’re struggling with a professional setback, remember: you are not your job title, and you are not your termination letter. Putting the hat back on is the hardest, but most necessary, next step.