I have written in the past that comedian, columnist, and advocate Jenn Sterger is one of my online writing influences. We were at Florida State University at the same time. I was in grad school, preparing for a life in International Affairs when she arrived on – or was thrown into – the sports culture world. When I saw she had a blog and was writing for Sports Illustrated, I was inspired to also find a place to write online. Blogging was the thing to do and I was a former Writer of the Year at the Florida State student newspaper. Writing had gotten in my blood.
Fast forward twenty years (jeez!), and Jenn and I are still writing. Her move to substack, combined with a few conversations with my other writer friends regarding a push-mailing list-based blogging platform, led me to create my own substack, which is probably how you are reading this. Outside of writing, our careers have had some other parallels, albeit in very different fields. I am not comparing my trials, tribulations, and career turmoil to hers, but I will say that career-caused mental health is understudied and under-served. We both needed help to get through some tough times and we have both found solace in the creative arts.
Pause: if you haven’t read, listened to, or watched Jenn’s story, this is a good time to do so. Seriously, she is a warrior. Duck Duck Go is your friend.
These days, after years of survival and reinvention, Jenn is in the stand-up comedy circuit. She is kicking ass, and touring America with some of the biggest names in comedy. I’ve seen her perform in Tampa a few times with names that sell out arenas. People are discovering her now because of her comedy, and that’s what she wants.
Although I have never gone through the public scrutiny she has, I completely identified with a line she wrote in her recent blog post. When discussing how she thought of herself as a high achiever who couldn’t settle down anywhere because she was labeled “difficult”, she wrote:
“Maybe the issue was that I kept trying to grow in environments that were never designed for me.”
Woah.
First, let’s admit that I have never been called “difficult” and how that term carries different weight for men and women in the workforce. That’s a thing.
Label aside, I have also had a difficult time settling down. A dating interest asked me recently what I have not been able to find that has led me to being single at 48. I told her stability. The longest I have been at one job in the last twenty years was almost four years, and that was my first job from mid-2006 to early 2010. Since 2010, I have had 15 jobs, to include side gigs and 1099 work. I average a new company every year. Very successful people have told me they don’t understand how I can’t keep a job.
For the numerically inclined:
- Layoffs: 5
- End of contract job terminations: 4
- Internships left at end of term: 2
- Resignations: 1
Some people have a list of ex-girlfriends or ex-boyfriends, I have a list of ex-companies. When I did stand-up years ago my opener was “I lost my job recently. Let me rephrase that, I didn’t lose my job. I know exactly where it is. But when my boss handed me my notice, I knew I would never see it again.”
Let’s look again at Jenn’s statement:
“Maybe the issue was that I kept trying to grow in environments that were never designed for me.”
I have tried to make a career of government contracting. I have tried to hop from one contract to another, developing skills and moving up in salary and status. But that’s not how government contracting works. I was trying to do something no one else does. I was trying to fit a square career in a circle hole.
Career growth and career development were never talked about when I took jobs. The last time I was promoted in a work place was when I was in military uniform in 1998. Seriously.
The type of government contracting I did was designed for people who were already experts or proficient in their field. They are hired to come in, do a job for a certain amount of time, and then leave. It is very transactional. Only the program managers, contract writers, business development folks, and senior staff have long term positions. The rest of the employees are at the whim of the contract. If the government doesn’t renew, or ends the contract for whatever reason, employees on the contract are advised to “go to our website and find any open positions”.
Why was I always seen as expendable? I only willingly left one job out of 15. The other jobs dumped me.
Was it because I don’t have the background of the career military people who look out for their fellow retirees? Was it because I was too expensive – often the case for the internships? Was it because I lacked skills? Was it because I didn’t fit in socially, militarily, or politically in workplaces that are becoming more governed by red-hat groupthink?
Could be any one of those reasons. It could also be because “I kept trying to grow in environments that were never designed for me”.
In her blog post, Jenn wrote:
“At my best, I’m the classic high-achieving gifted kid turned star employee, the one who sees patterns others miss and solutions others don’t think to look for. I work hard, think fast, and push past limits because that’s what I was trained to do.”
She writes in order to fit in, she “masked”, hiding her true self in environments where she wasn’t a good fit for the benefit of her career. That was my time in the defense contracting space. I fit in amongst old white male military retirees who think a certain way politically and watch the same news channel. I found my job interesting, did it to the best of my ability, and got a good paycheck. But I couldn’t grow in a world where promotions and advancement don’t exist. And if I am not growing, I am probably getting frustrated - on top of the social workplace frustrations.
As Jenn developed a passion and success in comedy, I built recognition in my novels and books. I am good at writing, selling, and hustling. As a self-published author, I grow through experimenting and running with what works.
I have designed my own environment, albeit one that doesn’t pay the bills. But there is growth. I am developing a reputation as a writer that I am proud of. I have almost more pride in my writing than in my twenty years in defense contracting. That was a job. The creative arts are my passion.
I was laid off from my last defense contracting job in April 2025. Although there are good people there, some of whom I am still friends with, I have no intention of going back. I was hurt too bad by defense companies and their bad management. I had to get therapy to get over that. When I explained my pattern of reapplying to a field that has treated me poorly numerous times, my therapist said my career was similar to an abusive relationship.
Every time I went back, I thought it would be different. I thought it would be better.
That’s a phrase commonly echoed in abusive relationships. I need to break free, take the skills I have acquired, and pivot someone where I can be myself. I am currently exploring fields such as Business Continuity, Disaster Response, or Emergency Management. Preferably at company that provides stability.
Somewhere where I can grow.
Thanks again, Jenn, for another writing inspiration.
