Career Grief: What Might Have Been

Grieving what we thought a career could have been and the opportunities that we never knew about.

Source: Adobe Stock

Our journey through the waters of career grief continues this week with more reader contributions. I’ve separated them with pull quotes. I’ll keep this going as long as people send things in, so if you have something to add, drop me a line at jaredpaventi@substack.com.

Kids & Death returns next week.

ALSO, I’m looking to you, dear reader, to tell me about the loss of a pet. We’re going to talk pet death and overcoming that grief this summer. Use the same email as above if you are up to talking about your dearly departed companion.

Here's what I know now: what you major in during college won’t always define your career path. I studied broadcast journalism, but I'm not a broadcast journalist. That said, I'd choose the same majors today if I had to decide all over again. I use my education every day. It's OK to change your mind about what you want to be when you grow up. It's OK if you don't have a flipping clue what you want to be when you grow up. And when it feels like it's not going to be OK? It will be.

I graduated with a job at an ABC affiliate. While I'd signed a contract to be a television reporter, I certainly didn't start on-air. That line in the contract that reads “shall perform other duties as management sees fit?” That defined my job for several months. I gave tours of the TV station. I dubbed stories for parents who wanted lasting memories of their kids’ television debuts. I went out with photographers and did interviews, then handed the stories over to anchors to voice them and take credit for them. Frustrating as that time was, eventually, I was on the air every day. I was on my way to fulfilling my dream of being Katie Couric.

But as time went on, I grew miserable. M-i-s-e-r-a-b-l-e. Every day at work, I'd make connections with the people I interviewed for stories, but I’d put together a one-minute, 20-second story and never really get to follow up or see them through, never get to REALLY tell those stories from beginning to end. Or I'd be assigned to stories that, to me, felt meaningless. Tomorrow would always bring a new story, and some were much more difficult than others. I was fulfilling a dream, but I didn't feel fulfilled.

Being a journalist is an amazing job for some people. But it wasn't the right fit for me. I cried. A lot. I felt like I would be letting my parents and about 298,428,937,482,374 other people down if I left television. Turns out...that wasn't the case at all. Change is scary. But change is OK. In fact, change is often great.

I have been a teacher in New York since 1999. If I complete 30 years as a public servant, I earn a pension and medical benefits from my employer in retirement. These “golden handcuffs” are nearly extinct in the private sector and I am grateful for these benefits. However, for the last 25 years it has felt more like a prison sentence than a reward at the end of a successful career.

When I began my career, I just thought I would need to adjust. It would take time to understand my role and expand my skills, and I would have to be patient to feel happy. I was assured over and over that it could be years before I had a repertoire of plans, years before I knew what to do when the unexpected and unplanned was thrown at me. I was 22 and I didn’t know a fucking thing about how I should feel in my first full-time job. I was thankful to have a job at a time when getting into the classroom was competitive. Nobody talked about toxic culture and mental health issues in 1999.

So, I told myself it would get better. I would get better at the job and it would get more manageable. I told myself that it would improve once this principal left or that superintendent moved on. I had to because there was all this adult responsibility. My parents paid for part of my college costs (there were loans to pay the rest). How could I just say, after all that money and struggle (on their part), this wasn’t what I expected or maybe even wanted?

Honestly, the whole situation was further complicated by the fact that I am good at my job. I have strong instincts about how to break down material and I learn fast. I could see the results in my students and their accomplishments. My principals and bosses were happy with my state testing results and my formal evaluations were glowing. So, why at the end of August in 2003, was I hysterical in my house, weeping uncontrollably on my husband’s shoulder (who must have been baffled), about having to return to work?

I still hate September, 25 years later. I still fucking hate the start of each school year.

It was around 2008 when I finally figured out it was never going to get better. The administrators changed, students cycled through and I had hundreds of lesson plans, but it wasn’t getting easier. It was getting more difficult. I was better at predicting what would go wrong, understanding the toxic culture of public education, but it wasn’t getting better.

By the time I figured out that I should have changed careers and was at a point where I could still legitimately wiggle out of the handcuffs, I was 31 years old. Now, there was another kind of clock ticking. We wanted to have kids. Summers off, time to spend with my babies, plenty of sick time, a sub to call when the kids were sick, and flexibility and health insurance that made my friends jealous... I saw how hard it was being a working parent in other fields. The golden handcuffs tightened.

Mortgage payments and daycare costs… You can’t change careers coming off maternity leave. You can’t change careers in the absolute hurricane of learning how to parent while working full time. Plus, there was still so much responsibility. I carried the health insurance for the whole family, my pension would be for BOTH of us to retire on as my spouse worked at a non-profit. At this point, the handcuffs were so tight that it hurt.

I hurt.

I kept mourning every September and life kept moving. I know now that there is no good time to make a life-altering change and you have to seek out those opportunities. But when you are in the hurricane all you are trying to do is survive.

(For the record: I give 110% to my students, my content and my responsibilities while I am at work. The amount of unpaid labor I have done is staggering. There has not been a single day in 25 years where I didn’t do my best even when I wasn’t feeling like I was the best. I’m not coasting into retirement. I’m working my ass off like I am in year one.)

I will be 47 soon and it’s only in the last few years that I figured out what my “skills” are, and (shocker) they transfer to other jobs and other roles, and would have allowed me to evolve and grow as a professional. The grief is all about what I could have been as a professional. I have no regrets about any other part of my life except my career. I grieve what I could have accomplished and the achievements I never reached. I grieve the confidence I lost as an educator, where you are never good enough. I thought for so long that all I was was “a teacher.”

And I mean just a teacher. The cultural language and criticism of educators over the decades deeply impacted my ability to see myself outside of my classroom or anything more than my job title. I also grieve all the time I spent unhappy, anxious, stressed and overworked.

Realizing that much of my identity surrounded my job title put me in a downward spiral that was epic and was pushed along at warp speed by the Covid-19 pandemic. It sent me into a mental health crisis, where my depression and anxiety became a living thing that sat with me every day as I drove into work (often in tears). It took me years of therapy, self-reflection and hard work to crawl out of the hole I was in.

I want to point something out too about the pandemic. The Great Resignation was a moment when changing career paths (not just jobs) was embraced and encouraged. There was so much language around making skills transferable that suddenly the cultural shift was profound. (I know that not everyone had a choice about their job and making changes, and many people lost their jobs because of Covid.) I had always understood that most people changed jobs three to five times before they retired. But, changing jobs or changing companies is entirely different from changing careers. Going from a public school teacher (with no other job experience) into some other role outside a school setting was unheard of prior to 2020. The cultural shift came too late for me to ride that wave and while I tried to find a key to unlock those handcuffs, they remain.

The regrets are deep and my 25 years in education followed the five stages of grief. First it was denial, and then anger and bargaining took turns for about 10 years. The last decade has brought depression and, finally, acceptance.

I have accepted (maybe even made some peace) with finishing out my time. I want to pursue opportunities that will allow me to find my career change after I retire. Maybe I can find a role where I can be proud of my skillset and make it work towards something other than classroom teaching. I’m putting a lot of hope and faith in timing, staying healthy and my skillset. I wonder, though, will anyone want what I can offer at 55 years old?

When I graduated from my master’s program, I landed a very cool, Big Name and demanding job…a job that even I don’t know how I landed it and I am sure just about everyone I knew probably felt the same way. This job forced me to be regimented. There was NO room for failure and I prided myself at succeeding in this position.

So when the time came for me to leave the Big Name, and work for Big Name II, I knew I’d be okay; I was ready to jump into something new where I could use all the new tools I had acquired for a greater good; and that I did. This new job with Big Name II required me to be more of a go-to on projects, where I was supervised by someone who was constantly on the road. I was left without guidance quite often, which I took to mean that there was trust and room for creativity in getting the job done.

In May 2014, I received a phone call from a 3^rd party HR rep who told me that I was no longer required to come to the office and that I was being let go because of “differences with my manager.” I hardly saw the guy, and he rarely gave me guidance on a job that I always got done, but I was fired. I failed, but I didn’t know how.

The weeks that followed were full of anxiety, not knowing what I could learn from this. The only reason I was given was empty. What did I do wrong? How will I know to not do that again? And more importantly, how was I going to make money so that I could pay my rent? SOOOOO much anxiety that I never got a chance to be angry or sad or grieve what I had a lost.

Ten years later, I think I am only just beginning to grieve the loss of that job. Currently, I have very big job with an even bigger title (literally, it’s 10 words long). While I’ve worked hard to learn and show my value to all who needs to see it, I leave my desk each day wondering, did I do enough today? And those are the thoughts that often keep me at my desk until 8 p.m. wondering what more I can do. The answer is nothing.

It’s not a flip of a switch or a simple check box. Grieving doesn’t start when you think and end when you want. It sneaks up on you when you least expect it, takes different forms during, and will end when IT is ready to be done.

“Congratulations!” was the sarcastic response from my doctor, who I saw when a bright, itchy, red rash appeared on my skin three days after I was laid off, unexpectedly, from a job I loved. Steroids were just what I needed to help my sleepless job search and 3 a.m. LinkedIn browsing.

We were told that there was no plan for a reduction in force, and, then, six short weeks later, I was laid off. People ask me if I was expecting it, as if I should have known and was looking for a new job prior to the news that forced gigantic sobs out of my body (to my embarrassment) in front of my HR VP. “I was not,” I say, “but I am optimistic, naïve, and thought all of my frantic, great, value-added work would keep me safe.”

(NARRATOR: It did not.) 

No amount of great work was going to keep me “safe” from corporate redundancy and individuals evaluating my work without even speaking to me about what I did. Yes, I am bitter.

It’s still raw and fresh and sneaks up on me in many different ways. I have heard from colleagues who are shocked and sad, and I think of all of the breakup songs I have been listening to and think: I hope it’s shitty there. I hope you leave, too. I hope, I hope, I hope you are safe. 

Job searching is filled with highs and lows. I’ve never been so busy frantically trying to find a job and networking, applying, trying to prove myself, fitting myself into different shapes to be considered for interviews, preparing for interviews, getting pissed at job openings that say “remote” and “flexible work” to only hide “30%+ travel” deep in the requirements.

But! Don’t forget to be cheery, to be excited, to show how wonderful everything is because no one wants to hire someone who is sad, bitter, and frustrated. 

I am waiting for the next “Congratulations!” I hear to include a job offer immediately after it. Then, I’ll be professionally optimistic, but probably still naïve.

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Dirt Nap is the Substack newsletter about death, grief and dying that is written and edited by Jared Paventi. It’s published every Friday morning. Dirt Nap is free and we simply ask that you subscribe and/or share with others.

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