My boss died

Now what?

If ever the universe put a banner up across the main highway of my life, screaming, “Pay Attention!!!!”, this had to be it.

Two years ago my old company merged with a new one and my future was, let’s say, less than clear. Really it was foggy AF. That probably should have been my first clue but being the biggest cheerleader for this merger, I was optimistic and positive there was something big ahead for me.

I had no idea it was one of those giant Amazon delivery trucks.

My second clue? Frustration.

During the transition, I lost count of the number of times someone said, “Well, we don’t know what your role is going to be,” every time I asked to join a training. I started thinking my new role is going to have an inmate number attached to it if this keeps up. I was desperate to learn and, admittedly, be relevant again.

Still I persevered and someone finally came to my rescue.

Ironically enough her name was Karen (No joke.) but she was nowhere close to the metaphorical/meme “Karen”. She was an angel.

When she asked me if I wanted to work with her in what had to be the most nebulous, vague job possible, unofficially known as the “Everything no one else knows how to do but has to be done so Karen does it and she’s drowning so you’re going to help her” department, I was 100% down with it. It didn’t matter that she was in Texas and I was in New York. This role fit me perfectly. In my old company, I was Karen for 20 years so it was a natural progression.

We worked together for three short months before she went on a two and a half week vacation. When she got back, we talked everyday, even if it was just for a few minutes to catch up, and I knew this was going to work out!

Three weeks after she got back, though, she went out on medical leave.

And two months later, she died.

I was devastated. Not because of the job but because I really liked her. We had gotten to know each other. I learned about her family and that she loved baby goats. She was unquestionably the kindest person I’d met at this new company. I would miss her deeply.

Am I the only one who sees a stick person looking at me and pointing to my left? Photo by Roger Bradshaw on Unsplash

And, yes, there was also the question of my job.

Without Karen, there was no role, mostly because no one in Texas knew me. No one knew how to do what Karen did and I hadn’t learned enough yet, so that made me useless.

I hate being useless.

I advocated for myself, hoping to find a spot, and was finally offered a position working with the CFO. Fantastic! She said she’d connect me with someone who would train me on my new role.

That was summer of 2025. I have yet to start a single day of training.

Here’s my dilemma: Financially, my family and I lean heavily on my job. And I may be an idiot sometimes but I’m not blind. I know the hammer is going to fall, sooner than later.

I’d rather eat snails (You cannot convince me they’re “delicious”.) than start looking for another full-time job. I’m too old and ornery to try to assimilate into another company culture.

I’m also too young (Weird to say at 56 but here we are.) and financially insecure, staring down medical and other debt, to retire. Not to mention the necessary medical insurance.

No, seriously. Now what?

I’ve already decided that jumping ship right now would be monumentally stupid. There’s no Plan B, no financial safety net, no happily ever after I can see from here.

So what else is there to do but jump on the middle-aged reinvention bandwagon! 🫤

The situation reminds me of how we pieced together ways of making a living when my kids were young. The difference is now I have an inventory of skills and talents to tap into and no childcare concerns (Hooray for middle age!!!). Back then I just had a lot of youthful enthusiasm and a high willingness to please, which is ridiculously hysterical now! Still, maybe that’s some evidence that I can pull this off? Imperfect but still moving forward?

I can’t be the only one going through something like this, can I? Maybe I am. But I doubt it.

Now I’m just trying to pull it all together, one piece at a time, building a foundation of skill AND desire, out here in the wild. Trying to figure out what I want. Asking myself what I could write about forever and not get tired of it. And maybe I could possibly help someone else along the way.

In case it’s not already abundantly clear, this is not “I did it and I’ll show you how you can do it, too!” That’s funnier than the fact I’ve been waiting almost a year for a job description! 🤣 🤣 🤣 🤣 🤣

This is a new adventure and experiment. Nothing about my situation is in perfect alignment for success. It’s exactly the opposite. And as the person who was the go-to for fixing situations for other people, I’m feeling pretty on my own and embarrassed that my reinvention isn’t clean, self-assured, or on schedule.

But here we are, a very public, visibly messy, unconfident, off schedule, and on purpose rerouting towards a new life. I may have missed that banner on the main highway two years ago but ready or not, it’s time to start keeping an eye out for the exit.

I’d so love for this all to be magazine-spread-ready but there’s nothing more unrealistic than believing you should be good at something you’ve never done before.

No, this will be proof that you can be a near-total mess and still move forward. Here, perfectionism is a casualty. We’re doing this messy.