An old work colleague contacted me a couple days ago, unexpectedly, right out of the blue. She got in touch via a LinkedIn message. It was a pleasant and unexpected surprise, and for one of the few times in my life, I was thankful for social media.
I hadn’t heard from her in a decade. She and I worked together for a couple of years in the mid-1990s. That was enough time to forge a friendship, and we kept in touch for the next 20 years or so. Then we fell out of touch, as happens.
Like me, she’s a writer. And like me, she has a sometimes jagged worldview (or did back then), and a sometimes caustic sense of humor (or did back then). We found a common bond and became pretty close, despite differences in age, background, and certain values. She gave me the affectionate nickname of “asshole,” which I did my best to live up to.
Before she contacted me earlier this week, we hadn’t traded any correspondence in exactly 10 years to the month. The last time we corresponded, in May 2016, I had just been downsized from a job I’d held for 16 years. I was 50-something at the time.
In an odd twist, she contacted me in May 2026 – just as she was being downsized from a job. In another odd twist, she also held that job for 16 years. In the final odd twist, she is also now 50-something – as I was the last time we touched base, and am still, having not aged a nanosecond in 10 years.
Ok, I’m no longer 50-something…..
Anyway, I shared these bizarro coincidences in a LinkedIn dialogue this past Sunday.
She replied: “Wow…[it’s] eerily similar with the job losses. And the fact that you popped up in my LinkedIn feed right now is even more weird. I feel like this definitely happened for a reason…”
The job she had for the past 16 years was in financial services. But now she wants to get back to writing, something more creative.
She shared a Substack blog she just wrote about her final day on the job. It was a brilliant little piece of writing, which didn’t necessarily surprise me, but still impressed me in countless ways. She’s a very sharp woman, my old friend, with a gift for stringing words together and making them hit all the right notes.
Her blog was poignant without being sappy, world-weary without being jaded, funny in places, heartbreaking in others. It ended on a hopeful note, and yet I couldn’t help but feel a little melancholy after reading it. Leaving a job behind means turning the page on another chapter in life. And when you reach a certain stage of life (as I have), those chapters become fewer and fewer. And melancholy raises its silly little head.
I let her know how much I enjoyed the blog, and she seemed genuinely appreciative. I have a feeling it meant a lot for her to share it with me.
When we worked together lo those many decades ago, she was a young writer/journalist not too long out of college, landing what I think was her first newspaper job. She was eager and ready to learn.
I was a news editor/reporter and quasi-mentor to her. I tried to impart my professional wisdom, having worked in the business for more than a decade off and on.
I’m not exactly sure how much I helped her, though. I certainly tried. But looking back on it now, so many years later, I’m overcome with the feeling that I could have done more. Should have done more. Offered better guidance, a better road map.
I became a better mentor to others, later down the road. But I’m not so sure I served her that well.
Ah, our sad little regrets. Always overstaying their welcome……
In any case, it appears that she turned out just fine, professionally and otherwise. She seems to have a nice life, and much to be thankful for. It was good to hear from her, and good to know she’s back to writing again.
*****
This isn’t a blog about hearing from old friends or colleagues, though that might be a good one. This happens regularly in my life, some soul from the past touching base out of nowhere. What always amazes me is how quickly we can pick up where we left off the last time, no matter how much time has passed.
I’ll file that blog for later.
But for now….
…hearing from my old friend and colleague the other day, and trading messages about the vagaries of the working world, reminded me of something.
That something is this: I haven’t had what you would call a “real job” in 10 years. What I mean is, a job where you are employed by a company, and receive a regular paycheck, and report to work at a certain time on certain days, with set duties, and an expectation that you’ll do what you’re supposed to do when you’re supposed to do it.
This seems sort of incredible to me, being so long out of the mainstream working world. Not that it should be incredible. I’m not a young guy, after all, and many people of my vintage have already retired. It’s just that I don’t feel like a guy who should be retired.
From a pure career standpoint, I feel like I’m around the age of 51. In most jobs, this is the age when you’re still at or near the professional summit. Maybe you just passed it, and are heading back down again, on the other side. But you’re still in the sweet spot when it comes to experience, knowledge – and earnings.
My career as a salaried employee ended when I was still near that summit, still near the height of my powers. I had built up decades of experience. I had absolute confidence in my ability to do the work well. There was nothing about my job that was a mystery to me anymore. Yes, you can always keep learning, always keep improving. But I had long ago stopped worrying about whether I was worth the money they paid me.
By all rights, I should have felt a sense of professional fulfilment. I should have skipped into work every day, with a song in my heart and a cup of robust coffee in my hand.
Instead, I was miserable. Fucking miserable. I detested every single moment of every single day I spent at that job, every little bit of every little bit of every little thing that involved going to work there.
It wasn’t the employer’s fault. They did okay by me – better than okay, if I’m being honest (although our cheapass owner could have matched our 401k contributions, the penny-pinching old geezer).
No, the fault was entirely mine. Nobody to blame but me. I hated the job because I just hate jobs. If there is a neuron in our human chemistry that sparks a negative vibe at the mere thought of having a salaried job, mine must be the size of Jupiter.
It’s not the work, mind you. There’s a difference between “work” and “job.” I don’t mind the work. In fact, I like the work. I’ve been an independent contractor for a decade now, a free-lancer. And every day I look forward to hitting the desk and taking on the workday. I really, really like it.
What I hated was working for someone else. Being an employee. Having to answer to someone else. Having a boss – or two bosses, or three, or eight, or twenty-three. I hate bosses, hate taking orders.
I really, really detested the mainstream working life, and don’t miss it at all.
Except when I do.
*****
Here’s something weird:
Sometimes, when I’m out riding around on my bike, or walking around town, or driving hither and yon, I’ll pull up in front of an office building or worksite and sit there and watch. Just sit and watch.
I’ll look at the worker bees, buzzing around the grounds. I’ll study them. Try to put myself inside their heads, their workplace skins.
I’ll imagine what it’s like inside the office. I’ll envision them sitting at their cubicles, chatting with their work mates. Grabbing a cup of shitty coffee from the shitty office coffee machine. Planning. Strategizing. Problem solving. Geared up, focused, exhausted, sick of it all, failing – and then succeeding.
I’ll envision the camaraderie, the sense of community that comes with spending a large chunk of your life with your workmates, during your most productive waking hours, in the prime of your life. I’ll think about how nice it must be to have a job you sometimes enjoy, and often hate, with people you really like being around.
I’ll remember what it was like to do good and important work, with people who shared a common mission.
I’ve known that feeling. You probably have, too. It can be pretty special, when all the gears work the way they’re supposed to.
My friend’s out-of-the-blue message rattled those memories, and her blog brought them into clearer focus. It reminded me that sometimes, being on the job can be a pretty great place to be. I needed to be reminded of that.
As my friend wrote in the LinkedIn message: “I feel like this definitely happened for a reason…”
To which I say: Touché, mon ami.
Image: AI, instructed to look like the classic ‘90s work office.
Vance Cariaga 