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Reflecting on a career
Another year, another decade.
I turned 40 years old yesterday.
(And I scheduled this in advance, so I’m writing while I’m still 39!)
It feels… weird. I spent most of my career in an industry that valued experience and tenure. I was 22 years old, guiding bankers through enterprise software implementation.
Now I’m in a field that moves fast. Marketing and journalism are about what’s right now.
I’ve been working for twenty-four years, more than half my life.
Three years as a bank teller
Three years in loan operations
Seven years in software implementation
Eight years as a product manager
Six years managing a customer success department (overlapping with my PM role)
Two-and-a-half years at content marketing agencies
One year as a freelance writer
I began my career wanting to be a stellar employee, always willing to go above and beyond. I recently found a performance review from 2008 where my manager wrote: “The amount of work Anna can produce is phenomenal!”
Having a baby in 2009 changed my attitude toward work. It was no longer about working hard, but about working smart.
From one employer to another
I spent six years working at a bank as a part-time employee, throughout high school and college. It was, in a sense, lucky. I enjoyed community banking and ended up pursuing a career in financial technology.
After graduating from college, I spent sixteen-and-a-half years with three different employers. 90% of that time was with a single employer. 97% percent of that time was spent as a remote employee. I only worked in an office for the first six months of full-time employment.
Over the years, I treasured my flexibility more than anything — and my employer was very flexible. When I first started working, I traveled up to 50% of the time to client sites. Once I had a baby, the company changed the model to web-based client training. I almost left the company in 2010 (was at the end stages of interviewing), when the company announced fully flexible work, with no requirements around set hours worked per week.
That flexibility was the reason I stayed and tolerated a lot. As a product manager, I straddled the customer service team and development team. The customer service team was wonderful. The development team was downright toxic. I look back now in utter disgust at how much was tolerated. And the CEO was driving the company into the ground due to a lack of vision and innovation.
Yet I thought that was part of work life. Something I should grit my teeth and charge through. I thought there was no way I’d be able to find another job that would give me as much flexibility.
Then the pandemic hit. I saw the opportunity and I quit.
But I found myself in a chaotic environment, one with a “growth at all costs” mindset. Employees were exhausted, burned out. The good ones were leaving in droves. I thought I could help — I had experience in operations. And even with the ear of the COO, everyone was too busy to take a breath and make things better.
With so many red flags, I left. Eight months after I started. And the company has continued on a downward spiral since.
Then I went to a tiny company, joining as employee #9. It was clear that the general manager was wholly unqualified to run a company and had no idea what he was doing. The requirements of my job shifted constantly, and became a very bad fit for me. And since my job ended, about a year ago, the company has all but collapsed.
I look back now at three very different companies. All dumpster fires — but in very, very different ways.
I was so, so tired. The idea of looking for another job and interviewing again was overwhelming. Especially since the two jobs I took in 2021 had no obvious signs of dysfunction during the interview process.
So now here I am. 40 years old and confident that I’ll be self-employed for the rest of my working life.
What’s interesting is now the concept of “retirement” seems weird. I could easily wind down, but not stop. Maybe I pull back on client work, but keep writing about topics I care about (like this Substack, if Substack even exists in 25 years).
The untraveled road
I look back on the years since I graduated from college and wonder where I’d be if I’d chosen a different path.
I didn’t pursue writing because I didn’t trust myself. I didn’t think I was good enough. I thought that I’d never be able to earn enough money as a writer to support a family.
So I abandoned the idea of writing professionally and pursued what I was good at: banking and technology.
And perhaps I couldn’t have been a successful writer back then. The world was a lot different back in 2006. The “creator economy” didn’t really exist. It was harder for people to build their own audiences. Perhaps I craved stability far more than my passion. I wasn’t hungry enough to take on the risk.
That’s what I tell myself, perhaps as a consolidation for “lost years” in a writing career.
I can’t change the decisions I made over the first sixteen-and-a-half years. And to a large extent, those decisions paved the way for the work I do now.
Instead, I have to look forward. To what I want to accomplish next.
Cheers to the next 40.
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