Starting over

Lake Mendota | Photo by the author

Three times in my life, I started over.

The fact that I got to three is a miracle.

Because my whole life, I hated change. I ran from it. I hid from it. When I lived in Michigan, I stayed in the same crappy half-basement studio apartment the entire six years I lived there. Because my mother and I moved so many times when I was in high school, I grew to loathe moving. Cardboard boxes were my constant and unwanted companions.

It wasn’t about cardboard boxes, of course. It was the chaos and instability that they represented.

I could have easily afforded a better place. But I stayed.

And I stayed in Michigan for six years, constantly thinking I was a professional fraud as a reporter. I loved the writing and research, but I wasn’t in love with journalism the way my colleagues seemed to be. I had actual dreams where official people in suits came into the newsroom and escorted me out, saying, “You don’t belong here.”

I should have stayed two years. But I was making a good living, and change terrified me. Velvet handcuffs.

ONE

There came a day I was thinking about how my lease on that crappy half-basement studio apartment was up that summer. And something happened. A switch flipped. And I decided I needed to get the hell out of Dodge.

So I did. No plan, no new job.

I moved home to Wisconsin, and actually lived with my mother for a year. (That’s another story.) I had a few interviews for writing or reporting jobs between the time I decided to leave and when I got in the car pointed home, but I tanked them all. Even then the market wasn’t great for reporters, anyway.

I started working for the state teachers’ union, WEAC, first as a freelancer and then in the communications department. I transitioned eventually into working on the web for them, designing an intranet system for the statewide organization that was widely praised.

I thought everything was going swimmingly.

Then, a new business division manager was hired. She was one of those people who had taken a lot of business courses but had never actually managed anything.

At our first meeting, she told me that we would be doing no more custom development; we would only be using off-the-shelf software from then on.

“But custom development is my whole job,” I said, incredulous.

“We’ll figure it out,” she said.

The writing was on the wall.

TWO

The day I decided to leave WEAC was legitimately one of the best days of my life. I could tell that my job was going to be minimized or eliminated under the new management, so I wanted to beat them to the punch.

I don’t know how this switch flipped. Because I had a secure job with a union, and I enjoyed my co-workers. Some of them are my good friends to this day. But the switch flipped, and I was out.

Which started me on nearly a decade of working for myself, making websites and content management systems for small businesses and non-profit organizations.

I wouldn’t trade that time for anything. But it was financially incredibly challenging. I was hanging on by a thread the entire time.

Eventually I became a state employee, doing web work for an agency that no longer exists. I left not because of any switch flipping, but because my job (and everyone else’s there) was eliminated.

At the time I naively thought that the work I was doing making the agency’s website work better for its audience might be the beginning of something big to revamp how government websites functioned.

That was a pipe dream, and when the agency was dissolved, all that work was thrown away.

After that, I found myself working for a company called TeachingBooks, which sells subscriptions to schools of an online database of reading resources. I loved the mission and the people, and I ended up staying there seven years, the longest I had worked anywhere.

THREE

Then, I had a brain tumor.

And I decided that I didn’t want to spend the rest of my career making small changes to computer files.

As I got older, the web began to feel too…insubstantial for me. Almost all of the work I poured my heart and soul into didn’t exist anymore. I wanted to get back to my roots: writing and editing.

As much as I felt connection to what we were doing at TeachingBooks, and my co-workers were bright interesting people I loved working with, I needed to move on.

Switch flipped again, this time aided by my brain trying to kill me.

Leaving my secure job for the third time wasn’t the only huge change I made in response to the tumor. I also lost a ton of weight.

Like the previous two times I started over, I didn’t have the next thing lined up. Like the previous times, I realized that if I waited for the perfect time to make a change, knowing me that time would never come.

This one has been orders of magnitude harder.

I’ve had lots of interviews but no offers. I’m also in my late 50s, trying to pivot back to a profession I had more than three decades ago. I’m also living in a college town stuffed to the gills with talented, motivated 25-year-olds who are a lot less expensive to hire.

That’s just the landscape.

But that’s why I’m creating projects for myself, like writing this “job hunting after 50” book and this newsletter to workshop content for the book.

I know now that I need to make my own opportunities, not send out tons of resumes to places with 250 applications for each job. That’s called doing the same thing over and over and expecting a different result.

The moral

Write your own story. Make your own opportunities. Don’t depend on other people to make them for you.

Also, don’t wait until the perfect time. There is no perfect time. Do it now.

Definitely don’t stay in a job or career path that drains you. Life is way too short for that.

I haven’t figured everything out. But I’m making the effort, day by day. And I know that we only have so many chances to change our lives. Turning away from those chances because we are scared is such a waste.