5 Reasons I Made a Midlife Career Jump at 40

(ed. note: This essay dates back a few years. People have been asking me recently about how I got started as a writer, so I figured it was time to dust it off and get it posted again. I also recently published it on my other blog/newsletter, I Like How You Think)

I’ll be the first to admit that jumping from IT operations manager to writer seems, well, a bit far-fetched. When you look at some episodes from my working life, however, it will start to make more sense. I hope.

I always did great in English class. My college papers consistently received high marks and praise from my professors and peer reviewers (BA in Anthropology, I know, from that to IT is itself quite a leap).

Then I hit the working world and got a bit…sidetracked.

I was never that IT guy. You know the one. He goes home after work and builds gaming PCs in his basement man cave. First off, never had a man cave. Second off, I’ve always preferred to spend my free time outside.

The story of how I ended up with my first real-world job as tech support for a real estate company is one for another time. What matters today is that I was supporting an in-house productivity suite and property search tool used by realtors and office staff.

My days were spent fielding calls that started something like this: “Hi, I can’t do the thing.”

My job was to ask enough of the right questions to figure out what the thing they were trying to do was and what was happening instead—then either walk them through the right way to do the thing or take the issue to the developers. This entailed translating from realtor-speak to dev-speak as I walked to the back of the office. Then, once they fixed the thing, translating what they did back to realtor-speak on my way back to my desk.

So, I got real good at a couple of things, real fast:

1. tech-to-English translation

2. listening through the frustration to understand what someone meant, rather than stopping at what they said

With that much of an intro out of the way, let’s dive a little deeper into my reasons for leaving the IT world behind (well, sort of, I still do a lot of writing about tech) and jumping into writing as a career. Stay with me through the sidetracks and seemingly random ramblings, I almost always bring it back around.

Words Have Power

From the time I learned to read, I’ve known that words have power. Whether spoken or written, words are how we as humans get our point across. Words are how we make ourselves understood and how we express our discontent with a situation. Words are how we inspire others, and ourselves.

Maybe I was deluding myself. I mean, come on, how important is it that the legal department of a software company have their spare laptop repaired? But to the people on that team, it was the single most important thing I could do to help them. So I focused on that importance and overlooked my own growing discomfort with IT and my role in the companies I was working for.

People Fascinate Me

Sounds strange coming from a former IT guy who now works from the solitude of his home office, I know. But this deceptively simple-sounding fact has been a primary driver behind many of the choices I’ve made over the years—including the decision to go over the career fence in search of proverbially greener pastures.

I say it’s an ability to read silence because it’s in the silence between words that people often give away their true feelings. Back in the day, I used this to understand the source of their computer troubles. Today I use it to fine-tune the tone and tenor of my writing so I know it’s not only hitting the intended target but also resonating with the client.

This sweet spot between client companies and their audiences is where I dwell these days, and that’s not a bad place to make a living.

Learn Something New Every Day? Yes, Please.

Back in the day, I learned about fixing laptop screens and the latest in solid-state memory speeds. Now, it’s whatever I want to learn about to write about it and share that knowledge with you wonderful people.

I’m a Creative Heart

Do you know those personality tests and assessments given by everyone from school guidance counselors to potential employers? By now I hope you’re not surprised to hear that not one of those ever said I was perfect for a role in IT support. Every single one of them said I was “a creative.” The thing about those tests is that they never seem to offer any concrete advice or suggestions for how to “creative.”

Being told that you’re a creative thinker is awesome, but then to have zero follow-up on how to make use of that in the real world…sucks.

So I let the fates guide my hand and off I went into the world of help desk. All through my time in the IT realm, I had people surprised to hear that that was what I did for a living. Including bosses.

When your manager tells you they’re surprised to see “someone like you in this line of work” it’s time to make a change.

As an Introvert, Open-Plan Offices Were Causing Me a Lot of Pain

Open-plan offices don’t work. For anyone.

As one who falls squarely on the introvert end of the introvert <—> extravert spectrum, these offices are particularly stressful. I need not only personal space to do my best work but even just to exist in an office environment I require space and quiet. Neither of which is particularly possible in an open-plan office. Even noise-canceling headphones don’t work when people don’t respect them, tapping you on the shoulder right as you get in the zone…

Speaking of which, I’ve been in my writing zone long enough for today. What I hope you can take away from this essay is that there is soul-searching involved in making a serious career jump. I did mine over the course of something like 6 years before finally getting up the nerve to jump that fence. I’ll have more to say on these, but for today here’s a ‘getting started’ list for you:

• Get your proverbial (and if you got ’em, literal) ducks in a row.

• Dive into your current working skill set and see what you can put to use elsewhere.

• Get some training if your chosen career track is something that can be taught.

• Consider starting slowly with a side gig.

• Then, when the time is right, go for it.