I’ll be the first to admit that jumping from IT operations manager to freelance 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’ve never been 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 for 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.”
And my job was to ask enough of the right questions to figure out what the thing was they were trying to do, what was happening instead, and 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, real fast, at a couple of things:
- tech-to-English translation
- 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 a species 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.
And from that early age, I also knew I wanted to know as much as I could about how to use words to help people. First I aspired to be a journalist, then a teacher, and finally I realized that my way of processing and using words was best suited to a looser framework. Then life got in the way.
So I made the best of it and found ways to keep using words to help people in whatever capacity I could. When someone called for help with their computer because they can’t get their job done, I used words to help them work out what was wrong and get them up and running again. Soon, I was using even more words to rewrite instruction manuals and how-to guides. It was the power of words that I relied on, not some innate love of computers, to help people do their jobs more effectively and efficiently.
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 greener pastures.
Back at that first IT gig supporting realtors I would often find myself having 20-minute conversations with callers that had not one single thing to do with the tools I was supporting. I would ask questions on the trail of a source for the issues they were having and before either of us realized it we would be talking about city council happenings or the coming ski season. Later in life, I came to find out that the ability to ask the right question at the right time, then shut up and listen to the answer is part of my personality typology. Back then, I just liked hearing people’s stories and occasionally telling a couple of my own.
I have a knack for knowing what someone is not saying. I say it’s an ability to read silence because it’s in the silences 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.
Freelancing brings opportunities to learn something new, every day. In just my first year, I wrote about artificial intelligence (this was some years before the current generative AI ballyhoo), business process mining, supply chain logistics planning solutions, recruitment marketing, chatbots, and gamified recruiting platforms. I did not know the first thing about any of those subjects before being assigned to write blog posts, ebooks, and whitepapers about them.
At the same time I’m learning about these subjects, I have 5 books on my coffee table in various states of read. They range from one about how to resist the attention economy, to one about the technology that one futurist sees as shaping our future as a society, to a collection of essays by a former rock drummer turned Buddhist lay leader.
Right before getting back to work on this piece, I was reading up on emission tracking in the supply chain so I could fix up an article for a client. And when I finish writing for today, I’m going back to that book about the attention economy. None of this is offered as some sort of humblebrag. It’s simply meant to explain where I’m coming from when I talk about my love of learning.
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 in order to write about it and share that knowledge with you wonderful people.
I’m a creative at heart
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 killing me, slowly
Are open-plan offices good for anyone? Or anything? Increasingly, it’s becoming clear that the answer is a resounding NO. Study after study is coming out that prove not only are they hard on the majority of the workforce, they’re also not good for the thing they were supposedly designed to be good at—collaboration.
All they do is encourage people to not respect their coworker’s personal space and boundaries by walking up and interrupting them while they’re working. And for creatives and tech workers alike (developers are, as a sidenote, some of the most creative people I’ve ever met), this means zero deep work gets done. See the writings of Cal Newport for more on deep work. Suffice it to say that it takes approximately 20 minutes for someone to get back into the work task they were involved in when someone interrupts them to ask about their drink preference for the upcoming office happy hour.
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 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
Was it hard? Hells yeah. Do I regret it? Hells no.