I Was The Boss From Hell
Hoo boy, this was a hard lesson to learn…
Way back when I was in the Flight Sim group at Microsoft, I was leading the documentation team charged with creating all the instructional materials for that product.
Along with management, my role focused on the overall instructional design for Flight Simulator – starting with flying a Cessna 172 all the way up to piloting a Boeing 747. But I had to also make sure the Software Development Kit for the product also got produced.
So I handed it over to someone who everyone had told me would do a fantastic job. “They’re a rockstar!”
So I thought, “Great! They’ll nail this.”
But no matter how much I encouraged, cajoled, or reminded this person, they just couldn’t deliver what I wanted. It drove me nuts. We kept going back and forth on that project, but it just couldn’t get any traction.
I was so frustrated I eventually went to my manager and said, “Maybe we should just get rid of this person.”
Fortunately, that didn’t happen. We moved them over to a different project that they totally killed it on. Huzzah!
But in looking back on that time, I realized with great regret that I had been truly AWFUL in my dealings with them. I hadn’t really listened or provided the right environment for them to succeed. Our styles of how we work was just too different.
And that taught me something hard but vital: I’m a great boss—for people who are exactly like me.
I thrive when I’m managing driven, self-sufficient people. You give me a goal, a mission, a deadline—and I’m off to the races. No need for hand-holding or micromanaging. That’s also the kind of employee I’m best suited to lead.
But when I’m working with someone who’s not wired exactly in that very same way? Yikes. I’m the worst boss EVAH. No patience. No empathy. A nightmare who can type like the wind.
It was a hard realization. I’d always thought I was a good manager. Turns out, I was a terrible one—in fact, the literal BOSS FROM HELL – at least for anyone who wasn’t a carbon copy of me.
Fast forward to today, and I’m no longer managing teams at Microsoft. Now, as a copywriter running my own business, I’m the boss of… myself.
Except that’s not entirely true.
Because now I have a new team.
I’ve built a number of custom GPTs to help me in my business. Now they’re team members. I go to them to quickly dash off copy and content. I’ve built bots to help me with overall strategy and reviews.
And here’s the kicker—I designed each one to work exactly how I want them to. They don’t need endless oversight. They don’t push back or get confused. They take a goal, run with it, and if I need to tweak something, they respond immediately and get it done.
It’s like I’ve created a dream team of me-clones who do what I ask exactly how I like it done.
And I’m really growing to like this model of operation…
You see, when AI first hit the scene, I was terrified. I thought it would take over my job, do all the writing, and leave me irrelevant.
But that’s not what happened.
Instead, I discovered that AI isn’t here to replace me. It’s here to work with me. It’s a team member—a powerful tool that lets me do what I do best, only faster and better. When you create a GPT trained on your expertise and your own voice, you’re not just a copywriter anymore.
You’re a manager.
You’re a strategic leader.
You’re responsible for directing a team (even if that team is made of bots). And when you see your "team" produce incredible copy under your guidance, it’s an amazing feeling—like the pride a manager feels when their team crushes a goal.
The other day, I was writing copy with one of my GPTs, and the results blew me away. It was just so good.
And for a split second, I thought, “Wait. I didn’t write this.” But then I realized—it didn’t matter. I directed the process. It was my vision, my strategy, my voice. That GPT was working as part of my team.
And that feeling? It was pure joy.
Not because I’d typed every word, but because I’d led the process. I’d managed the mission. I’d leveled up.
So here’s my challenge to you: stop thinking of yourself as “just” a copywriter.
As I say all the time, you’re NOT a writer – you’re a Project Manager in charge of delivering Marketing Assets.
But even more so, start thinking of yourself as assuming the role of a CEO – a leader, a strategic thinker. And with AI on your team, working for you and with you, the team under your command can produce work faster, better, and more creatively than ever before.
Not only will you amaze your clients—you’ll also amaze yourself.
Write Faster. Write Better. Right Now.
- Jack Turk
"World's Fastest Copywriter"