Carpe Potestatum: Career Interview with Greg Shields

This week, I spoke with technology author, speaker, and all-around bright guy Greg Shields. We were business partners for a while and are now coworkers at Pluralsight. Greg’s career trajectory was a bit… different from most of us, and I wanted to highlight some important lessons from his journey.

So, your career took a little bit of a hard left turn at one point. But before we get to that, what was your career, say sixteen or so years ago? What were you doing, what did you feel was on the immediate horizon, and where were you kind of aiming yourself?

Indeed, it did take quite the turn. I actually started out my IT career as a technical writer.

I had always been in and around “computers” growing up. We got our first Apple IIe when I was eight or nine years old. I was that kid in high school who got called into the library to fix the IBM mainframe system when it went down. I ran the help desk for the University of Illinois in college.

Even considering all those experiences, at the time I didn’t really think of myself yet as “an IT professional”.

I honestly didn’t have much in the way of career direction for a lot of years after graduating college. I worked for a ski resort for a year. I spent a summer as a host at a Dave ’n Busters, essentially a glorified bouncer at the door. I mountain biked a lot.

Completely randomly, I eventually took a temp job at a major defense contractor helping them complete the documentation to pass an ISO-9001 audit. Once that project concluded, they needed an entry-level person to build PCs “down in the tank” as they called it. It was in the basement of a building with no windows, one that was designed to survive a near-miss by a nuclear detonation. Some winter months in that building you’d go days without seeing the sun.

The job came with a salary and benefits. I leapt at the opportunity.

My first few months in the tank pre-dated all the OS delivery automation tools you think of these days, like Windows Deployment Services or even Symantec Ghost. We manually tossed Windows XP disks into drives and built each PC, one at a time, by hand. We installed the OS and all the applications, and then pre-configured the settings, before sending them out the door.

I got my first lucky break in desktop administration by making a bet with our Chief Scientist that I could build 300 desktops in a month. At the time, this was such an outlandish proposition that he took the bet. If I succeeded, he’d promote me past the help desk and into the Tier III/Tier IV systems administration group.

What he didn’t know was that I’d been toying around on the side with Symantec Ghost – something you can do in the long waits while installing operating systems – and knew I’d win the bet. A month later, I did.

My promotion elevated me to a new group of systems administrators who weren’t all that excited that I’d so quickly jumped several levels. They assigned me to the Terminal Services infrastructure as a kind of punishment because at the time nobody wanted to admin it.

It was that decision that eventually introduced me to Citrix’s technologies, Configuration Manager, and later VMware and its desktop solutions, essentially all the earliest editions of the solution set we know of today as “End User Computing” or EUC.

OK – now for the hard left turn. What happened? There was an inflection point—did you know it at the time?

I had several great years at that defense contractor. I helped build a polar-orbiting weather satellite that circles the planet today. But, I eventually started to get bored with the pace of things. The defense industry doesn’t move quickly.

At the time, I was devouring any IT content I could find. I took every certification exam I could. Our company had a policy that they’d raise your salary by a not-insignificant amount for every passed certification exam, so I took all of them.

I also read everything I could on the industry. One of my favorites was Microsoft Certified Professional Magazine, which later became Redmond Magazine. One day, I was browsing the website and I noticed they were sponsoring a contest. The contest was their Editor for a Day contest. It offered, “tell us in 500 words or less why you’re the right person to be our Editor for a Day. The winner gets an all-expenses paid trip to our TechMentor conference, and gets to choose the theme for an issue.”

I figured, “Heck, I started as a technical writer. Let me give it a go.” I submitted my 500 words and forgot about it for months.

Quite a bit later, I came into work one day to see a voice mail message on my work phone. The message was, “Hi, my name is Dianne Schaufhauser. I’m the editor in chief for MCP Magazine. You submitted an essay to our contest a few months ago, and I’m pleased to tell you that … you won!”

Now, the crazy part about this contest was that part of the prize was to pick that theme for an issue. My company was going through a big “enterprise process” activity, which was oddly interesting to me, so I chose that as my topic.

On the call with the editorial staff, I proudly announced this and got … crickets. Nobody said anything for a solid fifteen count. Eventually, Dianne spoke up and said, “You know, that’s great Greg, but we don’t have anyone here who can write on that.”

Without really thinking, I shot back, “Well, I can.”

The call quickly turned into chaos with people talking over each other. “No, that wasn’t the deal.” “We can’t have some random person doing this.” “Dianne, we never really wanted to do this contest.” And, so on it went for several minutes.

Eventually, I spoke up and took control of the chaos by saying, “Hey! Everyone! I seem to remember that this is my prize, and so I do get to choose. So, how about this? You give me three days to write a 4,000-word piece on enterprise process. If you like it, you run it as the next month’s cover story. If you don’t, you’ve still got twenty-seven more days to find somebody else.”

The room got silent – for a long time. After a few minutes, Dianne got back on and said, “You know, I admire your moxy, Mr. Shields. I’ll give you three days. Come back with 4,000 words, and we’ll see what we think.”

I was shaking when I got off the call, because I knew that I’d just agreed to do something so outlandish, so very different than I’d ever done before, and the success of an entire magazine hinged on it.”

Needless to say, three days later I returned back with the piece. They loved it. They ran it as the cover, and flew out a photographer (who also worked for National Geographic) to take dozens of photos over an entire day. The magazine was plastered with them. It was the first article I’d ever published.

It was also the beginning of a new trajectory in my career. That article led to writing several more in later issues. Those articles eventually got me the job as columnist for the magazine’s flagship column. That column eventually led to me presenting sessions at their TechMentor conference, which later still had me becoming conference co-chair.

All those experiences blossomed further into me leaving the company and starting out on my own, with my own business. You and I, Don, eventually joined our two businesses together for almost seven years. That led to meeting the right people who brought us to Pluralsight, where I continue to serve today as Author Evangelist.

Tell me a bit about what happened to your career after that. Was it… scary? Did you ever wake up in a cold sweat at night? And where has it taken you since?

Oh, most certainly. I have made some profoundly scary decisions, any of which would have huge repercussions on mine and my family’s well-being. Some of those were made with eyes wide open. For others, you just didn’t know. You kind of had to … guess … based on what you knew. Those were the hardest decisions, and often they ended up with the best results.

Looking back, what are some general things you feel you’ve learned about recognizing and seizing opportunities? Maybe you had a plan, maybe you didn’t, but it all went a very different direction. What would you want other people to know about taking chances?

Was there a plan for all this? No. Very much no, in fact!

There were ideas that got tried, and projects that were attempted. Some succeeded, others failed. Some projects cost far more in time than we ever got back in cash. Others were almost embarrassingly lucrative when you look back on them.

All too often, there was as much of an idea of “how do I make enough money to pay my mortgage this month” as was there “who do I want to be in five years”.

There were days, particularly early on, when it wasn’t entirely certain that the mortgage would get paid. But we got smarter over time and with each iteration. We wrote better contracts. We made smarter decisions on pricing for our efforts. We turned down projects that we knew weren’t best for us and our families. We met new people, or stopped working with – or for – other people.

We made decisions.

And, that right there is what I sometimes think is the biggest difference between going out on your own versus working for somebody else: You made the decisions. Those decisions are sometimes awesome, and sometimes they’re not – but you still get to make them.

I can’t conclude this story without addressing the reality that after so many years of working for myself, I eventually did go back to working for someone else. It’s that part of this story that’s worth highlighting as well, because a career working for somebody else can be as fulfilling as one working for yourself. It’s just different.

Working for someone else after working for yourself has been an exercise in being OK with no longer making those decisions. In a lot of ways, it’s easier. The hours are better, even if the potential upside isn’t.

More than anything, my current role here at Pluralsight is narrower, but perhaps deeper. I’m responsible for fewer things – I’m no longer marketing, and sales, and accounting, and all the other functions – but those projects I work on now are interesting.

They are because probably the one thing I’ve learned in this wild-and-unexpected career I’ve had is that you’re ultimately responsible for your own career path. A person’s success really is measured in just a few key traits: Show up when you’re supposed to, bring a good attitude, deliver on your promises, be easier than the other person just doing it themselves, and always remember the golden rule: “It’s more important to be on-time than perfect.”

So, there are a few lessons I think we can all keep in mind in terms of our own careers.

  1. Seize opportunity when you see it. Carpe Potestatum! Greg’s 500-word “Editor for a Day” entry might not have gone anywhere, but he tried. And he didn’t just poke the opportunity—he grabbed it. Even when the magazine was pushing back against the topic, he pushed to make his opportunity a reality. “Moxy,” Dianne said. Show moxy.
  2. You cannot predict your career. Don’t try. Define what you want from life, imagine a career that can provide that, and then look for the first step toward that destination. Take that step, and then the next. It’s a journey.

Thanks for reading—I hope you found some useful thoughts!