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James Green – IT Origins

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James Green is a Partner at ActualTech Media

You can follow James on Twitter and LinkedIn

What’s your IT origin story? How long have you been in the field?

My gut reaction to reflecting on my origin and career path to date is that it involves a great deal of luck. No one is quite sure where this saying originated, but it’s often attributed to Seneca: “Luck is what happens when preparation meets opportunity.” In light of that statement, I suppose what really happened is that I had a series of opportunities that I was prepared for and motivated to capitalize on.

I’ve always been interested in technology, and computers in particular. I’ll get to my first computer later, but my first experience with one was at a young age and I never stopped tinkering after that. When it came time to get a real job, I already knew enough to be at least somewhat useful.

I got my first IT job working for the IT guy at my dad’s company. He was busy doing important things (especially development-related) and was happy to pass off more menial admin tasks like going around the office and upgrading everyone’s system, backup administration, directory/messaging stuff, and so on. The company had <50 people at the time, so it was a great introduction to IT in the business world without too much pressure.

I was also 16 and more interested in girls and video games than work, so I made excuses not to show up 25% of the time and squandered plenty of great opportunities to learn. Probably really embarrassed my dad, too! Fortunately, the IT guy was pretty patient with me and only threated to fire me two or three times…

After graduating from high school, I tried going to a state university to get a Computer Science degree, but I found out pretty quickly that I didn’t have the attention span or patience to become a developer. There’s obviously other avenues in ComSci, but for my first few semesters, classes were focused on programming and data modeling, and I couldn’t be bothered to do the exercises or finish my homework. Still more interested in girls, but now instead of video games it was beer. After three semesters of doing terribly, the university let me know that I should sit out for a semester and re-think my life choices. I figured I’d just deliver pizza, keep doing the video games and beer thing, and enjoy life for a while.

And here’s one of those “opportunities I was prepared for” things: while I was just having fun and being a kid, I had a roommate with a real job at a VAR, and he was able to help me land a 3-month internship in their managed services division. My first day or two there, I realized that THIS was the sort of thing I had always envisioned myself doing. These folks were managing infrastructure of all kinds (from single server in the back closet sort of stuff to casinos and large healthcare systems and some pretty substantial deployments). And I loved it.

Seneca Approved

I dug in hard and put in 8-9 hour days at the office but then another 3-4 hours learning at home every night. I devoured training material. I grew pretty quickly as a result, and management took note. 2 months into my 3-month internship, they asked if they could just hire me, and of course, I said yes. And I’ve devoted myself to growing uncomfortably fast ever since. My one career rule is that if I’m not uncomfortable, then I’m not pushing myself hard enough and I need to step it up. By my own measures, I’ve been pretty successful since then, and I attribute that to the relentless pursuit of growth. That’s the only way to continue fostering this “luck” thing – the growth ahead of the opportunity keeps me prepared to capitalize on it when it comes. Three or four more opportunities taken advantage of led me to where I am today.

What’s been the biggest change in IT since you started your career?

When I started my career, IT was still seen as a necessary expense in most organizations. They spent money on technology because they needed it to do their jobs, and in some cases, it gave them a competitive edge. But it was always a game of “how little can we spend and still get what we need?”

Now, in many organizations, IT is more than just an enabler; it IS the business. Rather than use IT services because they need it to do their job, many businesses today look to IT to create core parts of their business and to generate revenue rather than purely expenses.

 Current worst trend in IT?

AI & ML-washing. Just like everything has been “cloud this” and “cloud that” for the last decade, the next few years are going to see an explosion of the same treatment of anything remotely resembling AI or ML. Just because one of your developers looked over the README.md for TensorFlow once doesn’t mean you’re using Machine Learning!

 Current best trend in IT?

There’s a big push for IT and the business to become more closely interconnected and one of the requirements for success in that endeavor is for IT professionals to become more business-savvy. I think that it ultimately benefits everyone if the IT folks in the server room understand the needs of the business and how the money is made (or people are or helped, or whatever the business purpose is).

 How do you approach organization at work? What are your must-use apps? How do you approach organization? What’s your ideal workspace?

My life would be a complete dumpster fire if it weren’t for Airmail, OmniFocus, and my Zirtual assistant Charity.

Airmail – There’s a few reasons I love my mail client: the hotkeys I’ve got set up are awesome and allow me to crank through e-mail (with one hand!). Dare I say…they’re better than Gmail’s! Also, it’s the only mail client I’ve ever used with a modicum of success that features nice integration with OmniFocus. I’ve always wanted to like Outlook, but even with some scripting hackery and third-party tools, it never plays nice enough with OmniFocus.

OmniFocus –  I’ve always been fascinated with organization, and as anyone with a similar persuasion knows, GTD is king. Many people try it. A few adopt it fully, and most people – like myself – wind up with their own modified version of it that works for them. So my workflow is based on something GTD-esque which lives inside of OmniFocus. The only reason I don’t drop the ball daily is because of this tool.

Zirtual – Today, there’s a virtual assistant for any budget. If you really have no money to spend, you can get somebody in the Philippines doing stuff for you for pennies on the dollar. (I’m not commenting on the ethics of that.) I’ve personally chosen to work with Zirtual, who paired me up with a great and experienced assistant. They provide the infrastructure and billing and all of that, and they go through the hard process of vetting the candidates. Zirtual assistants also back each other up, so if my assistant gets hit by a bus, one of her colleagues can help me out until she recovers.

I think that focus begets success, so it’s worth spending money on low value tasks to allow me to focus on higher-value tasks. Sure, I spend some money that would otherwise be profit for me on what seems like a luxury, but my belief (which would be really tough to actually quantify) is that it pays for itself and then some. And even if it doesn’t, it makes me a heck of a lot less stressed.

My ZA handles e-mail (she filters out all the crap and just sends me the stuff I want, based on policies I’ve created), she manages my calendar, and most importantly, she takes my tasks out of OmniFocus and puts them on my calendar so that they get accomplished before the due date. This is the crux of my entire workflow (which I find to work extremely well).

  • I make sure everything important is in OmniFocus and has a due date and estimated duration. If I fail at this, the whole thing breaks.
  • My assistant puts it on my calendar with enough time to complete it before the due date.
  • Most important: I have mentally decided that Charity is the boss of my time. I need to be doing what she put on the calendar for me at any given time, or I will fail.

I have created and documented the policies that guide her decisions, so I’m still really in charge. But here’s why I do this and here’s why I think everyone should have a virtual assistant: I have a commitment to her to get the tasks done and do what the calendar says. If I don’t, I have to go tell her I didn’t do it and ask her to schedule it again for next week and that is embarrassing. Does she really care if I did it or not? No. She could care less, I’m sure. But I don’t want to go tell her I didn’t do the task that I categorized as most important today. My commitment to her means that more important work gets done and less time is spent dorking around.

Book recommendations for other IT pros (besides The Phoenix Project?). What are you reading now?

To my earlier point about growing at an uncomfortable pace – books are the fuel that run that engine. I read 50ish books each year besides my RSS/Pocket habit. The books I read mostly fall into 3 categories:

  • Health
  • Spirituality & Relationships
  • Entrepreneurship

 Here’s a small selection from each category that I think are the most broadly beneficial:

First computer you owned.

This will sound like a futuristic rocket ship compared to the first computers of many of my peers… We’re not quite sure, but my parents THINK it was a whitebox 386 with maybe 4-8 MB of RAM from a local computer store. I have fond memories of playing Commander Keen, Jill of the Jungle, Heretic (editors note: YES), and, of course, Doom.

What do you do when you’re not working in IT?

We just bought an RV fit for full-timing (a Forest River fifth wheel, for any other RV’ers out there) and plan to travel quite a lot in 2018. Visiting national parks is a hobby for my family, so we see lots of those. We’re also pretty involved in our local church where I play bass in the band and my wife hosts a faith exploration group called Alpha.

 How do you caffeine?

I’m pretty excited about this question, because the way I caffeine literally changed my life. The first book in my list of recommended books was The Bulletproof Diet, and the way I caffeine is with Bulletproof Coffee. It’s becoming more and more popular, but I was doing it before it was cool! 😉 If you’ve never heard of BPC, it’s essentially a specially grown and processed coffee crafted to reduce mycotoxins. You brew this like normal coffee but then blend in butter and a special kind of oil (caprylic acid). The result is a delicious fatty beverage that replaces breakfast and makes intermittent fasting easy and painless.

I said BPC “changed my life” which is quite an endorsement. But I really mean that, and here’s why: after beginning my BPC regimen, I lost about 20 pounds. That’s literally the only thing I changed. That was enough motivation to become interested in how this could possibly work, why, and what the long-term health consequences were. I dug deep into the latest in nutrition and figured out how to eat in a way that supports my goals. As I learned, I lost another 25 pounds. 2-3 years down the road, I’m 45-50 pounds lighter than when I started this endeavor and a few things have changed: I have more energy, I’m happier with my physique, my mental clarity is much higher, and I generally feel like I have more to give. All that is fallout from trying Bulletproof Coffee.

 Who do you want to see answer these questions?

I’d love to see my partners Scott D. Lowe and David M. Davis do this.

Best career advice you’ve received.

The best career advice is also the best life advice. He certainly didn’t pioneer the idea, but to give credit where credit’s due, I first started to understand this concept when I read Brian Klemmer’s book The Compassionate Samurai. The advice is this: you are ultimately responsible for everything good and bad in your life right now. And you have a choice in everything. Even in situations where you think you aren’t in control, you have a choice in how you respond, how you process the situation, and what you make it mean about yourself.

Example: “My boss says I have to do XYZ thing I don’t want to do!” It seems like you don’t really have a choice, but you have tons of choices such as:

  • Quit your job
  • Reason with your boss and work towards a compromise
  • Punch your boss
  • Suggest alternatives you do want to do, but that accomplish the same goal

In the end, you might decide that the most helpful response is to just do what your boss asked. But understanding the level of control and personal power you have over your life changes your mindset and makes you unstoppable. “I weighed all the options and choose to do what my boss asked” gives you WAY more personal power than “My boss made me.” No one makes you do anything.

When it comes to career, you are 100% responsible for your situation and 100% capable of changing it if you want to. If you’re answering phone calls at the help desk and you’d like to be the CIO, you can do that. Start doing things that a CIO would do – read more, hone your interpersonal skills and communication skills, understand business as well as you do technology, and so on. Don’t wait for someone to give you permission, because you’re never going to get it. You’re in charge. If you’re a CIO and you’d rather be traveling in Europe with your family…you’re in charge! Slash your household expenses and start a new career as a travel writer. 

About the author

Rich Stroffolino

Rich has been a tech enthusiast since he first used the speech simulator on a Magnavox Odyssey². Current areas of interest include ZFS, the false hopes of memristors, and the oral history of Transmeta.


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