AMA: Which Path Should I Take?

A reader writes:

Hi Don, here’s a Q for AMA: I work at a fast growing software company as a Microsoft stack admin. The IT dept is small. I have good pay, benefits, opportunity for annual bonus and work/life flexibility, but corporate IT runs Linux and Windows server like it’s still 2006. All on-prem hosted VMs. No cloud. Also no dev environment. Just getting better server automation off the ground slowly. And I have to do a lot of incident ticket escalations for end-user support and spend a lot of time focused on end user workstation patching. The other side of the company developing the software is very progressive: DevOps, agile, tons of scrum teams, CI/CD pipelines and lots of stuff in the cloud.
I have an opportunity to work at an Ivy League university in their large central IT department. They run cross-functional DevOps teams where Windows, Linux, and Database admins all cross train. Plus they have a huge initiative underway migrating systems into the cloud and the tooling around that. I’d be a part of all that. The role has no direct end user support at all, which I prefer. The cons are longer commute, more processes/people to navigate, and 5% less pay to start. But also a 5% retirement match, so that’s kind of a wash, and very valuable as it compounds in the future. I have no match today.
Taking into consideration these different environments, which one do you thInk is better for my professional development moving forward? Curious what your gut reaction is, and other angles or perspectives I might want to consider.

I hope you’ll submit a question, too!

FWIW, a 5% retirement match against a 5% pay drop is actually a win; you probably get to keep 22% more income from the match as it’s pre-tax, and as you note, compound interest is a magical thing.
Well, it depends a lot on what you want your professional goals to be. One of the things I touch on pretty heavily in Be the Master is the need to define your success, and to define yourself. You’re doing almost exactly what I used to do when weighing opportunities: I’d kind of create a comparison chart (sometimes literally) like I was shopping for a car. I’d often find, as you’re finding, that the “hard” facts tend to balance each other in some way, and it’s the “soft” factors you have to start weighing. See, when you’re buying a car, you know what the goal is: transportation. With your career, unless you’ve defined your success, you don’t know what the goals are, so you can’t make decisions that lead to those goals.
When I’d first gone independent back in 2001, I was making most of my living off book advance fees (this trick no longer works, but it wasn’t bad back then), meaning I wrote about six books a year (I know, I know, it’s my thing). But when confronted with different book options, I started to do the same thing you’re doing – which is better for me to pursue? I wound up bouncing more or less aimlessly all over the place. Application Center. E-Commerce for Dummies (not proud, but it paid). Commerce Server. Pretty much everything. And while it paid the bills, as any of the options in front of you will do, none of them furthered my career. 
It wasn’t until my partner and I sat down and started discussing who I wanted to be when I grew up that some clarity emerged. That was around 2003, when I wrote my first book on VBScript. I switched to speaking almost exclusively on VBScript at conferences, and promoting private VBScript classes. That’s when my career took off.

…which one do you thInk is better for my professional development moving forward?

The problem is that there’s no way to evaluate these opportunities because you haven’t stated an end-goal. Money needs to be part of that end goal, of course, because “food” and “shelter,” but it isn’t the only factor.
Who do you want to be when you grow up, and which option is going to point you in that direction? Sure, you may find that you need to make some sacrifices – money – to get pointed in that direction, but if you focus on the end game, then you’ll eventually make that back and then some.
So my advice is to sit down with the fam and decide who you are and who you want to be. Then evaluate these options with that in mind. Which one is going to help you be who you want to be? Which one is going to get you, or help you toward, your success?

The role has no direct end user support at all, which I prefer.

Dude, we all prefer that. 🙂

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I went to a Tier 1 university from a consulting position with a Fortune 50 company, and it's exactly what I (capitalized) was looking for. It was a substantial pay cut, but no travel, 1.5 miles from my home, relaxed work environment, and small team. Am I on the bleeding edge of technology, no I had to overhaul 15 year old "best practices" to prepare them for cloud migrations, which we're doing now. Fun fact, another person came over from my last company and they didn't come for the culture like I did. They're trying to run the org like a for-profit corporation and it's not going well. It's all about the "soft" qualities, because happiness is what you're after - and you won't get it from an unsatisfying job, even if it pays well.


Why not just try to jump to the other side of your company? If you like the life you have at your current job and are looking for more technical challenges or to move closer to the cutting edge, and those exist for you right there, work your way in there! I did that very thing 3 years ago at my company and it's paid dividends for me. I'm vested in the 401k plan, I have more vacation days, I am the "senior" guy, and so on, that I was never before when I'd jump companies to improve my work situation. Plus, if you move to a bigger place like a university, while it may see fast moving from the outside, chances are you'll never get as much agility as you have at a smaller shop.
If I'd have thought of my career this way 20 years ago, I might not be on my 10th company.