The 6 Pillars


One thing you’ll hear me talk A LOT about are the six pillars I’ve observed very successful people follow in their IT careers. All of these will be continuously discussed and developed on the blog and podcast as we go along.  These aren’t everything you’ll ever need to know, but following these gives you SIGNIFICANTLY more room to run in your career.  So without further adieu, here they are in summary, pillar by pillar.

Pillar 1: It’s WAY easier to help people up a ladder than keep them down on the bottom rung.

Maybe for you, it’s the Golden Rule, treat others the way you want to be treated.

Or, maybe for you, it’s Karma – what comes around goes around.

In my career, I’ve been very fortunate to have outstanding career mentors throughout my working life. However, they’ve almost always been older dudes that weren’t in IT. So a lot of the knowledge, while somewhat portable, just doesn’t work in an IT environment. Now, you might be saying, yeah man, but this is just a blog and a podcast.

Yeah, you’re right. BUT – hopefully, you’ll glean something out of it. Maybe it’ll pique your curiosity.

I run a side-gig called CareerMap.Tech. We have a fantastic community, and I offer custom consultation on your brand of YOU.


Pillar 2: Congratulations, you’ve just been promoted to the head of sales for your career.


Here’s the thing, in IT there are tons of different personalities working throughout the career verticals you might be looking to move towards. And for a very few of you, it might ACTUALLY be sales. But for the rest of you, you’re probably thinking ‘ah, man, I don’t know anything about sales, and I sorta don’t like salespeople‘.

Don’t worry, I’m not going to turn you into a used car huckster, and I’m not going to teach you ways to lie during interviews. Because as Pillar 1 states, I want to help you get higher up the career ladder. If you get a job and get canned because you lied (but really, really well) that is not helpful. But I might challenge your beliefs in yourself, because frequently us IT folks are a little bit timid, demure, maybe the word you’d use is shy. And you may not be getting your brand out there properly because you’re worried about how to do that. DON’T WORRY. We’ve got your back.

So, we’re helping you move your way up, and maybe you just feel stuck or bored, but you don’t know how to get un-stuck. This is where we’re going to bring up pillar #3:

Pillar 3: It’s OK to pivot, and you’ll probably be more valuable when you do.

Now – here is where I may have had a few of you feel a bit of a check in your conscience. A good majority of us in IT are pretty loyal.  BUT, Here’s the thing: I’ve been at two jobs for over 4 years, and unconsciously, I was pivoting from one tech field to another. But, that experience never left me.

At this point, I’ve been in Networking, Systems, Security, Coding and Cloud / big data. I’ve been called a bit of a purple squirrel or a unicorn (though I prefer purple squirrel). And know what, my paycheck reflects that. And I’m not saying that to be boastful. I want you to do what I did: Over the course of 8 years, I’ve more than doubled my income with my career moves. Part of this is seniority, sure, but I know people who have multiple CCIE’s who make the same as I do, and I don’t have a CCIE. I know lead programmers at huge companies that make less than I do. And I want them to know their worth as well.

This comes to pillar #4

Pillar 4: Stagnant skills is career death.

I’m all for picking parts of a niche, but only if it’s a niche, YOU OWN. And I’m not going to tell you ‘Ah, start your own company, be an entrepreneur! Storm the castle for yourself!’  Hey, I’m all for that if it’s your jam. You will ALWAYS make more money when you own a company (period, end of story).

BUT, that’s not what I’m saying.

What I am saying is don’t pick a skill that boxes you in when it dies off through obsolescence. Because it will, I 100% guarantee it.

Left to my own ‘initial devices’ when I joined the IT workforce in 1999, I would be the master of all things “Fax over IP”.

Which you now do on your smartphone.

For free.

To set apart that negative statement, I’m going to give you pillar number 5 which I promise isn’t some self-help-hippie-drivel:

Pillar 5: Keep your dreams and goals, even if people mock you.

I can’t tell you how many people told me my career shifts were dumb.

My favorite quote from a former colleague who is not-so-good with the H.R.-P.C. talk was “Damn, that idea is more special-ed than you are.

I ended up explaining to him how to get out of a commodity tech job and become an SME 18 months later.

Wanna know what else people have told me in the past “Don’t focus your time on virtualization, that’ll never catch on.” “Security will eventually kill off all cloud products.” “Information Security is a terrible career path.” “Know what Preston, they’ll never automate the network.” “VoIP is definitely going to stay in-house; you can’t outsource it.”

All of these things were false. And by looking around and seeing the shifting tides of our industry I’ve Looked at my dreams, pivoted, added new skills, sold myself into a new role and usually bring people with me when I do it (see Pillar 1).

Finally – my favorite and most challenging pillar – #6:

Pillar 6: Make sure you surround yourself with smarter people.

Hey – I think you’re fantastic and you should think you’re fantastic too!

I had the fortune of marrying my wife Emily incredibly young. We were poor as church mice when we first started out and my wife picked up some sales training videos. Most of them came from a phenomenal trainer named Zig Ziglar.

Zig had this iconic quote “We tend to become the people we hang around the most.” So here is my point about this pillar – be intentional with your relationships! I never, ever, ever purposefully spend time with people who are toxically trying to bring me down.

If I did I would most likely be level 1 helpdesk ticket-taker-McGee.

And if that is your job description and I offended you, I’m sorry. But you are better than that, so am I.

I actively survey my colleagues to see who are the best – and hang out with them.  I do this at clients and friends as well.

And that’s not all we’ll tackle.

We’re going to delve into some seriously hidden knowledge in the IT industry. Mystical questions in our field like the following:

Why is it you need experience but can’t get experience without getting a job ?!

Why did my college train me on crappy tools that no one uses anymore?

Why haven’t I gotten a raise in the last two years?

What does it take to be a senior leader in my field?

How the heck do I get out of on-call hell?

How do you not suck in a 1 on 1 interview?

How do you not suck in a group interview?

Join us in this adventure, you’re now part of the Navigators!