Month: December 2017

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

6: Make sure you surround yourself with smarter people.

This pillar, #6 extends outside of work as well as inside.  Make sure you are constantly surrounded by high-quality people.  So how do you go about this at work?  First off, say you’ve got like 10 people in your department.  Find the 3 smartest people and see if you can be put on projects with them, or accompany them.  Go eat lunch with them.  See what things they’re reading and working on – are they things that would benefit you as well?

Now I’m not saying you need to BE them, just be around them.  It’s a weird, but the universal truth that when you hang out with high performers, you perform better.  When you hang out with the slackers, you start to let your productivity drop and work ‘dumber’ instead of ‘smarter’.  For more information on slacker and Debbie Downers, see pillar 5, because 99.98% of the time they’re the ‘actively disengaged’ employees that are NOT the people you want to emulate in your career.

Maybe you work solo or have work with what I would off the cuff dub ‘the actively disengaged’ employee. Even President Camacho from Idiocracy understood this concept, so if he gets it – we should too!  Make sure you are AROUND people you want to be around all the time, and act the way you want to be, or grow into career-wise.

Hey – I think you’re awesome and you should think you’re awesome too! But in reality, I had the fortunate event 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 from a phenomenal trainer named Zig Ziglar. Zig had this amazing 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.

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 so should you!

A breakup letter

Hey there Navigators – I thought I’d share a post I put on the soc-med’s that I found very freeing.  A financial and tech lifestyle pivot if you will.  Hopefully, you enjoy my prose and don’t get too much PSTD from reading it!

It’s not me, it’s you: My breakup letter to my constant digital companion of over a decade.

Well, we both must have imagined this time would come, although I’m sure I’ve been contemplating it much more than you.  The constant “Things will get better” but never did.  It seems we outgrew each other.  12 years.  12 years and approximately 15k USD.  FIFTEEN THOUSAND DOLLARS.  That’s how much I gave to you over the years.  And yet, you never gave me that much in return value.  Sure, there were some pretty good times at first, but as I grew as a person, you never met my needs.

My 4g used to be awesome, but you didn’t keep up.  When I asked you what the problem was, you blamed me, and said it must be my issue.  Your response was ‘you can fix this problem with a $250 repeater that you buy yourself to make me look better’.  And when I said I needed more from you – more of your attention and your 1’s and 0’s, you said that’s fine, but you needed more from me too.  Approximately 50 dollars more a month.  For 2 phones only.  On the phones I already had.  To add the boys, the bill would be somewhere around $410.  As our family grew, I knew I had to get out of this relationship.  It was toxic.

I found someone new.  Someone who is giving me 4 iPhone 8’s, 4 lines of service, unlimited data, and some various accessories.  For 30 dollars more per month than you wanted to charge me for unlimited for 2 phones.  Oh, and a streaming service to boot.  When I called you to give me an ultimatum, your answer was ‘You can’t leave me. No one is better than me, and you’ll regret this’.  That made me scared at first, but then it JUST MADE ME ANGRY.


So, Verizon, I feel it’s only fair I tell you that I’ve left you for T-Mobile.

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

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. The thing is, when you make an educated decision based on what our industry is doing, a lot of the time it looks SUPER weird.  This isn’t to say that you have to be a ‘futureologist’ or anything like that.  Just look at what’s new.  What are people talking about being ‘the next big thing’.  For instance, right now the ‘next big thing’ is IOT.  If you have IOT on your resume and LinkedIn profile, you’re going to start to get more and more recruiter calls.

The reaction to this decision to pivot spawns all kinds of salty memes out there that reflect this. “Wolves rarely bother with the opinions of sheep” is one that comes to mind.  A more positive version of this are the goofy pictures posted by 15 year-olds on Instagram like “sunshine in, darkness out”.

In all honesty though, the message is the same for this pillar.  It points to the fact that there are a TON of people in hopeless jobs that are negative and actively disengaged.  These same people WILL TRY TO SUBCONSCIOUSLY TAKE YOU DOWN WITH THEM. Did you notice that?  That was in ALL CAPS, bold, and italics for a reason.  I have been this guy.  Maybe not as deplorable as other miserable people I’ve worked with, but pretty damn close.

When I started to make career decisions based on what was best for me, versus what a corporate agenda or comfort level of myself and others was, I got pushback.  A LOT of pushback.  My favorite quote from a 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.

This has happened to me time and time again.  Proof in the pudding of things other 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”.

The funny thing about this pillar (5) and pillar 6 is that they could actually be the different sides to the same coin.  But they take different mental approaches.

All of these things above were false statements. 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).


Pillar 4: Stagnant skills is career death

Pillar 4: Stagnant skills is career death

OK, Navigators, here it is – the pillar I’ve been hinting to you about – Pillar 4.

Let me paint the backstory – I had found THE job I wanted.  Or so it seemed to me at the time.  It was awesome.  It was amazing.  I worked internationally.  I had challenging problems every single day, but I mostly had some kind of work-life balance going on.

And … I stopped getting certs.  And I just focused on one thing for a few weeks.  Then another.  I made no reasonable progress during this time, however.  Then I sorta just stopped doing advancement of myself and my skills altogether.  And as well, I started getting lazy at work.  Not feet-up YouTube all day lazy, but not as crisp.  Started missing deadlines.  As I look back now, I KNEW it was time to bounce, but my sexy oil and gas job in 2014 was more money than I’d ever made.  I bled the colors of my company and would be the ‘hero’ every chance I got when I would be texted in the middle of the night by overseas folks.

Here’s the funny thing – as I started to spiral, and I DID start to spiral I could have EASILY pulled myself out of it.  What it would have been was to start saying NO and start investing in myself.  But I felt desperation set in.  If you are feeling the desperate throes of ‘I’m about to get canned’ focus on building up ONE skill alone – Interviewing skills.  I have rarely seen someone pull out of a nosedive once they’ve lost favor.  Just make sure you validate your ‘I’m about to get canned’ feelings are a real thing and not just unfounded feelings of insecurity.  We will talk about these in later posts.

As I said, I was in a spiral.  My work was less than it should have been.  My engagement was lacking, and if anything, I was beginning to try and sabotage parts of my leadership (see pillar 1).  Subconsciously, of course, and only now can I fully realize this. I was disenfranchised and upset at my pride being injured as I was ‘replaced’.  Instead of asking further questions, and finding out there was a significant political issue impacting our brand in Israel, I just began to internally rage.  And it was a systematic politics issue I’d have never touched – like ‘politics’ political, not office politics.

Fast forward a few months and I had a horrible on-call rotation.  The 30-thousand foot viewpoint is that some Senior VP I had never known to exist was trying to call an office we were operating in stealth on our landlines.  And it failed.  So he had to use his cell phone to call resulting in a large bill.

Here’s the thing about a message that gets propagated from the C-Level down to an individual contributor:  Every layer adds their own particular layer of paranoia and ‘spin’ to the message.  So, a message that traveled down a few layers of management.  I know the SVP that it came from, and he wasn’t a terrible person.  I imagine in the game of ‘telephone’ it changed from ‘What the hell?  Wonder why this phone can’t call that number – secretary can you call the IT people??’ and became ‘ZOMG!  STOP WHAT YOU’RE DOING NOW.  GET INTO THE OFFICE AND FIX IT.  DO IT!  DO IT NOW!

My boss wasn’t a bad guy, but he wasn’t a particularly great manager for me either.  Many times, my leadership has been phenomenal at air cover from messages from above.  Right now, my current boss has been fantastic on this.  But as I retrospectively look backward, I had not done him any favors with my work.  I was consistently a pain in the butt and this was the proverbial straw that broke the camel’s back.  I had not been teaming well with him and making the two of us look good.  Because here’s the universal truth:

When you look bad, your boss looks bad.

As the message tends to get more severe and extreme as it moves from C-Level folks to the average workers it became a SEVERE AND INTENSE problem.  So much so that my boss called me during the dinner I was at on my anniversary.  And like a good lemming, I answered, ended dinner and went into the office.

What would I do today?  I would say ‘shoot’, let me get back to you tomorrow with a resolution.  But as I was so freaked out, I started panicking and called long distance providers and all sorts of other people who were legitimately NOT MY PROBLEM.  I took on the entire problem and then much, much more.  I compounded the issue by not having good boundaries.  Because I was living in fear of the ax falling.

Having a select number of skills and procedures running on auto-pilot gives me that peace of mind.  The complete irony of this peace of mind is that I’m a better employee.  I keep my skills up so that I can walk away at any time.  The irony is that once I’ve had that freedom, I’m not going to lose it again so I always have my skills increasing and evolving from old-n-janky to new-n-swanky.

To put the final nail in the coffin of this concept, let’s talk Niche-markets for a second.  My viewpoint is that you can exploit a Niche for maybe 5 years.  Maybe.  So – if you were a data processes implementer for dairy farms, you might have a cool niche.  But if you don’t evolve with technology, data process implementation 2.0 (I’m just making these up, BTW) will eat away your opportunities.  And you will be left out alone.

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.

Travel down the road with us and we’ll get you the mindset and skills to compete and succeed in this industry!

Sidebar:  the skills I’m currently working on:

NSX-T, AWS, and Ansible.

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

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

Pillar 3 is so EVIDENT on LinkedIn.  Go look at 95% of all profiles out there and what do you see?  Bob F Everyman – IT guy at universal megacorp and Sally T Jenkins – programmer for ultrahuge programming

If I’m honest, this was me.  I was ‘Preston Kilburn, Network Engineer at International Oil Company’.  Until I wasn’t (but that’s pillar 4 – I know right – I’m totally stringing you along for that pillar 4…)

And if I’m even slightly a bit deeper cutting – fellas – this is much more of an issue for us.  Men tend to have their identity almost wholly wrapped around their careers.  And … Maybe that’s OK if you’re a professor or an accountant.  But guess what – unless you’re staying a front-line help desk ticket taker – you’re going to have a ton of different roles.  If you’re not straight up support – 10 to 20 years from now your job has a huge extinction rate.  Most likely, it won’t be there.

I’m not saying don’t pick a niche.  But what I am saying is make sure your niche is an INDUSTRY not a specific JOB.  Let me give you an example:

My father-in-law is a former IBM and Cray Super Computer operator and programmer.  We were talking about work ethics at the time, but then he mentioned something that took me by surprise.  He was frustrated with a guy back in the day.  What stuck with me was what his job was:

Computer Maintenance Tech (AKA – the guy who vacuums out dust from inside the computer).

He was literally a hard drive maid.  That was his job.  That’s not a ‘thing’ anymore.  At least not that I know of.  And I know a lot of people.

What I am saying is that I’ve had careers in VoIP, Networking, System Administration, Virtualization, and Security.  Because I have shifted verticals many times, I rarely find myself in a position where I don’t understand more than the cursory facts of an issue a customer is trying to solve.  And in many senses, I’m a bit unique for this, because when opportunities have come along I haven’t’ said ‘Nope, I only do X’.

Honestly, I think my varied experience has opened a LOT of doors up.  Perhaps closed a few, but for the most part I think it has opened more than closed.  And it has given me one of the coolest nickname a recruiter has ever given me:

‘The purple squirrel’

When I was on the phone, this guy said ‘Look Preston, we need someone who has a good understanding of Cloud, Voice, Security, Virtualization, Networking and QoS.  I’ve looked at around 125 candidates – and you’re my purple squirrel!’

Want to know what the nice thing about being the purple squirrel is?

I say ‘NO’. A lot.

I actually turned down that very friendly recruiter, because honestly it would swing me back into a commoditized area – which I want to avoid.

What pillar 3 is about is freeing yourself from the oldskool confines of ‘Well, I was trained to do X, so I can’t do Y’.  Allow me to give you some real-life examples:

“I’ve gotten a CCNP voice, so I’m not going to work on an Asterisk VoIP system

I know Ruby, I’m not about to look at Python

I know linux, I’m not touching Microsoft (or vice-versa)

When the opportunity presents itself – and it will if you’re keeping your eyes open – expand your skillsets! From a core ‘you’ perspective, this does 5 things:

1: You are not your job at your employer. 

I struggled with this concept until I got fired (hang on to pillar 4 for this story).  Canned.  Let go.  Pink Slipped.  Whatever the euphemism, my employer, (and at the time a huge chunk of my identity) said “See ya!”  What happens when this event rolls around is one is faced with two choices “I am better than that situation” or “Surely I can’t go on anymore”.  Rarely does someone walk away from a firing and go ‘meh.’

2: You are not what you know now. 

The concept of constantly doing and learning more is super daunting for some people.  I totally get that. But it’s a thing in IT.  You can NEVER assume in this career that you will be doing the same thing even 18 months from now.  And what you know now might be completely irrelevant, but YOU are not.  You are not what you know now, get uneasy and out of your comfort zone.  Once you get comfy – do something new.

3: Your work is probably better than you know.

Frequently we will receive feedback on what sucks about our performance and internalize this to N+2 degrees.  “I got yelled at for not doing this report” might turn into “I’m absolutely horrible at reports and all administrative stuff”.  Now, you might legitimately suck at that area, but on the whole, your work is probably better than you think it is.  Don’t be afraid to take inventory of what you’ve done and be proud.  You’ll need it come review and role-shift times.

4: The desire becomes: Embrace Automation.

No matter how awesome and fast you are at something, find a way to automate it and let a robot do it.  NEVER DO SOMETHING MORE THAN TWICE.  If you find you’re doing something a third time you’re doing it wrong.

5: You start to do your due-diligence.

The hardest question I get asked when I work with folks considering a vertical or career shift is ‘Does this company suck’ or ‘Does this role suck’.  I’d take a semi-crappy job and a turd company with an amazing boss.  And then I’d move 45 minutes after that boss left.  Stick around to find out how to do the due-diligence of figuring out if a team is new and swanky or old and janky.

If you embrace the pivot, I promise your bottom line and your opportunities will start to reflect it.

Pillar 2: Congratulations, you’re head of career sales.

Today we’re talking about Pillar #2.

2: Congratulations, you’re head of career sales.

It’s entirely possible that this pillar might be the hardest for some of us in IT.  As a whole, we may not tend to be the most social of people outside of our close-knit group of friends.  Especially not at work, and perhaps most poignantly when first starting out as the first line of defense where everyone always seems to want a piece of you.

It can be daunting to think about IT-based social groups.

But the irony is this:  The more you move around in groups of peers and thought leaders, the more you grow as an SME (Subject Matter Expert).  And that is the EXACT reason to put on your sales hat and go meet some new people and build a network.

How is this helpful you ask?

Simple – when recruiters ask for people someone knows, you’re now ‘Oh, hey I met them at that OWASP meet up” or “Yeah, we met at Cisco Live – super cool person, great aptitude from what I could tell”.  And don’t be afraid to attend an event.  Everyone there (well, ok 99% of everyone there) is thinking the same thought in their head:

‘I shouldn’t be here, and I don’t know if I am good enough to even hang with this group.’

You’ll notice I said 99%.  Because there is that other 1%.  And they are that good, and you will definitely learn from them (this ties in with Pillar 6 as well).

Another function of Pillar 2 is that you MUST confront the awkward conversations that most of us just don’t want to have.  Things like

Hey, boss, why is it that I seem to get on-call and Jimmy doesn’t?


Hey, I’ve been here 18 months, and I haven’t gotten a raise.”

-or- perhaps the universal:

When did you say the bonus hit?

Because here is the thing – If you’re thinking it, and there are ten other people in your group, the other nine are probably thinking it.  Being in charge of your career destiny is quite scary when you first start out.

For some of us, the concept of sales is BONE CHILLING SCARY.

But the funny thing is, the more you do it, the faster you start to consider your decisions and get a little bolder.  Not cocky.  Not stupid.  But brave – willing to ask questions that might feel weird or stupid. I’M FANTASTIC AT ASKING STUPID-SMART QUESTIONS (but more on that later).  Once most of us get past this odd societal ‘workplace stage fright’ something happens:

You gain momentum.

Just a little.  Not all at once.  But if you keep putting yourself out there, meeting new people, asking questions no one else will, you begin on the way to owning your career path.  In a book I read years ago “Good to Great” – the author Jim Collins describes a well performing company like a heavy flywheel that’s 5,000 pounds (or, you know 2,262 Kg) that is 30 feet tall.  Getting it spinning is initially very tough.  But once you get going, it’s easier to go forward than it is to stop.

Your career is like that flywheel.  Big. Seemingly impossible to move.  But trust me, getting that forward motion is possible, and the more you push forward, the faster and farther you’ll go.


Historical Note

Just as a total sidebar, you can read about Good to Great’s flywheel concept (here)  and as a preview to Pillar 4, you can read this amazing Freakonomics article about some of the Good to Great companies that suck or just flat out don’t exist anymore (here).  And I’m not picking on Jim Collins – he’s a fabulous writer who pointed out what was working when the book came out like 15 years ago.  I’m pointing out that if you get complacent – you have almost more work than if you never started.

But that’s another story for a later date.

Pillar 1 – Helping people up the ladder is easier than holding them on the bottom rung.

Today we talk about Pillar #1:

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

I hesitated before even documenting this pillar, but the older I get, the more I realize that people don’t innately get this concept.  It is so important to help other people out. Call me weird, old-fashioned, or too good of a person – but I like helping people. But even I had to learn this lesson.

Screwing someone over is never ever a long-term win.


No matter how much you dislike someone, you have to at least try to help them out, especially when we are in a service area like IT.

By the way – did you know that?  We are in a service job.  I legitimately didn’t consider this until someone pointed it out to me.  We exist to serve other people with our tech knowledge.  Not to say that you are a SERVANT plebian who doesn’t proceed far in your career!  Far from it, I want you to become an SME (Subject Matter Expert).  But that’s the rub.  It’s VERY easy to become cold and calculating the more you know.  I know because this happened to me once.  Let me paint the picture:

I had just been promoted to a new position of authority for networking at an oil and gas company, and I was responsible for all of IT infrastructure in a region.  Kinda.  Sorta – it was weird because I had not-quite-peers in the office, they were junior-to-mid level folks.  There was a skill gap… NOT an aptitude or attitude gap though.

Therein lied the rub.  I felt ever so much superior to my hard working really smart peers.  Why?  Because… science?  Pride? Fear?

Who knows. One plausible reason was that I was a blind-spotted idiot, that’s why. I was so afraid of not being the smartest guy in the room that I built myself a sand kingdom.  Ironically, what happened next was really quite humbling.


That’s right – REPLACED.

Not on paper mind you, but corporate sent out a guy who would ultimately become the architect of the network.  He was going to tag along to ‘help out’.  What I learned next was oh so very humbling.  In order, what I learned was:

#1 – I had done wrong by not empowering the guys in the office more.

Being a control-freak did not help me.  Instead of doing deep dive training, I delegated stupid tasks I didn’t want to do.  Don’t get me wrong – delegation is NOT bad.  But expecting people you work with as a peer and leader to JUST do grunt work is wrong.  I kept all the ‘good stuff’ for me, but there was too much of it.

#2 – I got a dose of what I SHOULD have done when I got mentored.

Instead of sweeping in and telling me what garbage my network design was (and there was room to poke a few holes I think, looking back) – this guy took me under his wing.  We were having a really weird delay with some protocols.  Instead of going ‘Hey jackass, go fix this problem’, no he did it the right way:

1: He walked me through why it was a problem. 

2: Then he showed me how to fix it. 

3: And had me show the other guys how to fix it.

I walked away changed.

Was I a little chaffed at being replaced?  Yeah, I was, but I learned a MUCH DEEPER truth than setting a native VLAN on a trunk port because of random Israeli rules.

I learned ‘Show one, Do One, Teach One’. 

I didn’t have those words, but I got the concept.  And by God, it stuck (thanks Ronnie).  For more about WHY I got replaced, stick around for my explanation on Pillar 5.

So who in your career can you mentor instead of delegating to?

If you can’t think of anyone, who should be mentoring you?

Leave a comment with any insights or experiences.

Welcome to your new IT career advice home!

Hey – welcome home!

What is this place and how did you get here you ask?  Probably sweet, sweet writing, and maybe some subtle SEO magic.

Who am I / Who are you/ Who are we?

I am Preston Kilburn, the cartographer here at

YOU are now a Navigator.

WE are now going to kick your career goals in IT on overdrive.

So you might be asking why I would make a blog and a podcast about this subject?  Well, because quite honestly because nothing out there doesn’t have a HUGE ANGLE when they’re giving you advice.  I know you’ve seen these websites out there:

Search result for ‘How to get ahead in networking’ = ‘Take some classes at <fill in the blank training center>’.

Search result for ‘How to get a non-on-call IT job = ‘Find degree programs in your area at <fill in the blank university>’.

And honestly – I’m sick of it.

Sick and fed up of corporate recruiter shops offering lame-ass cert advice that is either so far out of the common range it’s not funny.

Sick of Universities promising that for an 80k degree, you might get a starting rung help desk job (with the dude who worked with no degree for 6 months at Geek Squad, btw).

Here are my core commitments to you, dear reader, listener, and occasionally – viewers:

1: I won’t recommend stuff I don’t absolutely think is helpful to your career in some ways.

2: If I get a referral fee for something I recommend, I will let you know.

3: I’m ACTUALLY in IT, and I plan to stay this way.  I’m not some mythical career coach looking to find a niche. For more info about me (Preston) here is my LinkedIn profile: (

4: I’m actually here to help you, not make a few bucks off of you.  There are a LOT of smart people I’ve met in IT who are stuck in dead end jobs and they don’t know how to break free.  I want to help you with that.

5: I take giving this advice seriously, because sometimes people gave me terrible advice just off-the-cuff and it set me back.

6: I value diversity of opinion.  We are going to have a LOT of different opinions.  Sometimes they might conflict – and that’s OK – because not every map is drawn the same way.  No two IT careers are the same either, but once you start to know the topology of this career, you’ll be able to go faster.