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.

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.