My Three Pillars

In the last six years I have been lucky enough in IT to be fairly successful and advance my career.  Lately I’ve been reflecting on what I did right, and what I might change.  In looking to the future and where my path is going, I find I have to look into the past and better understand how I got here.  While there was no definitive five year plan, I think there were three pillars that served me faithfully to enable growth and advancement.

Make Yourself Uncomfortable

In 2010 I had been at the same job for six and a half years.  I had started as a desktop admin and progressed to be in charge of servers, networking, and storage.  But I had definitely reached the zenith of where I could advance in the company.  Short of taking my boss’ job, unlikely, there was really nowhere to go.  The job was fairly easy, I knew everyone in the company, and I had a sweet three mile commute from my house.  It was all very comfortable, and you know what?  I could still be at that company doing the same work, with roughly the same people, and the same easy commute.  It would be easy, not challenging, and completely boring.

If you want to advance in your career, you have to make yourself uncomfortable.  You have to do things that make you uneasy or uncertain.  Now I am not saying you have to do something that terrifies you.  That seems counterproductive and likely to backfire.  Instead, I think you have to make yourself a little uncomfortable in increments.  For instance, I am not a huge fan of traveling to new places and working with people I don’t know.  So naturally I went into consulting, wherein I meet new people and work in new places constantly.  When I first started, it made me uncomfortable, and honestly sometimes it still does.  But I know that each new place and person comes with new opportunities, so there is a benefit to all that discomfort.

Discomfort is usually a sign you’re doing something right.

Plan to Fail

After I left my comfortable job in 2010, I worked at a university for two years.  And that was a great job.  In two years I learned a ton about enterprise systems and working at scale that I never would have discovered had I stayed in my previous position.  In 2012 opportunity knocked in the form of a move to consulting.  There was a promise of working with cutting edge tech, and a healthy increase in salary to go with it.  Even though the idea of consulting made me uncomfortable, I still went for it.

Four months in I knew I had made a bad decision.

There was a lot more travel than I had bargained for.  I was being asked to implement tech that I wasn’t qualified to configure, and install it in a fraction of the time it should have been necessary to do properly.  The team was me and two other people, who are both really nice guys, but it felt like we were totally disconnected from the parent company and pretty much making things up as we went.  The phrase “fly by night” and “by the seat of one’s pants” come to mind.  Smoke was being blown into orifices, and I was fairly miserable.

My first foray into consulting and I was failing.  And that is okay.

Not that it felt okay.  It felt pretty awful.  Failure isn’t supposed to feel good.  If I wanted to sit back and never fail, I would have never left the comfy couch.

Six months in I resigned.  And that was okay too.  I found a new job in consulting, and based on my prior experience I had a much clearer idea of what kind of company I wanted to work for and what type of consulting I wanted to do.  I had two kids under the age of two, so travel was out.  I wanted an established practice with subject matter experts I could rely on if I didn’t know the answer.  And I wanted to be able to prepare myself before I was pushed out in the field to implement or design a solution.  I ended up getting all of those things!

You’re going to fail.  And that failure will help you succeed.

Be Nice

I had a boss who once introduced me as the nicest person he knew.  I was a little embarrassed, and it made me sound a bit milquetoast.  But he was totally right.  I am nice.  And I strive to be nice to other people.  Being pleasant works for me, and I think it has greased the wheels a little when it comes to career advancement.  Can you climb the ladder whilst being a total asshole?  Sure you can, I’ve seen it.  But those people tend to burn bridges, and unless you are especially smart, indispensable, or absurdly attractive, eventually you’re going to piss off the wrong person and find yourself in the unemployment line.  I’ve seen that too.

I am not saying you need to be a doormat.  You can be nice and still be assertive.  You can be nice and still have an opinion.  You can be nice until it is time to stop being nice.  But the point here is the IT community is not that big, and people talk.  I’d rather have a reputation as someone who is easy to work with, than a total dick.

I’ll let Dalton have the last say on that one:


All other things being equal, people would rather work with someone who is pleasant.


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