Pride or Confidence. Pick One.

A few years ago I took a frank look at my career – past, present, and future – and made a stark assessment: I had two serious gaps to fill if I wanted to reach my ultimate goal.* So I set out to do something about that.

The gaps were these:

First, a gaping ignorance of IT – of all things computer-related, be they hardware or software. This was frustrating when I was CEO, even once I had an IT staff. In theory I didn’t have to understand IT, just employ others to explain it to me in layman’s terms, a la Henry Ford with his staff of experts. In practice, this ignorance led me to wildly over-invest in an online project whose scope I simply did not understand.

Ignorance of IT hobbled me in growing my business.

Second, I had never worked for an enterprise, or “really big company,” and I didn’t have a true insider’s feel for how they worked. I sensed they were much, much different in some culturally fundamental way from an SMB (a Small or Medium Business), but how, exactly?

This one was important because I wanted to help enterprises as I was helping SMBs. And I wasn’t getting any further within enterprises than the division or business unit level; often not even that.

Ignorance of the enterprise was holding me back in growing my career as a speaker and outside expert.

I knew I had to make a change, to fill these two gaps. This wouldn’t be easy: I was up against two very daunting obstacles of my own creation. The first was my utter distain of IT as “geeky.” I came of age in the eighties, when most college kids still only used computers to type out their term papers. But that contempt was itself uncool, and I knew it was long past time to get over it.

My second obstacle was that, if I wanted to gain an insider’s understanding of the enterprise, I needed to swallow my CEO-sized ego and allow myself to take an entry-level role for a few years while I learned.

Ouch. The first one was tough. The second…? One needs a tremendous amount of confidence to subdue his ego and let someone else play boss while he plays novice. But, despite my career highs to that point, within the enterprise I was in many ways a novice, an uninitiated outsider.

Pride is dysfunctional; it is self-limiting by its very nature. And here is the important thing, the very hard thing I’ve had to wrap my head around: pride is rooted in insecurity, in lack of confidence.

The confident leader is comfortable allowing others to lead.

I’ve been on a remarkable adventure of learning over the past three years. Has it been hard on my ego to allow others to lead so I can learn? Of course it has. But the result is fundamentally greater knowledge. I have filled my two gaps. I have also grown in my inner security; I’ve matured as a person.

In future posts, I will share more of my adventure with you. In the meanwhile, I want to leave you with this question: what are you willing to give up in order to get to your ultimate goal? Are you strong enough to give up your ego, to subdue your insecurities?

Maybe this type of journey is harder for a man, with the pressure (real and imagined) we put ourselves under to be strong, to be certain at all times. Maybe it’s harder as we get older, for similar reasons. But then again, I’m not so sure. Maybe it’s just hard, and those are just lame excuses.

Weigh in now in the comments below, and tell us your experience. Share links to your own blog if you’ve written on this. This is fundamentally important stuff; soul-changing stuff, if we allow it to be. What has your own journey toward true confidence been like? I’m eager to learn from you.

 

*Some other time, we’re going to get into my ultimate career goal, and yours. But one thing at a time.