Originally posted on: http://geekswithblogs.net/robz/archive/2013/06/25/career-defining-moments.aspx

Fear holds us back from many things. A little fear is healthy, but don’t let it overwhelm you into missing opportunities.

In every career there is a moment when you can either step forward and define yourself, or sit down and regret it later. Why do we hold back: is it fear, constraints, family concerns, or that we simply can't do it?

I think in many cases it comes to the unknown, and we are good at fearing the unknown. Some people hold back because they are fearful of what they don’t know. Some hold back because they are fearful of learning new things. Some hold back simply because to take on a new challenge it means they have to give something else up. The phrase sometimes used is “It’s the devil you know versus the one you don’t.” That fear sometimes allows us to miss great opportunities.

In many people’s case it is the opportunity to go into business for yourself, to start something that never existed. Most hold back hear for a fear of failing. We’ve all heard the phrase “What would you do if you knew you couldn’t fail?”, which is intended to get people to think about the opportunities they might create. A better term I heard recently on the Ruby Rogues podcast was “What would be worth doing even if you knew you were going to fail?” I think that wording suits the intent better. If you knew (or thought) going in that you were going to fail and you didn’t care, it would open you up to the possibility of paying more attention to the journey and not the outcome.

In my case it is a fear of acceptance. I am fearful that I may not learn what I need to learn or may not do a good enough job to be accepted. At the same time that fear drives me and makes me want to leap forward. Some folks would define this as “The Flinch”. I’m learning Ruby and Puppet right now. I have limited experience with both, limited to the degree it scares me some that I don’t know much about either. Okay, it scares me quite a bit!

Some people’s defining moment might be going to work for Microsoft. All of you who know me know that I am in love with automation, from low-tech to high-tech automation. So for me, my “mecca” is a little different in that regard.

Awhile back I sat down and defined where I wanted my career to go and it had to do more with DevOps, defined as applying developer practices to system administration operations (I could not find this definition when I searched). It’s an area that interests me and why I really want to expand chocolatey into something more awesome. I want to see Windows be as automatable and awesome as other operating systems that are out there.

Back to the career-defining moment. Sometimes these moments only come once in a lifetime. The key is to recognize when you are in one of these moments and step back to evaluate it before choosing to dive in head first. So I am about to embark on what I define as one of these “moments.”  On July 1st I will be joining Puppet Labs and working to help make the Windows automation experience rock solid! I’m both scared and excited about the opportunity!