Making the decision to leave your job and career is daunting.  It requires you to face a some significant issues head on: money, pride, security, opinions of others, uncertainty, and fear.  I admit that making the decision to step off your career path and head in a new direction is not for everyone and certainly not to be taken lightly.  However, I hope my story helps give you pause to consider the possibility.

First, a confession:  My name is Warren, I am 38 years old, and I have a wonderful job.  Yes, that’s right, I like what I do for a living.  I work at Microsoft (insert your favorite “evil empire” joke here).  My role allows me to influence and define Microsoft’s long term strategy, albeit for only a portion of their business and is the culmination of 15+ years in the software industry and I am fortunate to have this opportunity.

But the decision to leave this career path has little to do with what I do, how much I make, and what I will be leaving behind. Instead, as with every major decision in my life, I ask myself a simple question – “Am I running away from something or towards a new experience?“.  This simple question has had a tremendous impact on how I approach life and the barrage of choices that inevitably arise when you are open to the possibilities.

I approached the decision to embark on a new direction by asking myself a few questions, and spending time discussing with my amazing partner:

How important is this dream to me/us?

If you have been reading our blog for some time you will know that our choice to travel around the world was spurred by the realization that life is too short.  When we evaluated what really made us excited it was the joy of travel and exploring new cultures.  While I may enjoy my job, it has never ignited the passion and excitement that I get from travel and meeting new people.

What will happen to my career?

As I was making the decision I reached out to friends and the blogosphere to seek some council.  What I found was the concept of the “gap year” in careers was more common than I had expected.  Many people had stepped out of their jobs for a year or two and came back to the workforce and were able to pick up their careers when they returned.  I realized that my career would be here for me, just where I left it, IF I want it.

How will I identify myself without a job?

To be an American means that a large part of ourselves is identified by what we do.  When we meet new people we ask the question “Where do you work” or “What do you do”.  We begin to associate WHO we are with WHAT we do and the ability to separate these becomes more difficult over time.  For 15+ years I have defined myself by my job and life working in and around technology.  But why?  Why should how I get paid have any reflection on who I am as a person?  I realize now, after a lot of internal reflection, that I can be comfortable changing this internal perception.  I will not be defined by what I do for a living, but instead I want to be defined by:

• The friends I surround myself with
• My life experiences OUTSIDE of work
• The impact I have on other’s lives
• My willingness to fulfill my dreams
• The happiness I share with my wife

The decision:

I feel this should come with a big drum roll as you sit on the edge of your seat wondering which way I decide.  But like every “Three’s Company” and “The A-Team” episode, you knew how this was going to end when you started.  Ultimately I realized that my job and my career are means to reach retirement instead of a specific goal.  I was working to hit some arbitrary date when I could stop working and start living.  By identifying a different goal I was working towards it has changed my perspective on work, and in many ways how I approach life.  While I cannot promise you that life in the future is going to be perfect, I can say that I have never been happier since making the decision.

Here are some great resources I recommend for your own decision process that have inspired me:

• Briefcase to Backpack – I just found this site, but wish I had had it when I was making the decision
• Almost Fearless – her story was easy for me to relate to
• Zen Habits if you cannot find inspiration from Leo, I don’t know how to help you
• Helium.com – good collection of stories that you can find one to relate to
• The A-Team – not really helpful, but absolutely hysterical to watch

Have you taken the plunge and stepped out of your career?  What inspired you to take a different path?

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1. Question everything and embrace the possibilities
2. Mourn the death of your career
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