A couple of weeks ago I was sitting in a conference room with many of my peers when I suddenly realized that they are all going forward without me. Every person in that room would be further ahead in their career in 3 years, and I am just walking away. The feeling was overwhelming and without time for rational thought it felt like a punch to the gut. It has taken me some time to become comfortable with this realization and talk about it, but I was quite upset by the knowledge that others would pass me by in the one area I have always prided myself…work.

Yes, I have spent the last 18+ months planning the next phase of my life, selling our house, picking our rough path around the world and enjoyed every minute of the process. But in that one moment I was knocked on my ass and forced to confront what I was walking away from instead of what I was heading towards.

For 20 years I’ve been on a generally upward career trajectory, always building to the next opportunity. I have funneled my passion directly into each job, and put all my energy towards doing what was needed to get ahead. I am extremely pleased looking back on my career and all that I have accomplished. Frankly, I would not change a thing because each of those accomplishments and failures put me in this exact moment preparing for a change. However, the idea of not following my teammates up to the next rung of the ladder is hard to swallow.

Now, with less than 6 months until this chapter of my life closes, I have a feeling of remorse for what all I am leaving behind. My decision to walk away from a career I have become pretty damn good at is proving to be harder on me than I could have imagined.

At this point I have decided to just allow myself to reflect on what I have accomplished and celebrate my successes. From landing my dream job, to starting my own company, to being CEO of another, and to my current role at Microsoft I have a great deal of fondness for the journey to this point. In many ways, leaving my career feels like a death to me. There is not a single thing in my life to date that I have put this much work into and on September 30 I am walking away, and I am not quite comfortable with this yet.

For those of you seeking to embark on a similar lifestyle change, I warn you that there may be a moment when the reality crashes into the “dream” and you realize you are giving up more than you thought when you were drunk on the fun of planning. Be ready for it, embrace it, but don’t be surprised. Here is how I am dealing with it:

1. Realize that platitudes suck – everyone will have one for you “…better things ahead”, “…focus on the future”, “…you won’t remember this in 3 months”, “…you were not that good at this job anyway” (ok, the last one may not apply to everyone). Sorry, but none of these sayings will help but it is what people need to tell you in polite society. It will not give you comfort, but knowing it is coming will help to ensure you just smile and nod.
2. Focus on your successes and achievements – make an actual list of what you achieved in your career. Don’t worry about sounding cocky, this is your list. Write about what you did, how it make you feel, why it made you so happy, and how important it was to you and to the company/employees/etc.
3. Mourn the loss of your career – that’s right, ball up into the fetal position cry your eyes out, scream into the night, turn on some Enya and a good Scotch…whatever it is that you need to do to express your pain. Accept that losing your career is hard for you and thus spend the time to mourn it’s loss.
4. Remember why you made the decision – now that your eyes are dry, focus on why you made the decision. Remember that you are not running away from your career or job, but instead you are running towards a new lifestyle.
5. Create a list of all the things you put off doing – if you are like me, lists make the world go ‘round so having one is true comfort. Build a new list of those things you want to accomplish in the next phase of your life and begin building your new “career” in whatever is it that makes you happy and fits within the new lifestyle design you are building.

Each step has taught me something about myself and made me a better boss/employee/worker. Now as I embark on a different path I am looking forward to what life will be like without the career to be my guiding forward. At different points in my life I have wanted to write, learn a language, become a better photographer, learn to SCUBA dive, skydive (ONCE) and so much more…but I have always put my career objectives first. While I am struggling to say goodbye to my career mistress, I know the future holds more than I can fathom.

Click here to read my update one year after walking away from a career and following a new path.

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