Career Choices: Courage or Luck?

I often describe to my friends that my career progression has been a “long and crooked path.”  I have worn many disparate hats during my work evolution, from tester, coder, project manager, director of software, CEO, and now fractional COO.  While I have certainly advocated for myself through all these career changes, it is not at all clear that I have had a real plan.  The only common thread through all these moves is my instinctive desire to reach out for more challenges, and my dread of being bored.

I’ve been thinking recently about the transition period between being CEO of a medical device startup to my current career track of fractional executive (COO/CFO).  Specifically, I’ve been wondering what role courage or choice had in this, and contrarily, what was simple luck/fate.  When I first decided to leave the CEO role at ActivArmor, it was a risky move.  I did not have anything lined up.  Perhaps, that was a sign of courage — or maybe it was just desperation.  The stress and frustration in my CEO role was increasing, and becoming untenable.  So, it may have been less courageous, and just necessary.

I had an instinct and basic plan that I aspired to be a COO, and really was not crazy about working for just one company again.  It was clear that working with a single company, and single Founder, was too risky for me — all my eggs in one basket.  This being said, I was not sure how to create such a fractional career.  So, I also pursued “full time” opportunities.  (This dual track approach just seemed like prudent risk mitigation — perhaps, the opposite of courage.)   I had several interviews, for jobs that I could easily kick ass with.  But, I kept missing these.  It became clear that my age and experience was actually working against me.  This was most obvious in my last attempt in this track, at a medical device company call SwissLog.  They needed someone to fix their rampant quality issues, and given my record of long years of doing just this, and considerable medical device experience, it was a slam dunk.  However, I was rejected, and was actually told that they were “looking for someone who could come in and build their whole career around SwissLog.”  Besides that blatant naivety of this statement (have they ever met a Millenial?), it was explicit ageism.  That being said, failing to secure a full-time track position, in retrospect, was the best thing that could have happened to my career.  I could not have known this at the time, but now I have a dream job — working with multiple clients as fractional COO/CFO, solving widely variant problems, preparing for their eventual exits, making a real difference to my clients’ success, and getting WAY more revenue than I would with any job I had interviewed with.

Professional courage … involves an ability (or an instinct) to sense opportunities and then sus out the right response and timing.    — forbes.com