What Do I Want to Do?

So, I had spent the last number of years figuring out what I don’t want to do – work at large companies that lack sufficient entrepreneurial opportunities.  But now that I am out the more difficult question remains – what do I want to do?

In this early stage of exploration I have come to realize this question has more dimensions than I first thought.  Yes, there are the obvious ones:

  • What technology?
  • What market?

But beyond these questions there are others as well:

  • Start my own company or join an existing one?
  • Early- or late-stage start-up?
  • Role:  CEO?  VP Marketing?  VP Engineering?
    (Does it matter that much in a startup?)
  • Location:  Boston?  US?  Foreign?

And there are yet even further ones revolving around how I reach my end point:

  • Immerse myself at the first reasonable opportunity that I encounter and see what happens?
  • “Survey the field” for some number of months and then pick the most attractive opportunity?
  • Mentor/coach one or more startups and see where that leads?
  • Other?

As I write this I come to realize that I probably have the wrong objective in mind.  Instead of thinking in terms of “finding my next job” I probably need to have a more meaningful and audacious objective in mind – something along the lines of “be a founder/leader of a successfully exited startup”.  My next position might be as the founder of the next Google or it might be something else that serves as a stepping-stone. 

So, of all the questions whirling around in my mind the most important to answer first might be whether I should be looking for a startup or an idea for a startup.  If I can answer this then I will better able to answer the question I commonly get at networking events:  “So, what do you want to do?”