The other day I had coffee with someone in the midst of a career change.  It was one of these “networking” coffees, he was referred to me by a mutual friend, that sort of thing.

He was a good guy, wicked smart, personable.

After a career spent in large organizations in one specific industry, where he successfully navigated  from a feet-on-the-ground salesman to a top management spot, he finds himself wanting a new challenge and is looking seriously at a few online ideas.  His experience is relevant, even if only on the edges–and I have no doubt that he will  make his new business work–if only because he has  a track record of success, he simply won’t allow it to fail.

But here are some things to think about if you find yourself in a similar situation, thinking “THERE is what I should be doing.  I can do THAT!”

1.  Yogi Berra.  For a lot of us growing up, our first experience with ICANDOTHAT was with someone famous.  For me, I just knew I could be the next Yogi Berra.  How hard could THAT be, playing baseball everyday—I was already doing THAT.  Soon, however, the reality of his skill was made evident and more, his dedication to developing it.  I have seen  big company guys look at starting their own companies like I looked at Yogi.  He made catching look easy, simple, uncomplicated, fun.  Don’t under-estimate what goes into creating something from scratch.

2.  The grass is always greener.   I am not saying my friend should stay in his own industry.   At upper levels of management, you see leaders going from one business to another all the time, like John Sculley going from PepsiCo to Apple (oops, bad example).  You seldom see them  go from a large company environments to  successful startups.  A startup guy can more easily go from startup A to startup B, than a BIG Company Person can go to his first startup.  Can it be done?  Sure.  It is just harder.  A venture guy once explained it to me this way, “they can understand the music, even the lyrics in a startup; they don’t get the tune.”

3.  Use developed skill and accumulated knowledge.  My friend knows his industry backwards and forwards.  His knowledge is wide and deep.  My advice was to use this skill and knowledge to fix  unacknowledged problems within the industry.  This industry is known to have a lot of “issues.”  With his skill, he could attack and solve problems he has seen  every day.  This has successful startup written all over it.

4.   Think from the ground up.  In a startup, market size is important if only because you want to have a big enough opportunity.  But when I hear startup guys talk about the 40 Billion Dollar Marketplace for their product, my eyes glaze over.  I know, I know, Sergei and his buddy got there with Google.  But still….far better to talk about how to sell one customer in a repeatable, scaleable fashion within your new marketplace.

5.  Know when to give up, when to buckle up.  Certain industries are dying, others simply need a better idea.  Almost every ‘dying’ industry did so for lack of a visionary who had the ability to save it, but didn’t.

I hope my friend buckles up.

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