The road less traveled

ca. 2010:

In his “Four Roads” post, Seth Godin outlines four possible models of thinking about your career/job progression and experiences. Unstated, but this leitmotif of experience, value, and art is tied in tightly with his linchpin model.

  1. stuck in a loop – doing the same thing, better & faster, but not getting anywhere
  2. always getting on a new road – rarely getting better
  3. wrong road – getting better at the wrong things
  4. right road

This sounds like a description of my career path(s). Need a big reset button, or at least a path to one that takes better care of my family in the meantime.

One friend commented that he saw his last years as a sort of treadmill. My [lightly edited] response:

That’s funny because I think of 9 years of experience as generally better than 1 year 9 times, which is my situation. I know that half or more of the reason I’m in the mess I’m in is that I haven’t focused on anything for a substantial length of time, not really.
5 year Army
3 years law school
4 years lawyer
8 years quasi-banker/consultant
2 years lawyer

Other than this past two years or so, I feel like everything sort of fit together if I could just put it all in the right perspective, like that scene in Sneakers where they are jumbling some scrabble tiles around because the they think the company name is an anagram for something important. I’m at the middle step where they have something pretty non-sensical and silly. “Setec Astronomy” turns into COOTYS RAT SEMEN and then into “too many secrets.”

I guess I just compared my last 21 years to rat semen. Hmmm. Take that as a sign you’re not doing so bad!

Perhaps it’s not quite so bad as that, but there’s more to this discussion (as always). My personal challenges [as of this writing in late 2010] have been affected in large part by my choices from 2001-09. It’s added stress, more than I knew or understood or would have wanted, to someone important to me. And the outcome has not been good.

Here is another reply:

Well, you’re not on road #1. The problem with roads #2-4 is that you only know after the fact which one you were on.

My lengthy response:

I’m not on 1 or 4. [___] thinks I’m on 2, either fickle or vaguely dissatisfied. I feel like I’m on 3 because the problems I’m solving don’t seem to match up well with what I’d like to be doing.

I’m reminded of the profile on Freeman Dyson, at Princeton’s Institute for Advanced Study: [___] and I both read it and said “This sounds like Rick’s dream job.”

But I’m not sure that’s really accurate in the details. In any case, it’s not in my immediate future to go get a Ph.D. and become an expert in something. Plus, I think that the thing I’m an expert in is already developed and I’m just not quite there yet at describing it to other people. I think it has something to do with learning quickly, grasping complexities rapidly, readily thinking in terms of systems and big picture connections/ecosystems, and making decisions about all of that analysis pretty rapidly.

I guess that makes me sound like a VC or perhaps a politician or cabinet member of some kind. I also think of myself with labels like “board member” or “judge” (but arbitrator/mediator are good stepping stones to that road that I am starting on in any case).


And now it’s 2016, and I’m going through and liberating draft posts from the queue.

What do I think about when I look back at this one? First, that things have turned out better than I feared. It took me a little bit longer to figure out what path I’ve been on. Now I’m working to strengthen the trunk of this tree while pruning some branches and grafting others.

I am a startup lawyer. I work on their legal issues, on side projects to improve startup legal documents, on investing and advising, on board governance, consulting and interim management outside the purely legal realm, and on startups with a mission to improve outcomes for startups.

The things I tell people I like about what I do:

  • I like hearing peoples’ individual stories about their path from the past to the future they’re trying to create
  • I like helping specific individuals through my efforts – I see founders with better work and lives as a result
  • Startups need more than purely legal advice, meaning my leadership, management,  finance, and technical skills get exercised

So this is my path. I expect I’ll get to the point where I live out my years focusing on board-level interactions. It seems like the role that will Mass my skills for greatest impact.