Maximizing Career Optionality

Since graduating from law school I’ve had a lot of conversations with peers to discuss alternative careers and how I landed in the most unconventional of spots for a law school grad — a startup in Silicon Valley. Throughout these conversations, I found a consistent concern ever present: the number one hesitation folks had when making career choices was sacrificing optionality.

This was an interesting point that got me thinking about optionality and its relation to career decisions. Specifically, was there a systematic and simplistic framework — regardless of industry — that could be used to explain optionality and how to maximize it over the course of your career? In discussing career retrospectives with senior VCs and Execs, I continually heard a clear theme: the more value you can drive for an organization, the more optionality you will have in your career.

As you progress in your career, the accumulation of skill — hard and soft — is more attractive to an organization than the promise of potential. This shift is not linear; rather it happens relatively swiftly.

This makes intuitive sense. The problem comes in practice. All of our lives we are judged on our potential — college admissions, internships, first few jobs, and even graduate school. To rise to the top we become masters of what it takes to succeed at this game, continually optimizing our performance to satisfy certain pre-defined requirements helping us reach the next milestone. Given our training in this environment, we think about optionality linearly and intimately relate it to convention; as long as we continue on the well-trodden path we preserve optionality.

The logical flaw in this thought process however lies in the shift of the relative importance of skill and potential as we progress in our careers; that is, as we progress into our careers, the accumulation of skill — hard and soft — is more attractive to an organization than the promise of potential. The market has a different value network and judges what we bring to the table differently than the environments in which we play from ages ~15–30.

Applying the practices by which we have traditionally succeeded in life to a game that fundamentally values something different is akin to bringing a knife to a gun fight. It’s a pure misfit and a recipe for underperformance. Gary Vaynerchuk really brings this point home when he talks about the psychological challenges would-be entrepreneurs go through, especially those that were good students:

“There are a lot of people, especially when they were built to be good students…after a life full of winning because they understood that system, they go into the actual marketplace and have no clue how to be a true-bred entrepeneur because they don’t have the stomach to deal when the market says go f*ck yourself.”

The one consistent theme I have noticed in successful Execs is their mentality of thinking about optionality through the lens of skill acquisition— soft and hard. This mentality shift helps makes sense of the seemingly counterintuitive perspective to the hesitation of sacrificing optionality early in one’s career.

Sacrifice optionality early, so you can get more of it later. Play chess, not checkers.