The Danger of Optionality


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When I was in law school, the golden phrase my peers used for evaluating initial opportunities was “exit options.” In plain English - the question was “What job could I take that would preserve the most and best optionality after I left the job?”

At the time this was gospel. And to be honest, I was definitely drinking the Kool-Aid. If every one of my smart peers was thinking this way, surely I should be as well right? Wrong. In fact, in hindsight I realized how dangerous of a mentality this is; to date, I believe “solving for optionality” is one of the biggest mistakes ambitious people make early in their careers.

When you’re solving for optionality, you’re unknowingly doing 3 things: (1) you are attempting to predict an unpredictable future, (2) you are trying to orchestrate a meta-game of “if this, then that” and (3) you are playing by rules of a game that will be shortly outdated.

The flaws embedded in the first two are self explanatory - the future is not static, it’s dynamic. The third is more counterintuitive, but most important to understand. There are 2 curves that matter in your career: potential and value. Over time, the importance of these 2 curves change dramatically.

Curve 1 is the Potential Curve. In the early part of our lives we are judged on potential - college admissions, internships, graduate school, your first job. Think of the filters people use on you early in your career: How smart are you? How hard working are you? How much drive and ambition do you have? These are all “potential” metrics. Organizations do this because it is highly rational - a candidate with less knowledge but more horsepower (vs. more knowledge and less horsepower) will outpace the latter in short order.

The danger - as an individual - is digging your heels into this curve and thinking that potential is the metric by which you’re continually judged. As you can see from the graph, the Potential Curve wanes in importance. The reason for this is it was never a curve that actually mattered; from Day 1 it was a “proxy” curve. A proxy for future value.

As you progress in your career, all that matters is the value you can drive for an organization. There’s less rope, less latitude, less patience. The more senior you become, the more binary the metrics you are judged by. Your performance becomes your track record.

The exciting thing about the Value Curve - especially today - is there is no gatekeeper to it. In fact, the faster you realize the world disproportionately rewards those on the Value Curve vs. the Potential Curve, the faster you can play by those rules of the game.

An advisor told me this early on in my journey and it always stuck with me: the more value you can drive, the more optionality you will have. Too many people focus on titles, optics and “what if” scenarios. Be great, put your head down, give it enough time and the rest will take care of itself. More pointedly - sacrifice optionality early, so you can get more of it later.

Have a great weekend,

Romeen


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In The Trenches

Bootstrapped my business to $60M, brought in PE and currently in the next leg of the journey. Angel investor in 75+ companies. In this weekly newsletter I break down lessons learned, practical frameworks, tools & tactics to level up in business and life.

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