Stochastic Futures

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Imperfect leadership, future forecasting, and systems design

19 December 2018

Starting a company, launching a non-profit, changing cultural attitudes, or doing anything that involves change comes with seemingly insurmountable challenges; hundreds of them. I believe there are three themes one must embrace to be successful in bringing about any sort of change.

Imperfect Leadership

I want to emphasize the imperfect part, as every leader is flawed, stressed, and makes decisions with imperfect information. There is no right answer for most difficult problems, and I hope that one day the myth of a “perfect leader” will be dispelled. Even though we can all rationalize that no such leader exists, most employees, investors, students, and children act as if those they look up to should not be capable of being wrong.

Realizing that every leader is a fallible human being is liberating. Government leaders make decisions based on research and analysis, but they also fall prey to fears and insecurities, or even basic biological challenges like hunger or insomnia. People get egotistical, self-assured to a fault, or simply have biases that lead them to overlook information or ideas.

Forecasting the future

Being a great leader assumes you have a vision or idea of where the world is headed. To some, this sense of knowing about the future comes naturally, but I believe one can develop a system to gauge where the world is headed1.

Forecasting specific political events is difficult but having a point of view on where the future is going and why, is something that every leader needs to do. You don’t need to be right all the time (see the point on imperfect leadership!) but knowing where the world – or your small part of it – is headed, is critical. Pushing this further, applying decision trees to your plans to understand your breadth of options, possible responses of your market, and other challenges is a great way to build a plan.

Systems and models

The best way to describe this succinctly is via Scott Adams: “Losers have goals, and winners have systems.” Another version of this is creating useful filters for yourself: creating a world view that limits your information, while also doing a good job of predicting the future2. Having frameworks, systems, and approaches to accurately make forecasts about the future and respond to them is critical to being ultra-successful.

I also use the word “system” very loosely here. Ultimately, the job of a small-project-aiming-to-become-big is to find a repeatable way of executing whatever it is they want to execute… It could be raising money for a charitable cause, or selling a product, or something else altogether. Building this system – whether a daily operating model or a process for repeatable revenue or a way to generate new products quickly – is key to success. This is something I noticed when reading Ben Franklin’s biography: no matter what he was working on, he was keen on creating playbooks and processes3. The same is true for today’s major companies in protecting their markets and generating revenue4.

So, whether you are building a government or starting business, your success as a leader will require you to accept the themes above. You’ll have a point of view for the future, and you’ll be designing systems to scale your ideas and tackle the forecasts or trends you think will be relevant in the future. You’ll be doing so knowing you’re imperfect, but always improving nonetheless. And when your plans, attitude, and execution is consistent across these three themes, you achieve greatness as a leader.


  1. A fantastic book on the topic is Superforecasting.
  2. Scott Adams discusses this in Tools of Titans, and has a deeper discussion in Win Bigly.
  3. See Benjamin Franklin: An American Life.
  4. Steve Blank has a great discussion on this.