How I decide

Two rules do most of the work. One decides what I will and will not do. The other decides which of the remaining options to take.

Principles over outcomes

I judge a decision by how well it fits my principles, not by whether it produces the best result in this particular case.

That sounds naive, and the reasoning is the opposite of naive. The world is complex and you frequently cannot foresee the consequences of your choices, so outcome-based decision making is often guesswork wearing a suit. In an unpredictable environment, values are the more reliable instrument.

Deciding this way has three practical effects. Decisions come faster and cost less, because you are not simulating branches you cannot actually see. People find you predictable, which makes them more willing to work with you than against you. And you avoid the slow erosion that happens when every principle is negotiable against a sufficiently good outcome, which changes who you become in ways that are very hard to reverse.

The principles themselves are mostly unoriginal, which I think is the point. Fairness, meaning rewards follow contribution. Integrity, meaning I do not break a promise because keeping it became expensive. Honesty, including when the truth costs me the deal. Human dignity, including my own. Service, quality by choice rather than by neglect, and a bias toward whatever produces growth over the long run rather than the quarter. Most of this framing I take from Covey.

To those I would add a few of my own: every person is responsible for their own actions, focus on what you can control, accept reality as it is because truth is the highest value there is, accept yourself as you are, and treat freedom of will as close to absolute. Anything is permitted as long as you are not forcing your will onto someone else.

An acceptable worst case, then maximum optionality

For the choices that survive the first filter, the question is not which option has the best expected outcome. It is:

What gives an acceptable worst case, while leaving the most optionality?

Note that it is not the best worst case. Any acceptable one will do. A worst case is acceptable when I survive it and it is reversible, meaning that with the time available I can get back to my last good enough position.

With that floor in place, I take the option that keeps the most doors open. Optionality means being able to make many small bets where one of them can pay off disproportionately. This is Taleb's idea and I have found it more useful than anything else I have borrowed.

Some consequences of taking it seriously are not obvious. Credentials and savings are worth having mostly because they raise your floor, not because they raise your ceiling. A rare, very well paid job cuts both ways: it can fund optionality, or it can raise your standard of living to the point where no other path is reachable from it. And the cheaper you can live, the freer you are, up to the point where lack of money starts closing doors of its own.

Where this has been wrong

I ran a different rule at FunnelBud for years, optimising the next decision rather than the direction, and it quietly took the business somewhere I did not want it. I wrote that up in the strategy mistake I made at FunnelBud. The post carries its original 2024 diagnosis and the replacement rule I only settled on a year later. I would rather show the method that failed, and how long the gap was, than only the ones that worked.