On Making Decisions

Our decisions, when we fully trust ourselves, often don't end up being decisions at all. They can feel like a river, carrying us towards an inevitable and luminous outcome.

In my experience, this happens when decisions are about what we really want, not what we feel like we should be doing. The people I know who are great runners really want to run. For me, I only run when I feel like I should, and then it becomes a chore. In other words, it's a decision, instead of a natural force carrying me through to the inevitable conclusion.

And yet, we're not always at that expansive place where we can listen to the universe and trust ourselves. Given that, here's a few tips (in no particular order) on how to make decisions.

1. Practice discernment. Listen to yourself in silence, true silence. Imagine yourself before you make the decision, during the decision, and after the decision. Do you feel expansive? Do you feel contractive? What does your body do? You have in-built knowledge in your gut that really can't be intellectualized out.
2. The lack of a decision is still a choice - you're just choosing not to make a decision. Sometimes, it's the best choice. But just know that you're in control of this - you're deciding not to decide.
3. The most important thing is not the decision, it's learning how to make decisions.
4. Decision velocity is so important. Changes can always be made later. But you should find yourself making many decisions as quickly as you can, especially in an executive role.
5. Any successful enterprise is the result of a courageous decision.
6. Your assumptions are worthy of challenge. Make sure you interrogate them as part of your "how" process before you make a decision.
7. You don't need to be involved with your own story of the decision. Try to untangle yourself from it - practice remaining uninvolved.
8. Most things we think are decisions actually aren't. Power, authority, biological determinism, family culture, social construction, tribalism, memetic desire, all of these contribute to the choices you think are yours. To quote Devil Wears Prada, these decisions are "chosen for you by the people in this room".
9. Despite this, it's critical that we take direct individual responsibility for our decisions. Yes, this is a paradox. But it's an important one. You must be radically self-reliant on your own decision making, even though there is very little chance that you actually have the power you think you have. The perception of control matters, and you can hold both of these ideas at the same time.
10. We get caught up in opposites and binaries because they're easier to deal with. Most of the time, decisions aren't an either/or.
11. When in doubt, maximize for optionality.
12. When you're really, really in doubt, flip a coin. Really.
13. People will actively avoid information that will help them make a better decision when their intuition is already decided.
14. We believe that we have precise and well-articulated preferences and we are wrong
15. We (humans) prefer control. That preference, when combined with insecurity, makes us react in a dominant or submissive way to power. The proper response is to respond as a peer - in peer conversations you are always in control.
16. Maturity is living in the tension between two different conflicting choices.
17. Genuine discernment arises from wisdom, rather than automatic pattern response.
18. To remove fear and judgment from your decisions, apply iteration to everything.