OVERALL TLDR/SUMMARY:

• Effective decision-making can be counter-intuitive.
  • You assume that a good decision is supposed to look and feel good, and a bad decision is supposed to look and feel bad.
    • Some decisions do follow that pattern, and those are the easy ones– the ‘freebies’. Everyone can make those decisions.
  • The hard, counter-intuitive thing is when a good decision feels bad, or when a bad decision feels good.  That’s when you’ll have to steer against what ‘feels’ right. (random aside: Interesting parallels to countersteering? 1 2 3 4)
  • Apart from luck, making the right decisions in these difficult situations is what separates the successes from the also-rans.

• Posssible intro: talk about bikeshedding as a counter-example– choosing errenously to focus on a simple problem instead of digging into the difficult/shitty problem.
  • “There’s a funny yet troubling story that says a lot about the limitations of human decision-making…”
  • (probably even better: tell a story about a bad decision that felt good, and a good decision that felt bad)

Obvious preamble, can probably cut: The quality of your life is, after accounting for starting conditions and other variables beyond your control (genetics, upbringing, environment), ultimately a function of the quality of your decisions.  So you always want to make the best decisions you can. To do that, you need to identify what the optimal decision is, and then you need to execute on it. That much is obvious. So why is it that we don’t see people making optimal decisions all the time?

Sometimes identifying the optimal decision is easy,

• • because it jumps out at you as the obvious and right thing to do,
  • because there’s a wealth of information that points out that it’s the right thing to do,
  • because everyone who evaluates the problem has the same opinion as you.
• • Those almost aren’t worth discussing– they’re “solved problems” with obvious solutions.
  • Execute them quickly, pat yourself on the back and move on to the hard stuff.
  • (In fact, if you find yourself making a series of easy good decisions, it’s a strong sign that you might be too far inside your comfort zone and avoiding the real, important decisions that need to be made.)
  • (It’s often tempting to spend an excessive amount of time and energy on the clean, tidy problems – so much so that there’s a name for the phenomeon: Bike-shedding.)

• Startups that get caught up in bikeshedding can “do everything right” and yet run out of money and get shuttered.
• Startups need to focus on staying alive, and staying alive is a hard, messy problem that involves confronting shitty decisions and systematically making the least shitty decision.
• That’s the optimal thing to do.
• It’s optimal, but it’s emotionally draining, because even when you make the right decision, you’re going to look and feel like you failed.
  • When you fire someone early rather than late, you’re going to feel the emotional cost of asking someone to leave.
  • Even though that might be the right decision!
  • You may have to ship something that’s imperfect, even though you feel that it’s right to wait until you get everything right.

• Ultimately, your success is going to be determined primarily by the decisions you make in the difficult quadrants – how you use your judgement, discipline, focus, discernment to make good decisions even when they feel bad, and to avoid bad decisions even when they feel good.
• This is obviously easier said than done, but acknowledging that this is how it is is the first step towards making it happen.
  • If you want to achieve significant success, you’re invariably going to have to make hard decisions, and you’re quite probably going to be tempted to go with what feels right.
  • Be wary of your feelings(?).
  • (Maybe some extra bit about how… it’s tempting to follow the herd and be wrong with the herd, because you at least don’t have to endure the discomfort of being deviant.)

Possibly relevant quotes:

“Either way could be a big mistake. You’re not going to get any confirmation from anybody or anything. If you change and succeed, that might be great, but you might have succeeded even better at the last thing. If you change and fail, you’ll never know if you might’ve succeeded if you hadn’t changed.” – Marc Andreessen, to Tim Ferriss

“No matter how good you are, you’re going to lose one-third of your games. No matter how bad you are you’re going to win one-third of your games. It’s the other third that makes the difference.” ― Tommy Lasorda

“Life is not always a matter of holding good cards, but sometimes, playing a poor hand well.”  ― Jack London

“Being a good company doesn’t matter when things go well, but it can be the difference between life and death when things go wrong. Things always go wrong.” – Ben Horowitz