It's a very good blog - albeit getting a bit too much 'commercialized' in the last years. The guy also wrote a book, which I found pretty good: https://fs.blog/clear/
That being said, you can read all this stuff, but more importantly - you need to apply it. This is the hard part.
If you've never heard about him, and you want to learn about thinking and decision making, he's THE guy.
I will often go for a walk or sit in a cafe with a sheet of paper and just think about the problem. I try to define the problem properly before I even start thinking about solutions.
For trickier problems, you just need time. I go on a long bike ride and let ideas simmer until they break down into something simpler and more manageable. I get my best work done after my weeks-long hikes and rides.
Above all, know thyself. Having some awareness of your own biases and irrationality helps you correct the course. Knowing what you like, where you tend to get stuck and what you suck at helps a lot.
Do I make mistakes, sometimes? I also beat myself up over them more than I should. The important thing though is to learn from the mistake to be better prepared next time. Here are a few tips that may be suitable for you.
1. Always view your problem from different perspectives instead of sticking with your initial solution. ... 2. Do not make a decision just because it is the most comfortable. ... 3. If you already have your mind made up, do not just seek information that supports what you want to do. ... 4. Focus on the decision that is in front of you and your present situation.
Some time ago I read an insightful article here however I do not remember exact URL: https://www.lifelords.com/success/
As for books, Jocko Willink's Extreme Ownership is a good place to start. Take ownership of yourself and become the best version of yourself.
80% of sales come from 20% of the customers > yes, fire the customers who bring in 80% of the work.
80% of goals come from 20% of the players > no, your formation should not change everyone to forwards
Opportunities come 80% from networking, 20% from working hard > if you spend all your time networking, people would avoid you
Very often there's a support structure in place which leads to to the results.
Here's a very simple decision matrix web app https://www.ruminate.io/.
I'm also building a tool for analyzing problems, which includes functionality for a decision matrix: https://ameliorate.app/. Most of it centers around clarifying causes and effects of problems/solutions, which can also help you grasp a situation. Here's an example of a decision I've made with the tool for picking which ORM to use for building the tool itself: https://ameliorate.app/examples/ORM?view=Tradeoffs+scored+as....
I understand the resistance of developers to such frameworks. Maybe Scrum misuse killed all enthusiasm.
Both inside and outside of work: 5 whys is good.
Think of 1 and 2 way doors. If the decision is reversible it is almost an experiment. Travel for 4 weeks or 12 weeks? Doesn't matter as you can fly home at any point.
Even buying a house is fairly reversible although selling immediately will be costly.
Having children is a one way door. Having dogs or cats is really too (or should be considered as)
Quitting a job may be 1 or 2 way. If you are high level at Google it may be impossible to get back to something like that soon. If you have a regular web dev job you can probably get something like that again if you decide to take time to do something else.
Sorry to disappoint but quality of your decisions grow only proportional to your expertise in some area.
There are adjacent and similar areas, so by getting better at one you improve your decision making in others as well.
But any book that tries to sell you generic “decision making” skill is a piece of garbage.
This is how skills work fundamentally.
Meta-skills cannot be learned, can’t be trained. This is why they are meta
Focus on exact narrow areas (even “startups” is way to generic, “startups fundraising” or “hiring in startups” are better examples) you want to improve.
And slowly (with life experience) you’ll build up a good intuition in those areas. But don’t expect it will help you be great in other distant fields. Though it may happen by accident or because you’re generally smart enough to avoid mistakes.
Also nobody likes this answer, but religion writes the manuals to life. All major religions have done their research and wrote books. There's a stark contrast between ancient Greek philosophy to when Christianity came in. There were unsolveable problems that the philosophers couldn't tackle, like Aristotle believed that if a great made a mistake they were done for. And then Jesus came in with the idea of repentance and flipped this on its head. The word "hamartia" changed from "missing the mark" to "sinning", and sins are recoverable.
Then Islam based the ideal lifestyle around every behavior and action by the Prophet Muhammad, from sleeping, headaches, eating, treating guests, treating enemies, and so on. Philosophy became necessary because later there would be scenarios where there was no precedent for decision making, so they wanted analogies. Aristotelian philosophy became a tool for this. Then you had Avicennian philosophy, which developed into inductive logic... things we take for granted today like symptoms. Then al-Ghazali came in and labeled all of the philosophers as nonsense, and Greek philosophy was buried until the 19th century.
So if you want a tldr, read al-Ghazali. His big work was Tahāfut al-Falāsifa ("Incoherence of the Philosophers"), but if you want something simpler and much more practical, try Ayyuhal Walad ("Advice to a Son/Student"). It's hard to find an English translation that properly captures the sarcastic bite in his writing though. Plenty of religious figures were funny and sarcastic too.
Honestly, as a society, I think we've gone full circle. We're rediscovering meditation/mindfulness. Which is a fair point - approach all decisions from a fresh mind. But that works up to a point. There's just so much that it takes a while just to go over what to cover and what not to cover.
As an overview and primitive generalization of some more or less obvious ideas about human nature to read for fun - good enough.
As a real learning tool - garbage.
What you mention only confirms my point - you can improve your decision making only in a certain area.