Edit: If you are interested in this subject, I'd like to interview you to learn about your own experience with making difficult life mistakes. Hearing people's stories will help validate my framework and give me material for future essays. And I might be able to offer some interesting insights to you also. Please add me on Discord (username: chrisw5823). I would really appreciate it!

Making mistakes is fine; making major life-altering mistakes is something I recommend trying to avoid. In this post I will introduce a framework that can help with this.

The study of mistakes is fascinating from the perspective of rationality and biases. And from a practical perspective, it's very high impact. In my case, there are several mistakes I've made in the past that I'd be willing to pay at least a year of my salary to undo.

Below is a short intro to a few of my main principles. I also compiled various heuristics/principles in a diagram here. It's a graph where related heuristics are connected to each other by an edge. (I made this for my own purposes and am uploading as-is for now, sorry if some terms/lingo don't make sense to others.)

A few of my most important principles

Asking "what's far?"

A major human bias is "near vs. far": we focus on the "here and now" and discount everything else:

  • We discount pain that will come to us in the future (hyperbolic discounting)
  • We forget the pain of mistakes that happened far in the past, so we keep repeating them.
  • We neglect things that are far from our senses/awareness/focus ("out of sight, out of mind").

To correct for this, make a frequent habit of asking yourself "what's far right now?". This is like your "radar" that will alert you to things you should be paying more attention to.


How many of you have had the following experience:

You have a decision to make. You carefully evaluate your choices and decide. Then, it is revealed that your decision had a bad outcome. Immediately you have an "oh no" moment and realize why it was a terrible decision. You see the obvious things you failed to consider, ask yourself "what was I thinking?", etc., but it's too late.

It's remarkable that within seconds of seeing the bad outcome of your decision, you can produce insights that you failed to produce during days of contemplating beforehand. Wouldn't it be nice if you could somehow force those insights to occur before the decision is made?

Here is one way to make that happen: conducting a pre-mortem. A pre-mortem is a kind of role-play where you pretend that you already made your decision and are learning that it had a bad outcome. In addition to the benefits you can read about elsewhere, I want to emphasize that a pre-mortem allows you to leverage different emotions, in particular regret (even though it is simulated/acted). When you're feeling regretful your brain becomes very effective at noticing the negatives of a course of action.


Be cautious with new things. Not all that glitters is gold. Start new things minimally and ramp up gradually, and wait long enough to see the results. In most cases it costs you very little to do this, just a bit of extra time and patience.

Beware of testing limits. If you keep piling straws onto the camel's back, eventually it will break. If you are sure you will be able to recover from that breakage, then fine, go ahead. But if it's something you might not be able recover from, then it's better to draw a red line and not go past it (even an arbitrary red line is better than none at all). It's usually better to choose your own punishment than to have fate choose it for you.

Stay several degrees of separation away from danger. Better to just stay home rather than go someplace where a hazard is present, even if you think you can avoid that hazard by being vigilant and smart. The reality is that unexpected things will happen, you will forget your plan or get lazy, etc.

To determine how cautious you should be, look to your past. Have you caused yourself more pain by being overly cautious, or by not being cautious enough? Adjust your level of caution accordingly. My rule of thumb is that your optimum is reached when the pain of over-caution equals the pain of under-caution.

Willpower to interrupt things

Many big mistakes happen when you're caught up in the moment and continue with something that you would usually know better not to do.

For example, you might be enjoying drinks with some people, and that little voice inside tells you "maybe I shouldn't be drinking right now because (insert reason here)". There are many forces working against you making the right decision: (1) the enjoyment of the alcohol, (2) peer pressure, (3) inertia, (4) excuses/rationalizations/"good intentions", e.g. "i'll just have 1 more drink" / "we're almost done anyway", etc.

There are countless situations like this. Sometimes they involve other people pressuring you, and sometimes it's your own weakness/temptation.

The key is to develop the ability to suddenly interrupt something enjoyable even when there is high pressure/temptation to go with the flow, e.g.:

  • Walk outside
  • Ask the other person for a time-out
  • Stop drinking that bottle of beer and pour it down the sink

Once you get outside and away from the pressure/temptation/disorentation of the situation, it becomes much easier to think rationally, and from that point you can make a better decision about whether to leave or to go back in.

This is sometimes really hard to do in a high-pressure situation. It is an ability you need to develop like a muscle. So I recommend practicing on a daily basis doing this in lower-pressure situations. For example, the next time you are engaging in a minor vice such as eating a candy bar when you're supposed to be on a diet, or watching a TV show when you're supposed to be studying, practice suddenly interrupting it. Getting yourself out of these situations gets easier the more you do it.

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You might also find some food for thought by ordering from these menus:

This is all good advice, but I wonder whether in 10 years maybe the first step will be "don't forget to take your willpower increasing pill, otherwise you will predictably fail to follow most of this advice".