There are many ways losing, making mistakes, or doing something wrong makes you stronger.
First of all, there are the direct effects. If you make some mistake, you can learn from it and adjust your actions in the future. If you do something wrong, the regret can teach you in a similar way.
I also think losing more in a way that doesn’t teach you anything might be valuable. Let’s say you want to make more friends. You currently have a 100% success rate of making friends, because you’ve carefully vetted everyone before talking to them. You only approach people you’re certain you’ll get along with. By doing so, you’re missing out. You should aim for a lower-than-perfect success rate, and talk to more people.
This is true even if you learn nothing in the process! Let’s say that the reasons certain people decide whether to be your friend or not are completely inscrutable to you. There are the people you approached before, with a 100% success rate. Everyone else has a 30% success rate, which looks as good as random to you. If you talk to 10 people at the 100% rate, you’ll make 10 friends. If you talk to 34 people at the 30% rate, you’ll also make 10 friends. However, you don’t have to stop talking to the 100 percenters! So if you talk to 10 at 100%, plus any significant number at 30%, you’re making more friends.
There are costs here, which we shouldn’t forget. You might try to explain this away as a waste of time, but really how long does talking to someone new take before you know the friendship potential there? Two minutes? Five? In this contrived scenario, if you spend a couple extra hours talking to new people, you double the number of friends you have. Even if you ruthlessly only value your friends for the time savings they bring you, it seems likely to me that a group of ten friends will be able to save you that amount over the course of your friendship, with their access to time-saving resources you might not have yourself.
The reason the new strategy works so well is that the main cost of talking to new people—our fear of embarrassment, or saying the wrong thing, or whatever—isn’t really a cost at all. Sure, there might be some awkwardness, but how long does it last? Again, only a few minutes. Our anxieties make us undervalue the prospects of talking to new people, when the downside is in fact extremely limited. (This is not to say those anxieties are trivially overcome, however.)
Let’s put this more abstractly. Imagine a distribution over all possible outcomes. You can shift this distribution around, but it’s very hard to change its fundamental character. If you’re trying harder, or putting yourself out there more, you’re probably losing more (more of the distribution falls over negative outcomes). However, if you’re increasing the amount you’re winning after subtracting out negative outcomes, this is (by definition) a net gain! Your job usually isn’t to minimize failure, at all costs. Your job is to maximize the sum total value of experience that you get from doing something.
Too often we’re stuck in risk-avoidance mode. Any half-competent investor will tell you that if you want to maximize your gains, you’re going to have to take on a little risk. Doing nothing with your money (or in this case, your personal resources in general), just sitting on it and letting it rot, is a surefire way to lose out.
I understand that it’s very hard to do things you’re not used to doing. It’s hard to say just how much fear and anxiety can affect people—it’s not trivial to overcome any of these things. This is just a lot of what I’m thinking about and slowly improving on. How do we get better at taking these little risks and shifting our distributions towards maximizing total greatness, rather than minimizing all risk, thus missing out? So far the best I’ve come up with is finding various ways to keep practicing these slightly scary skills, and slowly working up to things that would have been unthinkably terrifying before.
There are very few areas where losing is so bad that trying more is a bad idea. These tend to be pretty obviously risky, and easy for the average person to stay away from. If you work as a heart surgeon, then by all means, minimize failure! In the usual lower-stakes environment of everyday life, though, it probably makes sense to be trying more things and risking more failure than you currently are.