The second dubious virtue is recklessness. As with desperation, there are many bad ways to be reckless. There is a nihilistic recklessness, in those with a muted ability to feel and care, that is self-destructive. There is a social recklessness, when peers push each other towards doing something dangerous that none of them would do alone, in a demonstration of commitment that can become needlessly dangerous. And there is a fiery, destructive recklessness in those too quick to anger, which can lead people to actions they will regret for a lifetime. I caution against all these types of recklessness.
Nevertheless, there is a type of recklessness that is a virtue. This is recklessness in the pursuit of an external goal, and I have found it to be rather rare.
I get a lot of questions from people about how cautious they should be as they make changes in their lives. If they remove their guilt motivation, will they be able to do anything at all? If they really try to understand how screwed up the world is, on a gut level, will they break? If they devote their efforts to the pursuit of something larger than them, will they lose touch with their humanity, and with their ability to connect to other human beings?
And I tend to answer: You are not made of glass.
Dive in. Change things. Fix problems. If more problems crop up, fix those too.
Imagine that you look upon yourself, detect harmful guilt-based motivation, tear it out, and then notice that this leaves you with a Zen-like lack of drive, such that most of yourself is now happy to let days slip by but some small part of you is crying out that something is wrong. Recklessness-the-virtue is about being in that state and deciding to push forward rather than retreating; deciding to make a desperate effort to acquire a new drive, rather than panicking and retreating back towards guilt.
Recklessness is about ripping off the blinders that prevent you from seeing the dark world on a gut level, and knowing that if this happens to be debilitating then you'll find some new way to handle it, rather than being forced to retreat.
Always forward, never back. Be unable to despair. Have confidence all the way up. Think of all the people you know who are too stagnant, too cautious about breaking something important, to ever change at all.
You can recover from breaking a few parts of yourself, so long as you're modular rather than fragile. You can become able to roll with a few punches.
(This seems like a good time to insert a heavy-handed reminder about the law of equal and opposite advice! Many people would do well to gain a little recklessness, but many others need less recklessness and more caution. If you're in a particularly fragile mental state, consider disregarding this post entirely.)
During my undergraduate education, I was the president of an entrepreneurship club. The first most common type of person who would drop by asking for advice was that young wannabe founder all full of naïve excitement about some half-formed notion that they're about to make the next facebook. The second most common person was that competent programmer with an idea that wasn't half-bad — maybe they had some idea for an app that would let couples communicate in a way they couldn't yet easily do, six years ago — but, being tempered and level-headed and well aware of the naïvety of the first folks, were entirely unable to commit to their idea.
Both sets of prospective entrepreneurs were doomed to failure. The first set, for all the obvious reasons — they'd focus too narrowly on writing code that no one would ever buy, or fail to find their first users, or fail to make a minimum testable product, or they'd dramatically misunderstand and underestimate the difficulty of the technical challenges, or whatever.
The second set would fail because they didn't really expect themselves to succeed. They could make themselves work on their idea, while reciting to themselves some story about being risk-loving, but they couldn't get their head into the idea, to the point where they were spending fourteen hours a day working feverishly while plans and paths and strategies dominated their waking thoughts.
There's a fugue state that successful entrepreneurs report entering, which the second set of people had rendered themselves unable to enter. Somehow, their realistic understating of their odds destroyed their ability to commit.
In one fashion, this makes some sense: they, knowing that great success is likely a lie, cannot fool their innermost self into believing in their own vision, which precludes them from entering the fugue state.
But in another fashion, is silly. What do the odds have to do with your ability to commit? Why is their epistemic state preventing them from entering the emotional state that would most help them succeed?
I think there are a few different skills it takes to be able to ender the fugue state even while knowing that your odds of success are low. One of them, I think, is the virtue of recklessness.
Recklessness is in the ability to say "screw the odds, I'm going to push forward on this path as hard as I can until a better path appears." If the odds are low, a better path is more likely to appear sooner rather than later — but the reckless let that be a fact about the paths, and they don't further allow low odds to prevent them from pushing forward on the best path they can currently see, as fast as possible.
If you want to become a successful entrepreneur, or if you want to succeed at other very difficult tasks, it helps to be able to take the best from both types of hopeless entrepreneurs. Become the sort of person who can enter the fugue state and give an idea your all, while also being able to see and avoid all the common failure modes. The fact that you are unlikely to succeed is an epistemic fact, you do not need to give it dominion over your motivation. Be a little reckless.
Recklessness, as a virtue, is about being able to throw caution to the wind. It's about being able to commit yourself fully to the best path before you, and then change your entire life at the drop of a pin as soon as a better path appears. It's about being free to act without worrying too much about what happens if you disrupt the status quo — too many people are already too stagnant, and we need to move faster.
So if you find yourself knowing what it is that you need to do next, but worried that doing so will break something else important…
then I say, do it.
Try not to break anything vital, but if you do, fix it and keep moving.
Always forward, never back.
Be a little reckless.