"If I don't try, I can't fail"
Go back to the job advert from chapter 1, open in its tab for four days and closed on the Friday. Or take the quieter version of the same move. You do apply, but you leave it until the last evening and send something rushed. If it fails, it was the rush that failed.
The belief underneath is that not trying is safe. If you expect little and risk little, you can't be badly let down. A rejection would hurt, and a rejection after your best effort would hurt most, so you hold the effort back.
The part that's true is that rejection hurts. I'm not going to tell you it doesn't. Closing the tab did spare you a possible "no" in three weeks' time.
Psychologists have studied the half-hearted version of this under the name self-handicapping. In a well-known experiment from 1978, Steven Berglas and Edward Jones gave students a set of problems. Some students got problems that couldn't be solved, and were then told they'd done very well, so they had a success they couldn't explain. Before a second test, everyone was offered a choice of two drugs, one said to help performance and one said to harm it. Among the men, those with the unexplained success were much more likely to pick the drug that would harm them. If the second test went badly, the drug would be the reason, and their good opinion of their own ability would be safe. The women in the study didn't show the pattern.
I think that's what the closed tab protects. It doesn't protect you from failure, since you still don't have the job. It protects a possibility. "I could have got it if I'd gone for it." "I could write a good book if I ever had the time." It's like keeping a lottery ticket in a drawer and never checking the numbers, so that it can go on being a possible winner. An unchecked ticket pays out exactly what a losing ticket pays. You also have to keep not looking at it.
The comparison with failing is worth making plainly. If you apply and get turned down, you lose an evening and have a bad day or two. You also learn something, even if it's only that this sort of job attracts two hundred applicants. If you don't apply, you lose the same job and you learn nothing. The question of whether you could have got it stays open, and an open question like that tends to get heavier over the years.
This is where "I can't be disappointed" goes wrong. The disappointment does come. It comes slowly, when you hear who got the job, or when you notice how long the novel has been in the drawer. Thomas Gilovich and Victoria Medvec studied what people regret. Over the short term, people tended to regret things they'd done that turned out badly. Looking back over their lives, they more often regretted the things they hadn't done. Gilovich and other colleagues later found the same long-term pattern in China, Japan and Russia. A large repeat of the original studies in 2022 found it again in three tests out of four, with weaker effects, and its authors describe the wider evidence as mixed. All of it rests on what people recall or imagine, and nobody has followed people for decades to check. Still, it fits what older people tend to say when you ask them.
It's also doubtful that low expectations cushion the blow as well as they promise. In three studies by Sarit Golub, Daniel Gilbert and Timothy Wilson, people who expected a bad result felt worse while they waited than people who expected a good one. Once the result arrived, what they'd expected made no measurable difference to how they felt. Expecting the worst cost them something and bought them nothing. Test that against your own memory. Think of a disappointment you'd braced for, and ask whether the bracing helped much on the day.
You might say, "Some things I really wouldn't get." That's true, and you can't tell which ones from the feeling, for the reasons in chapter 3. The costs of trying are usually small and fixed. An application is an evening. A question at a talk is fifteen seconds. Showing a friend the drawings is one slightly awkward minute. Set against those, a "no" tells you less about yourself than it feels like it does. Most rejections come from things you never see, such as an internal candidate, a budget, or forty other good applicants.
So I'd suggest a different aim. Give up trying to be someone who never fails, which can only be managed by never trying. Aim to be someone who finds out. People who find out fail more often than you do at present, and they also get more of what they wanted, because they were in the running.
In practice, start by spotting your own half-tries. They're harder to see than a closed tab. Watch for the application sent at the last minute, and for the idea introduced with "this is only a rough thought". Watch for the piece of work you describe to everyone as something you threw together. Each time you catch one, ask what the full attempt would have looked like. If the stakes are small, make it.