"I'd rather not send it at all"
So far I've written about work that goes out late. There's a quieter version of the habit, and it costs more. Some things never go out.
There's the job application you worked on for a fortnight and didn't submit, because the covering letter never sounded right. There's the email to an old friend after their father died. You drafted it four times, and every draft seemed clumsy next to what they were going through, and then so much time had passed that sending anything felt worse than sending nothing. There are the holiday photographs you meant to make into an album once you'd edited them properly, which are still on a memory card from three summers ago. You may also have a short story, a business idea or a letter to the council that never went anywhere.
The belief underneath is that a flawed thing is worse than no thing. While the application is unsent, it can still be excellent in principle. Once it's sent it's only as good as it is. Holding it back keeps the excellent version alive. It also guarantees a result of nothing, and that gets forgotten.
Look at it from the other end. Your friend didn't need a well-written email. They needed to hear from you, and three awkward lines in the first week would have done it. The employer can't hire someone who didn't apply. They'll appoint someone whose covering letter was ordinary and was in the pile. In each case the comparison you were making was between your draft and a perfect draft. The real comparison was between your draft and silence, and your draft would have won easily.
There's some evidence that this shows up in output, even among people whose careers depend on output. Simon Sherry and colleagues studied psychology professors. They measured how much each professor demanded perfection of themselves, and then counted publications. The more perfectionistic professors had fewer publications in total and fewer as first author. They had fewer citations too, and appeared in less influential journals. That held even after allowing for how conscientious they were. The authors suggest that demanding perfection of yourself can turn into a kind of overstriving that defeats its own purpose.
It's a single study in one profession, and it's a correlation. But it goes against a natural assumption. You might expect the perfectionists to publish less and better. They published less, and what they published was cited less. Whatever the extra care was doing, it wasn't producing the masterpieces that would have justified it.
Perfectionism also connects with plain delay. Fuschia Sirois, Danielle Molnar and Jameson Hirsch pooled the studies on perfectionism and procrastination, using the two dimensions from chapter 3. People high in perfectionistic concerns procrastinated more, across 43 samples and about ten thousand people. People high in strivings procrastinated less. The association was modest in both directions. It fits the picture so far, though. The dread makes you put things off, and the high standards on their own would have got you started sooner.
If not sending has been your pattern, here's a different way to think about the unsent things. Each one is currently scoring zero. A mediocre application scores something, even if it's only practice at applying. A clumsy note to your friend scores a great deal. An album of unedited photographs gets looked at, and a memory card in a drawer doesn't. You aren't choosing between flawed and flawless. You're choosing between flawed and nothing, and nothing is the option you keep taking.
There's one action I'd suggest now and not at the end of the book. If there's a message to a person that you've been failing to write well enough, send a short plain version today. "I've been meaning to write for ages and kept not finding the right words. I'm so sorry about your dad. I'm thinking of you." It isn't polished. It will land better than you fear, and far better than the fifth unsent draft.