A friend asked me how I knew when a piece of my writing was good. I told her that when I finish a first draft (or 2nd, 3rd, …) I always think it’s garbage.

She looked shocked and asked, “Do you revise it a lot?” I nodded. “But how do you know when you’ve revised it enough and it’s finished?”

Accomplished writers will tell you to let the work sit awhile, maybe even as long as a few weeks. When you go back to look at it, the parts that aren’t working will jump out at you.

But what if you always find something wrong with your writing? Famous writers talk about never looking at their work after it’s published because they’d want to trash it. Gustave Flaubert wrote Madame Bovary over 5 years. He’d spend an entire week revising one page. And that book was brilliant.

As a child, my wise young son noticed my constant rewriting and said, “You’ll always be a better writer today than you were yesterday, so you’ll always want to improve it. You’re going to have to stop some time so you can write something new.”

How do you know when to move on?

This question arises in life as well. When do you leave a job you don’t like? You can try to improve it, change your thoughts about your boss or co-workers, or struggle to make it meaningful. In the end, you might have to quit.

I counseled an unhappily married couple for an entire year. The wife complained that her husband always gave her unwanted advice about her job, didn’t want to spend time with her on vacations, and accused her of wasting money. The husband complained that his wife always rejected his advances, didn’t value his greater experience in the career they both shared, and spent a suspicious amount of time texting male co-workers.

This couple learned communication skills, arranged fun outings with each other, and made romantic gestures. They were still miserable.

If you’re married, it makes sense to do whatever you can, for as long as you’re able, to try and make the relationship work. But there’s an old cowboy saying: When your horse dies, get off.

You don’t want to fall for what economists call the Sunk Cost Fallacy. (Gamblers call it throwing good money after bad.) Just because you’ve sunk 10 years of time into a relationship, it doesn’t mean you should sink more time into it. Most people leave a marriage only after years of pain and suffering and wished they’d ended it sooner.

Too bad we can’t hop into a time machine and travel to the future to see how it turns out before choosing. Listing pros and cons, asking others for advice, taking classes, joining writing critique groups, and going to a therapist go only so far.

In the end, you’ll go with your gut feeling. Then, whatever happens, you’ll tell yourself it was the right thing to do. Telling yourself anything else will only cause needless suffering.

We can’t always move through life with baby steps. Sometimes we get to the edge of a cliff and the only way forward is to make a giant leap to the other side.