How do you know when you’re done? You never do.

Claude Monet

Like many artists, Monet was temperamental. His mood was usually an extension of how his painting was going that day. Now, he’s a master, so you’d think his painting would usually go well. This wasn’t the case, at least in his eyes. Regardless of public opinion (he was hated at the beginning and loved at the end), Monet was consistently critical of himself. He also constantly pushed himself with new techniques and subjects, trying to capture increasingly fleeting plays of light and color.

Still, many of his early paintings are considered masterpieces. Not just as forerunners of coming work, but as fantastic accomplishments in their own right. Yet during all this time, Monet fretted and bickered and scratched out hundreds of paintings in progress. Something inside him drove him to push harder with each painting, to reach new levels of accomplishment that others may not even have been able to notice.

Alexa Johnson

My wife. A talented poet and copywriter, she proofs much of my writing. I had pushed a recent copywriting project as far as I could see to take it. And while I was happy about some of my work, other parts I wasn’t so sure about. Confused, stressed, I gave my work to my wife.

Her feedback was insightful and gave me confidence that I was on the right track. But as she said, I needed to take it even further. With that confidence, I took up my pencil again and tightened the writing even more, pushing it forward again until I wasn’t sure if it was any good at all.

John Cleese

I recently watched a speech Cleese gave on writing and creativity. In it, he made an unusual observation:

To know how good you are at something requires the same skills as it does to be good at that thing. Which means, if you’re absolutely hopeless at something, you lack exactly those skills you need to know you’re absolutely hopeless at it. This is a profound discovery. That most people who have no idea what they’re doing have no idea they have no idea what they’re doing. It explains a great deal of life….It explains why so many people who are in charge of so many organizations have no idea what they’re doing. They have a terrible blind spot.

How do you know when you’re done?

John Cleese is right. We can’t fully judge our own success — at least in subjective, fuzzy pursuits like art and management and creativity — unless we’ve previously been successful in that specific way. Now turn that on its head. If you can attest to the high-quality of your work, you’re not pushing yourself forward. If you’re happy and confident about your work, you’re just going through the motions.

Part of Monet’s greatness was consistently working beyond his comfort level. My worry that my work may have been drivel was actually a good sign. It meant I was growing as a writer. Of course, my work may well have been bad writing (and some of it was), but that’s alright; failure is a part of growth.

How do you know when you’re done? You never do. But if you still feel good about your work, you’re not there yet.