Ira Glass and the Years Your Work Will Disappoint You

“Your taste is why your work disappoints you.” That is the line people quote from Ira Glass, and it is better than most advice about creative work because it describes a feeling instead of prescribing a cure. The feeling is the gap between what you can recognize as good and what you can currently make. Glass’s claim is that the gap is real, that it lasts for years, and that the only exit is a large quantity of finished work.

The harder claim, and the one this post is about, is that most people never test any of it. They meet the gap in month two, read it as a verdict on their talent, and leave. The gap does not stop them. Their interpretation of it does.

What Ira Glass actually said, and where it comes from

The source is an interview about storytelling that Glass, the host of This American Life, recorded for Current TV in 2009. The version that spread online a few years later was a film by the German designer Daniel Sax, who set a portion of the interview to hand-made typography: “disappointment” carved into a cucumber, “taste” sprayed across a painting in a hotel room. That film is what most people mean when they say “The Gap.”

The argument runs in four moves. People who do creative work get into it because they have good taste. For the first couple of years, what they make is not very good. Their taste, though, is “killer,” as Glass puts it, so they can see exactly how far the work falls short. And the people who survive are the ones who keep producing anyway until the work catches up.

Note what the structure does. The disappointment is not a bug in the process. It is the evidence that your taste is working. A person with no taste would be perfectly content with the early work, and that contentment would be the worse sign.

Why does the gap feel like proof you are bad?

Because the gap and the verdict produce the same sensation. When a draft is embarrassing, the immediate experience is identical whether you are three weeks into a long climb or whether you simply lack the ability. Nothing inside the feeling tells you which one you are in.

So the feeling gets read at its worst reading. And the people most vulnerable to this are the ones with the best taste, since they see the shortfall most clearly. This is the unfair part of Glass’s observation: the more discerning you are, the larger the gap looks, and the more convincing the case for stopping.

There is also a timing problem. The gap runs for years, but nobody checks in on a schedule that long. The feedback you receive in the first six weeks is the feedback you use to decide. Six weeks is almost entirely gap.

A related pattern shows up at the other end of a project, where people stall when the finish is in sight; that one is covered in the post on why people quit at ninety percent. The gap is the same failure at the front of the line.

Glass’s fix, and a second example that makes it concrete

Glass’s prescription is volume: do a lot of work, set yourself deadlines, and force yourself to finish things, because the work is how the skill arrives. It sounds like a platitude until you see it run as an experiment.

In Art & Fear (1993), David Bayles and Ted Orland tell of a ceramics teacher who splits a class in two on the first day. One half will be graded purely on quantity: fifty pounds of pots earns an A, forty a B. The other half will be graded purely on quality, and needs to hand in a single pot, a perfect one, to get an A. At the end of term, the best pots came from the quantity group. While the quality group sat theorizing about perfection, the other half was busy making mistakes and learning from them.

Is it true? Partly, and the details matter. According to Orland, the ceramics story is true, “allowing for some literary license,” and its real origin was a teaching gambit used by the photographer Jerry Uelsmann on his beginning photography students at the University of Florida. Orland and Bayles changed the medium to ceramics for the book. So it is neither a pure parable nor a transcript of a documented class. It is a real teaching exercise that was retold, and I would not cite the pound figures as measurements.

What survives that caveat is the mechanism. The quantity group did not out-try the quality group in the sense of effort per pot. They simply had more cycles of make, look, adjust.

Where “just do more” breaks down

Volume is half of the answer, and the other half is usually left out. The quantity group in the story could pick up each pot, see the crack, and change the next one. Output came with feedback built in.

Remove the feedback and the advice fails. Someone who writes the same unedited paragraph a thousand times is practicing the paragraph, mistakes included. Taste only closes the gap when it is pointed at the work: you compare the output against the standard that bothers you, find the specific distance, and aim the next attempt at it. Without that step, volume is just repetition.

This is also why a bare count of hours is a poor measure. Three small pieces you finish, review, and revise teach more than ten you abandon at the first sign of embarrassment. Finishing matters because an unfinished piece never gets the comparison.

If you have been calling an unfinished project a work in progress for some years, the Tolkien story of Niggle and his unfinished painting is a stranger and gentler take on the same problem. And for the practical version of tolerating bad output on purpose, Anne Lamott’s case for shitty first drafts is the place to go.

What closes the gap is mostly attendance

Put the two examples together and the gap turns out to be less about talent than about attendance. The quantity group won by showing up to the wheel, repeatedly, including on days when the results were ugly. Glass’s survivors are the people who sat down again after a bad draft.

That is a dull answer, and dullness — not difficulty — is the reason it goes untried. The motivating part of the work, the idea and the taste, is already in place. What remains is repetition on days when you do not want to, and nobody feels like repeating something they are currently bad at.

One place this touches mornings: DontSnooze is an iOS alarm app built around the same dull requirement, applied to mornings. When the alarm goes off you record a short video that your small group of friends can see, and if you do not, a random photo from your own camera roll goes to the group for 48 hours. It cannot make you better at anything. It can make the first act of the day, getting up and showing evidence of it, something other people can see you do. If you are going to spend years in the gap, that at least makes the start of each day count as one more attempt at the wheel.

The cucumber in Daniel Sax’s film has the word “disappointment” carved into it. It is a good image to keep around: the word is fresh, it will not last, and it was cut by someone who kept the knife moving.