Oulala: On Iterative Design

The name "oulala" comes from the French expression of pleasant surprise—that moment when something unexpected clicks into place. In design, these moments rarely arrive on schedule. They emerge through iteration, through the patient work of trying, learning, and refining.

The myth of the perfect first draft​

There's a persistent fantasy in design: that if you just think hard enough, research thoroughly enough, plan carefully enough, the right solution will emerge fully formed. Experience teaches otherwise.

Good design almost always looks inevitable in retrospect. The final interface seems like it could only have been that way. But trace the path backward and you'll find sketches that went nowhere, prototypes that revealed unexpected problems, and assumptions that testing proved wrong.

This isn't failure. This is how design works.

What iteration actually looks like​

Iteration isn't the same as revision. Revision implies you had something right and are fixing what's wrong. Iteration is more exploratory—you're not just polishing, you're discovering.

Early iterations are about exploring the problem space. You're not trying to get the design right; you're trying to understand what "right" might mean. Low-fidelity sketches, rough prototypes, early conversations with users—these help map the territory.

Middle iterations narrow the focus. You've learned enough to have hypotheses worth testing. Prototypes get more detailed because the details start to matter. You're still learning, but with increasing confidence about direction.

Late iterations refine within established constraints. The fundamental approach is set; now you're optimizing. This is where small changes can have significant impact, and where it's tempting to keep going forever.

Creating conditions for productive iteration​

Iteration requires certain conditions to work well:

Time and space​

Obvious but often overlooked: iteration takes time. If the schedule assumes the first idea will work, there's no room for learning. Build exploration time into project plans, even when it feels like a luxury you can't afford.

Cheap failures​

The faster and cheaper you can try things and see them fail, the more iterations you can fit into the available time. This is why low-fidelity prototypes matter—not because they're faster to make, but because you're more willing to throw them away.

Learning loops​

Each iteration should teach you something. If you're changing things without understanding why the previous version didn't work, you're just shuffling deck chairs. Build in reflection: what did we learn? What are we trying next? What will tell us if it worked?

Psychological safety​

People need to feel safe proposing ideas that might not work. If only "good" ideas are welcome, you'll get cautious suggestions optimized for not being wrong, rather than exploratory thinking that might lead somewhere interesting.

Iteration in practice​

Some practical approaches that support iterative design:

Design studios: Time-boxed sessions where multiple team members sketch solutions to the same problem. The variety surfaces assumptions and generates options. Nobody's idea needs to be "the one."

Progressive prototyping: Start with the cheapest representation that can answer your current question. Paper sketches for flow questions. Clickable mockups for interaction questions. Coded prototypes only when you need real behavior.

Hypothesis-driven testing: Frame what you're testing as explicit hypotheses. "Users will understand this icon means settings" is testable in a way that "is this icon good?" isn't. Clear hypotheses focus observation.

Time-boxing: Give iterations boundaries. "We'll explore this for two days, then decide whether to continue or pivot." Without boundaries, exploration can expand indefinitely.

Common iteration traps​

Analysis paralysis: You can always gather more data, explore more options, consider more edge cases. At some point, you have to commit to a direction even with incomplete information.

Attachment to early ideas: The first solution you thought of has emotional weight. It's yours. But being attached to a specific solution can blind you to better options that emerge through exploration.

Iteration theater: Going through the motions of iteration—making prototypes, running tests—without actually being open to changing direction. If the conclusion is predetermined, the process is performative.

Perfecting the wrong thing: Meticulous refinement of a fundamentally flawed approach. Sometimes you need to step back and question the basic direction, not just the details.

The oulala moment​

After all the sketching and testing and refining, occasionally something clicks. The interface that seemed forced starts to feel natural. The flow that was confusing becomes clear. The design arrives at a place that feels right—not perfect, but right enough that further iteration yields diminishing returns.

These moments can't be scheduled or forced. But they can be made more likely by creating conditions for genuine exploration, by staying open to surprise, and by doing the work of iteration even when the destination isn't clear.

The oulala moments don't come from individual brilliance. They emerge from process—from the accumulated learning of many small experiments, from the willingness to try things that might not work, from the patience to keep going when progress isn't obvious.

Applying this to your work​

If your current project feels stuck, consider:

1. Are you iterating or just revising? Are you exploring new possibilities or just tweaking what you have?

2. What are you learning? Can you articulate what each round of work teaches you? If not, you might be going in circles.

3. Are failures cheap enough? Is it easy to try something and see it fail? If not, can you reduce the cost of experimentation?

4. Is the direction clear? Sometimes the problem isn't iteration—it's lack of clarity about what you're trying to achieve. Step back and check your foundations.

5. Is it time to commit? If you've been iterating for a while, maybe you have enough information to make a decision. Endless exploration isn't progress.