This excerpt reminds me a lot about how very much relates to startups in general - Jay

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ROBERT ANDERSEN – CREATIVE DIRECTOR, SQUARE

As a product designer, most of what I do is twofold: understand the problem you want to solve and approach it from as many angles as you can. After executing on a well-defined and accurately constrained problem in multiple ways, it soon becomes obvious what the true or best solution is. Creative block generally arises from a breakdown in this process.

If you’re stuck in the middle of the design, it probably means that you’re not asking enough questions. Who is the audience? What do they feel? What do they desire? What will improve their life and create joy? How do other designers tackle similar problems? At the core of every successful design is a set of simply defined constraints that you measure your ideas against. It’s all about determining the soul of a product before laying down the first pixel or pen stroke.

Using constraints and understanding as a foundation, you should then execute as many variations you can within those bounds. There are limitless ways to tackle a problem both functionally and aesthetically, which is why you need to uncover a wide spectrum of possibilities to see what feels right. This is crucial to determining quality. Creating various options also means that you don’t need to put pressure on yourself to form one perfect solution from the start. Explore the good and explore the bad—creative block does not exist here, because even a bad direction can move you closer to the right one.

Accurately understand your task and explore immediately. Give yourself the space to freely fail, and that same space will give you the freedom to succeed.

He's kind of like the Wizard of Oz. He doesn't tell you anything you didn't already know.