I took Drawing 101 in college. On the first day of class as we set our easels, the instructor put a few objects in the middle of the room: bottles, Styrofoam orbs, a piece of striped cloth. We were supposed to draw the whole scene in 15 minutes, but I was paralyzed by that snow-white square of Strathmore staring back at me. After a moment of panicked internal monologue (and trying to steal looks at my neighbors' work) I picked a place to start—the mouth of a bottle seemed as good a place as any—and I forced my hand to start making marks on the off-white paper. I tried to fill in all the detail as I worked my way down from the mouth to the neck and finally to the bottle's fat middle part. I was standing very close to the easel and making lots of small, tight movements with my wrist, erasing errant strokes as I went.
The artists reading will know that this is the exact wrong way to start drawing a scene. It's suffice to say I took no pride in what I produced at the end of those 15 minutes. I had a poorly drawn wine bottle—rendered in high detail—sitting awkwardly and incorrectly in the rest of the scene, which had been hastily dashed together in the final moments of the exercise.
What I learned that semester stayed with me: Start fast and loose. Use softer, lighter marks as a way to discover the scene. If you start focusing on tiny details right away, you get overly invested too quickly. Don't erase stray marks. Let them remind you where not to go. They provide a scaffolding for you to build on.
Years later I realized this isn't bad advice for starting to design products either.
Here's what I keep reminding myself. Don't hold anything too close to your heart: a strategy, a feature, a logo. Experiment a lot. And it's okay to be wrong. Being wrong helps you discover the shape of the opportunity.