The Tao of Bob Ross

Yesterday I wore my Bob Ross shirt. It says “No mistakes, just happy accidents.” While not a mentality I’d advocate for the implementation phase of a project, it captures a philosophy I like for the early stages of design, because it makes space for innovation to take root. 

When we present a winning app design, it may seem to the client as though we followed a precise path, mathematically arriving at the best possible solution through formulaic expertise. That is an illusion. In reality, our Figma boards are often littered with discarded attempts just off the field of view. But one or several of those discarded attempts probably contains a kernel of an idea that actually works. And that idea sparked another iteration, which may have led to a collaboration session with cross-functional team members, which eventually yielded (after a couple more revisions) a design that matters.

Why did those attempts bear fruit? Because people had mental space in the design process to play. Play is different from experimentation. Play involves an element of fun. Play means trying something for the heck of it. The reason play is so important is that freed from the constraint that we have to make it work right now, the brain is free to come up with things that probably won’t work, but have some intriguing element within. By engaging with those ideas, we learn more about the properties of the problem and how it responds to different methods. New, even more creative ideas spawn from the original attempts. 

Sometimes in the midst of the play, we take an idea far into never-never land and then reel it back in. This is intentional – it is often much easier to push past the point of pragmatism and pull back, than play it safe and try to punch it up a little later. Once you’ve settled into the alluring safety of feeling like you have it solved, it’s hard to later smash the constraints and come up with something truly novel. That period of play is the time when the new and innovative can begin to take shape.

What’s the best recipe for innovative play?

  1. Research early. Gather all of the information you need about the problem. Ask all the good questions. Understand the small aspects of it. The devil, as they say, is often in the details and you don’t want to overcommit to a solution that works at a macro level but falls apart in implementation.

  2. Ponder. Take some time to just think about the problem and the people who experience it, without trying to solve it. What is important to them? What do they hope for? What do they fear? 

  3. Play. Commit to try things with no expectation that this session leads to a solution. Resist the urge to check the box. If you’re having trouble with this, play a game with yourself where you try to come up with at least 3 outlandish ideas that won’t work. A note on this: you want direction, not quantity. If you have 26 variations on the same thing, you are not playing, you’re fiddling. Fiddling is for later. Try things that are dramatically different from each other, informed by the pondering you did in step 2.

The trick to all of this is time and mental space. Some people have guts of steel and can engage in play the night before a deadline, but many of us can’t. Start early, when you can’t yet feel the pressure of having to come up with an answer. 

Once you’ve played, then expertise and experience come into the game. They help you narrow down the options faster and avoid being drawn in by sexy ideas that just won’t work. After a certain quantity of projects you begin to recognize opportunities and best design patterns and some if it happens by rote. But that is in the nuts and bolts, the bits and bytes. You can nail all of that and still have something that’s thoroughly forgettable and fails to generate any user enthusiasm. 

The key to capturing hearts and minds is to connect with people in a way that makes them feel seen and heard. That means reaching people in a way that is core to who they are, that touches our humanity. And when do we feel more truly ourselves than when we play?

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