Uncertainty is in my experience one of the most frustrating aspects of creativity to deal with, and to improve on. It’s common to feel the urge to get to a conclusion as quickly as possible, as a way to resolve the tension that uncertainty arises.

Uncertainty is a powerful yet fragile thing. If we observe it too closely, we risk compromising it by reframing it through our existing ideas, approaches, and mental models. If we let it go too much, it’s impossible to go anywhere and reach goals.

Creativity requires the courage to let go of certainties.
— Erich Fromm

Our ability to deal with uncertainty can be improved in different ways. The first step is obviously to accept its existence, and how fundamental it is to the creative process. Resist the urge to find a solution immediately.

It’s going to be very uncomfortable, especially if you haven’t done it explicitly before. That’s ok. It’s the same feeling you get when you start practicing a new sport and you discover you have muscles you never used before. It gets better over time.

It’s however my experience that this discomfort is never going to go away. It’s there and it will always be there. If might get less daunting, hide in different corners of the process, or change shape, but it won’t go away. The ability is to bear with it.

The creative architects had this tolerance for this discomfort we all feel when we leave things unresolved.
— John Cleese

Reframing certainties is another useful approach to break through from safe ground. Take all the assumptions you’re making, write them down to make them explicit, and then try to break them. “What if this isn’t true?”, “What if the opposite is true?”, or “What if I remove this for a moment?” can be good questions to ask.

It might be that you’ll circle back to your certainties in the end. That’s ok: the idea isn’t to break them because they are wrong, but because this process can lead to more insights. While I think it’s rare for assumptions to end up radically changed after reframing, sometimes it will happen. Be open to it.

Creativity involves breaking out of established patterns in order to look at things in a different way.
— Edward de Bono

We should also try to seek opposing views. Sometimes it’s useful to purposefully search antagonistic, different, and even completely unrelated views. Knowing these views exist is useful, if anything because they allow you to say “No, because…”: that because is extremely valuable.

More often than not, however, there are interesting things we can take from these opposing views: maybe not in their entirety, maybe just a detail, but there’s value in them.

Don’t discard ideas too soon either. “Bad” ideas are valuable, and sometimes they can make a comeback in different ways. It’s very easy to label an idea as “not working”, but it’s important that even if our brain tells us “it’s bad” we keep it around, in a corner, being open to revisit it later. “Bad” ideas can also help breaking a frustrating moment by being hilarious or absurd. This kind of break is welcome too.

There are two parts to any failure: there is the event itself, with all its attendant disappointment, confusion, and shame, and then there is our reaction to it. It is this second part that we control.
— Ed Catmull, Pixar

This because sometimes we start with some supposedly “good” ideas, put them together, and we find out that they are not quite getting to the result we are looking for. Then, later, we find out that the “bad” idea, combined with others we ignored before, form something that is far better than the original “good” ideas together.

I was a kid playing with LEGO the first time I experienced this. I often spent hours trying to build the “perfect” spaceship for the hero, ending up frustrated in not being able to fulfill all my tight requirements. Then I threw together something quick for the antagonist… and loved it so much more that I had to weave a role reversal of some kind in the story I was creating, for the antagonist to become the hero. From a creative process perspective the build-up to the “perfect” spaceship worked as a preparation for the moment when I let myself free from constraints and produced something truly creative.

Sometimes we don’t know exactly where we are going, we just have a loose idea of the final goal, and we pursue it. Not knowing exactly where a path is leading is another side of the uncertainty: the process, the steps themselves can be questioned and shuffled.

Mistakes aren’t a necessary evil. They aren’t evil at all. They are an inevitable consequence of doing something new.
— Ed Catmull

I sometimes think of this approach to uncertainty as finding all the puzzle pieces. Imagine that you have to build a puzzle but you don’t have the pieces to begin with, you have to find them before you can start putting them together, and you don’t even know if they are from the same puzzle. It’s obvious that if you give yourself time to find more pieces, the larger and more complete the puzzle will get. It’s also obvious that you don’t know exactly which image is going to form from the puzzle, so you combine the pieces together, see if they fit, two of them, three of them, and so on, and maybe after a while you have a 20-piece block and then… you suddenly discover a different combination that makes another image with twice the puzzle pieces.

The frustration of not knowing the final image, not knowing where to find the pieces, and the ability that comes from having many of them, and even being able to discard a semi-formed puzzle for a new one: that’s managing uncertainty.