Creative Confidence

Recently, someone I was interviewing asked me what I looked for in the perfect maker.

Immediately, reams and reams of qualities came to mind. I opened my mouth to call forth what have been a ten-minute projectile of words. I’ve written about some of them. I’ve drawn pictures of others. After all, it is the endless fascination of my career, analyzing and exploring and asking and learning the nuances of this simple little question: what does it to take to make a good new thing out of nothing?

Alas, a long list of traits is inherently unhelpful. The candidate would have sat politely, eyes glazing over as I prattled on. We humans are designed for parables, proverbs, simplicity. An answer is not really an answer if it is too complex to be remembered.

So I said this instead: creative confidence. These days, this is most top of mind for me when talking with candidates.

I first came across the term in the title of David and Tom Kelley’s book. The term rolled off my tongue and danced in my ear with its pleasing chime. I knew instantly what it meant. This was the quality I had been questing for, the holy grail of creatives everywhere, the unwavering faith that, at the end of this mess, the thing we have touched and molded will be something wonderful.

But here is the double-edged truth of makers: the act of creating anything original is uncertain. By virtue of the fact that what you are trying to do has not been done before, you cannot know how it will turn out. You cannot know how long it will take to get to something good.

At the same time, we humans crave certainty. We like knowing where our next meal will come from. We like folks who keep their promises. To get a group of people to accomplish anything together, planning is essential.

The magic trick is keeping these two facts in balance. When the unpredictable forces of creativity take over, you get situations that can’t scale. Would you back a director who couldn’t tell you whether her next movie would come out in one year or seven, even if her movies are brilliant? Would you work with someone who was a genius but who was completely unreliable when it came to when and how you two would work together?

Similarly, when the desire for certainty trumps everything else, you get derivative and mediocre results, like too many movies with the same predictable ending. Overvaluing certainty means you end up choosing the same paths that have already been trodden, so while you may have a good idea of exactly how the budget, schedule, process and product will turn out, you’ll also rarely find yourself winning awards for innovation.

A person with creative confidence understands how to strike this balance. She understands and accepts that uncertainty, false starts, and mistakes are part of the creative process, but she also projects a sense of stability and progress to those around her. Yes, she makes you believe, there is indeed a beautiful story in this collection of random footage, the mistakes we are making are teaching us new lessons and making us better, and when we premiere our movie, the applause will roll through the auditorium like thunder.

How can you tell if someone has creative confidence? Ask yourself if she…

1. Remains stable despite the shifting winds of momentum. When it feels like 20 people have 20 different opinions about the product and its viability, it’s easy to get swept up in trying to please all the various stakeholders or drawing conclusions from how the “average” feels. A person with creative confidence does not lose her direction. Her feet remain firmly planted on the path, following the guidance of rational first principles, a solid internal process, and research and learnings straight from the people she is building for.
2. Takes a rigorous approach to her work. That means it is hard to poke holes in her recommended ideas because she has thoroughly vetted all the alternatives. You will ask have you considered X? and the answer is always, Yes, I have considered X, and here are the tradeoffs and my conclusion… You are left with the impression that this person did their homework and that you are learning something from their thoughtfulness, diligence, and quality of work.
3. Is crystal-clear on what she is trying to accomplish. A creatively confident person will frame all her work around the problem or opportunity she is going after, and will focus the conversation back on the priorities that matter if it starts to go astray.
4. Admits when she doesn’t yet have the answer, but can describe a clear plan to get to the answer. The plan can take any form — milestones with dates, a clearly outlined process, a change in people or plans, etc — but the key thing is that the plan inspires confidence and places some structure around how we are going to navigate the uncertain wilderness to get to a good path.

Okay, all that is well and good, but what if I don’t have creative confidence? How do I get it? This is the fun part.

1. Believe that confidence is something that can be acquired. Tom Stocky’s article, one of my favorites says it better than I ever could: growing in self-confidence is really about growing in two skills: self-awareness and growth mindset. The first is understanding yourself as objectively as you can — what are you good at, and what do you suck at? The second is being okay with that and realizing that where you are now is just a starting point for where you can get to, with time and sustained effort.
2. Go through the creative process again and again and again. There is no shortcut to this. You can read all the books in the world, but unless you have actually gone through experiencing the countless different ways you can try to make something from nothing and fail or succeed, it will be pretty much impossible to earn the confidence that comes from having done and survived. How do you know not to freak out when it’s the 11th hour and you’re bashing your head against the wall because you have no good ideas left? Because you’ve felt that exact same stress time and time before, and you’ve always gotten through it. This may not seem like good advice for the impatient, but I have always found it comforting, especially when paired with #1. In the simple act of doing, no matter how it turns out, we are building up the experience and learning that we can cash in for creative confidence later on.
3. Improve your skills. I have never seen somebody whom I consider to be creatively confident who wasn’t in the top 5% of some particular skill in their field, and who was also incredibly self-aware about it. You do not gain credibility and confidence by simply wanting it or acting it, even if you are well-liked. You must have the hard skills and the track record to be considered credible. Otherwise, you end up looking creatively arrogant (which is when you believe you have creative confidence, but nobody else thinks so because you don’t have strong self-awareness.) Take your craft seriously. Don’t just ask what’s the minimum I can do to finish the job? but what will push this to be better than anything I’ve done before? Hone your work until it gleams. Hold it against a rigorous lens. If you do not trust your own eye, ask for feedback from the most rigorous person you know.
4. Invest in your process. A rock-solid process — a series of repeatable actions — is the golden goose to building creative confidence. These actions include: a) thoroughly exploring every idea you or your trusted peers can come up with. This might feel time-consuming and unexciting, but it’s also a pretty simple math equation: if you have explored literally every single option, you will also have come up with the best solution. As you become stronger in your craft, you’ll develop a keener sense for how to discard unpromising paths earlier so you can more quickly get to the best solution, but if you are stuck, never doubt the power of brute force; b) getting lots of early feedback from as many smart people as you can. Even if you hear different or conflicting things, understanding the range of viewpoints ensures you will consider the tradeoffs carefully. And if you start hearing that everyone agrees your solution is obvious, then great. Your work here is done; c) connecting with the real people you’re building for. It’s hard to overestimate the power of user research. Done well, it gives you an unparalleled understanding of the why behind how people think and what they do. Nothing builds confidence like research that validates the problem you’re solving is real, and that the solution you’ve come up with is really working for people.

Creative confidence, as with all skills, can be built: step by step, day by day, project by project. Be curious, and make things.

And while I hope I do not know the ending to your movie on the night of your premiere, may it be wonderful, and may the applause be thunderous.