But it’s important to talk about the because that’s the critical part of any bold venture. With most projects, there’s a fine line between success and failure, and how you handle the determines which side of that line you end up on.

You talk a lot about the ups and downs of starting and growing a venture. How do you navigate this roller coaster of challenges, failures, and successes?

The middle is a constant cycle of successes followed by failures, setbacks followed by breakthroughs. Making it through that cycle depends on two things: enduring the lows and optimizing the highs. When things are terrible, you have to find ways to convince your team and yourself that you’re making progress, even if that progress is tiny. And when things go well, it’s not enough to just celebrate. You have to examine what worked and how to optimize it as opposed to just fixing what’s broken. It’s also important to recognize that we are not our best selves at the peaks (when egos grow and we falsely attribute success to the things that we did) or in the valleys (when we make decisions out of fear). So much of navigating volatility comes down to self-awareness.

What is the biggest mistake creative entrepreneurs make in business, and how do they avoid it?

collaborated with lettering artist and illustrator Jessica Hische to create illustrations of the book’s key insights. You can read more about it here.

By definition, creative people are constantly coming up with new ideas. In general, that’s a great quality. But it can work against you when you’re trying to launch a new business or a major project.

In the book I talk about the need to “kill your darlings,” a term writers use to describe the challenge of removing beautiful plot points and characters in order to simplify the narrative and stay focused on the core storyline. Similarly, in a productive creative team, you need  a strong immune system that can kill off ideas that get you off track or compromise productivity. Of course, every now and then, you need to suppress the immune system to allow new ideas to take hold. But nothing beats great execution, and your job as a creative leader is to not let new and shiny ideas inhibit your ability to finish the projects you’ve committed to.

We all know we can’t do it alone, but hiring the right people is easier said than done. What’s your advice for ventures that need to grow their team?

The greatest teams I’ve been on have been made up of extraordinarily different extraordinary people. So many studies have found that diverse teams come up with more creative, innovative solutions. An important part of that is the sort of racial and gender diversity we most often talk about, but it goes beyond that as well. Innovation comes from having people who look at a problem in a fundamentally different way than you do. Their perspectives may not even make sense to you at first, but by pulling together those very different points of view you arrive at a solution that no group of similar, like-minded people could ever come up with.

The other advice I’d give is not to avoid people who are polarizing. People who are opinionated and willing to fight for their perspective can be hard to get along with. But having those disagreements and embracing the conflict will bring you insights that would never come if everyone is willing to compromise and avoid conflict.

What was it like writing this book and reflecting on your adventures and lessons learned along the way?

At times, it was hard reliving things I’d gone through in the middle of Behance’s development. I got married during that time, and working on the book made me remember the feeling of being on my honeymoon, a once-in-a-lifetime trip, but at the same time worrying because Behance was a few months away from not being able to make payroll. As a result, I wasn’t fully present for my honeymoon and that’s a painful memory.

But in researching the book I spoke with dozens of other entrepreneurs, creative people, and leaders who have been on similar journeys. I learned that I wasn’t alone in having those painful memories, and that we all had great memories too. I became convinced that by sharing what we collectively had learned in our own middles, we could make that part of the journey a little easier for other people.

What is your ultimate mission and goal with writing “The Messy Middle?”

One thing that really struck me, as I became a part of a community of fellow entrepreneurs and makers, was how seldom people openly discussed the middle stages of their projects. Every project was always “going great” — until it failed. The bumps along the road were endured in isolation. Perhaps we don’t talk about the messy middle because we think it is unappealing or too revealing, but the isolation is maddening and just makes it harder.

This book is a direct result of the empathy and fascination I developed for the messy middle during my experience building Behance, leading teams at Adobe, as well as advising many other leaders, entrepreneurs, and designers.

Learn more about “The Messy Middle,” and pick up your own copy.



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