Author, Entrepreneur + Behance Founder Scott Belsky’s “The Messy Middle” Book

130+ insights on navigating the most treacherous parts of a project

Everyone who’s sought to bring an act of creativity to fruition understands the struggle that befalls the dense journey between “aha” and “we’re done!” Scott Belsky—a multi-hyphenate entrepreneur, Behance founder, author and Adobe‘s Chief Product Officer and Executive Vice President for Creative Cloud—knows the journey quite well. He’s embarked upon it time and time again. And the lessons he learned from serial success now makes its way to others in the form of “The Messy Middle.” There are more than 130 insights penned, all with the mission of helping readers accomplish their goal in three ways. Endure, he employs. Optimize the good times, he adds. And don’t self-defeat in the final mile. The books represents a five-year project, and the inspiration and guidance within come not only from Belsky, but also interviews he’s conducted. Most importantly, it’s applicable to all types of projects—personal or professional, large or small. We spoke with Belsky to learn more about honing what falls upon the pages—and the widespread resonance he’s been met with so far.

Inherent in the name is the idea that there’s a beginning and an end to a venture. Beginnings come in many forms, but are generally identifiable. Ends, on the other hand, are nebulous. And for some of us there isn’t necessarily an end-game. Does that mean we’re perpetually stuck in the Messy Middle? Is that good, bad or otherwise?

The most humbling part of creativity is that you’re never truly done. While some finishes are momentous, most are merely mile-markers that make long journeys more manageable. But as you approach a major transition point or event in your work, the skills you need to succeed may suddenly change as you find yourself marketing your creation or negotiating a sale. I’d argue that we’re always navigating the volatility of the messy middle, but there are punctuation points throughout that have implications.

In the book, rather than talk about the state of being finished, I focus on what I call “final mile challenges.” Psychologically, you’ll ponder the implications of finishing and likely have mixed feelings. I’ve seen all kinds of counterintuitive behaviors, like cutting sections of a screenplay in the last minute, rushing a sale process after a decade building a company, and various forms of self-sabotage in the final mile of a project when people felt they didn’t deserve their success.

You summarize the middle as a series of ups and downs that marry optimization and endurance. Without giving it all away, can you summarize this for us?

No matter what it is you’re trying to create or transform, the myth of a successful journey is that it starts with an idea, followed by a ton of hardship, and then a gradual and linear rise to the finish line. But no extraordinary journey is linear. In reality, the middle is extraordinarily volatile—a continuous sequence of ups and downs, flush with uncertainty and struggle. Every advance reveals a new shortcoming. Your job is to endure the lows and optimize the highs to achieve a positive slope within the jaggedness of the messy middle—so that, on average, every low is less low than the one before it, and every subsequent high is a little higher.

But no extraordinary journey is linear. In reality, the middle is extraordinarily volatile—a continuous sequence of ups and downs, flush with uncertainty and struggle

I organized the book as a collection of insights that help you (1) endure the human-tendency-defying woes of the middle (your war with self-doubt, the roller coaster of incremental successes and failures, and bouts of the mundane amidst sheer anonymity), and (2) optimize the hell out of everything that works (constantly improving the way you hire, structure, and manage your team, relentlessly simplifying and iterating your product while staying anchored by your customers’ needs, and crafting your instincts to make better decisions and internalize what you’re learning while staying relatable).

On your journey with Behance, when did you know your end-game and how did that define your awareness of and empathy for the middle? Did defining the end help you get through the middle?

Our early team assumed Behance would be a lifestyle business and we held off on raising any venture capital for five years. Behance’s messy middle, especially the first five years without any end in sight, was very difficult and transformational for all of us. We endured long periods without any traction, had many fits and starts, and were forced to be remarkably resourceful. It was one of those classic “what doesn’t kill you makes you stronger” experiences.

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.

Learning to endure working amidst self-doubt without traditional rewards may very well be half the battle

This book is a direct result of the empathy and intrigue I developed for the messy middle during my experience building Behance as well as advising many other entrepreneurs and designers.

Do you hope this book will help creatives and entrepreneurs get through the middle faster? better? smarter? All of the above, I’d imagine. I guess the real question is, why write this book?

In part, I want to dispel the myth that the journey to make something great is linear. Even the greatest success stories were remarkably volatile and flush with struggle. Learning to endure working amidst self-doubt without traditional rewards may very well be half the battle. Not only must we tolerate the volatility, we must also learn to mine it for the insights that make our teams and products better. A big chunk of the book is devoted to optimizing how teams function, reducing process, and crafting better products. I want this book to be the ultimate companion for the middle stages of bold projects, especially at the toughest moments.

You always have several projects going on and each are at different phases. What are you in “The Messy Middle” of right now and how did writing the book help you with this moment?

Six months ago I took on the opportunity to lead product at Adobe, and I am very much in the messy middle of revamping some of our products and helping ship entirely new products. Leading change in any company is a challenge, and I find various insights from the book very relevant in my new role. For example, there is a whole section in the book about tackling “organizational debt” and valuing conviction over consensus as well as one about anchoring your product to customer needs and crafting a better first-mile experience for customers—all very helpful for my aspirations at Adobe.

Writing this book was very meta, since the project had a very messy middle of its own. For a while, I hesitated to share it with anyone. I wasn’t sure I’d be able to get it together. But when I started the research process and shared the outline with others, I became motivated by the widespread resonance. We’re all enduring and optimizing, but we don’t talk enough about it. The middle makes or breaks you, and ending up on the right side of this line depends on how you navigate everything in between.

Pre-order “The Messy Middle” online now for $24.

Portrait by Om Malik, all other images courtesy of Messy Middle / Scott Belsky