The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture - Hardcover

Scott Belsky is an entrepreneur, author, and investor. He is currently Chief Product Officer at Adobe, serves as a board member to several early stage companies, and is a Venture Partner at Benchmark, a leading venture capital firm based in San Francisco. He was previously the founder and CEO of Behance, a leading online platform to showcase and discover creative work. He is also the creator of 99U, Behance's think tank and annual conference devoted to execution in the creative world. Belsky is the author of Making Ideas Happen and coauthor of the 99U book series.

The Messy Middle
The journey of creating something from nothing is a volatile one. While we love talking about starts and finishes, the middle miles are more important, seldom discussed, and wildly misunderstood.
You survive the middle by enduring the valleys, and you thrive by optimizing the peaks. You will find your way only by reconciling what you learn from others with what you discover on your own. You'll get lost. At times, you'll lose hope. But if you stay curious and self-aware, your intuition and conviction will be your compass.
While difficult to withstand and tempting to rush, the middle contains all the discoveries that build your capacity. The middle is messy, but it yields the unexpected bounty that makes all the difference.
Introduction
When I set off to write a book about the middle of bold projects and entrepreneurial journeys, you might expect that I started with my own. Having endured five years "bootstrapping" my own business and facing my fair share of challenges as an entrepreneur, this was my chance to share everything I learned. But I couldn't remember anything. It wasn't memory loss-it was just all a big blur.
So I turned to the common source of answers to random ponderings these days: my phone. I flicked through years of random photos taken, back to the middle years of building Behance, my first company, hoping to jog my memory. I founded Behance in August 2006 and signed the documents to be acquired by Adobe in December 2012, so I made my way to 2009 on my phone, the absolute middle of my middle. Thousands of thumbnail images showed screenshots taken on my phone of website errors, bad copy, social media mentions of us and competitors, and various product ideas and changes. These screenshots spanned years and, in some months, outnumbered my photos. The sheer volume of them reminded me of falling asleep every night scrutinizing our product, anxiously looking for something but never knowing exactly what.
I also found another type of screenshot-customer messages and feedback. I remember capturing these insights to share with my team, but also I needed them. I wanted to hold on to and extend some early semblance of reward and significance at a time when nobody seemed to care.
Scrolling a little farther, I saw a reunion with college friends and then a special moment from my honeymoon during which my wife and I encountered elephants in Thailand. I was surprised to see how strained my smile looked. The memory rushed back, and I recalled the tension of wanting to relish this once-in-a-lifetime moment while realizing I had a team at home running on fumes and I was just a few months away from missing payroll. Being away from the team felt utterly irresponsible, and this burden followed me everywhere. Scrolling farther now, I stumbled on a team event at a restaurant kitchen where we all cooked a meal together-we couldn't afford it, but I knew the only thing that mattered was keeping the team together. As I scrolled through our team pics, I was struck by how close and dedicated we became despite the circumstances and our differences. When the odds are against you, without revenue or margin to protect you, teams and relationships are different. It's not work; it's survival and self-discovery.
These photos reminded me just how exhausted and uncertain I had been-fueled by my relentless determination to make something awesome. Perhaps, in such periods of struggle, our preoccupations and emotions take up so much mind share that the events themselves become a blur? Or perhaps we don't remember the middle because we don't want to?
YouÕre probably reading this book because youÕre about to embark on a massive journey-or are already trekking through the middle of one. Whether youÕre a writer, start-up entrepreneur, big-company innovator, or an artist, you share many of the same hopes and fears.
You might be working within a multinational company, a small nonprofit, a new creative studio, or on your own. No matter what it is you're trying to create or transform, the myth of a successful journey is that it starts with the excitement of 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. The notion of having a bold idea and making consistent incremental progress is impossible. Those seeking a linear journey with less instability can still be successful, but they often struggle to create anything new.
In reality, the middle is extraordinarily volatile-a continual sequence of ups and downs, expansions and contractions. Once the honeymoon period of starting a new journey dissipates, reality hits you. Hard. You feel lost and then you find a new direction; you make progress and then you stumble.
Every advance reveals a new shortcoming. Major upsets give rise to new realizations that lead to breakthroughs in progress. At best, you move two steps forward, one step back-at worst, you realize you've been walking the wrong path entirely for months. This is what that journey actually looks like.
I've come to call the journey of creation one of "relative joy." Your job is to endure the lows and optimize the highs in order to achieve a positive slope within the jaggedness of real life-where, on average, every low is less low than the one before it, and every subsequent high is a little higher. In the moment, you can see only the uphill or downhill in front of your nose, but over time, you come to recognize that there is a median that keeps you moving forward in the right direction.
The volatility of this tug-of-war is hard to stomach. You must pay less attention to the day-to-day incremental advances and more on achieving an overall positive slope. And that's entirely determined by how you navigate the messy middle.
It's not about the start and finish, it's about the journey in-between.
There are just a handful of thrilling and treacherous moments as an entrepreneur. Most of them happen at the start or finish of the journey (or one of the restarts or false finishes along the way). They're all we talk about, but they reveal very little about the journey itself.
We love talking about the starts.
The start is romantic. We love talking about it because it is inspiring without the complication of substance and strife. Conception is an adrenaline rush fueled by grandiose visions paired with naivety. You're inspired by a destination and have no idea how you'll get there. The solution in your mind's eye is rose colored. You don't yet know how the cards are stacked against you.
In this case, ignorance is not only bliss but also enables you to dream up solutions at the edge of reason. You're untethered.
We also love talking about finishes.
We imagine the rush, the exhaustion, and the pride of finally making it. This is what we dream of throughout the struggle of creating, isn't it? How relieved we'll be when the workout is finally over. A "finish" can happen at different parts of a journey: Launching a product. Publishing a book. Raising money. Reaching a key milestone. Being acquired. Shutting down. Going public. Closing the quarter. The press likes to write these headlines and we like to read them. But the superlatives obscure the fact that they are simply abstract mile markers. We learn very little from these moments despite their gravity.
One of the strangest parts of being an entrepreneur is being part of a community obsessed with starts and finishes. Investors tend to be interested only in starts (when they're able to invest) and finishes (when they get a return). Similarly, stories tend to be written only about public inflections. Even between entrepreneurs or big company CEOs, what is intended as a network of support becomes an echo chamber. Nobody wants to talk about their self-doubts and the insecurities that fuel them. Every business is "going great" until it fails. The bumps along the road are endured in isolation. The majority of the journey itself is unchronicled because it is unappealing and too revealing.
As a young entrepreneur, the focus on starts and finishes always bothered me. As a manager, I sought to hire people who were seeking a journey rather than a particular outcome. The more immersed I became in the start-up world, the more I wanted to operate without sensationalism. When the journey feels gritty and real, your potential becomes more tangible.
Then I went to work as an investor with dozens of entrepreneurs at all different stages of company building, where it became clear how destructive the spotlight on starts and finishes really is. As we celebrate the success of others, we're liable to draw lessons from a drastically edited story that excludes the middle. What's in the middle? Nothing headline-worthy yet everything important. Your war with self-doubt, a roller coaster of incremental successes and failures, bouts of the mundane, and sheer anonymity.
The middle is seldom recounted and all blends together in a blur of exhaustion. We're left with shallow versions of the truth, edited for egos and sound bites. Success is misattributed to the moments we wish to remember rather than those we choose to forget. Worst of all, when everyone else around us perpetuates the myth of a straightforward progression from start to finish, we come to expect that our journey is meant to look the same. We're left with the misconception that a successful journey is logical. But it never is. Don't let others' stories pervert your understanding of the journey. Emulating someone else's story is following a playbook without all the pages in the middle.
We don't talk about the messy middle because we're not proud of the turbulence of our own making and the actions we took out of despair. Sharing our challenges shakes our egos. And finally, the middle of a journey doesn't make for good headlines.
The middle isn't pretty, but it is illuminating and full of essential realizations to finish whatever it is you set out to start. It's time we start talking about it.
The journey to create a product or service is reflected in the outcome in ways you may not even expect. It matters, tremendously.
Consider a product you use in your everyday life-is it simple or complicated? Too many features or just the functionality you need? Is it enjoyable or is it a chore? The experience of using someone else's creation comes from the path the creator took to make it. It is not the plastic, metal, or pixels that make a successful product or service. Rather, it is the thoughtfulness and tough choices made by the makers-the team dynamic, the perseverance, the organizational design (and redesigns), the constraints, the battles fought, and the values that governed the path taken.
This book is about mining every insight from the volatility and the depths of despair to improve your team, product, and self. This book is also intended to help you survive the creative process when you lack any sense of traction, recognition, or significance.
A few years ago I set out to understand what founders and other leaders of bold new projects do throughout their journeys that they don't talk about. I sought to chronicle the pain-management techniques, the tactics for optimizing, and the instincts that not only help their teams survive the journey from start to finish but also thrive.
This book is the culmination of seven years' worth of scribbled notes, mobile memos captured on the run, and one-liners committed to memory. It covers insights witnessed and realized in boardrooms, on midnight calls with teams solving a crisis, during sleepless nights fretting difficult decisions, in brainstorming sessions with entrepreneurs, and often in the reflective haze of long-haul plane flights. The perspectives in this book are derived from experiences with many different people and teams, from entrepreneurs to writers from small agencies and start-ups to billion-dollar companies transforming their industries. When a tactic or tenet fascinated me, I'd capture it and share it with others for feedback or better ideas, and the ones that made the cut are in this book. The following pages cover insights garnered from interviews, from my own struggles and relative triumphs, and from working alongside the many entrepreneurs I have advised over the years. While the insights are organized into sections, the book is intended to be more of a buffet than a plated six-course meal. I encourage you to navigate to whatever parts of the journey resonate most at the moment, using the table of contents.
As they have for me, I hope these insights bolster your confidence, fortify your plans, and make you question your assumptions. As you seek to make an impact in what matters most to you, this book will help illuminate your path from start to finish.
The stories fall short
In 2006, I founded Behance, a company devoted to connecting and empowering creative professionals. The problem my team and I set out to solve was a simple one: the creative world was one of the most disorganized communities on the planets-there was no way to track a photographer's work, find out who designed a particular product, or track down the motion graphics artist or creative director behind a particular campaign. We wanted to help organize creative people, teams, and the community at large.
The problem was simple, but the solution was anything but. After several fits and starts, lessons learned the hard way, and five years of bootstrapping (building a business that relied on revenue rather than venture capital), we built a multifaceted business. The Behance Network grew to enable more than twelve million creative professionals to showcase their work, connect and collaborate with one another, and get jobs. Over the years, Behance became the leading online platform for creative careers and provided me with the opportunity to grow a large design and technology team. We then expanded Behance by offering content and events for the creative community, online and off, by creating a think tank, website, and annual conference called 99U in 2007. Influenced by the famous Thomas Edison quote, "Genius is 1 percent inspiration and 99 percent perspiration," 99U is dedicated to the execution of ideas rather than the ideas themselves.
In late 2012, Behance was acquired by Adobe, one of the world's largest technology companies responsible for products like Photoshop, Illustrator, and the PDF (Portable Document Format), among many other products for the creative world. It was an incredible and unexpected outcome for the entire team-certainly not the one I imagined for myself when I started designing paper products and running seminars for freelance designers to pay the bills. I joined Adobe as a vice president of products, leading an overhaul of the company's mobile and cloud asset strategies. The three years that followed were enlightening in ways I didn't expect. I had to wind down old products, help launch new ones, and lead teams through a great deal of uncertainty and change. I left this role with an appreciation for the frictions in a big company-how they hurt, how they help, and how to keep the ship moving forward, inch by inch.