The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture. By Scott Belsky

This is the story of author Belsky’s company: Behance.

“We bootstrapped the business for five years before one of our products, the Behance Network, eventually started to gain traction. This allowed us to raise some funding from a top-tier venture capital firm, which gave us the chance to build a dream team that turned our product into a ubiquitous global creative platform. When Adobe turned Photoshop and the rest of their software into a subscription service, they needed a network like ours. The timing and opportunity was great, so Adobe acquired us. It was a great outcome for the entire team, and we happily continued working together for years afterward.”

Pithy success stories like this one are missing the really important part: the messy middle. In this messy middle lie the dirty little secrets that entrepreneurs don’t admit. The line between their success and failure is wafer thin. They are filled with self-doubt and insecurities. The bumps along the road are endured in isolation. In the middle is a roller coaster of successes and failures.

If you have ever started a business or are starting one, the description of the messy middle will resonate.

Belsky’s focus is on what is in the middle mainly because there is so little written about this critical period. It is a paradox because nothing headline-worthy happens in the middle, yet everything important to your success or failure does. “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.” Theirs didn’t, and neither will yours.

This book is not a literary equivalent of a ‘pity party’, rather it is a collection of illuminating and essential realizations that will help you finish whatever it is you set out to start.

The content of ‘The Messy Middle’ is a collection of ideas derived from over seven years of gathering relevant experiences and insights, from many different people and teams. Included were entrepreneurs of start-ups, entrepreneurs of billion-dollar companies that have transformed their industries, as well as thinkers and investors. It is organized around two themes – ‘endurance’ and ‘optimization’.

These two complementary forces “will help you conquer the middle of any bold project,” Belsky promises. And I believe him. They will bolster your confidence and strengthen your commitment to your plans.

“The middle makes and breaks you – and ending up on the right side of this line depends on how you manage everything in between,” says Belsky. “These gems from the journey make you more capable for whatever comes next, and in my own life, they have made all the difference.”

The messy middle of this journey is all about “enduring the valleys and optimizing the peaks.” This is important because your journey to success and wealth, always starts with excitement and expectation. The reason is your blissful obliviousness of what you don’t know and of the painful obstacles ahead. Only by embracing the middle will you find your way through, and this is where Belsky’s book adds value.

“Realistically, you will need to commit to suffering for years to push your idea to fruition. It usually takes at least two years before you have any reasonable traction to show that your business might be working, then another few years of driving growth to create something that looks like a moat. Then you can afford to breathe. A little,” investor Doug Clinton is quoted as saying.

After much effort, it is not uncommon to realize that you are headed nowhere and need to change everything. This means losing years of work and comes with the soul-crushing feeling of having to start all over again.

This was the experience of YouTube, which was originally a dating site that never took off. Ditto for Twitter which started as a podcasting network, and similarly never took off.

Leaders need to be the stewards of perspective. The messy middle is like a long road trip without windows. There is often no sense of progress or landmarks. As a leader, you need to call out and describe the landmarks that you pass along the way. It is for you to make the past relevant to the future, even when it is dry and irrelevant. Your job is to be an energy-giver rather than a part of the energy-takers.

Every journey has heavy moments: Firing employees. Solving a PR crisis. Weathering legal battles. Each time you struggle to push through the muck, know you cannot avoid conflict or circumvent disappointing others. It must be done, and it must be done by you. The author says he steels himself by saying “Scott, do your ****** job!” At your most difficult and trying moments, one often has to push oneself to do the job – it is your job not anyone else’s.

The leaders Belsky seems to admire most have invested a great deal of time in understanding their own psychology and unpacking their past.

Self-awareness means understanding your own feelings well enough to recognize what bothers you. Scott reports that when he is taken advantage of, he would opt to right that wrong even if the economic cost of doing so exceeds the economic impact of letting it go. Being conscious of your triggers helps you take your finger off that trigger.

Self-awareness is also about preserving sound judgment and keeping relatable and realistic.

The more aware you are of yourself and your surroundings, the more data you have to inform your decisions, the more competitive you will be. At most points in the ‘middle’ you are probably many decisions away from success. But always one decision away from failure.

When times are truly rough, we are often told that you should ‘stick with it’, but when should you quit?

Ask yourself this question: Knowing all that I know now, would I pursue the project all over again? Would I invest the money and energy all over again to get as far as I’ve come in solving this problem? If the answer is ‘yes!’, don’t quit. Simply accept that life is a marathon, not a sprint

Feeling impatient with progress and deflated by process is just the way it is, so long as you still have conviction.

If, however, the answer to the question above is: “Hell, no! If I could go back to the day before I got into this mess, I would head in a totally different direction,” then ask yourself why you are still trying.

The book is a collection of quality lessons each short enough to be read in 5-10 minutes.

Readability       Light –+– Serious

Insights               High -+— Low

Practical              High -+— Low


*Ian Mann of Gateways consults internationally on strategy and implementation and is the author of ‘Strategy that Works’ and ‘The Executive Update.’ Views expressed are his own.