Book Summaries

Book Summary -The Messy Middle by Scott Belsky.

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The middle is messy, but it yields the unexpected bounty that makes all the difference.

In The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture, bestselling author of Making Ideas Happen and co-founder of Behance Scott Belsky describes the Messy Middle in every project, the behind the scene roller coaster, the sleepless nights, and also shares strategies for navigating the volatility of new ventures and leading bold creative projects, teams, products and ultimately yourself.

The book is a great read about the messy middle encountered in most projects. Scott shares his experience, lessons learned, anecdotes and insights gained as the co-founder of Behance and later Chief Product Officer at Adobe. 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 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.

The middle is messy, but it yields the unexpected bounty that makes all the difference.

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.


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.

The volatile terrain of the messy middle of a journey is the real story nobody talks about.

The Middle: Enduring and Optimizing

The middle of the journey is all about enduring the valleys and optimizing the peaks. After the joy of conception subsides, your objective is to make every setback less difficult than the one before it—and make every recovery hoist you slightly higher than where you were before.

The middle of the journey is an excruciating struggle. But there are momentary recoveries throughout the journey that keep you going, like the sensation of seeing your team’s DNA in your product, meeting a customer who sincerely thanks you, watching a culture take shape and the people you hired evolve to become entirely different leaders . . . there are so many moments along the way that keep you going. You just need to endure the lows and optimize everything that works.

Commitment to Suffer

In order to fight against the resistance, you’ll need more than passion and empathy. You’ll need to commit to suffering for the years required to push your idea to fruition. Not just a willingness to suffer, but a commitment.

“To create what will be, you must remove yourself from the constant concern for what already is.”

The Storms

Storms have the habit of feeling like their own little worlds, even though they’re just weather patterns and they move on.”

Compartmentalizing is just as hard on a daily basis as it is during a perfect storm. The more responsibility you bear, the more your collective concerns will limit your productivity. To move forward, unbounded by the anxieties and insecurities of the moment, you must apply controls to the energy you spend assuring yourself that all is OK.

Insecurity Work

No intended outcome, does not move the ball forward in any way, and is quick enough that you can do it unconsciously multiple times a day. Insecurity work puts you at ease, but it doesn’t actually get anything done.

The insecurity work we do every day is the equivalent of leading a journey focused only on what is immediately concerning us—beneath our feet—rather than focusing on where we want to be. But if you compartmentalize your ideas and look ahead, and worry less about day-to-day concerns, you’ll eventually look behind yourself to see the line you drew was much straighter. You will arrive much closer to your vision.


“Playing the long game requires moves that don’t map to traditional measures of productivity.”

The human mind is remarkably shortsighted. We’re very good at recognizing cause and effect and projecting the short-term implications of our actions. But we struggle when it comes to chain reactions and laying the groundwork for future opportunities. It takes an entirely different set of measures to engage and endure the long game.

Strategy is nourished by patience.

Companies are as impatient as people, if not more so. If your project is under the gaze of a large organization, often measured by its quarterly results,it is often exceptionally hard to get the necessary time and space for your bold strategy to materialize. Teams must therefore build systems to nourish patience, culturally or structurally, and you must be willing to defend your long game.


If you want to be the industry leader, sometimes you need to take the difficult path. Be wary of the path of least resistance. It may look compelling in the short term but often proves less differentiating and defensible in the long term. Shortcuts tend to be less gratifying over time. The long game is the most difficult one to play and the most bountiful one to win.

Resourcefulness > Resources

As your business grows and your plans become more ambitious, you will want to grow your team. When it comes to scaling, the easiest path most leaders default to is to hire. More heads, more hands, more work done. But the best managers know that growing the team is not always the answer. Too many teams hire when they should be optimizing the people they’ve already got. You can always get more resources, but resourcefulness is a competitive advantage. Resources become depleted. Resourcefulness does not.

“Resources come and go, but resourcefulness is a muscle that kicks in throughout the life cycle of any business. Without it, capital cannot be used efficiently. Focus on building your team’s resourcefulness.”

Change is painful

Change is painful and especially unwelcome when there is nothing dire to fix. But what you must realize—and relay to your team—is that proactive changes that feel premature are far better than reactive changes that feel inflicted upon you.

Your challenge is to develop a healthy rhythm to keep your team in a constant state of motion. If you don’t shake up life every now and then, life will shake it up for you. Too much calm exacerbates any disruption, so building up your and your team’s tolerance for change is a positive long-term strategy for increasing tenacity.

Process is the excretion of misalignment.

Process—the very thing you didn’t need in the early days. Training programs, daily staff meetings, organizational structure diagrams, approval processes: These are the mechanisms we throw at misalignment to ensure that a group of people think and act in tandem. Process is how we force alignment when it doesn’t happen naturally. You schedule meetings, you embed systems for tracking and accountability, and you install more managers.

Present your ideas, don’t promote them

Whether you are sharing an idea with colleagues or pitching an idea to investors, be less polished and more real. A little texture in the form of uncertainty and admission of challenge is helpful for everyone.

The right partners will see your challenges as potential rather than weakness, and your honesty will set the right tone for future collaboration and navigating the ups and downs of the journey together.


Most people’s natural tendency is to please and accommodate others. In the process of creating a product, this tendency often manifests itself as a generalized product vision that accommodates too many kinds of customers a little rather than one particular kind of customer a lot. The more wide open a product vision, the less likely it is to revolutionize one particular use case.

Boulders vs Pebbles

In every project, there are a few boulders and lots of pebbles. The boulders are hard to move up the hill, but they materially impact your project and differentiate you from others. Boulders could be a major new feature, a new architecture for your service, or writing the initial draft copy for your website. By contrast, pebbles are the innumerable little tweaks and changes you could quickly make that are rarely differentiating.


Although you should follow them closely, don’t become defined by your opponents. If you focus more on your competitors than on your own customers and your own unique approach to serving them, you lose your identity. Stay tuned but not governed by what’s going on around you.

Ask for forgiveness, not permission.

Society tends to eventually celebrate what was, at first, shunned. Companies are no different. If you can withstand some tyranny, you’ll be rewarded for it. Oftentimes, the best way to proceed is by charging ahead without too much reliance on the processes developed to maintain the status quo.

Simple is Sticky

The Product Life Cycle

  1. Customers flock to a simple product.
  2. The product adds new features to better serve customers and grow the business.
  3. Product gets complicated.
  4. Customers flock to another simple product.

    Simple is sticky. It is very hard to make a product—or any customer experience—simple. It is even harder to keep it simple. The more obvious and intuitive a product is, the harder it is to optimize it without adding complication.

“The pursuit of a great product requires discipline, endless iteration, and grounding your objectives with your customers’ struggles and psychology.”

Identify what you’re willing to be bad at.

“Productivity and performance are too often conflated. Instead, you need to decide what aspects of your team and product distinguish you most—and what you’re willing to be bad at. Your competitive advantage is a conscious admission and acceptance of your weaknesses as well as a recognition of your strengths; it’s as much about what you focus on as it is about what you choose to let go.

Optimize the first 30 seconds for laziness, vanity, and selfishness.

Within that first mile, the first 30 seconds of the sprint determine if people will keep running the whole distance. During these first 30 seconds of every new experience, people are lazy, vain, and selfish. This is not intended as a cynical jab at humanity. It’s an essential insight for building great products and experiences both online and off-. It is a humbling realization that everyone you meet—and everyone who visits your website or uses your products—has an entirely different mind-set before they’re ready to make the effort to care.

The lazy-vain-selfish principle

This lazy-vain-selfish principle is true for all kinds of product experiences, online and offline. In the first 30 seconds, your visitors are lazy in the sense that they have no extra time to invest in something they don’t know. They are vain in that they want to look good from the get-go when they engage with your product or service. And they’re selfish in that despite the big-picture potential and purpose of what your product stands for, they want to know how it will immediately benefit them.

“The consequence of starting a project out of sheer passion is making decisions without considering those you’re serving. Empathy for those suffering the problem must come before your passion for the solution.”

Build your narrative before your product.

Every creation needs a narrative. The narrative is the story of what you’re building in the context of why it matters. What inspired the idea? Why does it need to exist? What makes it relevant? How does it make the future better?

“The narrative is how early team members and investors make sense of what you’re building. The narrative helps you and your team take risks.”

Don’t let artificial measures abstract your goals. When you’re optimizing for a particular measure, reiterate for yourself and your team the real impact you desire to make, not just the metric you’re measuring.


The beginning stages of a business are more art than science. You must try to solve problems with new ideas that will feel strange and are in no way economical. You must run manual experiments, spend endless amounts of your own time with customers, and tinker until you find something special.

Reschedule your agenda

One reason we hesitate to audit how we spend our time is because we can’t bear the truth. Day to day, amid the gravitational force of operations and the desire to please others and immediately gratify ourselves, we spend time in ways we are likely to regret by the end of the week. Reconsidering your schedule can be a rude awakening, but it’s the only way to plan better the next week.

All the Best in your quest to get Better. Don’t Settle: Live with Passion.

Lifelong Learner | Entrepreneur | Digital Strategist at Reputiva LLC | Marathoner | Bibliophile |

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