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Lessons from Scott Belsky’s Book “The Messy Middle”

Scott Belsky is Adobe’s Chief Product Officer and Executive Vice President, Creative Cloud. He co-founded Behance in 2006 and served as CEO until it was acquired by Adobe in 2012. He is the author of Making Ideas Happen and his new book is The Messy Middle.

The messy

  1. “We love talking about starts and finishes, even though the middle stretch is the most important and often the most ignored and misunderstood. We don’t talk about the middle because we’re not proud of the turbulence of our own making and the actions we took out of despair.” Creating something from nothing is a volatile journey. The first mile births a new idea into existence, and the final mile is all about letting go.”No extraordinary journey is linear. In reality, the middle is extraordinarily volatile — a continuous sequence of ups and downs, flush with uncertainty and struggle.”

Anyone who has been though a startup experience will recognize what Belsky is depicting in the graphic below. When I first saw this depiction it immediately reminded me of the way Phil Knight described the ups and downs of Nike’s business in his fantastic book Shoe Dog. I also thought of many other businesses like OpenTable which encountered significant ups and downs along the way to eventual success that required both endurance and optimization.

real j

I saw this process first hand when I spent more than five years of my life working at a startup. I have also seen the same patterns as an investor. What Belsky writes about is just as applicable to working for one the largest business in the world. Might there be a dentist somewhere who started a dental practice and the trajectory was mostly up and to the right without any need for endurance and optimization? Probably not. But even if there is a dentist who experienced a smooth and steady upward slope they are inevitably not creating anything new. In other words, the more a new business is creating new value, the more what Belsky describes in The Messy Middle is true.

All businesses operate in an environment that is almost entirely driven by uncertainty and ignorance. Creating a business, a new product or improving an existing product involve processes that are almost never merely risky like playing games at a casino. Business inevitably involves a never-ending series of idiosyncratic decisions for which there are sometimes best practices. This means that making decisions based solely on statistical factors and recipes is impossible. This is why business is best described as an art that is often informed by science.

  1. “The book is broken down into three sections of insights (Endure, Optimize, & The Final Mile).”“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.”

Belsky wrote the introduction to my seventh book A Dozen Lessons for Entrepreneurs. When we communicated about the progress of my book I sensed that he was engaged in an intense effort to get his book “just right” from a design standpoint. Belsky’s struggle to find the right structure was part of the “Messy Middle” of his book writing journey. His elegant solution for The Messy Middle was create a four-part structure for the book, within which are discrete insights, best practices and lessons that apply to the value creation process. I really like the way that this approach allows the book to be read in a nonlinear manner. Belsky writes: “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 part of the journey resonate most with you at the moment, using the table of contents.” Other authors who have adopted a modular book structure include Elad Gil with High Growth Handbook and myself with my blog and seventh book. Adopting this a nonlinear structure in writing a nonfiction book is often more consistent with the way people read today. Many readers want just in time advice that doesn’t necessarily require long continuous reading sessions. This structure enables a “long read” to be the one method for getting value from the book and yet reading it in a linear way it is not required to capture value from the material. The Messy Middle, High Growth Handbook and A Dozen Lessons for Entrepreneurs are designed to be usable as reference books. People consume information differently today and book and web design must take this into account. Readers too must use tools in new ways. For example, if you want to know what I think about a topic, simply put the keywords “25IQ” and the topic that interest you (e.g., “wholesale transfer pricing”) into a search engine and it will search over a million words on my blog. You can do the same thing if you purchase an e-book version of The Messy Middle and use the search function.

This graphic below is a wonderful example of Belsky as a designer. The “Start” phase of the journey kicks off with a blast of goodness and favorable publicity and then the  reality hits in that this startup is going to be hard to make successful (red shading). Endurance (blue gray) depicts when negative things happen as an inevitable part of the process and Optimization (turquoise) is when the line depicting the process moves up when something positive is happening. The Finish phase of the journey (dark blue) completes the book. Each stage of the process calls for different approaches and solutions, some of which will be identified below. Within each of the four categories Belsky has identified so many different solutions that in this blog post I have been forced to pick just a few insights that resonate with me most and best enable me to embellish a bit on that insight. Picking just ten more insights from The Messy Middle to fit within my usual quota of twelve was really hard since there are so many in the book.

four color


  1. “The start is pure joy because you’re unaware of what you don’t know and the painful obstacles ahead…. after the excitement of a new idea dissipates, reality sets in.” “This is where the journey truly begins.” 

The beginning moments of starting something seem glamorous. Early team members may find themselves featured in articles in the press and on blogs. This is true both for startups but also for work done inside a big company on a new product. The reality of the zone which Belsky depicts in red in the graphic just above is that the team quickly realizes that creating a “new new” thing is hard. Some people have called this “trough of sorrow” or the “trough of despair,” but I believe a better term would be the “trough of reality.”  If someone is feeling sorrow or despair during this “start” phase, they are not suited for work like this. It is perfectly normal to think: “holy shit” during this process, but then to get to work creating value. It seems like I was born believing that there is no problem that more work by me can’t solve. This can create problems related to overconfidence but it does leave me free and clear of most sorrow and despair related concerns. People hate losses and so there is an arbitrage for someone like a  founder who can persevere though losing investments. People lose track of how much failure there is, but that is survivor bias, which is another topic I have written about before.    


  1. “[Endurance] is about developing a source of renewal energy and tolerance that is not innate.” “Our additions to short-term validation that trying to defy it is hopeless…. You must hack your reward system [with]… manufactured optimism.” “Celebrate anything you can, from again a new customer to solving a particularly vexing problem.” “We crave certainty but must learn to function without it.” “Accept the burden of processing uncertainty.” 

Every effective team I have ever observed has learned to manufacture milestones that create positive short-term reinforcement for the team along the way. The human species has lived as long as we do now for only a short period in its history. Thomas Hobbes wrote once that the life of a human for almost all of history involved living in “continual fear, and danger of violent death” and that it was “solitary, poor, nasty, brutish, and short.” It is no wonder that humans love immediate or at least near-term gratification. The instances in which humans make mistakes due to their drive for short term optimization of present moment benefits is endless. Rather than fighting these instincts Belsky believes the most effective teams create milestones that enable people to celebrate short term wins. The best milestones represent the retirement of different types of risks. Josh Wolfe of Lux Capital believes:

“The greatest entrepreneurs are risk killers. They think about killing failure paths. They also understand that risk and value can change form. When risk has been killed then value has been created and a subsequent investor should pay a higher price for a percentage ownership interest in a business.”

I heard Josh make this just point about creating team milestones in a board meeting we attended yesterday. If you create your milestones around killing or reducing technical, market, financial, people, regulatory and other risks you get a double benefit. The team is motivated in the short terms and you are killing the right risks. Sonali de Rycker of Accel “We advise breaking down the [process of building a business] into milestones. Don’t just look at it as a ten-year goal. …Getting to milestones around value creation will allow you to fundraise.” 

  1. “Leave every conversation with energy.”

People who are most effective on teams and the most effective teams separate discussion from energy and commitment. Amazon is well-known to have a culture that has adopted what they call “disagree and commit.” Jeff Bezos describes this approach as follows:

“This phrase will save a lot of time. If you have conviction on a particular direction even though there’s no consensus, it’s helpful to say, “Look, I know we disagree on this but will you gamble with me on it? Disagree and commit?” By the time you’re at this point, no one can know the answer for sure, and you’ll probably get a quick yes. I disagree and commit all the time. We recently greenlit a particular Amazon Studios original. I told the team my view: debatable whether it would be interesting enough, complicated to produce, the business terms aren’t that good, and we have lots of other opportunities. They had a completely different opinion and wanted to go ahead. I wrote back right away with “I disagree and commit and hope it becomes the most watched thing we’ve ever made.” Consider how much slower this decision cycle would have been if the team had actually had to convince me rather than simply get my commitment.”

Even if a meeting is acrimonious, people should strive to leave that meeting with energy. In other words, Belsky is saying that words “with energy” should be added to the phrase. Disagree and commit with energy. 


  1. “Optimize the hell out of everything that works.” “When something actually works… you need to tenaciously evaluate it. Why did that work? How do you do it again? How do you spread it to your team?” It’s less about fixing what is broken and more about improving what works.” “The best teams …are never ever satisfied with the current state of their product.” “A/B testing is not just for digital buttons. You can use it in all areas of your life, from A/B testing your daily habits to how you team functions.” 

The rise of modern data science has enabled individuals and companies to put the optimization process that Belsky describes on steroids. There has never been a better time to harness processes that use the scientific method to improve people, teams and processes. Many of the most successful new products introduced over the last decade are at their core about bringing the scientific method to some area of life or business that formerly relied on guessing. Even if something is seemingly “going great” it is wise to keep trying to optimize to find improvements. This is how the most effective businesses maintain their competitive edge. Part of the reason why cities last longer than businesses is that residents of cities are continually experimenting with new solutions and those solutions over time enable the city adapt to changing conditions. Businesses that are more top down operated than a city may not adapt quickly enough to change to survive. I intend to write more about this topic soon.    

  1. “Resourcefulness > Resources.” “In the startup world, resources are like carbs. Resourcefulness is like muscle. When you develop it, it actually stays with you and impacts everything you do going forward.” “Resourcefulness also makes you more creative. Any good designer will tell you that creative constraints help the idea generation process. With fewer resources and options you become more creative with what you have.”

Businesses die more often from indigestion than starvation. Finding ways to grow without new resources is often what creates new value value. If money is used as a substitute for creativity and a sound organizational culture, the business is weaker when challenged by a competitor which has found way to scale without just spending more money to “fix things.” Belsky said once in an interview:  “My former COO at Behance, Will Allen, used to always push teams to “refactor, refactor, then hire” when they came asking for more headcount and resources. Small teams can run circles around big teams faster and without as much tripping.” One significant problem that startups have is that people sometimes are hired from very large companies which have lots of resources and set processes. The arrival of people from a large business can be the kiss of death for a startup or small business since speed is a competitive weapon and cash resources are more limited. This is not always true about former big company employees but it is something that must be watched carefully.  A startup is not just a small version of a large business. What causes success or failure in one does not necessarily apply to the other.

  1. “Success fails to scale when we fail to focus.” “We navigate most of our lives and businesses with cursory knowledge rather than local knowledge. Only when we stick with and deeply explore one area, whether by choice or accident, do we learn better routes.” “Great products don’t stay simple by not evolving; they stay simple by continually improving their core value while removing features and pairing back aspects that aren’t central to the core. More once subtraction for every addition.”

Creating and staying within a circle of competence is a life and business superpower. It is amazing how much advantage a person can get by consistently not being stupid. Focus helps a business stay with its circle of competence and hone its competitive advantage. If a business crates new paths to failure the probability of failure rises. A business having a focused objective doesn’t mean that the goals should be small but rather that the level of risk the business takes on is optimal given resources available to that business and the competitive environment. Warren Buffett frames his approach to this set of decisions in terms of expected value:

“Take the probability of loss times the amount of possible loss from the probability of gain times the amount of possible gain. That is what we’re trying to do. It’s imperfect, but that’s what it’s all about. …coming up with likely outcomes and appropriate probabilities is not an easy task…the discipline of the process compels [you] to think through how various changes in expectations for value triggers—sales, costs, and investments—affect shareholder value, as well as the likelihood of various outcomes.”

In addition to what someone might call “business objective bloat” there is a different but related point that Belsky writes about in his book: customers want simple solutions and teams that have too many resources often reduce or even kill the value of the product by creating too much complexity by introducing new “features.” So-called “feature bloat” can be as deadly as the bite of a rattlesnake. Belsky once said in a New York Times interview:

“Indeed, new products win over users with their simplicity and add complexity over time to appeal to power users (and build a business), and then the process repeats itself. Teams that defy this practice continually simplify their products over time. For example, some teams try to remove or simplify features at the same pace as adding new features. Other teams attempt a reboot at some point in their product’s life cycle where they design a new version with a vastly simpler foundation. The first step is acknowledging when you’re catering too much to power users and failing to engage the latest cohort of new customers.”

Accomplishing what Belsky talks about just above in the interview is what makes great designers and “product people.” Some of the most talented people making the right choices about what to add and what to remove have savant-like skills in accomplishing this objective. Some of it seems like it is nature but the best designers I know what hard at nurturing their skills. Great designers are a scarce commodity and if your business has them, you should work hard to keep them.

  1. “Culture is created by the stories you tell.” 

Humans are storytelling creatures. A year never goes by that I don’t increase my belief in the power of stories. The best teachers know how to tell stories and the best founders and managers know that as an organization grows telling stories is often the best way to create a propagate culture. There some good books about how to write a story you can read and learn from including The Hero with a Thousand Faces (The Collected Works of Joseph Campbell). One key point to about stories is that it is best to show people what to do rather than telling people what they should do something.

What is the culture the stories must propagate in a business or other organization? Charlie Munger believes: “One solution fits all is not the way to go. All these cultures are different. The right culture for the Mayo Clinic is different from the right culture at a Hollywood movie studio. You can’t run all these places with a cookie-cutter solution.” The culture of a business is more than the sum of its parts. The totality of the vision, values, norms, systems, symbols, language, assumptions, beliefs, and habits of a business is what creates the culture of a business. Munger and Buffett are huge proponents of creating a strong organizational culture: “Our final advantage is the hard-to-duplicate culture that permeates Berkshire. And in businesses, culture counts.…Cultures self-propagate.” Bureaucratic procedures beget more bureaucracy whereas culture enables speed which is a critical competitive advantage in a changing world.

  1. “The more credit you need, the less influence you will have.” “A new type of professional has emerged in the twenty first century. You’ll find them working solo, in small teams or within large companies. “These ‘free radicals’ are the unbound energy sources of energy in the professional world.” 

Another superpower in life for getting things done is to let other people take credit for something. Making someone believe that X was their idea is the best way to get X adopted. This is why some of the best coaches are often so skilled in asking the right questions instead of always giving directives. Many businesses foster roles for a few of the free radicals that Belsky is talking about just above. These people naturally press an organization to think about new ideas and to try new approaches. They are insatiably curious and willing to help out wherever is needed. 

  1. “Foster Apprenticeship.” “A certain percentage of your energy should be devoted to mentoring others. Apprenticeships are mutually beneficial, as you’ll prepare emerging leaders on your team to take more senior roles while developing a culture of constant learning and teaching.” 

Anyone who knows me knows I am interested in finding ways to increase the ability of educational systems to prepare people for life and success in business. There is no better way to learn than to be an apprentice to someone who is skillful at something. I have been lucky enough to have been an apprentice to many very successful people. This experience naturally makes me think about this questions a lot: How can scalable digital systems provide something that approaches or supplements this same luck that I experienced as an apprentice? Relying on traditional analog systems (being an apprentice to real people) that I benefited from can’t economically scale to effectively serve billions of people on the planet. The value and importance of person-to-person apprenticeship will never completely go away, but how can it be made more effective using digital tools? Books are magical, but people are reading less rather than more. People are trying to solve this reading problem in clever ways. For example, Amazon has a created period that starts each meeting during which people must read a document about the meeting n a prescribed format. In other words, employees of Amazon are forced to read the material and the writer is forced to keep the writing tight and short.


  1. “Finishes come in all shapes and sizes and are never as certain (or desirable) as they seem. In fact, finishing should never be the end goal, and you shouldn’t aspire to ever feel truly ‘finished’; life loses value when the challenge dissipates.”

I believe the real “winners” in life are the people who accumulate the best stories based on real life experiences. This collection of great stories is an indicator that you never stop learning, creating and sharing. Belsky is saying that a finish is just a way station on the path to something else.

There are many other insights in The Messy Middle I wanted to write about that I have not mentioned in this blog post, but you can now buy and read the book yourself.  One objective when you write a review is to give the reader a taste of the book but not give so much way that their is less incentive to buy the book. I can assure you that there are many topics in the book I did not cover and many important insights and questions for you to think about. As an aside, in preparing to write these blog posts I nearly always read and listen to podcasts that feature people who I write about. Scott was a guest on a recent podcast with Tim Ferris in which he is asked what thinkers he likes to read he mentioned Ben Thompson of Stratechery and then me. Ferris responded by repeating my name “Tren Griffin” in the manner of “who the heck is that?” It was quite a funny moment for me actually and it makes for a good story.

In his introduction to my latest book A Dozen Lessons for Entrepreneurs Belsky wrote:

You can ask for tips, but you can’t adopt someone else’s approach in aggregate. More than anything else, the journey of building a company is really the construction of your own one-of-a-kind playbook to build a team, culture, and product.

Belsky’s words do a marvelous job of capturing an important part of why I write in the first place. I believe that while there are best practices entrepreneurs and investors should be aware of there is no single recipe they should follow. By better understanding the views and experiences of a wide range of successful the reader can better discern which of many possible paths will lead to success. In other words, entrepreneurs and investors should learn from past successes, but also be prepared to break new ground.

P.s., This graphic below not only describes Belsky’s “sweet spot as an investor,” but is an example of how he uses design to convey ideas and create value and the idea of circle of competence. Great design is a wonderful thing, which is something I get to experience most every day.  The Messy Middle challenges readers to think about design in new ways. How should a book be designed? How should my investment thesis be designed? How should my business be designed?



End Notes: 

Scott Belsky’s Official Site:  http://www.scottbelsky.com/

Publishers Note for the book: https://www.penguinrandomhouse.com/books/557330/the-messy-middle-by-scott-belsky/9780735218079/

Medium Post by Belsky: https://medium.com/positiveslope/navigating-the-messy-middle-7ca6fff11966

Scott Belsky’s blog:  https://medium.com/positiveslope

The Messy Middle post: https://medium.com/positiveslope/crafting-product-in-the-messy-middle-efed809a3f12

Podcasts and videos:




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