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The Messy Middle Tackles the Hard Work on the Way to a Big Idea





The Messy Middle Tackles the Hard Work on the Way to a Big Idea

Experts have a lot to say about starting a business, and even about finding success. But what about advice for how to manage the critical intermediate challenges that certainly appear when an organization is growing?

One author that tackles those challenges is Scott Belsky through his latest book The Messy Middle: Finding Your Way Through The Hardest and Most Crucial Part of Any Bold Venture.   Belsky is a veteran entrepreneur, having launched and sold ventures such as Behance, the world’s leading creative network, and 99U, a productivity conference and think tank.  He is currently the Chief Product Officer at Adobe.

Touted as “the opposite of a success memoir”, The Messy Middle delves into core truths Belsky learned from his entrepreneurial ventures that can help aspiring teams adjust their business models rather than scratch their heads in wonderment.

What Is The Messy Middle About?

Belsky wrote the book to address topics that he found fellow entrepreneurs seldom discuss.  No one talked about the bumps in the road — just how something was great until it failed.

The book is partitioned into three sections: Endure, Optimize, and Final Mile. Each is meant to expose the core influences on entrepreneurial struggles at each part of the journey.   Optimize is the largest section, containing segments that complement the varying aspects of a growing enterprise, from team formation and leadership to product development decisions and communication among the team.  I like how that decision of section size mirrors Belsky’s theme of a grand middle.

What I Liked about The Messy Middle 

I like the ambition Belsky brings to the subject material.  There are 416 pages that speak to just about anybody who is on the entrepreneurial journey, but it never feels as if Belsky is trying too hard to justify an idea.  Moreover, none of the ideas are stale, a refreshing feat for a book of this length.



Segment titles are very direct, such as “To Be Done Is To Die” — but Belsky makes sure each foray into intriguing explicitness is supported with specific advise or insight. When he writes about achieving leadership influence while avoiding narcissism, he delivers it with exquisite phrasing.  The segment titled  “The More Credit You Need, The Less Influence You Have” is wonderfully meme-worthy. Belsky writes to expand that clever title with superb clarity:

“It’s only natural to want short-term affirmation, and you’re liable to over attribute success to yourself and failures to others. But by doing the opposite, you’ll feed your team’s potential rather than assuage your own insecurities,” he writes.

A few ideas speak to solopreneurs, the introverts, and those laboring under imposter syndrome’s spell.  In the segment  “Take Note of Your Insecurity Work” Belsky helps the reader identify and organize tasks that may feel good but accomplishes nothing.

“When you’re anxious about your business, there is no easier quick-relief antidote than checking things,” he writes. “The problem is that you could spend all day checking things and fail to do anything to change things….When you spend 30 minutes going down a rabbit hole to answer a particular question , be sure to ask yourself “Why is this question important and how is the answer actionable?”

Belsky also leverages the experiences of other leaders. He shares the insights from Pinterest CEO and cofounder Ben Silberman.  Check out this comment on establishing a long view of entrepreneurship by envisioning steps along the way.



“Ben breaks up every period of his company into chapters, each with a beginning, goal, reflection period, and reward,” Belsky writes. “For example, a few years after the business was founded – once Pinterest’s website had a loyal and rapidly growing base of users – the company embarked on a new chapter to “become a mobile service”….What I liked about Ben’s chapters approach is that each one applies to everyone in the company and embodies a goal rather than a tactic. Each chapter requires a fresh perspective on the product, renewed empathy with the product’s users, ”

Other segments offer meaningful guidance, though some of the topics are only complementary material for other books with specific knowledge.   The segment Data Is Only As Good As Its Source and Doesn’t Replace Intuition does not have an in-depth rigor like Eric Siegel’s Predictive Analytics, but does offer the right perspective to consider data against intuition.

The last few segments, grouped under “Never Being Finished”, can seem a bit too quirky to be insightful, but when you do take the ideas in, you get a refreshed look into life balance (“You Are Not Your Work” and “Your Either Part of The Living Or The Dying”) and reexamining setbacks from wrong decisions (“Continuing To Learn Is An Elixir To Life”).

Other Reads to Consider

Readers seeking a deep subject treatment of business aspects may want  to pair this book with lslands of Profit In A Sea of Red Ink, Revenue and The CMO, or Data Driven Marketing.  My all-time startup favorite resource, David Gladstone’s Venture Capital Investing, is a good pairing with this book, too.  These book combinations can aid organizations that are in a messy middle of their own and must incorporate innovative problem-solving tactics.



Why The Messy Middle

Small business teams and evolving start up teams will find The Messy Middle useful for refining every aspect of their game.  The book will teach a team how to through hardships to the valuable lesson on operations or outlook on a market.

With The Messy Middle, Belsky delivers a brilliant book that goes past dogma and slogans into key tactics and ideas. While many authors claim their book will take you to the next level, Belsky makes an earnest and successful attempt to help business leaders and teams get to that level through logical decisions to keep a bold business venture alive.

Image: Amazon

4 Comments ▼

Pierre DeBois - Associate Book Editor


Pierre DeBois Pierre Debois is Associate Book Editor for Small Business Trends. He is the Founder of Zimana, a consultancy providing strategic analysis to small and medium sized businesses that rely on web analytics data. A Gary, Indiana native, Pierre is currently based in Brooklyn. He blogs about marketing, finance, social media, and analytics at Zimana blog.

4 Reactions

  1. Aira Bongco

    This is right. It is not just about the idea but how you tackle the hard work behind the idea.

  2. Pierre: Have you Scott Belsky’s other books?

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