The Messy Middle: A book review by Bob Morris

The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture
Scott Belsky
Portfolio/Penguin (October 2018)

“It’s not about the start or finish, it’s about the journey in between.” Scott Belsky

The “it” may refer to creating something that Steve Jobs once characterized as “insanely great.” His statement (quoted earlier) suggests that “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.”

As I began to read Belsky’s latest book, I remembered a scene in the film based on L. Frank Baum’s children’s classic, The Wonderful Wizard of Oz, when Dorothy and her companions first see the dazzling Emerald City in the distance. They leave the yellow brick road and begin to run through a field of poppies to reach that destination. Their nemesis, the Wicked Witch of the North, has other ideas.

Only after a series of severely difficult ordeals do they succeed. Dorothy and Toto return to their home in Kansas; the Tin Woodsman gets a brain, the Scarecrow gets a heart, and the Cowardly Lion gets courage. Belsky suggests that those involved in any bold business initiative also need a brain and a heart as well as courage. They also need to understand that “after the excitement of a new idea dissipates, reality sets in. You’ll become mired in logistics and daunted by the unknown. You’ll frantically attempt to level out your overworked synapses. You’ll be in a freefall without knowing how far away the bottom is — and that’s when the headwinds kick in. Everyone will doubt you. You will struggle to see your own progress. You’ll realize that your industry, your team, and your competitors don’t like change — and society doesn’t either. Not even your customers.

“And then finally the bottom arrives, and you hit hard. After scrambling to get your bearings and not lose too much time, money, or face, you’ll look back up to see a monstrous peak in front of you.” Welcome to the messy middle, “the hardest and most crucial part of any bold venture.” If it eventually succeeds, it can yield  “the unexpected bounty that makes all the difference.”

He goes on to reveal “the dirty little secret that entrepreneurs hate to admit is just how fine the line is between their success and failure. The middle makes and breaks you, and ending up on the right side of this line depends on how you manage everything in between . It requires immense perseverance, self-awareness, craftsmanship, and strategy. It also requires luck, harvested whenever [and wherever] you encounter it.”

These are among the dozens (hundreds?) of key points that Belsky examines with rigor and eloquence in the first two sections, ENDURE and OPTIMIZE:

o Accept the burden of processing uncertainty
o Friction brings us closer together
o Be the steward of perspective
o Leave every conversation with energy
o The only “sustainable competitive advantage” in business is self-awareness

o Sometimes a reset is the only way forward
o Strategy is nourished by patience
o Do the work regardless of whose work it is
o Diversity drives differentiation
o Hire people who have endured adversity

In this context, I am again reminded of Richard Branson’s suggestion that an entrepreneur is someone “who jumps off a cliff and builds a plane on the way down.”

When concluding, Belsky suggests that challenges of the messy miles of each perilous journey “don’t get easier and never repeat themselves, because they are the moat between vision and reality. The messy middle is a life’s work, and when anyone crosses the finish line and pushes the extraordinary [‘insanely great’] out to the world, we all benefit…The future is created by those who endured and optimized through the messy middle to create it. For you and the rest of us, stick with it.”

Not all journeys reach their destination. Fortunately, visionaries are not limited to only one. In Tennyson’s classic poem, Ulysses urges them “to strive, to seek, to find, and not to yield.” Scott Belsky offers more than a battle cry. Of greater value, he offers an abundance of information, insights, and counsel that can serve as a cohesive and comprehensive operations manual for those who are determined to navigate their way “through the hardest and most crucial part of any bold venture,” whatever its nature and extent may be. Bravo!


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