The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture
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You must pay less attention to the day-to-day incremental advances and more on achieving an overall positive slope. And that’s entirely determined by how you navigate the messy middle.
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This book is about mining every insight from the volatility and the depths of despair to improve your team, product, and self.
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When a tactic or tenet fascinated me, I’d capture it and share it with others for feedback or better ideas, and the ones that made the cut are in this book.
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So let’s get real: The pithy success stories we hear are missing something.
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How does an unqualified team recruit, manage, and retain very qualified people—often more qualified than ourselves?
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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.
Matthew Ackerman
Engineering momentum in your clock
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Volatility is good for velocity. The faster you move and the more mistakes you make, the better your chances of learning and gaining the momentum you need
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endless endurance and optimization.
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a section on endurance and a section on optimization—the two complementary forces that help you conquer the middle of any bold project.
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One realization I hope you have from this book is the relationship between volatility and preparedness.
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Without a fight against fate (aka the status quo), you’ll never venture beyond the expected.
Matthew Ackerman
Fighting against the momentum of life--of circumstance--to find your direction and build your own momentum
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we learned everything the hard way. I’m surprised we survived.
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I felt the weight of every decision, and the careers of those who quit their jobs to join me, on my shoulders. My shoulders alone.
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these years felt lost because we ran in circles. We had to rebuild the Behance Network’s core technology three times.
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we were determined to get it right. We didn’t make rapid progress with our product, but the hardship strengthened our resolve.
Matthew Ackerman
How do you process the psychology of this struggle?
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Endurance is about much more than surviving late nights and laboring without reward. It’s about developing a source of renewable energy and tolerance that is not innate.
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You must supplement this void with manufactured optimism.
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You’ll have to generate a unique and intrinsic sense of belief in yourself as you manage the blows to your plan and ego.
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running a marathon while hungry requires supernatural sustenance in the form of some key insights and convictions tha...
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Thus, physiologically, we’re hardwired to have a strong preference for actions, decisions, and projects likely to yield quick wins, because delayed gratification causes anxiety and discomfort.
Matthew Ackerman
Quick uncalibrated bet that feels like a win and relieves the uncertainty vs bullets that incomplete but slowly point you in the right direction
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As you craft your team’s culture, lower the bar for how you define a “win.” Celebrate anything you can, from gaining a new customer to solving a particularly vexing problem.
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Milestones that are directly correlated with progress are more effective motivators than anything else.
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actively searching for positive feedback provides false positives.
Matthew Ackerman
Confirmation bias
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I was looking only for the positive trends rather than objectively reviewing all the trends.
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To objectively observe the performance of your new creation or product, put yourself in others’ shoes. You can piece together something resembling the truth only from many different perspectives. How would a skeptical investor look at your numbers? How would an impatient new customer attempt to navigate your product? What are competitors saying about your product? Actively seek out the negative trends as well as the positive, as your longevity over time will be determined by your awareness of weaknesses as much as your strengths.
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Sometimes when leaders are trying to rally confidence and support, they are actually blunting a blow that must be felt in order to feel the reality and make difficult decisions.
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“You must tell the truth without destroying the company. To do this, you must accept that you cannot change the truth. You cannot change it, but you can assign meaning to it.”
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State the facts clearly and honestly—Don’t
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If you caused it, explain how such a bad thing could occur—What
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Explain why taking the action is essential to the larger mission and how important that mission is—A
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And when you find something worth celebrating, only applaud the progress and actions you want your team to repeat.
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Funding shouldn’t be celebrated. If anything, raising money should make you nervous: It means you have more to lose and more people you are responsible to.
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For strong companies, financing is a tactic. For weak companies, financing is a goal.
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What should you celebrate? Progress and impact.
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Celebrate the moments when aggressive deadlines are met or beaten. Pop champagne when the work you’ve done makes a real impact.
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By avoiding uncertainty and desperately seeking a quick answer, we’re liable to embrace premature or incorrect solutions.
Matthew Ackerman
Settling to avoid uncertainty—poverty of certainty