The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture

Forcing yourself to have a “one feature in, one feature out” guideline will help you develop your product with a bias toward simplicity. While simplicity benefits your newest customers and the majority of your current customers, it also benefits your own process to grow your product and solve problems as they arise.

Our in-person events for five thousand people around the world would generate tens of thousands of social media posts, and the images would ultimately reach hundreds of thousands of people. But more important, these events prompted conversations and relationships that went far beyond our brand as a service and instead made it a lifestyle.

Competing with your past is the purest and surest way to make faster progress without compromising your vision. The greatest successes are the aggregate of persistent optimizations of personal bests.

You also need a margin to mine circumstantial opportunities and explore the unexpected.

As someone who believes wholeheartedly that self-awareness is the greatest competitive advantage for a leader, I love the idea of developing tools and norms that promote it.

For leaders, no-drama days where everyone is just happily doing their thing feel great, so they assume a calm, hassle-free existence is the one that produces the best work. They optimize for a steady state, when there are no surprises and people do as they’re told. But comfort also breeds complacency. As learning curves plateau, we lose interest in

Apprenticeship is an investment in future talent, so actively encourage it.

When you find yourself working alongside polarizing people, try to appreciate the role they play and the origin of their struggle.

The only time you should force new behaviors or terminology is when they enable a

The volatility of this tug-of-war is hard to stomach. 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.