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

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

“This is the progress paradox,” Glei writes, “by dint of technology, it’s easy to see our progress when we’re doing relatively meaningless short-term tasks, while it’s quite difficult to see our progress when we’re engaged in the long-term, creative projects that will ultimately have the most impact on our lives.”

The perfect question is a key to clarity. It unlocks truth and opens minds. It is distilled by having empathy for your customers’ struggles and ignoring sunk costs and past assumptions to get at the root of a problem. When you’re building something new, focus on asking the right questions instead of having the right answers.

Empathy for those suffering the problem must come before your passion for the solution.

The aspiration for a “frictionless” experience is shortsighted. A truly frictionless experience, where you avoid or deny every ounce of struggle, is mindless. Friction makes you feel the texture of a process, and the texture helps you remember what you’ve experienced. Without friction, teams are liable to move too fast, and edges that are too smoot

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

James Murphy, the founder and front man of LCD Soundsystem, said it well: “The best way to complain is to make things.”

Whether you’re an author suffering from writer’s block or a start-up team struggling to satisfy its customers, the solution is to change the question you’re asking. If the original question plaguing you is “Why aren’t people signing up for our product?” maybe the better question is “What kinds of people would benefit most from our product?” When yo

One of the greatest motivators is a sign of progress. Hardship is easier to tolerate when your work is being recognized (either through external validation or financial rewards), but long journeys don’t show progress in the traditional sense. When you have no customers, no audience, and nobody knows or cares to know about what you’re making, the gr

Process is how we force alignment when it doesn’t happen naturally. You schedule meetings, you embed systems for tracking and accountability, and you install more managers. But if not implemented properly, process slows down progress. It can be painful, especially as teams that grew up eschewing mandates mature. Nobody likes more obstacles to doing