Navigating our "Messy Middle"
Welp, I held off using sports analogies for as long as I could
I love my daily commute: a twenty-minute bike ride during the Chicago summer meandering through my favorite neighborhoods (Lakeview to Lincoln Park to West Loop). This part of my day is sacred. It’s a buffer time to “drop into” work in the morning and an opportunity to “step out” of the workday in the evenings.
On my bike ride home from the office earlier this week, I thought about the percentage of my startup stress/anxiety that is externally delivered (a bad sales call, product issues, delayed roadmaps, etc.) versus internally manufactured (WTF are we doing, will this ever work, can I do this, etc.). Basically, a mental health metrics tree.
I was thinking about this after reading Scott Belsky’s latest book, The Messy Middle, over the weekend. The book is a deep dive into the part of a growth journey that no one talks about: the middle. The middle is what comes after the “joy” of the start has receded into a distant memory. It’s a long-dark period (years!) that is an onslaught of both external and internal anxiety. It lasts until the relief of the end finally comes to light.
Scott’s recounting his own “messy middle” experience with Behance will have you nodding along the entire way. There is nothing unique or special about these stresses: every founder will face them. Like most things, it’s less about what is thrown at us and more about how we handle it.
While the entire book is a must-read, one passage that quotes Justin Fried of Basecamp especially changed my thinking: “The best startups are really just ‘stay ups’. Outlasting is one of the best competitive moves you can make.”
Bear with me because I can’t help but turn this into a sports analogy near and dear to my heart: In tennis, there is a special type of opponent known as a “pusher”. These are players that just refuse to miss. They don’t chase the instant gratification of a big forehand ripped down the line for a winner. They are relentless and run down every ball. Regardless of how hard you hit it or where you place it, they will get it back over the net. They are annoying as hell.
Yet, they win. Being a “pusher” may not look glorious, but it is exactly the type of play that is necessary in a marathon match in which all of the odds are stacked against you.
I’m deep in my “messy middle” as I’m sure you are too. I guess we’ve just got to keep on swinging.
Happy weekend,
Raman at Rhetoric
📚 What’s made me a better storyteller this week
