
The Paradox of Control
Sometimes you need to let go to succeed
Sep 19, 2023 · 7 min readUpdated Jan 29, 2026
Sponsored By: Height
This essay is brought to you by Height, the first and only AI project manager.
Project management is necessary — it’s how we keep teammates in sync, minimize downtime, and hit deadlines. However, it’s often tedious, complicated, and most of all, far from your true ambition.
Height can handle organizing your team so that you can focus on the project and let AI handle the management.
When the U.S. Air Force developed rocket planes that could break the sound barrier, the pilots who flew them kept dying.
As planes reached speeds near Mach 2, pilots would lose control due to the thinner air in the upper atmosphere. As Tom Wolfe describes in his book The Right Stuff:
“A plane could skid into a flat spin… and then start tumbling, not spinning and not diving, but tumbling, end over end like a brick.”
You couldn’t maneuver out of a rocket plane tumble; anything you tried just made it worse. Pilots would claw desperately at the controls as they hurtled to their deaths, screaming into their radios: “I’ve tried A! I’ve tried B! I’ve tried C! I’ve tried D! Tell me what else I can try!” (Wolfe, page 99.)
During one of those tumbles, a pilot named Chuck Yeager got knocked unconscious. By the time he came to, he had fallen to 25,000 feet… and in the lower, denser air, he could maneuver again. He was able to right the plane and land it safely.
It turns out that in the upper levels of our atmosphere, the most effective thing you can do with an out-of-control plane is to take your hands off the controls. It goes against all instincts, but letting go—literally, doing nothing—is the only real move you have.
While most of us in tech aren’t flying supersonic jets, we still encounter situations where control works and others where it doesn’t. Exerting too little or too much control can both cause problems, depending on the context.
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In psychology, when you attempt to control something that is ultimately uncontrollable, we call it “misapplied control.” As founders, it’s important to learn to recognize this pitfall and work with the underlying fear that drives it—the fear that things might go terribly, horribly wrong.
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Casey Rosengren is a founder and executive coach based in New York. If you’d like to learn more about coaching, drop him a note.
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Thanks to our Sponsor: Height
Thanks again to our sponsor Height, the world's first AI-based project manager meant to lift the burden off your shoulders.
Height efficiently streamlines your tasks and projects, taking the grind out of your routine. It ensures your workflows are always in order, so you can channel your energy into doing the work that matters the most.
Say goodbye to hassle, with automatic project management that reduces your workload, not intensifies it. Height makes it possible for you to achieve more by doing less.














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