On Shortcuts and Ceilings

Some skills give you little choice but to struggle through them the right way. You can get clever, you can get creative, but eventually you come face to face with the limits of a shortcut.

Anyone who has become moderately proficient playing the guitar knows this. When you're just starting out, it's easier to use only downstrokes with your picking hand. For a beginner, this can be incredibly satisfying. You can play real songs. You can make music. It feels like progress, and it is progress—for a while. But this shortcut quickly turns into a ceiling. At some point, especially when you try to tackle faster pieces or more intricate rhythms, you realize that alternate picking is no longer optional. It is necessary. Upstrokes and downstrokes, used together in fluid motion, are what allow you to scale your skills. By that time, however, the muscle memory of the shortcut has settled in. Unlearning it is harder than learning it would have been in the first place. You are no longer advancing. You are untangling.

This happens everywhere. In youth baseball, it is common to see young pitchers throw with just their arm strength. They hurl the ball with raw energy, often to great effect. Coaches cheer. They strike batters out. It works—until it doesn't. Without learning the mechanics of the full-body throwing motion, a pitcher will eventually plateau or get hurt. Proper pitching involves a kinetic chain: legs, hips, core, shoulders, and arms working in sequence. That chain is what gives elite pitchers their speed and longevity. But if you never build that foundation early, the arm takes all the punishment, and the ceiling is lower than it looks.

This principle applies just as clearly to the development of organizations. Every growing organization experiences a phase where a handful of people make everything happen. A teacher volunteers to run the after-school program. The head of school handles all admissions decisions. The finance manager is the entire HR department. In the early days, this kind of hustle is not only admirable, it is often necessary. You do what you must with the resources you have. There is a gritty pride in it.

But then something changes. The school expands. The community grows. Programs multiply. Complexity increases. And suddenly, the same heroic efforts that once made the school run are now limiting it. The shortcut that saved you time and energy in the beginning has become a bottleneck. Because the work was never distributed. The process was never documented. The system was never built.

It is easy to see these patterns in hindsight, but much harder to recognize them in the moment. We mistake momentum for sustainability. We think because something is working, it is scalable. But anything that depends entirely on one person is not a system, it is a stopgap. It is a fragile arrangement that cannot survive transition, turnover, or even simple growth.

This is not just a leadership problem. It is a human problem. We naturally favor what works right now over what will work better later. We are drawn to efficiency and short-term wins. But skill building, like institution building, rewards the patient. It rewards those willing to do the harder thing first so that the path becomes easier later.

In schools, I have seen this play out most often in programs that are deeply tied to a single personality. A beloved music teacher builds a fantastic program, but when they leave, there is no playbook for how to continue. Or a school leader manages a complex budget through instinct and memory rather than a replicable process. These things can look like success until they are stress tested. And by then, the organization is left scrambling to rebuild from scratch.

The solution is not to eliminate all improvisation or passion. Those things are vital. But they have to be paired with intentional infrastructure. We have to stop and ask: could someone else do this if I stepped away? Is there a plan, a process, a system behind what I do? If the answer is no, we are not really building capacity. We are preserving dependency.

Skill, craft, and organizational strength all require the same discipline: resisting the temptation of the shortcut when the road ahead calls for something deeper. When we do the foundational work early, we create room to grow. We build something that lasts. And we lift the ceiling not just for ourselves, but for everyone who comes after.