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Blog

Why Experience Is Making Change Harder, Not Easier

  • Jamey Schrier
  • January 20, 2026
  • No Comments
  • leadership

Experience is supposed to make things easier.

You have seen cycles. You have solved problems. You have built something that works. On paper, you should be better equipped to adapt than ever.

Yet for many seasoned practice owners, change now feels harder, not easier.

That is not because capability has declined.
It is because experience changes how risk is perceived.

How Experience Trains You to Rely on What Works

Early in ownership, change is constant.

You adjust pricing. You shift schedules. You test systems. Decisions are made quickly because there is little to protect and everything to build.

Over time, success creates stability. The practice grows. Revenue becomes predictable. The team expands.

Experience teaches a powerful lesson.

This worked.

That lesson slowly turns into an assumption.

This should keep working.

When Confidence Replaces Urgency

Experience builds confidence. Confidence reduces urgency.

You know the business well enough to manage around problems instead of fixing them. You recognize issues early and step in before they escalate. You compensate for gaps with judgment, availability, and effort.

The practice keeps running.

From the outside, it looks stable.
From the inside, it requires more of you each year.

Experience allows inefficiency to survive longer.

The Patterns That Experience Quietly Reinforces

This is where experience begins to work against change.

 

Fixing Problems Personally Instead of Structurally

Experienced owners are good problem solvers. When something breaks, they step in, assess quickly, and get it handled.

That ability keeps the business moving. It also prevents the business from learning.

When the owner consistently fixes issues personally, the system never changes. The same problems resurface because nothing upstream was redesigned. Over time, the practice becomes dependent on the owner’s availability instead of its structure.

What feels like leadership is often compensation. (WSJ)

Trusting Instinct More Than Objective Data

Experience sharpens intuition. You can feel when something is off before the numbers show it.

The risk is when instinct replaces data instead of being tested against it.

As practices grow, complexity increases. What worked when the owner could see everything no longer scales. Without objective metrics, decisions rely too heavily on perception. That makes blind spots harder to detect and harder to challenge.

Experience without data feels efficient. It is often incomplete.

Delaying Changes Because Things Are Still “Manageable”

Seasoned owners know how bad things can get. Compared to that, today’s problems feel tolerable.

So change gets postponed.

As long as the practice is still functioning, discomfort is normalized. The owner adapts instead of redesigning. The business stays operational, but the cost of that stability is paid in time, energy, and attention.

Manageable is not the same as healthy.
It is simply familiar.

Protecting Familiar Workflows Even When They Limit Growth

Workflows that have “always worked” carry emotional weight. They represent survival, effort, and identity.

Changing them feels risky, even when they no longer fit the business.

Experienced owners often protect familiar processes because they know how to navigate them. That familiarity becomes a reason to keep operating inside constraints that no longer make sense.

The workflow stays comfortable.
The business stays capped.

Mistaking Stability for Sustainability

A practice can feel stable while quietly becoming fragile.

Revenue is steady. The team shows up. Problems are handled. Nothing is on fire.

But stability built on constant owner intervention does not last. It depends on energy, availability, and personal tolerance for pressure. Sustainability requires something different. It requires systems, leadership, and margin that exist without constant oversight.

Experience makes stability achievable.
Structure makes it sustainable.

These patterns are not errors.

They are adaptations that once served you well.

They are now the constraint. (MGMA)

Why Change Feels Riskier Later Than Earlier

Earlier in ownership, the upside of change is obvious.

Later, the downside is clearer.

You are no longer risking survival. You are risking disruption. Team morale. Short-term performance. Your own time and energy.

So change gets postponed.

You wait for space.
You wait for things to calm down.
You wait for the right moment.

Experience tells you that you can handle things as they are.

That is often true.
It is also what delays progress. (HBS)

How Experience Increases the Cost of Delay

When informal leadership and owner intervention persist too long, the business hardens around them.

Roles blur. Accountability weakens. Systems grow around workarounds instead of intention. The owner becomes the stabilizer for everything.

Experience makes this survivable.

Until it is not.

When change finally becomes unavoidable, it feels overwhelming because the gap between what exists and what is needed has widened quietly over time.

What Experienced Owners Must Relearn

The shift is not learning more.

It is recognizing that experience alone is no longer the solution.

At a certain stage, judgment must be supported by structure. Leadership must replace proximity. Decisions must be designed into the business instead of routed through the owner.

Experience still matters.

But only when it is used to build a business that does not depend on it.

What This Requires Now

If change feels harder than it used to, that is not a personal failure.

It is a signal that the practice has outgrown how it is currently being led.

The question is not whether you can keep handling more.
It is whether the business should require you to.

The Practice Freedom Assessment is designed to surface exactly where experience is compensating for missing structure, where decisions are bottlenecked, and where the business still relies too heavily on you to stay stable.

No pressure.
No selling.

Just a clear view of what your experience is carrying, and what the business needs next if it is going to support you instead of depend on you.

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