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Daily Reflection
August 24, 2026
“Things turn out best for the people who make the best of the way things turn out.”
— John Wooden

When Yesterday’s Strength Becomes Today’s Limitation

Have you ever discovered that the very approach that helped make you successful was now getting in the way of your success?

We naturally rely on what has worked for us before. Experience teaches us lessons, builds our confidence, and gives us approaches we know we can depend on. But when circumstances change, yesterday’s strengths can sometimes become today’s limitations if we’re unwilling to adapt how we use them.

Life as an entrepreneur is vastly different from life as an executive in a corporation.

After spending much of my career as an executive, I had developed a pretty good sense of what worked for me as a leader and what didn’t. By nature, I’m direct, I’m a quick decision-maker, and I’ve always been fiercely independent.

Throughout my corporate career, those qualities served me well. When something needed to get done, I relied on my own efforts and the efforts of the people on my team to make it happen.

Then I became a solo entrepreneur.

There was just one problem.

I no longer had a team.

Instead of adapting to this new reality, I initially approached entrepreneurship the same way I had approached much of my corporate career.

I would figure it out.

And I tried.

What I quickly discovered was that around every corner there seemed to be another skill I needed to master.

I didn’t just need to be a great coach. I needed to learn marketing and sales. I needed to understand accounting. I needed to figure out social media. I needed to build and maintain a website. And the list seemed to keep growing.

I had little or no experience in many of these disciplines, but for several years I tried to brute-force my way through them.
I learned a great deal.

But progress was slow.

More importantly, I wasn’t particularly happy. I was spending an enormous amount of time struggling with things that weren’t my strengths while taking time and energy away from the work I was actually best equipped to do.

Coach and develop leaders.

During that period, I read Dan Sullivan’s Who Not How, and it challenged one of the assumptions I had been operating under.

Instead of continually asking myself how I was going to learn to do everything, I began thinking about who could help me do the things I didn’t need to do myself.

I changed my approach.

I found someone to help with my website. I outsourced marketing. I got help with accounting.

And that freed me to spend more of my time doing what I do best.

Looking back, the problem wasn’t that I wasn’t working hard enough.

I was working very hard.

The problem was that I kept applying an approach that had worked in one environment to a completely different environment.

That’s one of the challenges of leadership.

Experience is incredibly valuable, but it can also convince us that because something worked yesterday, it should work tomorrow.

Leadership doesn’t work that way.

Conditions change.

People change.

Organizations change.

Missions change.

And as those things change, effective leaders have to be willing to change with them.

That doesn’t mean abandoning our principles or forgetting everything experience has taught us. It means recognizing that the destination can remain the same even when we need to find a different route to get there.

Had I adapted earlier, I could have prevented a great deal of unproductive struggling.

That’s a lesson I continue to carry with me.

Where am I continuing to use an approach simply because it worked for me in the past?

What evidence might be telling me that my current approach is no longer working?

What could become possible if I were willing to adapt?

CHALLENGE

Identify one area where you’re struggling today.
Instead of asking, “How do I work harder at this?”
Ask yourself, “What might I need to do differently?”
Sometimes the answer isn’t to push harder.
It’s to adapt sooner.

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