Lead Like a Leader

Personal Leadership Mastery

Blog Post #6 — Find Your Cool Series

Title: How to Define Your Own Version of Success

One of the first questions we asked in every innovation planning session was simple:

“What does winning look like — and for whom?”

In the corporate world, people often answered with metrics. In the healthcare world, they answered with outcomes. But what stuck with us most was what happened when people didn’t have a clear answer.

Confusion. Delay. Exhaustion. A cycle of overperformance and underfulfillment.

The same thing happens in life.
If you don’t define success for yourself, the world will do it for you.
And usually, it’s a noisy, status-driven version you’ll outgrow the minute you achieve it.

Your cool can’t survive in someone else’s version of success.
It only thrives in alignment with your core — your why, your values, your impact.


A Real Innovation Example: Redefining Metrics That Mattered

During a major supply redesign, our first draft of success was a traditional process scorecard. But after mapping the full ecosystem — end-to-end — a entire differnt model emerged.

So we changed our success criteria.
We added trust. Simplicity. Emotional confidence in the process.
And that’s when innovation actually began to work.

We stopped chasing efficiency and started designing real outcomes.

You have the same opportunity in your life.
What if you’re succeeding at something that doesn’t actually matter to you anymore?


Cool Exercise: Define It for Yourself

Set aside the titles, the accolades, the income brackets.
Ask yourself:

  • What do I want my life to feel like each morning?
  • What impact do I want to make on others — with my time, words, energy?
  • What am I no longer willing to trade away in exchange for praise or perceived stability?

Now write your personal definition of success in one clear sentence:

“Success for me means…”

Read it every week. Update it when you grow. Build around it.
Let it become your new metric.


Innovation Insight: What You Measure Shapes What You Build

In every transformation we led, we used this principle:

“You can’t manage what you don’t define.”

We saw it everywhere — teams with no clarity on success worked harder but produced less.

Your life is no different.
You might be pushing. But are you pushing in the right direction?

When your version of success is clear, your decisions get simpler. Your boundaries get firmer. Your confidence gets quieter, but stronger.

And your cool? It begins to rise — because you’re finally designing a life you respect.


Quote to Reflect On

“Don’t aim for success. Do what you love and believe in, and it will come naturally.” — David Frost


Final Thought

This isn’t about goals.
It’s about your inner criteria — the standard by which you’ll measure whether a day, a year, or a life was well lived.

Once you define success on your own terms, you’ll never again confuse motion with meaning.

And the life you’re building?
It’ll feel like yours — every step of the way.

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Embark on an extraordinary journey with John Dempsey and Tom Reynolds at “Lead Like a Leader,” where 80 years of collective wisdom meets a passion for Self-Discovery in Leadership. Dive into our blog, where we unravel the secrets of success from the corridors of one of the world’s largest healthcare companies to the dynamic world of start-ups. Join us in reimagining personal leadership and well-being, as we blend timeless insights with cutting-edge strategies. This is not just a blog; it’s a beacon of empowerment, a sanctuary for truth-seekers, and a roadmap to your fullest potential. Welcome to the straight-talking zone, where learning and sharing never stop.