Lead Like a Leader

Personal Leadership Mastery

Blog Post #5 — Find Your Cool Series

Title: Building Your Inner Compass: 5 Questions to Answer Now

Every successful innovation project we led — from reimagining care pathways to redesigning global supply chains — began the same way:

We immersed ourselves until we understood what really mattered.

Not just what people said they wanted. But what they valued. What they avoided. What they traded. What they endured.

In innovation, we map those tensions across the system. In life, your compass lives in those same questions. It’s not hanging on the wall. It’s buried in your values, patterns, and core beliefs — many of which are invisible until you stop to reflect.

The challenge? Most people don’t stop. They stay busy. Reactive. Over-scheduled.

But if you want to find your cool, you don’t need a calendar overhaul.
You need a compass reset.


Real-World Example: When a Team Got Stuck

In one project, a global team hit a plateau. The strategy was sound. The execution was flawless. But motivation was collapsing.

So we paused. Not to change the plan — but to recalibrate purpose.

We asked five foundational questions — not about the business, but about the people running it. That’s when clarity returned. Innovation restarted.

What changed wasn’t the system. It was the sense of meaning inside the system.

That’s what a compass does: it gives direction when movement alone no longer feels like progress.


Cool Exercise: Inner Compass Check-In

Grab your journal. Sit with these five questions. Answer honestly — no filters.

  1. What do I deeply value — even when no one’s watching?
  2. What activities give me energy — and what depletes it?
  3. Where in my life am I currently pretending or performing?
  4. If failure wasn’t a factor, what would I try this year?
  5. If I had just five years left, how would I spend them — and with whom?

These aren’t hypotheticals. These are design questions.
And the answers? That’s your compass.

Not for a perfect life — but for a true one.


Innovation Insight: Without True North, You Drift

In complex systems, drift happens when priorities become distorted by noise.
In human systems — your life — it happens the same way.

You start making decisions based on:

  • What others will approve of
  • What used to work
  • What keeps things quiet

And slowly, you drift from what you actually want.

Innovation taught us to always check for alignment before scaling. You should too.

You don’t need more motion. You need a clearer north.


Quote to Reflect On

“He who has a why to live can bear almost any how.” — Friedrich Nietzsche


Final Thought

You can’t outsource direction. You can borrow strategies, mentors, or models — but your compass has to be internal.

These five questions aren’t just journal prompts.
They’re design tools.
They reveal the architecture of a life that aligns with your values — not just your résumé.

Finding your cool isn’t about standing out.
It’s about standing true.

Start with your compass. Let’s navigate from there.


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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.