When Success Isn’t Enough: Conversations with CEOs About Purpose, Identity, and the Courage to Look Different

Hello Big Brains:

I was recently invited to sit down with 6 hyper successful CEOs to share my testimony, and to reflect upon the pursuit of "purpose" and "identity" in this world.

Each of these CEOs had achieved everything that the world defines as "success"... each of these CEOs had impressive titles, world class resumes, financial independence, generational wealth, appreciable "assets" (i.e., homes, cars, fancy things), power, respect, and status...

So why did they want to talk with me?

Because, despite their worldly success, they felt deeply unfulfilled.

To be clear, I did not know a single one of these CEOs. A former peer of mine shared my story with one of the CEOs, and they invited me to speak for two hours (they kept me for 3 hours). I also believe God gave me this unique and unexpected opportunity to encourage me during a period of transition and change in my life.

If you don't know my story - here is a short summary (see "Find My Next"): God called me off of the corporate ladder that I worked tirelessly to climb for 15 years, and into a radically different purpose. God called me into outdoor ministry - not simply to lead adventures, but to help create space where hearts are formed, priorities are reordered, and lives are surrendered to Him.

Here is a reflection that I wrote after my conversation with these CEOs. I hope it offers encouragement.

*****

Over the past few months, I’ve had the privilege of sitting across the table from CEOs - men and women who have reached what many would call the summit of success.

Impressive titles. Influence. Financial freedom. Resumes that command instant respect.

As I’ve shared my own testimony, many have opened up in return. And in more than a few conversations, I’ve encountered something unexpected: restlessness. A quiet disorientation. An unspoken question beneath the surface - Is this it?

Success answers many questions. But it does not answer the deepest ones.

So I’ve begun asking something simple: “Who are you when you’re not the CEO?”

Not what you do.

Not what you’ve built.

Not what’s on your LinkedIn profile.

Who are you apart from the title?

Jesus once asked a striking question: “What good is it for someone to gain the whole world, yet forfeit their soul?” (Mark 8:36)

In a culture that equates achievement with worth, it’s easy to anchor identity to performance. To believe our value rises and falls with quarterly results and public perception.

But Jesus never anchored identity to achievement. He anchored it to sonship. To belonging. To being known by the Father.

If identity is fused to position, what happens when the position changes? When retirement comes? When influence fades?

If success is the foundation, identity will always feel unstable.

Many high-performing leaders eventually realize that climbing the ladder can quietly narrow your world. Time becomes scarce. Relationships become transactional. Decisions become calculated. Purpose slowly gives way to preservation.

Yet Jesus offered a completely different framework for greatness:

“Whoever wants to become great among you must be your servant.” (Matthew 20:26)

Not visibility - but humility.

Not control - but surrender.

Not self-preservation - but self-giving love.

In my own journey, I’ve learned that choosing service over status is rarely applauded at first. It can look inefficient. It can look like you’re stepping backward.

But the Kingdom of God often moves in what appears to be reverse.

The world says: climb higher.

Jesus says: kneel lower.

The world says: secure your name.

Jesus says: deny yourself. (Luke 9:23)

The world says: protect your power.

Jesus says: wash feet. (John 13:14–15)

Servant leadership is not weakness. It is strength under control - power surrendered for the good of others. It is influence rooted in character rather than control.

Success itself is not wrong. Influence is not the enemy. Achievement is not the problem.

The real question is: What is it anchored to?

When success is rooted in ego, it becomes a prison. When it is surrendered to purpose, it becomes a platform.

Jesus also said, “For whoever wants to save their life will lose it, but whoever loses their life for me will find it.” (Matthew 16:25)

That paradox is where many of these conversations are leading.

The most fulfilled leaders I’ve encountered are not the ones with the most accolades. They are the ones who know who they are apart from them. Anchored. Secure. Willing to look different.

Because following Christ will often make you look different.

If you find yourself successful but unsettled - admired but uncertain - perhaps that discomfort is not failure. Perhaps it is invitation.

An invitation to redefine success. An invitation to choose service over status. An invitation to build a life that serves many, not just self.

And perhaps most importantly: An invitation to anchor your identity in something eternal rather than temporary.

As Jesus reminded His disciples: “Seek first the Kingdom of God…” (Matthew 6:33)

Everything else finds its proper place when that foundation is secure.

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