There’s a moment I think about often — the final one.
Not morbidly, but honestly: that last look back.
It’s the reckoning we all face, the point at which the real story of our life is told back to us. I try to live in service of that moment — not in fear of it, but as a compass. It reminds me to choose well so that one day, when I look back, I feel pride rather than regret.
I still have a great deal to do (and undo), but I’m grateful for the marker. It keeps me honest.
One thing I’ve come to see clearly is how profoundly our work shapes that final reckoning. Not exclusively — marriage, family, health, friendships all matter deeply — but it’s hard to deny that our vocation is a major contributor to our “life story.”
And if most CEOs had to end their careers tomorrow, I suspect many would feel… middling.
Not disastrous, not triumphant — just fine. And “fine” is a hollow victory.
If today were the end, how would you answer these questions?
- Has your career left you better off — emotionally, spiritually, or even physically?
- Have you been joyful (at least some of the time)?
- Have you expressed your full talent, or have you been holding back?
- Have you worked with people who energise you?
- Has your impact mattered?
- Has the business you lead made the world even a fraction better?
In my experience, most CEOs begin their journeys with me answering these questions with a polite but painful “sort of.” The reason? Most businesses are not built for remarkability. They are wired for risk mitigation, efficiency, and predictability — not for boldness, not for self-expression, not for meaning.
Last week, we released the re-imagined Lockstep — not just a consulting firm, but a platform for the idea of the Transcendent Business. It is, without question, the boldest expression of my vocation. And whatever becomes of it, I already know this: it will not be a hollow victory. It is the truest card I have to play.
If your own “deathbed moment” feels uncomfortably uncertain, listen to that instinct.
Everything required to create a deeply fulfilling career is available to you. CEOs are fortunate — autonomy is built into the role. Within reason, you get to shape both the business and the experience of leading it.
Being a CEO does not need to deplete you. It can — and should — be one of the most meaningful, expansive, and soul-satisfying paths a person can walk.
So declare the beginning of your own pre-parade.
Mark the moment.
Choose the path that will make that final look-back a joyful one.