Life After Fortune 500 CEO: When It’s Time to Chart a New Course

Brad D. Smith  •  May 6, 2026

One of the harder truths in leadership is recognizing when your role is shifting. Earlier this year, I shared something on LinkedIn that I had been thinking about for quite a while. I wrote briefly about life after Intuit, and about realizing that after 11 years as President and CEO, it was time for a new chapter. I expected a few people might connect with it. What I didn’t expect was how many people would reach out, from so many different walks of life, all recognizing some version of that same feeling.

At some point, many of us sense a chapter may be ending, even if what comes next isn’t clear yet. For me, that realization came with gratitude, and with a growing sense that it was time. But I’ve learned that if you care deeply about the organization, part of leading well is helping prepare the people who come next. In this first post, I want to share what helped me recognize that shift in my own life.

Rarely does a major career transition come down to one defining moment. Most of the time, it’s a collection of signs that keep showing up until you finally have to pay attention. When I look back now, a few markers stand out more clearly:

1. The Organization Was Entering Its Next Chapter

One thing I’ve come to believe pretty strongly is that every organization benefits from a fresh perspective. That doesn’t mean something is broken. In fact, sometimes the healthiest time for a transition is when the organization is strong. I found myself asking whether we had taken the company where we needed to take it in that season. I wanted to leave it stronger, not simply stay longer.

2. Successors Were Ready Behind Me

I think one of the best measures of leadership is whether you have built something that does not depend on you alone. Life is a team sport, and building a high-performing culture means developing the skills and capabilities in others. Leadership transitions grow and stretch individuals, while also bringing fresh perspectives to the organization. That can be exactly what keeps an organization healthy. 

I was privileged to have 3–4 viable successors who were ready to advance the organization, while envisioning what could be even better. My aspiration when I assumed the role was to play a part in choosing the timing, with an acknowledgment that one of the key inputs to that decision was when the board had a slate of viable successors. This would ensure that we grounded the decision in what was right for the company and fair to the people who had invested so much in it.

3. I Still Had More Questions Than Answers

This third sign was more personal. I never wanted to be that individual who stayed past their prime. We have all seen an aging athlete who is no longer able to contribute at the same level, and we grimace when we see them falter. My goal was to leave when I still had more questions than answers. That intellectual curiosity would enable me to stay fresh in the role as long as I remained in the position, while serving as fuel to think differently about what the next phase of life might hold. 

That curiosity led me to reach out to those who had traveled a similar transition in their lives. Individuals who had concluded a successful chapter and had embarked on another exciting journey in ways that were meaningful to them and impactful for others. My question was what I should consider doing next. Thankfully, they challenged me to think more deeply than that. One friend said, “You’re asking the wrong question. You shouldn’t be asking ‘what’ but rather ‘why.’ ‘Why does it matter?’”

That was the trigger that got me thinking about time, and about how I wanted to spend it. It was those reflections that led me toward more narrow questions, a clearer sense of purpose, and a growing signal that it was time.

A new course must start with honest reflection. And sometimes part of leading well is knowing when it’s time to hand it off. If this season of your life is raising new questions for you, I hope you’ll give yourself the space to listen to them.

Next time, I’ll share more about what came after my initial realization — and how I began figuring out my ‘why,’ and how that led me to ‘what’ I was actually meant to do next.

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