What is Success? What a Dying CEO’s Final 48 Hours Taught Me

Success is not how high you have climbed, but how you make a positive difference to the world. – Roy T. Bennett 

The morphine drip wasn’t doing much anymore. Richard Hartwell, CEO of Meridian Industries—a name you’d recognise from your 401k statements—lay propped against hospital pillows at 3:47 AM, staring at his phone with the desperate intensity of a man running out of time.

He wasn’t checking stock prices. He wasn’t reviewing quarterly projections. For the first time in thirty-seven years, Richard Hartwell was scrolling through LinkedIn, frantically searching for someone—anyone—who might remember him for something other than increasing shareholder value by 12% annually.

“I built a $4 billion company,” he whispered to his night nurse, Maria, who had heard variations of this monologue for three consecutive shifts. “Four billion dollars. Do you know what that means?”

Maria, a woman who’d held more dying hands than she could count, adjusted his IV and said gently, “What do you think it means, Mr. Hartwell?”

The question hung in the sterile air like a challenge. Because here’s the thing nobody tells you about success: it’s remarkably easy to climb a ladder that’s leaning against the wrong wall. And sometimes you don’t realise it until you’re at the top, looking down, wondering why the view feels so… empty.

The Meridian Man

Let me back up. I didn’t know Richard personally—not at first. I knew of him, the way you know of most Fortune 500 CEOs: as a name in business journals, a quote in earnings calls, a figure who transformed a mid-sized manufacturing company into a global powerhouse. The business press loved him. Harvard Business Review featured him twice. He was the kind of success story that made other executives wake up at 4 AM to hit the gym, determined to unlock whatever secret sauce had made this guy so phenomenally… successful.

But success, I learned, is a trickier beast than we imagine.

I first encountered Richard’s story through his daughter, Jennifer, who attended one of my Purpose Pursuit Protocol courses last spring. She sat quietly, arms crossed, looking like she’d rather be anywhere else. During the lunch break, she cornered me.

“This purpose stuff,” she said, voice tight with something between anger and desperation. “Is it real? Or is it just another self-help fantasy for people who don’t have real problems?”

Jennifer had real problems. Her father—this titan of industry, this master of the universe—was dying. And in his final weeks, he’d become obsessed with a question that was slowly driving him mad: What was the point of any of it?

“He keeps asking me to help him find people who remember him,” she said. “Not business associates. Not board members. People who remember him as… him. And the list is getting shorter every day.”

The Success Trap

Here’s what Richard had accomplished by age 64: He’d increased Meridian’s revenue by 2,400% over his tenure. He’d created 47,000 jobs. He’d been featured on the cover of Fortune magazine three times. His net worth was north of $200 million. He owned homes in seven countries and a yacht that required a crew of twelve.

He was also, by every metric that matters to dying people, completely alone.

“I worked 80-hour weeks for three decades,” he told me during one of our later conversations—yes, I eventually met him, thanks to Jennifer’s persistent advocacy. “I missed Jennifer’s piano recitals, her graduation, her wedding rehearsal dinner. I missed Christmas mornings and birthday parties and Saturday afternoon soccer games. But I told myself it was worth it because I was building something important.”

The morphine made him brutally honest. “I was building other people’s wealth. I was making rich people richer. And I convinced myself that was a noble calling.”

This is the dirty secret of success culture that nobody wants to acknowledge: we’ve created a system that rewards the appearance of purpose while systematically destroying actual purpose. We celebrate people who sacrifice their relationships, their health, their authentic selves on the altar of achievement. We call it “dedication” and “drive” and “leadership.”

But lying in that hospital bed, Richard could see the truth with crystalline clarity: he’d spent forty years optimising for metrics that ultimately meant nothing to the person he actually was underneath all those accolades.

The 3 AM Revelation

It was during one of those sleepless nights—the kind where pain and medication conspire to strip away all your comfortable delusions—that Richard had what he called his “3 AM revelation.”

“I realised I couldn’t answer the most basic question,” he told me, his voice barely above a whisper. “If someone asked me who Richard Hartwell really was, beyond his job title, I wouldn’t know what to say. I’d become so identified with my role that I’d lost track of my actual self.”

This wasn’t just philosophical navel-gazing. Richard was experiencing what psychologists call “identity foreclosure”—when we commit to an identity without exploring alternatives, often because external pressures make one path seem like the only acceptable option.

But here’s the kicker: Richard had never actually chosen his path. He’d defaulted into it.

“I was good at math in college,” he explained. “Got recruited by a consulting firm. Did well there. Got poached by Meridian. Worked my way up. Each promotion felt like validation, like I was winning at life. But I never stopped to ask: winning at what, exactly? And for whom?”

He’d been playing a game whose rules he’d never questioned, pursuing a definition of success that had been handed to him by… well, by whom? Society? His parents? Business school professors? The metrics were clear—revenue, growth, market share—but the meaning behind those metrics had always been fuzzy.

“I optimised my entire existence around numbers that looked impressive in annual reports,” he said. “But I never asked whether those numbers aligned with anything I actually cared about.”

The Inventory

In his final weeks, Richard embarked on what he called “The Inventory”—a systematic review of his life choices through the lens of authentic purpose rather than external achievement.

He made lists. Lots of lists. (Old habits die hard, even when you’re dying.)

Things that energised him: Teaching his daughter to drive. Mentoring young employees. The early days at Meridian when the company was small enough that he knew everyone’s name. Solving complex operational problems. Building systems that actually worked.

Things that drained him: Board meetings. Quarterly earnings calls. Networking events. Golf with investors. (“I hate golf,” he confided. “Always have. But everyone assumed I loved it because I was good at it.”)

Moments he felt most alive: When he was solving problems that mattered to real people. When he was building something, not just managing it. When he was learning, not just performing.

Moments he felt most dead: Most of the last fifteen years.

The pattern was clear, even to someone pumped full of painkillers. Richard’s natural gifts—systems thinking, problem-solving, teaching—had been channelled into a role that utilised maybe 20% of what made him feel genuinely alive.

“I could have been a great teacher,” he mused. “Or an engineer working on infrastructure projects. Or started a company that actually solved problems I cared about. But I got seduced by the external validation of climbing the corporate ladder.”

The Course Correction That Never Came

Here’s where Richard’s story gets really heartbreaking. About ten years into his tenure as CEO, he’d started feeling restless. The initial challenge of turning around a struggling company had been replaced by the grinding routine of managing a successful one.

“I remember sitting in my office one Tuesday afternoon,” he said, “looking out at the city and thinking: ‘Is this it? Is this what I’m going to do for the next twenty years?’ I felt this… emptiness. Like I was living someone else’s life.”

That was his moment. His chance for what I call a “Purpose Pivot”—when life circumstances align to offer you a clear choice between continuing on autopilot or intentionally redirecting toward something more aligned with your authentic self.

But Richard didn’t have the tools to process what he was feeling. He didn’t have a framework for distinguishing between temporary dissatisfaction and deeper misalignment. He didn’t know how to evaluate whether his restlessness was pointing him toward something important or if it was just midlife malaise.

“I told myself it was normal,” he said. “Everyone gets bored with their job sometimes, right? I figured it would pass.”

Instead of investigating the feeling, he doubled down. Took on bigger challenges. Pursued more aggressive growth targets. Convinced himself that the solution to feeling empty was to achieve more, not to reconsider what he was achieving.

“I medicated my existential crisis with workaholism,” he admitted with a wry smile. “It’s socially acceptable addiction.”

Haunting Questions

In those final weeks, Richard became obsessed with questions he’d never allowed himself to ask:

What if I’d had the courage to change course when I first felt misaligned?

What if I’d defined success based on my own values instead of society’s expectations?

What if I’d prioritised becoming the person I wanted to be over becoming the person I thought I should be?

What if I’d understood that purpose isn’t something you find once and then forget about, but something you have to keep choosing, again and again, as you grow and change?

These weren’t just hypothetical musings. They were urgent, practical questions about how to live a life that feels meaningful from the inside, not just impressive from the outside.

“The tragedy,” he told me, “isn’t that I made the wrong choices. It’s that I never realised I was making choices at all. I thought I was just following the obvious path, but there were dozens of other paths I never even saw.”

The Legacy Situation

Three days before Richard died, he asked me something that I haven’t been able to stop thinking about:

“If someone else was living my exact life—same challenges, same opportunities, same pressures—but they had a clear sense of their authentic purpose, how differently would they have navigated it?”

It’s a profound question. Because Richard wasn’t fundamentally flawed or uniquely misguided. He was intelligent, capable, well-intentioned. He got trapped not by personal failings but by a cultural system that conflates external achievement with internal fulfilment.

How many of us are living versions of Richard’s story right now? How many of us are optimising for metrics that don’t actually matter to who we are underneath all our roles and responsibilities?

How many of us are climbing ladders without ever checking whether they’re leaning against walls we actually want to reach?

The Plot Twist

Here’s the thing that surprised me most about Richard’s story: despite everything, he wasn’t bitter. Regretful, yes. Wistful about roads not taken, absolutely. But not bitter.

“I had a good life,” he said. “It just wasn’t my life, if that makes sense. I lived the life I thought I was supposed to want instead of the life I actually wanted.”

In his final days, Richard did something extraordinary. He started reaching out to people—not to network or maintain relationships, but to apologise. To Jennifer for being absent. To employees he’d been harsh with. To friends he’d neglected.

But mostly, he started having conversations about purpose with anyone who would listen. Warning people about the seductive trap of external validation. Encouraging them to get clear about what actually mattered to them before they got too far down someone else’s path.

“If I can save even one person from living my life,” he said, “then maybe all of this wasn’t completely pointless.”

The Framework He Wished He’d Had

In our conversations, Richard and I developed what he called “The Deathbed Test”—a framework for evaluating life choices through the lens of what will matter when everything else falls away.

The Questions:

• If I was lying in a hospital bed looking back on my life, would I be proud of how I spent my time?
• Am I building something that aligns with my deepest values, or just something that looks impressive to other people?
• When I feel energised and alive, what am I doing? When I feel drained and empty, what am I doing?
• If I could design my ideal day with no external constraints, what would it look like? How far is my current life from that vision?
• What would I do if I weren’t afraid of other people’s opinions?

“These seem like simple questions,” Richard noted, “but they’re actually revolutionary. Because most of us never ask them. We just assume that if we’re successful by conventional metrics, we must be on the right track.”

The Two Paths Forward

Richard’s story illustrates something I see constantly in my work: there are two critical moments when people need support in aligning their lives with their authentic purpose.

The First Moment: When you’re feeling generally restless or unfulfilled but can’t quite put your finger on why. You know something’s off, but you don’t have clarity about what you actually want instead. This is what I call the “Purpose Pursuit” phase—when you need tools and frameworks to discover what actually energises you, what you value most deeply, and how to translate those insights into concrete life choices.

The Second Moment: When you’ve had some clarity about your purpose but life circumstances have knocked you off course, or when you’ve evolved as a person and your previous sense of purpose no longer fits. This is the “Purpose Pivot” phase—when you need support in course-correcting without throwing away everything you’ve built.

Richard never got support for either moment. He powered through the first with willpower and alcohol. He ignored the second entirely until it was too late to do anything but regret.

The Conversation We All Need to Have

Here’s what Richard taught me: the conversation about purpose isn’t a luxury for people who have their basic needs met. It’s not self-indulgent navel-gazing or privileged philosophical meandering.

It’s literally a matter of life and death. Not physical death, necessarily, but the death of your authentic self. The slow erosion of whatever makes you uniquely you.

“I succeeded at someone else’s definition of success,” Richard said, “and failed at my own life.”

We live in a culture that’s incredibly sophisticated about optimising for external metrics—productivity, efficiency, growth, achievement—but remarkably primitive when it comes to optimising for internal fulfilment. We have detailed frameworks for strategic planning in business but wing it when it comes to strategic planning for our actual lives.

We spend more time researching which car to buy than clarifying what kind of person we want to become.

The Gift in the Tragedy

Richard died on a Thursday morning in April. Jennifer was holding his hand. His last words, according to the nurse, were: “Tell people to figure it out sooner.”

But here’s the beautiful thing: Richard’s story doesn’t have to be your story. The questions that tortured him in his final weeks can guide you toward a different kind of life right now. The regrets that haunted him can become wisdom that liberates you.

Because the truth is, it’s never too late to ask the hard questions. It’s never too late to course-correct. It’s never too late to choose alignment over achievement, authenticity over approval, purpose over prestige.

But it’s also never too early to start.

Your 3 AM Moment

I’m willing to bet that something in Richard’s story resonated with you. Maybe you saw yourself in his early career trajectory. Maybe you recognised the feeling of climbing a ladder without checking whether it’s leaning against the right wall. Maybe you’ve had your own 3 AM moments of wondering whether you’re living your life or someone else’s expectations.

If so, you’re not alone. And you’re not stuck.

The difference between Richard’s story and yours is that you still have time. You still have choices. You still have the opportunity to align your external life with your internal truth.

But—and this is crucial—purpose doesn’t just happen. It requires intention. It requires tools. It requires support and frameworks and communities of people who understand that this work is not selfish but essential.

Whether you’re in the “Pursuit” phase—trying to get clarity about what you actually want—or the “Pivot” phase—needing to recalibrate after getting knocked off course—the work of aligning your life with your authentic purpose is both the most challenging and most rewarding thing you’ll ever do.

Richard spent his final weeks wishing he’d had the courage to ask the hard questions sooner. You don’t have to wait until you’re running out of time to start living the life that’s actually yours.

The only question is: what are you going to do with the time you have left?

If Richard’s story stirred something in you—if you recognise yourself in his journey or felt that familiar pang of “there has to be more than this”—you’re ready for the conversation about purpose. Whether you’re just beginning to question your current path (Purpose Pursuit) or you’ve lost your way and need to find it again (Purpose Pivot), the tools and frameworks exist to help you navigate toward a life that feels authentic from the inside, not just impressive from the outside. Because the most successful life isn’t the one that looks best on paper—it’s the one you’re proud to have lived when you’re looking back from your own hospital bed. The choice is yours. The time is now.