The lessons learned—and regrets revealed—towards the end of the lives of history’s greatest founders

Founders are often celebrated for their vision, determination, and achievements. ?But as their journeys wind down, their reflections often reveal more than just lessons—they also uncover regrets.? For many of history’s greatest founders, the end-of-life perspective sheds light on what truly mattered and what they wish they had done differently.

The biggest regret shared by many of these influential figures? ?Neglecting relationships—whether with family, friends, or themselves—in their relentless pursuit of success.

Here’s what we can learn from the lessons and regrets of history’s greatest founders:

1. The true measure of success is impact, not wealth

Andrew Carnegie, the steel magnate, spent his later years giving away the fortune he had spent decades amassing, famously stating, “The man who dies rich dies disgraced.” ?Despite his towering success, Carnegie recognised that wealth itself held little meaning unless it was used to uplift others.

Regret: like many industrialists of his time, Carnegie often put business above personal connections.? His later philanthropic work was, in part, an attempt to address this imbalance.

Lesson: wealth and success are hollow if they don’t contribute to a larger purpose or enrich the lives of others.

2. Neglecting relationships is the greatest regret

In his final days, Steve Jobs reflected on his extraordinary career and its cost.? He noted, “The wealth I have won in my life I cannot take with me.? What remains are only memories of love and relationships.”? While he transformed the world with Apple, he expressed regret over time lost with loved ones.

This regret echoes the findings of the famous Harvard Study of Adult Development, which revealed that the quality of relationships—not professional achievements—determines long-term happiness and fulfillment.

Lesson: success is fleeting; the connections you build with others endure far longer.

3. Failure is a teacher, but balance is key

Thomas Edison spent much of his later years reflecting on his experiments and tireless work ethic.? While his perseverance gave the world incredible innovations, his family life suffered greatly.? Despite his achievements, Edison’s relentless focus on work created distance from his loved ones.

Regret: focusing so single-mindedly on success that personal relationships and self-care were neglected.

Lesson: failure and hard work are vital teachers, but success becomes hollow if it comes at the expense of balance and well-being.

4. A mission is bigger than its founder—but don’t forget yourself

Walt Disney, towards the end of his life, emphasised creating a legacy that would outlive him.? He famously said, “Disneyland will never be completed.? It will continue to grow as long as there is imagination left in the world.”? Yet Disney also faced health issues exacerbated by his unrelenting work ethic.

Regret: pushing himself to the limit without prioritising personal health and relaxation.

Lesson: building something bigger than yourself is noble, but self-care is essential to sustain your mission.

5. Balance ambition with life’s fragility

Benjamin Franklin, known for his civic contributions and wisdom, spent his later years emphasising the importance of balance.? While his professional achievements were vast, he also expressed regret about neglecting family in his younger years, particularly his relationship with his son.

Lesson: life’s brevity should inspire balance—not just ambition.? Reflect often to ensure your actions align with your values.

The common thread of regret: relationships, health and balance

Across these stories, one thread ties their regrets together: relationships, health and balance. ?Founders who achieved extraordinary heights often admitted neglecting personal connections, health, or moments of stillness in their pursuit of greatness.

The takeaway for today’s leaders and entrepreneurs is clear:

• Nurture relationships.? Time spent with loved ones is never wasted
• Seek balance.? Ambition is powerful, but it should not come at the expense of health and well-being
• Define your own success.? True fulfillment lies in alignment with your values, not just external accolades.

Final thoughts

The lives of history’s greatest founders serve as both inspiration and cautionary tales. ?Their lessons remind us that success is not just about what we build, but also how we live—and who we live it with.

As you navigate your own path, ask yourself: What will truly matter when you look back on your life?? Are you building something that enriches both your legacy and your present?

History’s founders have shown us the way.? Let’s learn from their lessons—and their regrets.?