Lessons from 25 Years in Leadership: What I'd Do Differently Now

After more than 25 years in leadership across the tech and construction industries, I’ve had the privilege of building enterprise products, guiding global teams, and mentoring leaders through periods of rapid change.

It’s been rewarding, but not without hard lessons. Leadership, like life, is a journey of trial and error. Looking back, there are things I would do differently. These reflections now shape my work as an executive coach, helping midlife professionals and leaders avoid the pitfalls I faced and embrace healthier, more fulfilling definitions of success.

Here are the five biggest leadership lessons I’ve learned:

1. Success Without Joy Isn’t Really Success

Many leaders equate promotions, income, and recognition with fulfillment. I did too. But one of the greatest lessons of leadership is this: external success doesn’t guarantee inner satisfaction. If I could start over, I’d focus more on aligning my work with joy, purpose, and energy, not just achievement.

2. Invest More in People Than in Processes

I spent years designing systems and processes to drive efficiency. But the breakthroughs that mattered most always came from people. Mentoring, coaching, and empowering others delivered far greater impact than any new workflow. Leaders who prioritize people over process create lasting cultures of trust and innovation.

3. Don’t Ignore Burnout

Burnout is one of the most dangerous and overlooked challenges of leadership. Like many executives, I treated exhaustion as proof of commitment. The truth is, ignoring burnout drains creativity, resilience, and relationships. Today, I help leaders recognize early warning signs and treat rest as a strategic investment in performance and well-being.

Don't Ignore Burnout

4. Lead With Curiosity, Not Certainty

In my early career, I believed leaders needed to have all the answers. Over time, I realized that the best leaders ask the best questions. Curiosity unlocks creativity, builds stronger teams, and inspires more innovative solutions than certainty ever could.

5. Redefine Success Along the Way

What motivates you at 30 may not be what drives you at 50. One of the most powerful leadership lessons is to regularly redefine success. Ask yourself: What does success mean to me now? Pausing to realign your goals prevents stagnation and ensures your career evolves with your values.

Looking Forward: Leadership Growth and Reinvention

I don’t regret the journey, every step taught me something valuable. But if I could go back, I’d focus less on chasing external validation and more on aligning with joy, people, curiosity, and balance.

Today, through my coaching practice, I guide leaders through this same process of reflection and reinvention. I help professionals pause, reassess, and consciously design their next chapter, whether that’s advancing their leadership, avoiding burnout, or pivoting toward something entirely new.

Because leadership isn’t just about hitting targets or scaling teams. It’s about creating a career and life that feel as successful on the inside as they look on the outside.

👉 If you’re a leader at a crossroads, maybe it’s time for your own reset. Book a free Clarity Call and explore what your next chapter could look like.