Leadership Is Like Painful Experience: Lessons Learned the Hard Way
Experience alone doesn’t make us wiser it often leaves us wounded. In this post, Dr. Marion Mouton explores why painful experiences are not the best teachers unless leaders intentionally reflect on them. Drawing from research in leadership, adult learning, and organizational development, he unpacks how reflection transforms scars into strategies and mistakes into momentum. Using the framework of Educate, Empower, Equip, this article offers practical ways for leaders to turn challenges into growth, build cultures of psychological safety, and ensure that no pain is wasted.
9/13/20254 min read
During my first principalship at Sunrise McMillan, I believed that experience alone would make me a better leader. I thought that if I simply endured enough storms, survived enough difficult meetings, or handled enough crises, I would eventually arrive at wisdom. What I discovered was far more sobering: experience is not the best teacher. It is the most painful. The true teacher is reflection. Without it, pain only lingers as scars, repeating itself in different forms.
Kolb’s Experiential Learning Theory shows that adults do not grow significantly from experience alone. In fact, studies suggest we retain less than half of what we go through unless we intentionally reflect, analyze, and apply what we’ve learned (Kolb, 1984). Research on deliberate practice supports this growth doesn’t come from time spent, but from targeted reflection and adjustment (Ericsson, Krampe, & Tesch-Römer, 1993).
Experience has a way of humbling leaders. It doesn’t wait for you to be ready, and it rarely arrives wrapped in comfort. It teaches through sleepless nights, broken trust, failed initiatives, and the sting of words you wish you could take back.
But experience by itself is just pain. Too many leaders wear their scars like trophies without ever asking, What should I have learned? Pain becomes wisdom only when we pause to reflect. Reflection is the bridge that carries us from survival to growth.
Without reflection, failure repeats itself.
With reflection, failure becomes feedback.
Without reflection, pain makes us bitter.
With reflection, pain makes us better.
Schön (1983) called this the work of the “reflective practitioner” leaders who intentionally step back from action to consider meaning, implications, and future practice. Without reflection, leaders risk what Argyris (1991) called single-loop learning repeating cycles without questioning the underlying causes. With reflection, they move into double-loop learning transforming not only actions but beliefs and systems.
This is why the strongest leaders don’t just collect experiences; they evaluate them. They create rhythms of reflection through journaling, debriefing with mentors, or walking their team through after-action reviews. They take the sting of mistakes and turn them into strategies for success.
Educate:
Leaders must first understand that experience alone is not enough. Education begins by teaching ourselves and our teams that pain only becomes progress when it is reflected upon. Provide clarity around this truth: failure is not final, and mistakes are not endpoints. By teaching the “why” behind reflection, you help your team see that learning from pain is not about punishment it ’s about purpose (Brookfield, 1995). Leaders can use professional readings, reflective discussions, or case studies to illuminate how others have transformed setbacks into stepping stones.
Empower:
Once people understand the value of reflection, they must feel empowered to practice it without fear. Too often, organizational cultures treat mistakes as career-ending events. True empowerment means creating safe spaces where staff can admit missteps, analyze them openly, and explore better paths forward (Edmondson, 1999). Empowerment is also about shifting the mindset: leaders can say, “This was painful, but what can we gain from it?” instead of “This was painful, and that’s the end of the story.” By modeling vulnerability sharing your own hard lessons you give permission for others to turn their scars into strength (Brown, 2018).
Equip:
Education and empowerment are meaningless without tools. Equip your team with structured practices that transform raw experience into actionable insight. This could include:
After-Action Reviews: A simple three-question process: What went well? What didn’t? What will we do differently? (U.S. Army, 2011).
Reflective Journaling: Encourage leaders and teachers to capture lessons learned weekly, then revisit them during planning sessions (Moon, 1999).
Mentorship and Coaching: Pair less experienced leaders with mentors who help them process painful moments with perspective (Kram, 1985).
Red Team Thinking: Use structured frameworks that test assumptions and expose blind spots before repeating mistakes (Bryce Hoffman, 2017).
Equipping is about giving people strategies to do more than just endure difficulty it’s about helping them extract meaning and apply it consistently.
Communication Clarity and Consistency
Be clear with your team: we do not glorify mistakes, but we refuse to waste them. Communicate consistently that challenges are opportunities for reflection, and reflection is what transforms pain into progress. Model this by being transparent about your own lessons learned showing them that leaders don’t just experience, they evaluate.
Final Thought
Every leader will face painful experiences. That’s unavoidable. The question is whether those experiences remain wounds or become wisdom. Pain alone doesn’t make us stronger. Reflection does.
"Experience is not the best teacher; evaluated experience is." – John Maxwell
Call to Action
Choose one painful leadership moment from your past year. Instead of letting it sit as a scar, revisit it with purpose. Write down what happened, what you learned, and how you will lead differently because of it.
Three Reflective Leadership Questions
Am I simply enduring experiences, or am I extracting wisdom from them?
How do I model reflection so my team sees it as strength, not weakness?
What structures can I create to ensure that mistakes are always turned into momentum?
Journaling Prompt
Think about the most painful leadership experience you’ve had. What wound did it leave, and how can you transform that wound into wisdom by reflecting on it today?
References
Argyris, C. (1991). Teaching smart people how to learn. Harvard Business Review, 69 (3), 99–109.
Brookfield, S. D. (1995). Becoming a critically reflective teacher. Jossey-Bass.
Brown, B. (2018). Dare to lead: Brave work. Tough conversations. Whole hearts. Random House.
Edmondson, A. (1999). Psychological safety and learning behavior in work teams. Administrative Science Quarterly, 44 (2), 350–383.
Ericsson, K. A., Krampe, R. T., & Tesch-Römer, C. (1993). The role of deliberate practice in the acquisition of expert performance. Psychological Review, 100(3), 363–406.
Hoffman, B. (2017). Red teaming: How your business can conquer the competition by challenging everything. Crown Business.
Kolb, D. A. (1984). Experiential learning: Experience as the source of learning and development. Prentice Hall.
Kram, K. E. (1985). Mentoring at work: Developmental relationships in organizational life. Scott, Foresman.
Maxwell, J. C. (2018). Leadership gold: Lessons I’ve learned from a lifetime of leading. HarperCollins Leadership.
Moon, J. A. (1999). Reflection in learning and professional development: Theory and practice. RoutledgeFalmer.
Schön, D. A. (1983). The reflective practitioner: How professionals think in action. Basic Books.
U.S. Army. (2011). The after action review (AAR) in training and combat. Department of the Army Field Manual FM 7-0.