The feeling of guilt is real. It’s like an unbearable weight, pressing down on your chest, making it hard to breathe, hard to focus, and sometimes, hard to even function. As leaders, we are often faced with situations where decisions must be made quickly, and sometimes those decisions leave us feeling like we could’ve done better, should’ve done something else, or would’ve if we had the chance. These regrets can weigh us down, leaving us trapped in a cycle of self-doubt and reflection that, if not handled properly, can hinder our progress as leaders.
I often think of the 1994 Disney movie The Lion King. There is a scene where young adult Simba encounters Rafiki after being away from Pride Rock for years. Rafiki tells Simba that whatever happened doesn’t matter because it’s in the past. Simba disagrees with Rafiki, saying that the past still hurts. Rafiki then hits Simba on the head with his rattle stick. When Simba asks, “What did you do that for?” Rafiki simply responds, “What does it matter? It’s in the past.”
Like Simba, many leaders carry the weight of their past decisions, allowing regrets to hold them back from their future success. It’s easy to get caught up in the should’ve, would’ve, could’ve of leadership. But, just like Simba had to realize, holding on to past mistakes does nothing for your future. The ability to forgive yourself, to learn, and to let go of the past is essential to moving forward with confidence and purpose.
In a world where leadership is scrutinized more than ever, these feelings of regret are often amplified by the sheer pressure of expectations, both external and internal. However, there is good news: Healing and moving forward is possible, and with the right tools, any leader can learn to manage their regrets and channel them into opportunities for growth and transformation.
One of the biggest challenges for leaders is learning to forgive — not just others, but themselves.
The Weight of Regret in Leadership
Regret is not an uncommon emotion in leadership. A study by the American Psychological Association (2020) found that 70% of leaders admitted to experiencing some form of regret in their careers, whether related to missed opportunities, tough decisions, or strained relationships. Yikes! This regret can lead to feelings of guilt, stress, and anxiety, which in turn can affect decision-making, team morale, and overall productivity. And honestly, who needs the additional stress? Like we don’t have enough to worry about already.
Leadership, by nature, involves making tough decisions that don’t always have clear right or wrong answers. Whether it’s deciding to let an employee go, choosing between two equally important projects, or navigating office politics, leaders often face decisions that leave room for second-guessing and self-doubt. While this is normal, it’s critical that leaders learn to manage these feelings rather than let them take over. I had one job as a leader in which I had to fire staff my very first day of employment. Talk about stress.
Each decision, whether right or wrong, gives us the opportunity to reflect, grow, and become better leaders.
The Importance of Life Lessons
Every decision we make as leaders comes with the potential for both success and failure, but more importantly, every decision provides a lesson. John Maxwell, a renowned leadership expert, once said, “Sometimes you win, sometimes you learn.” Leadership is a journey, not a destination. Each decision, whether right or wrong, gives us the opportunity to reflect, grow, and become better leaders.
In many cases, what feels like a failure is actually a lesson in disguise. It is through mistakes and missteps that we build resilience and wisdom. Research from the Center for Creative Leadership (2022) shows that leaders who embrace a growth mindset — the belief that abilities can be developed through dedication and hard work — are more successful in overcoming challenges and bouncing back from mistakes.
Think about some of the most admired leaders in history — Abraham Lincoln, Steve Jobs, Oprah Winfrey — they all faced significant challenges and setbacks in their leadership journeys. Yet, they didn’t let their mistakes define them. Instead, they used them as stepping stones to success. Leadership is not about never making mistakes; it’s about learning from them and growing stronger as a result.
Forgiveness: For Others and Yourself
One of the biggest challenges for leaders is learning to forgive — not just others, but themselves. As leaders, we often hold ourselves to a higher standard than we hold anyone else. We expect perfection, and when we inevitably fall short, we are quick to criticize ourselves harshly. It is a terrible and unproductive cycle. However, true leadership requires self-compassion.
Harvard Business Review (2021) notes that self-compassion is critical for effective leadership. Leaders who practice self-compassion are more likely to recover from setbacks, maintain their well-being, and inspire their teams to do the same. By learning to forgive yourself, you create space for healing and growth.
Forgiving others is equally important. Holding onto resentment or anger towards a colleague, employee, or superior only creates a toxic work environment. When people feel safe to make mistakes and learn from them, the organization as a whole becomes more innovative and resilient.
Let go of the mistakes, the regrets, and the “what ifs” that are holding you back.
Healing Takes Time: Have Grace for Yourself
Healing is not a one-time event; it’s a process, and as with any process, it takes time. As a leader, it’s important to have grace not just for others, but also for yourself. Understand that you are human, and humans make mistakes. What’s more important is what you do after those mistakes. Do you learn from them? Do you take accountability? Do you make efforts to improve?
It’s easy to dwell on past mistakes, but it’s far more productive to use them as lessons for future decisions. Each day brings a new opportunity to be better, to lead more effectively, and to make a positive impact on those around you.
Tomorrow is Another Day
The beauty of life is that each day is a new opportunity. If you’re blessed with another day, make the most of it. Holding on to the regrets of the past will only weigh you down and prevent you from reaching your full potential. Instead, focus on the present and what you can do today to improve.
In the famous Disney movie Frozen, Elsa sings the now-iconic line, “Let it go.” While it might seem like a simple children’s song, the message is powerful. Let go of the mistakes, the regrets, and the “what ifs” that are holding you back. Focus on what you can control and take proactive steps towards becoming the leader you know you can be.
Believe in Yourself
At the end of the day, the most important thing you can do as a leader is believe in yourself. No one else is going to believe in you if you don’t believe in yourself first. Confidence comes from within, and when you exude confidence, it inspires those around you to have faith in your leadership.
If you’re struggling with the weight of leadership regrets, remember that you’re not alone. Every leader faces challenges, and every leader makes mistakes. What sets great leaders apart is their ability to bounce back, learn from their mistakes, and continue moving forward with grace and determination.
At American Management and Leadership by Design, we believe in empowering leaders to move past their regrets and embrace their full potential. Our executive leadership coaching is designed to help you get back on track, find your center, and develop a clear action plan for success on your own terms. Contact us today to learn how we can support your leadership journey.
📲 Scan the QR code or visit our website to book a consultation with Dr. Andrea Diese and take the first step towards reclaiming your leadership journey. 🌟
#Leadership #ExecutiveCoaching #LeadershipDevelopment #LetItGo #RegretManagement #WorkplaceCulture #SelfCompassion #GrowthMindset #LeadershipLessons #AskDrAndrea #LeadershipVisibility #AMLD #AMLDLeadership #LeadershipSuccess
🔽🔽🔽
American Management and Leadership by Design – We Fix Businesses and Strengthen Leadership 💼💪🏽
