Redeeming Regret: A Path to Grace and Growth | Beyond the Classroom
How Reflection, Repentance, and Redemption Transform Our Failures into Hope
I was recently thinking about the regrets I have as I reflect on leading Dakar Academy for ten years. I regret not being bold enough at first to say what needed to be said. I regret not making hard decisions quickly at times. I regret not always having the gentleness I desired in conversations. I try not to dwell there, but I do go there.
That process of reflection is very different from the sentiment expressed in a tattoo I saw recently, which simply read, “No Regrets.” While the idea may sound appealing, the truth is that regret, when approached rightly, can be a powerful tool for growth.
Regret, often seen as something to avoid because it is painful, is one of the most common emotions people experience — second only to love. Psychologists and researchers, including Daniel Pink in The Power of Regret, have even found that regret can significantly boost performance and improvement. In studies, participants who practiced “if-only” reflections after challenging tasks performed much better in subsequent attempts than those who avoided regret or focused only on what went well.
Properly managed, regret spurs growth, counteracting a cultural emphasis on unwavering self-confidence. In fact, a complete inability to feel regret is often associated with severe neurological conditions like Huntington’s and advanced Parkinson’s — reminding us that never feeling regret isn’t liberation but the loss of a God-given moral compass.1
However, the key is not to linger in regret or let it lead to self-condemnation. Rumination — dwelling obsessively on regret — almost always causes people to deteriorate in performance. We have all had the experience of ruminating because we did not do well on a test, perform well in a game, or go through a breakup with a loved one.
These moments, while deeply human, show how easily rumination can consume our thoughts and energy. We often believe that by thinking about something long enough, we can improve, but rumination rarely makes us think more clearly or perform better. Instead, regret should propel us to once again approach God, seeking His never-ending grace.
Similarly, in 2 Corinthians 7:10, the Apostle Paul contrasts “worldly grief” with “godly grief.” Worldly grief focuses on self — how the situation impacted me and how it makes me feel. It centers on personal loss, shame, or inconvenience, often leading to a cycle of self-pity or defensiveness.
In contrast, godly grief shifts the focus outward and upward. It acknowledges how our actions have impacted others, recognizing the pain we may have caused them. Even more importantly, it confronts how our actions have wronged God. This perspective leads to a deeper understanding of sin and the need for repentance, not just as a way to move past guilt, but as a pathway to restored relationships — with others and with God.
Godly grief — the kind sparked by healthy regret — leads to repentance and often a healthier new direction. It turns potential despair into a spark of hope, as regret opens the door for us to approach Christ for His grace once again.
Regret and sin become good news — not because sin is desirable, but because acknowledging our sin offers a pathway to transformation. Unlike psychological flaws we can’t fully control, sin can be repented of and forgiven. Repentance turns potential despair into a spark of hope. Especially as Jesus promises that when we trust him, all our efforts are never in vain.
This promise of hope and transformation resonates deeply in the Christmas story. At Christmas, we celebrate that Jesus came into the world not only to forgive our sins but to give us new hearts and new desires. Through Jesus, regret can be redeemed into a pathway for growth and renewal, showing us that our failures are not the end but an opportunity to draw closer to God and embrace His transformative grace.
In Christ, we discover that our past does not trap us, our failures, or the world’s brokenness. Jesus’s coming means we can move beyond a victim narrative, embracing a grace-filled life. Regret becomes a tool, not a trap.
As we reflect on our regrets, let’s see them as signposts guiding us to acknowledge our failings, seek forgiveness, and embrace the life-changing mercy found in Jesus. That is the true wonder of Christmas.
1 Pink, Daniel H. The Power of Regret: How Looking Backward Moves Us Forward. Riverhead Books, 2022.
Robb Warfield has over 25 years of experience as an educator, principal, and director across four countries. He holds a Master’s degree in School Administration, a Master’s of Arts in Education, and a Bachelor of Arts degree in History. Robb joined Dakar Academy as the principal of Central Campus in 2015, became the director in 2016, and has since led the expansion of the school, opening DA West in 2019, DA Co-op Campuses in Guinea in 2020 and Liberia in 2023, and DA South in 2022.