Dear colleague,
We're well into the school year now, and if you're anything like me, you've maybe not done it all perfectly. I mean, SUPER close to perfectly, sure… but not quite. Once in awhile, you find yourself filling up your coffee, looking around your classroom, and thinking, “Man, I wish I had….”
Perhaps it's a student interaction you could have handled better or a colleague relationship that's gone off the rails. Maybe it's that new strategy you intended to try but haven't yet. Or it might be something deeper, like a missed opportunity to truly see a struggling student or a moment when you chose efficiency over humanity.
Today's article is an invitation to take a look at those with fresh, keen eyes. Because regrets, some argue, are less a sign of failure than they are an indication of wisdom.
Dan Pink, in his 2022 book The Power of Regret, makes the compelling case that we've got regret all wrong. That whole “no regrets” mentality, according to him, is both unrealistic and counterproductive. In his survey of over 24,000 people across 110 countries he actually found that regret, when rightly used, can become one of our most powerful tools for growth and improved decision-making.
In his survey study, Pink found that 83% of people regularly look back and wish they had done something differently. This huge majority, Pink argues, demonstrates that regret isn't a character flaw but is instead a feature of being human.
Pink's Four Types of Regret
Pink identifies four core categories of regret that appear across cultures and contexts, and they translate well into our work as educators:
- Foundation Regrets = the basics we didn't tend to. Not establishing clear routines. Skipping that parent phone call. Letting dust accrue on our MGC clipboard. Letting grading pile up until it felt insurmountable.
- Boldness Regrets = the risks we didn't take. That innovative project we wanted to try. Getting Pop-Up Debates going. The necessary but difficult conversation with a colleague. The chance to speak up in the meeting.
- Moral Regrets = when we took the low road instead of the high road. The time we were dismissive of a student's question. When we chose convenience over what we knew was right for kids. When we used sarcasm to “handle” a behavior problem.
- Connection Regrets = the relationships we didn't nurture. The student whose name we know but who is still a stranger. The colleague who was clearly struggling, but we were too busy to talk.
When I take an honest gander at the last few months, small vignettes flash through my mind. I can check all those boxes.
How This Connects to Student Motivation
And that all got me thinking about how well the connects to the Five Key Beliefs methodology in The Will to Learn. Our regrets as educators often cluster around moments where we failed to cultivate the Five Key Beliefs with our students:
- Credibility: Times when we weren't fully present or prepared, sending signals that we didn't care about our craft
- Value: Lessons that felt disconnected from anything meaningful, leaving students wondering why any of this mattered
- Effort: Moments when we didn't Woodenize a learning behavior or didn't help students make the connection between their work and their growth
- Efficacy: Times when we implied that grades = success or didn't take the 10 minutes to unpack outcomes after a test
- Belonging: Moments where a student clearly felt left out and we didn't do anything; kids who failed in public despite our best efforts and scaffolding
Again: I check all those boxes. This job's got a lot of breadth and depth to it, and that pretty much guarantees that there are times where we'll miss the mark.
According to Pink, regrets like this are actually helpful. Why? Because they guide us toward how to improve the quality of signals we're sending.
The Gift of Mid-Year Regrets
Unlike resolutions in January, mid-year regrets come with built-in wisdom. We've been in the classroom long enough to see patterns. We know our students now. We understand again, in our bodies, the rhythm of our school.
Theory detached from practice? That was summer stuff. Now we're in the spot where the rubber of theory meets the asphalt of reality.
Pink suggests a simple three-step process for transforming regret into forward motion:
- Relive it briefly (meaning think on it, but don't ruminate).
- Reframe it as a learning opportunity.
- Extract the lesson and apply it going forward.
My Questions to You
As we careen or coast or race to the winter holidays, here are some questions worth pondering:
- What's one student interaction you wish you could have handled differently? What belief (Credibility, Value, Effort, Efficacy, Belonging) might have been undermined?
- What's one teaching risk you've been avoiding? What would boldness look like in your classroom?
- When have you chosen the easier path instead of the right path? What would moral courage look like with your students?
- What relationship — with a student, colleague, or parent — have you let drift when you could have invested in connection?
And before I close, let me be clear on something: taking this positive spin on regret doesn't mean it doesn't still feel bad. Pink found that it's actually normal to feel bad about our regrets. 24,000 people or so basically said the same thing: regret is not fun.
It feels bad.
So, we may as well let the bad feeling do something good for us tomorrow.
The central trick, I think, is in doing the things Pink recommends at the heart level.
- Our regrets don't define us. We're not our jobs. We're not our performance.
- Next month is a new month of school. The school year's not done.
- The fact that we regret belies a wisdom that we have, the values we hold, the things that called us to teaching in the first place. Are they big and heavy sometimes? Yes. But I'd rather have these things and have to process regrets than not care and live superficially.
The path to the head truly does go through the heart. And sometimes, the heart speaks loudest through the things we wish we had done differently.
Regretting some stuff right beside you,
DSJR
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