What Teachers Can Learn from The Top Five Regrets of the Dying
Mr. Alvarez ran into a former student at the grocery store, now well into her thirties with kids of her own, who thanked him for a comment he had made about her writing fifteen years earlier. He barely remembered saying it. Driving home, he thought about how many of his own college friends he had lost touch with over two decades of grading, coaching, and summer school, and how he always told himself he would reconnect once the school year calmed down, a season that never actually arrived. He also thought about the classroom lesson plan he still followed out of habit, long after it stopped exciting him the way it once had.
The whole book, compressed
This edition works through 4 core lessons — take them one at a time, not all at once.
What's different for your conditions
Tap whichever ones sound like you. Nothing here is sent or saved — it's just for your own noticing.
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The core lessons, applied to you
Teaching in a way that is actually yours
It is easy to keep running a lesson or a whole approach because it is familiar and expected, long after it stopped reflecting what actually excites you about the subject. A teacher who periodically checks whether their practice still fits their own values, not just the curriculum's expectations, tends to avoid a slow drift into going through the motions.
Curriculum requirements and standardized testing genuinely limit how much personal reinvention is possible in a given year.
Redesign one small piece of your teaching this term purely because it would excite you again.
The friendships that grading season crowds out
College friends, old mentors, and colleagues from an earlier school often fade not from any falling out but from years of grading, coaching, and summer prep leaving no space for anything else. The loss tends to go unnoticed until a chance encounter, like running into a former student, brings it back into focus.
The school year genuinely leaves little room for anything beyond the classroom during its most demanding stretches.
Message one old friend or mentor this week, no agenda beyond reconnecting.
Working hard versus staying honest about burnout
Long hours grading and planning can be genuine dedication to students, and they can also become a way of avoiding a harder truth about your own exhaustion or doubts about the profession. Both patterns build slowly, rarely announced as a single decision.
Some seasons, finals, report cards, genuinely require the extra hours, and that is not avoidance.
Tell one trusted colleague this week an honest thing about how the year is actually going for you.
The throughline beneath the routine
This book is not a research study, it is one caregiver's synthesis of what she heard repeatedly while sitting with people near the end of their lives. The regret beneath the others was that people had not let themselves be happy along the way, waiting for a break that kept getting pushed to next semester. For a teacher, that is worth sitting with honestly, not a fixed prediction of your own future regret.
Teaching in a way that reflects your own values can mean pushing against a curriculum or schedule you do not fully control. Reconnecting with old friends takes time the school year will always claim first. Being honest about burnout can unsettle a professional identity built on quiet endurance. These pulls tend to be sharpest exactly when the year is busiest.
Name one thing, honestly
- Does your current teaching practice reflect what excites you, or mostly what is expected and familiar? - Which friend or mentor from before this career have you let quietly fade? - Where have you called exhaustion normal instead of naming it honestly to someone?
Good. Now look back at the "Try this" line under whichever lesson feels most connected to what you just wrote, and treat that as this week's actual assignment — not all 4 at once.
The practices from this edition
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Run this for seven days
Tell one trusted colleague this week an honest thing about how the year is actually going for you.