Wishing You a Regret-Free Winter Break 😁

Dear colleague,

This'll be my last article of 2024; thank you for reading and teaching right beside me this year. (This is the halfway mark of the eighteenth year of my teaching career. Just when I think I've got this job figured out, providence brings along a set of challenges that make it feel brand new. I'm tired and grateful and looking forward to time away from that bossy bell that runs the school week.)

As we go into break, I'm thinking about this idea of living with no regrets. As a middle-aged guy, it can be easy to go through the motions. This is what most folks do. The trouble is, going through the motions leads to regrets over time. This is what palliative care nurse Bronnie Ware's book The Top Five Regrets of the Dying: A Life Transformed by the Dearly Departed is all about.

The regrets she writes about are pretty straightforward. Below I'll list them (in bold) but also mention a thought or two that I have about each heading into this winter break. And remember: the stuff in bold below, that's from folks on their deathbeds reflecting back on their lives. This isn't middle-aged guy perspective; it's much more substantive than that.

1. I wish I had the courage to live a life true to myself, not the life others expected of me. If you're attending holiday parties, it's easy to run into folks who have expectations about you, opinions on how you should be living or working, and so on. The questions I'm asking this break are these: What do I expect of myself? What do I want my life to look like? I'm going to find some quiet mornings to write and pray about these things.
2. I wish I hadn’t worked so hard. I've got 17 days off of school once this Friday hits. I'll give myself three or four of those days to do work. Any work-related thoughts that intrude on the other 13-14 days, I'll write them in my journal and keep on with my life. The goal is presence over productivity. Easy to write, harder to do, possible to practice.
3. I wish I had the courage to express my feelings. For me this break, I want to focus on expressing feelings that are helpful, positive, true. Think of it as MGCs but outside the classroom and from my heart to someone else's.
4. I wish I had stayed in touch with my friends. This is probably the most convicting regret from Ware's whole book — at least for me. I'm bad at staying in touch with folks. But Crystal and I decided to use a few days before New Years to visit with old friends from our Baltimore days, and I'm grateful for the chance to practice the above points (not working so hard; expressing my feelings) with these old friends.
5. I wish I had let myself be happier. This one is pretty nuts because, too often, I forget that happiness is a choice. It goes back to that book I wrote about a couple days ago, 13 Things Mentally Strong People Don't Do. It reminds me of the experiment with zero alcohol I wrote and did an interview about this past fall. It was a choice to pause my drinking just over a year ago, and it's a choice that's led to a surprising increase in my overall happiness. Tiny example. But for this break, how could I choose to laugh more? Do more puzzles with Dean? Play more games with my kids? Ask more questions to my teenagers? Face my fears with hard relationships?

Lots of stuff to consider, right? This is the stuff we get to do, colleague. I pray your break is great and filled with blessings big and small.

Resting right beside ya,

DSJR