How Hard Is It? (A Teacher’s Rant Driving Him to Retirement)

Every once in a while I look around my workplace — a public school in Chicago — and ask myself a question that has become almost a mantra:

How hard is it?

Not in the philosophical sense.
Not in the “teens are complicated” sense.
I mean… literally… how hard is it to do the absolute simplest things?

Because lately, the gap between “this should be easy” and “apparently this is impossible” feels wider than the Grand Canyon.


1. The Master Calendar That Does Not Exist

Let’s start with the calendar — or rather, the lack of one.

My school does not have a shared, school-wide master calendar. That means I often have no idea when field trips are happening, when testing is scheduled, or when some random event is going to hijack half my class.

Imagine trying to run a class with structure and planning while operating in an administrative environment that seems allergic to… well… structure and planning.

And here’s the part that drives me nuts:

A shared calendar takes ten minutes to set up.
Google Calendar → Create → Share with staff → Done.

How hard is it?

Apparently very.


2. “What Can I Do to Raise My Grade?” (Asked With One Week Left)

Another classic:
Students approaching me a week before the end of the semester, asking what they can do to raise their grade.

Not in week two.
Not in week five.
Not even in week ten.

Week seventeen.

And the answer — the simple, painfully obvious answer — is always the same:

Do the work during the semester.

It’s astonishing how foreign that concept feels to many of them. We’ve created a school culture where deadlines are flexible, missing work can be made up months later, and every consequence can be negotiated.

So kids have learned that nothing actually counts until it’s too late.

But still… how hard is it to keep up with assignments as they come?

Harder than I thought, apparently.


3. Being Where You’re Supposed to Be

You’d think this one would be simple:

Be in your class, not your girlfriend’s class.
Be in Civics during Civics, not wandering into the gym.
Go where you’re scheduled to go.

And yet, every day I have students drifting in from hallways, from other rooms, from places they absolutely shouldn’t be — usually with an expression that says, What? Why is this a problem?

It’s not that the rule is complicated.
It’s that enforcement is inconsistent, consequences are rare, and many kids have learned that rules are more like suggestions.

So again:
How hard is it?

Too hard, it seems.


4. Why This Feels Like a One-Way Ticket to Retirement

The truth is, none of this would bother me if it were the result of complicated, unsolvable problems.

But these aren’t complicated.
These are the easy problems.
The low-hanging fruit.
The quick fixes.
The “we could have solved this in 2009” issues.

What wears me down — and what makes retirement look more attractive every day — is living in a system where:

  • the simple things don’t get done
  • the obvious things aren’t enforced
  • the preventable problems repeat endlessly
  • and the people who notice sound like the unreasonable ones

I’m not asking for perfection.
I’m not asking for reinventing the wheel.

I just want a calendar.
Students who do their work.
Kids who go to the class they’re assigned to.

How hard is it?

Hard enough, apparently, that I’m starting to think the answer might be:
Too hard for me to keep doing this forever.

 



This Week in Training – Week 11: Back on Track (Mostly)…

IMWI 2026: The Long Crawl to the Base Phase
(Recovering from turkey, travel, and general chaos — one workout at a time.)

Solid week, even if I missed two workouts. The important thing is I got back to it after the Thanksgiving dip. I’m starting to feel that rhythm again — the familiar soreness, the satisfaction of checking sessions off, and the creeping sense that I might actually be getting fitter.

Swim 🏊

  • Workouts: 1
  • Total Distance: 2,000 yards
  • Total Time: 41 minutes
  • Notes: Only one swim this week, where I missed a workout. Felt fine, though I was rusty and bored. The pool is my quiet place, but sometimes it feels like Groundhog Day with goggles.

Bike 🚴

  • Workouts: 1
  • Total Distance: 17.84 miles
  • Total Time: 1 hour
  • Notes: A one-hour Power Zone Peloton ride. It was a challenge, but I made it through. I’m sure my zones have slipped over the past year, but I stubbornly used the old ones anyway. Didn’t hit every minute perfectly, but I didn’t bail either. Win.

Run 🏃

  • Workouts: 2
  • Total Distance: 10.05 miles
  • Total Time: 1 hour 39 minutes
  • Notes: Both runs outside — cold air, steady pace, good energy. I love running in winter. There’s something about the quiet and the crunch of snow that makes it easier to keep going.

Strength/Other 💪

  • Workouts: None
  • Notes: Still nothing formal, though I probably should start mixing in some core and strength work before “base” sneaks up on me.

Relative Effort 📈

  • Total Weekly Effort: 541 (up from 411 over Thanksgiving, down from 552 before that)
  • Notes: Overall trajectory is trending upward again, which is what matters.

Reflections ✍️

Not perfect, but a solid rebound. I felt good this week and kept moving forward. The Power Zone ride reminded me what real effort feels like, and the runs helped shake off the post-holiday rust.

Next week will probably look similar, but I’m hoping to hit every planned workout. After that, things should ease up — no more after-school class twice a week, which means more flexibility and fewer excuses.

Goals for Next Week 🎯

  • Hit every scheduled workout.
  • Stay consistent with running — maybe stretch one a little longer.
  • Add a second swim (and try not to complain about it).
  • Keep building toward that elusive “base phase.”


Something Good Every Day — Memories…

Today’s good came from memories—specifically the silly or unexpectedly fond ones that pop up and tug you back to another version of yourself.

The first hit while I was watching a movie at work. Someone slammed down a phone to end a call, and I felt an immediate wave of nostalgia. I was never the “angry hang-up” type, but there was something satisfying about physically slamming a receiver onto a cradle. It had weight. It had oomph. People today will never know the catharsis of hanging up with authority. Now it’s just… tapping a red circle. Very civilized. Very boring.

The second memory arrived courtesy of an algorithm. YouTube recommended a tutorial series for a video game I barely played—but it transported me straight back to the COVID shutdown, when I spent two months skiing in Utah.

The first month I lived in this great little apartment that overlooked a mountain. End of the block, trailhead right there. On days I didn’t ski, I hiked or biked the trails. I had a nook where I could sit, read, and stare out at the ridgeline. I downloaded that video game and messed with it a little—not much, but enough that it’s braided into the memory of that view, that quiet. I also remembered the Thursday “live” online trivia nights with Bob and Sheila. Something small, but I miss that.

The second month I stayed somewhere less charming—no mountain view—, but it was attached to a coffee shop, which was its own kind of cozy. I’d teach in the mornings, then drive twenty minutes to Snowbasin, where by 12:30 I’d be clipping into my skis. Weekday skiing meant no lift lines. I’d ride down the mountain and ski straight onto the next chair. That kind of solitude-in-motion stays with you.

These were good memories, and I hope I make more like them—not all as goofy as landline-phone theatrics, but still. I’m at the point in life where I look back and think things were better when I was growing up in the ’70s and ’80s. The 90s and early 2000s weren’t bad either.  To be fair to myself, I’ve been able to appreciate and enjoy every stage of my life, though the 50-59 age group has been a lot more challenging.  Still, I’m sure when I’m 70 (if I can hold out), I’ll look back fondly on now, too.

Today, the good was remembered. And being grateful, I’ve had moments worth remembering.

It’s great to be alive.



Perfect Friday Winter Night

Martini…catalogues…dark/cold.



Something Good Every Day — Coming Home…

The last two days, going to work has felt like a chore. I’m over it. Walking into that building has taken more effort than I like to admit, and finding something “good” during the school day hasn’t come naturally. Some days the well feels dry.

But the good for today wasn’t at work.
It was coming home.

Home is peaceful right now. My wife, the pets, the familiar calm of the evening settling in. I’d say the kids, but they’re out of the house these days—though two will be back for a month over Christmas, and that will bring its own kind of good chaos.

Tonight we have ASL lessons early, but after that? We’ll have time. Time to read by the fire, or watch a Christmas rom-com, or play a game. Nothing flashy, nothing huge—just the kind of quiet, comfortable evenings I live for.

After-work nights are where the day finally exhales.
That’s the good for today.

It’s great to be alive.



Something Good Every Day — Dinner

Tonight’s “good” was dinner.

Not some gourmet masterpiece—Blue Apron did most of the heavy lifting—but still, I cooked it.

My wife had a long, chaotic workday, and the rest of her week is going to be just as bananas. Normally, cooking is something I do because… well, I do 95% of the cooking around here. It’s habit. Routine. A task to be crossed off before I collapse on the couch.

But tonight I put my mind in a different place. Instead of treating it like a chore, I treated it like a kindness. A small act to make her day a little softer around the edges.

I put on a fantastic playlist, let the music carry me, and cooked without rushing or resenting or watching the clock. Just chopped, stirred, plated, and felt good while doing it. When she walked in the door to a warm meal after a punishing day, it felt like I’d done something meaningful—even if it was simple.

Not every act of love has to be grand. Sometimes it’s dinner. Sometimes it’s mood. Sometimes it’s just deciding to do the same thing differently.

(And let’s be clear: this new mindset does not extend to picking up the clothes on my side of the bed. That’s a bridge too far.)

Good playlist, good food, good deed.

It’s great to be alive.



This Week in Training – Week 10: Oof, Thanksgiving….

IMWI 2026: The Long Crawl to the Base Phase
(A reminder that snowstorms and road trips are not part of any structured training plan.)

Oof, Thanksgiving. It did not end well — and not entirely my fault this time.

I started strong with a swim on Monday before we headed out of town. Got in two runs and some island biking while away, but the Midwest snowstorm torpedoed the weekend. Instead of flying back early Saturday and finishing strong, I spent 14 hours sitting in a car doing absolutely nothing. The only endurance event was my patience.  I lost that event.  It’ll be a funny story once my family starts speaking to each other again.

So no, not the week I hoped for. But it was a vacation week, and it is what it is.

Swim 🏊

  • Workouts: 1
  • Total Distance: 2,025 yards
  • Total Time: 40 minutes
  • Notes: Got this one done before traveling. Felt good to move, knowing the rest of the week might get messy.

Bike 🚴

  • Workouts: 3
  • Total Distance: 5.85 miles
  • Total Time: 38 minutes
  • Notes: Island riding — short, easy, mostly for fun. The scenery was better than the mileage.

Run 🏃

  • Workouts: 2
  • Total Distance: 10 miles
  • Total Time: 1 hour 42 minutes
  • Notes: Two solid runs early in the trip before the weather and travel schedule took over.  Plus, running along the ocean is always a nice change for me.

Strength/Other 💪

  • Workouts: None
  • Notes: Unless car-seat core tension counts.

Relative Effort 📈

  • Total Weekly Effort: [Not tracked this week, but probably “Low to Moderate Frustration” on the perceived exertion scale.]

Reflections ✍️

Not a great week, but not a total wash either. I did what I could around travel, weather, and long hours of sitting still. The important part is that I’m itching to get back into it — a good sign heading into the next stretch.

Goals for Next Week 🎯

  • Get back on top with consistent training across all three sports.
  • Aim for three solid weeks before a planned rest week over Christmas.
  • Rebuild rhythm and routine — the real victory after a disrupted week.

 



Something Good Every Day — Introduction

If I’m being honest, I tend to lean negative. It’s not that I walk around gloomy or cynical, but my brain has a talent for cataloguing what’s wrong, what’s broken, what’s irritating, and what’s disappointing. I even gratitude-journal every morning, and while that helps, I’ve realized I want something that comes after the day has happened—a way to end it on a note that reminds me there is still good everywhere if I pay attention.

So: a new project. “Something Good Every Day.”
Every evening I’ll write about one thing—something I saw, heard, read, or experienced—that was simply good. Not profound, not life-changing, not a solution to the world’s problems. Just something human, something hopeful, something that cuts through the noise.

The idea came to me right before we left for Thanksgiving break. I was walking down the street and saw two friends saying goodbye on the sidewalk. They had clearly just had breakfast or coffee together. They hugged, laughed, wished each other a warm Thanksgiving, and split off in opposite directions still smiling. That tiny moment stuck with me. In a world that feels like an endless scroll of Tumblr-drama, “going no-contact” announcements, and performative takes about everything under the sun, there are people out there who simply live their lives and enjoy each other. It lifted me more than it had any right to.

And then today’s “good” arrived while I was walking the dog.

Two houses down, a kid shot across the sidewalk on a sled like he was at the top of Vail. His dad had shoveled only half the front steps; the other half he had packed down into a tiny makeshift hill. Same with the sidewalk. Near the curb, he built a little snow ramp to stop the kids—not reckless, just thoughtful, and honestly kind of genius. The two kids were having the time of their lives sledding down those stairs. You could tell, even from down the street, that this would be one of those childhood memories that sticks forever.

Meanwhile, the four boys next door were all bundled up, playing in the snow, while their dad loaded them into the sled for a trip to Cricket Hill. Two dads, two sets of kids, a cold afternoon turned into something warm. Memories being made. Screens nowhere in sight. And maybe, just maybe, giving mom a well-deserved break.

That’s today’s good.

If I can find one moment like that each day—something simple, something real—I think it might tilt my perspective a little. Or at least remind me that the world isn’t as bleak as the algorithm wants me to believe.

It’s great to be alive.



This Week in Training – Week 9: The Turkey Trot Shuffle…

IMWI 2026: The Long Crawl to the Base Phase
(Still pre-base, still moving forward, still calling commutes “training.”)

Life got in the way this week, so I ended up one workout short. A few other sessions ran long, though, so it all balances out time-wise. The week wrapped up with a 10K Turkey Trot – not a race effort, as my pace made clear, but longer than my usual runs, so I’ll count it as a win.

Swim 🏊

  • Workouts: 1
  • Total Distance: 2,000 yards
  • Total Time: 39 minutes
  • Notes: This was the missing workout. I would’ve liked a second swim, but time didn’t cooperate. Felt fine in the water – need more of it.

Bike 🚴

  • Workouts: 3 (sort of)
  • Total Distance: 25.46 miles
  • Total Time: 1 hour 47 minutes
  • Notes: Mostly commuting rides – to work, back, and a round trip to packet pickup. Not “workouts” in the strict sense, but still time in the saddle, and it all adds up.

Run 🏃

  • Workouts: 2
  • Total Distance: 11.18 miles
  • Total Time: 1 hour 51 minutes
  • Notes: The week ended with the 10K Turkey Trot. I wasn’t racing, but it was nice to stretch the distance beyond my usual five miles. Felt steady throughout.

Strength/Other 💪

  • Workouts: None
  • Notes: I keep saying I’ll start yoga. Maybe this coming week will finally be the one.

Relative Effort 📈

  • Total Weekly Effort: 552 (up again from 534 last week)
  • Notes: Effort trending up even with one fewer session – proof that commuting miles and a 10K trot count for something.

Reflections ✍️

Even with life intruding, I’m happy with the week. I stayed consistent, ran a little longer, and logged solid time on the bike. The trend line is moving in the right direction, and that’s enough.

Next week will be tricky since I’m traveling, but I’ll swim before we leave and should have access to a cruiser bike. We’ll see how it goes. If I have to swap a workout for yoga, so be it — probably overdue anyway.

Goals for Next Week 🎯

  • Swim before heading out of town.
  • Get in any ride — even a cruiser counts.
  • Run when and where I can.
  • Substitute yoga if needed (and maybe pretend I planned it that way).


This Week in Training – Week 8: Burning Off the Static…

IMWI 2026: The Long Crawl to the Base Phase
(Still pre-pre-base, but at least it’s feeling like forward motion.)

Solid week. Everything clicked pretty well — good runs, good swims, and even some decent time on the bike. Progress.

Swim 🏊

  • Workouts: 2
  • Total Distance: 4,300 yards
  • Total Time: 1 hour 29 minutes
  • Notes: The second swim (Sunday) went a bit longer. I had that jittery, undifferentiated anxiety – the kind where it feels like every atom in my body is vibrating too fast. Swimming helps calm that. It’s one of the big reasons I exercise and why I feel better during marathon or Ironman training. I need that release.

Bike 🚴

  • Workouts: 2
  • Total Distance: 24.82 miles (15.82 outside)
  • Total Time: 1 hour 31 minutes
  • Notes: One Peloton ride (30 minutes) and one e-bike ride along the lakefront (1:01). The outdoor ride reminded me why I love this sport. The Peloton reminded me that convenience counts too.

Run 🏃

  • Workouts: 2
  • Total Distance: 10.16 miles
  • Total Time: 1 hour 41 minutes
  • Notes: Both runs felt strong and smooth – no significant soreness, which is a nice change.

Relative Effort 📈

  • Total Weekly Effort: 534 (up from 494 last week, and above my typical weekly range)
  • Notes: Despite the higher effort, I’m not feeling beat up. I’ll call that a win.

Reflections ✍️

It was a good week. Balanced, productive, and even therapeutic. I don’t feel achy, just calm — the kind of calm that comes from moving enough to quiet the static. This is the version of training I like: not obsessive, not burnt out, just steady work and a clearer mind at the end of it.

Goals for Next Week 🎯

  • Keep the swim consistency going.
  • Continue building the bike volume.
  • Hold steady on running — solid, not strained.
  • Stay in motion, stay sane.
  • Strong week before I have to adjust things for Thanksgiving vacation.