November 30th, 2025

 Yesterday wasn’t just a winter wonderland in Chicagoland, it was the annual Shepley CTA Christmas Train ride.

This year it was just the Oldman and his two boys. Hazel skipped out, tucked deep in that preteen “Dad-is-embarrassing” phase. PopPop and Grampa Don rode along in spirit, and I’ll admit there was a moment when that hit me square in the chest.

The snow gave the day a magical touch, and per Don Shepley tradition, the lessons started early. The drive to Harlem/Lake was part defensive-driving class, part master class on dealing with idiots who still drive like the roads are bone-dry. Some people will never learn that snow doesn’t lie.

Up on the platform, young families bundled up with strollers, all waiting to get their picture with Santa. We never waited in that line when my kids were little. We always went to the real star of the day, the motorman. Santa may have a sleigh, but it’s the guy driving the L who is the true hero on CTA Christmas Train Day.

After the engineer come the elves. CTA employees dressed up, handing out buttons and candy canes, smiling like they mean it. These are the real celebrities. We found Mr. Carr, the motorman who has been in most of our photos over the years. He said the boys were giants now, asked where Hazel was, and noticed again that there wasn’t a grandfather with us this year. That is what you get when you build a relationship with a class act.

George chatted up a CTA elf while we waited. At the end of their conversation, the elf told me the CTA was hiring, and that my son ought to apply. “His knowledge of the lines and equipment is impressive,” he said. I told him George was neurodivergent. The elf didn’t blink: “We work with several George’s already.” That meant more than he knew.

I thanked him for planting that seed with my son. I would be honored if one day George worked with Mr. Carr and colleagues who took time on their day off to spread joy to the world.

When the train pulled out toward the Loop, the city was covered in a blanket of white. We stopped at the station near my Oldman’s old house. It felt like he stepped on board right then and there. Fritz asked why I was smiling with wet eyes. I told him, “Your Grampa Don just got on at Ridgeland.” Fritz shrugged: “You always say heaven’s closer than Oak Park.”

The train packed in, riders soaking in the lights and music, faces glowing like they were seeing magic for the first time. It reminded me of the first time the Oldman and I rode it back in the nineties on the old Congress line. Just me and my dad, much like this year. A father with his son creating lasting memories.

As we entered the Loop, the crowd thinned. By the time we left the last downtown stop, it was just a handful of CTA elves, a few Black people heading home to the Southside, a couple Orientals going to Chinatown, and the Shepley men. It was peaceful and warm creating a small pocket of quiet in a loud world.

The Christmas journey arrived at our turnaround station. George sprinted down the platform at 35th to thank Mr. Carr one last time. From his window at the front of the train he yelled “See you next year! Bring Hazel!” through the snow and wind. That moment slowed us just enough that we missed the northbound ride home. The doors shut and that warm train was gone. Now we were stranded on an exposed platform near Comiskey Park, De La Salle, and IIT with the wind slicing right through us. The next train was in twenty minutes.

I wasn’t thrilled, but George needed that last goodbye. So, we waited under the heat lamp. That was when an older man, beaten and tired by life asked if I could help him get food and water. I turned away so he couldn’t see my wallet, then slipped him a couple bucks. We exchanged a “God Bless” and he wandered off into the swirling snow.

I didn’t give him money to feel noble. I didn’t do it for an audience. I did it because my boys were watching. They saw the street smarts and the humanity, two things Chicago demands in equal measure.

I asked if they were cold. “Kind of, Dad.” I told them when the train comes, we will go home to Riverside, to heat and dinner. That man was staring down a storm that could kill him. One storm is an inconvenience for us and a possible death sentence for someone else. That was a lesson no classroom teaches.

Our train finally arrived and just like that, we went from holiday joy to brutal reality. Litter on the floor. Smell of urine. A crack pipe lit in the corner. Four young Black kids laughing at the junkies, because that’s their normal. Fritz pulled out his phone, suburban innocence on display. George looked at him and said, “Put it away. Head on a swivel.” That’s the autism I love—straightforward, observant, unfiltered and correct.

At Roosevelt, a street woman shoved her shopping cart onto the car.

This is Chicago.

Not a brochure.

Not a Hallmark card.

Not tourists sipping hot wine at Christkindlmarket.

This is the real city and I was glad... yes, glad that the boys saw both sides. You don't plan these lessons. Life hands them to you when you pay attention.

Back in the neighborhood, George asked if we could go to PopPop’s McDonald’s. It was where we used to go whenever he was with us. Last time he was there, his nose was running like a busted hydrant; I grabbed him a stack of napkins as we sat and ate Big Macs together. Yesterday, sitting there without him, my eyes filled again. I missed him. I missed the joy he received spending time with his grandchildren on the train.

We got home and the boys disappeared to their rooms, silent and spent. A day of magic, snow, family, and hard truth will wipe out even the toughest kid. The CTA Christmas Train delivered again.

I’ll keep taking this ride every year. Riders will come and go. I know George will probably always be my constant. Someday I may ride alone and someday the train will leave without me. I will be with Grampa Don and Pop, watching to see if the lessons we passed down are still being lived.

Okay Chalkheads... shovel smart, fill the crockpot with something that smells like love, and hold tight to the person who fits your jigsaw.

End December with gusto and astonishment.

PopPop with the Shepkids on one of his last CTA trips.

November 29th, 2025

 The snow is gently falling on Chicagoland this morning, and it won't stop anytime soon.

It is our first test of the season. The kind that checks your patience more than your muscles. Because around here, winter doesn’t win, it just takes its turn.

Joni had it right... you can look at snow from both sides. Today’s storm can be a gift. It will moisture the fields need, a blanket for the earth, a fresh coat that makes even the ugly parts of Chicago look magical. It can be an excuse to feel a little joy, to go sledding, cross-country skiing, or even skitching like we did when we were young and stupid.

Or

You can take the other angle. You can gripe about the roads, the procrastinated snowblower, the salt chewing up your car, or the fact that every shovel in Cook County feels like it wants to send you into cardiac arrest. It’s all there if you want to see it in a negative way.

But today, I’m choosing the better side of the coin. I am taking the beauty. This snowfall sets the stage for December. A perfect opening act for Christmas lights, warm houses, and deeper breaths.

If I’m feeling ambitious and it isn't canceled, I might hop on the CTA Christmas Train. If I feel lazy, I will stay inside and decorate. Either way, I should probably grab some eggnog and brandy before the shelves look like Sox Park during a bad season.

Vivaldi’s Winter is already playing in the background, the first pot of coffee is percolating, and Big Al, the French Algerian, is whispering the truth we all forget:

“In the depth of winter, I finally learned that within me there lay an invincible summer.”

So feel the warmth, Chalkheads.

Step outside and taste the November snowflakes.

November 28th, 2025

 Hazel had her project boxes out, building whatever twelve-year-old girls build.

You know the drill... glitter, glue, scraps, cardboard kingdoms and always a mess for dad to clean up once the extravaganza is complete. While she worked, I told her a story from when I was in the fourth grade in Cub Scouts. We made our moms pendants out of old prescription bottles. We poured colorful aquarium gravel into the bottle cap, baked it on parchment paper, punched a hole through it as it cooled, and pulled yarn through the hole. Gramma CeCe loved the thing. I might still have it tucked away somewhere.

Hazel told me to go find it. So, we headed over to my old footlocker.

Now, this isn’t just a box, it is a time capsule. The kind you would expect to find hidden in the cornerstone of a municipal building. Mine just happened to be in a red footlocker I painted blue in 1976. It holds the story of John Shepley from the beginning: trophies, letters, pictures, ticket stubs, medals, certificates, treasures, and ghosts.

Hazel lasted about ninety seconds before she forgot all about the 1970s pendant for her grandmother. What grabbed her wasn’t the craft, it was the mountain of Polaroids and Kodachromes stacked inside. Pictures of her daddy growing up. Pictures of a life she never saw and probably never suspected.

The ones that caught her the most? The party years.

Me drinking a Little Kings at a high-school party.

Me doing a beer bong at a fraternity house.

Me leading a Second Line down Royal Street in the French Quarter.

Dad pounding pints in a London pub.

Dad with several empty Irish-coffee mugs at the Buena Vista Café in San Francisco.

Mardi Gras with Jumbo at Shanahan’s.

Dad hugging people of all shapes and colors, all smiling.

Bachelor-party golf outings with cart girls in bikinis.

A hot tub in Vegas with the Houston Oiler cheerleaders

Tailgates in Bloomington, Champaign, Iowa City, Baton Rouge, and South Bend.

And then came the pictures of me with a couple girls I knew BEFORE her mother. Hazel didn’t say much, just raised an eyebrow like only a twelve-year-old daughter can.

Eventually we reached the photos of her mom and me. The digital-camera era. The box-camera era. Those early years when everything was still ahead of us.

Mom and Dad at a Bears game.

Mom and Dad at a Cubs game, a Sox game, another Bears game, a Jayhawks game, then another Bears game.

Mom and Dad cleaned up for a wedding.

Mom and Dad in PopPop and JoJo’s house before the renovation she’s grown up with.

And then New York, a year after 9/11.

Oysters at Grand Central Station.

Standing in front of the Chrysler Building.

Near the Brooklyn Bridge.

Her mom laughing, smiling, hair different in every picture. Beautiful in all of them.

Hazel stared at those the longest. Her first real glimpse of her parents when they were in love, before the long chapters life eventually wrote. She asked to take a dozen photos home. Of course I let her.

The rest of the day was just as it should be. Baking, projects, homemade pizza rather than turkey, a Stranger Things marathon, and the sort of quiet Thanksgiving rhythm instead of the hustle and bustle.

I think the Shepkids will remember Thanksgiving 2025 for a long time, Hazel especially. It was the day she saw her parents in another lifetime, and her dad as a young party monster before he turned into the guy who sweeps glitter off the kitchen floor.

She’s used to seeing a thousand pictures on her phone. She wasn’t prepared for a thousand pictures in a cardboard box buried in a footlocker. Different world, same dad.

Thanksgiving is over now, and it is time for the first official Christmas song of the season. Everyone else can start with Mariah Carey or Bing Crosby. I’m going with The Pogues, "Fairytale of New York."

The Bears play this afternoon. The Hoosiers and Boilermakers battle for the Bucket around suppertime. I pray Chalkhead Nation had a spectacular Thanksgiving and is rolling into Christmas and Hanukkah with some fire in their step.

Gusto and Astonishment

November 27th, 2025

 I think about what I am thankful for today, and it always comes back to the Straight F’s in life.

If you have been hanging around the Chalkboard long enough, you have seen them appear from time to time. They are the Foundation, the cornerstone, the simple things that never fail me when everything else gets loud and chaotic.

It starts with the big three: Faith, Family, Friends. On Thanksgiving, I tack on Food and Football. Because if there is ever a day when those two belong on the list, it is today.

During the year, the list gets a few additions. Fundamentals is often applied. Fearless, Farmer, Fitness, Funk, Forgiveness and even flamboyant will make an appearance. Living on this lighted grid next to a big lake, Familiarity sneaks its way in on a daily basis. The feel of home, the comfort of knowing where the hell you are in this Fragile world.

... And yeah, sometimes I can toss in the most common F-word known to mankind. I am still a Chicago guy who worked on a trading floor.

But today I keep it clean and stick with the ones that built me.

Faith.

I will tell you straight: without the Holy Trinity and the Blessed Virgin Mary, I would be a busted-up mess. I am thankful every single day for the faith my parents planted in me, started in the baptismal font at St. Ita’s up in Edgewater. That wasn’t just water, it was the first brick in a foundation that has carried me through all the rough patches and all the stupid decisions.

I pray every morning driving into work and plenty of you Chalkheads get name-dropped in those quiet chats with heaven. You might not know it, but you have been prayed for more than a few times. I pray and I swear, that is what I do. I can be in the middle of a Hail Mary and if a guy doesn't use his directional signal, heaven will hear, ".... blessed art though amongst women (this jagoff can't use a directional?) and blessed is the fruit of thy womb, Jesus.

Family.

The Shepkids are the biggest blessing I have ever been handed during my crooked, awkward journey of life. They clog toilets. They spill shit. They push every button God installed in me, but then, out of nowhere, they flash these moments of brilliance that stop me dead in my tracks. That is the good stuff. That is the stuff that keeps this man going.

As years roll on, family disappears from our tables and our phone lists. They leave a hole, but I don’t wallow in grief or emptiness. I am thankful they shaped me when they could, and I am thankful I will see every one of them again in whatever great reunion comes after this storyline, even the Shepkids’ mom will be at the eternal table.

Friends.

My Oldman preached this one hard. He told me early on to learn the difference between an acquaintance and a friend. Then he would quote Yeats,

“Think where man’s glory most begins and ends, and say my glory was I had such friends.”

As I have gotten older, friends have sifted out. Some fade into memories. The true ones, the ones meant to stay have become the bedrock of my Foundation. You don’t get many of those in one lifetime. Guard them fiercely and cherish them.

Football and Food.

Thanksgiving doesn’t feel right without the Turkey Bowl, the Detroit Lions, and some good-natured tackles. Football is stitched into the fabric of today even if the Bears aren't playing.

Food glorious food! It is the bountiful symbol of all the hard work and sacrifice we go through. Every damn day, we grind for today's bounty. Give me stuffing, mashed potatoes drowning in gravy, and a slice of pecan pie to top it off.

When I get done chalking about Straight F’s, I will put on December by George Winston. Something I have done every Thanksgiving morning since Reagan was in the White House. Traditions matter and that album kicks off the day.

So today, give thanks for the Straight F’s in life. Stretch before you hit the annual gridiron. Hug the cook who made the turkey gobble just right, and don’t forget to tell the people around you that you love them.

Because next year’s feast isn’t promised to any of us.

One last thing...... I Love You

November 26th, 2025

 Thanksgiving Eve has always been its own kind of holiday.

When we were fresh out of high school and stumbling into young adulthood, the night before Thanksgiving carried a magic all its own. Folks who scattered off to colleges, jobs, or whatever roads life had shoved them down suddenly came drifting back home. Old friends reappeared like ghosts you actually wanted to see. For one night, everybody was in town, everybody was young, and everybody had a cold drink in their hand.

I have a handful of regrets in my life, Jumbo-sized and well-earned. One of them sits squarely on a Thanksgiving Eve in the mid-1990s.

The day started like any other trading day. After the closing bell in the Bond Room, I headed downstairs to Ceres. The legendary watering hole tucked in the lobby of the Chicago Board of Trade.

A place known far and wide for drinks poured like they were trying to drown you. Four gin martinis later, and mind you, a Ceres martini is basically a chilled bucket of gin with a nod toward vermouth...

...I hopped on the Congress CTA back to my Oak Park apartment, feeling bulletproof and stupid.

Once home, I did the standard bachelor reset: shit, shower, shave, and then right back out the door. I grabbed a Blue Cab and headed straight to Madison Street, Forest Park’s own “Street of Dreams.”

If you were young, single, and breathing in those days, that stretch of bars was where Thanksgiving Eve turned into Thanksgiving Morning without warning.

I hit it hard with my crew. Hard enough that the memories come back in snapshots rather than video. Luck, grace, or the guardian angel assigned to idiots got me a ride home before I made things worse.

I woke up around 2 a.m., sitting in nothing but my underwear in my hunter green La-Z-Boy. The smell hit me first. The unmistakable, unforgiving stench of a burning Home Run Inn pizza smoldering in the oven. The kind of smell that says, “You are lucky your dumb ass didn’t take out the whole building.”

I cleaned up what was left of the pizza, dragged myself into bed, and passed out.

At 8:30 a.m., my answering machine kicked on. It was the Oldman. His voice had that tone, the one every son knows.

“Where the hell are you? The potatoes aren’t going to peel themselves.”

Another call at 8:40.

Another at 8:50.

And so on.

When I finally picked up around 9:30, he didn’t need to hear details. One listen to my voice and Don Shepley knew exactly what kind of night I’d had.

He was furious as he told me to stay home. He said he didn’t want to see me.

Now, with the clarity that only comes long after you need it, I understand what he was really saying: Get your fat ass over here right now, but I took him literally.

I stayed home. Ate a can of soup and a couple peanut butter and jelly sandwiches for Thanksgiving dinner. My Oldman didn’t speak to me again until the eve of the eve of Christmas that year.

I didn’t just blow Thanksgiving. I blew the whole damn Christmas season. I would give anything to get back that Clinton-era holiday stretch and get a do over with my daddy.

Ceres Café was the birthplace of a lot of bad decisions, but that one kicked me in the ribs.

I never got wasted on Thanksgiving Eve again.

This year, I am staying put with the Shepkids. Making homemade pizza and definitely not burning it. Laughing, eating, keeping it simple.

And if there is one thing I’d tell anyone heading out tonight, it is this: Be safe. Be happy and tell someone you love them.

Because nights come and go, but regret hangs around longer than any hangover.

November 25th, 2025

 This week isn’t about gourmet meals, linen tablecloths, or trying to impress anybody.

It’s not the time to polish the silver or pretend your family behaves like the ones on TV. This week is about the simple meal the earth gives us, the stuff grown in dirt and hauled in by hands. It is sweatpants, old socks, and an oversized Dick Butkus jersey that has seen more gravy splatter than Soldier Field saw touchdowns in 2023. It is all the glory that a touchdown in the Turkey Bowl stands for... bruised shins, bad passes, and bragging rights that’ll last until next year's game.

You don’t need fancy decorations. You need the paper-mâché turkey your son made in second grade. The cardboard pilgrim and Indian that has been stuffed in the same bin for twenty years. That one construction-paper feather that keeps falling off. Those are the real decorations, the ones that remind you time is passing whether we like it or not.

I enjoy a buttery Chardonnay with that moist turkey. I like the cranberry out of the can; the ridges still stamped into the sides and a dollop of Kool Whip sliding down the mound like a slow avalanche. This week is built on simple tastes, honest recipes, and the kind of food that sticks to your bones.

Songs that stir memories.

Movies that never get old.

The kind that make you sink into the recliner you promised to replace before Thanksgiving.

Just around 7 p.m., someone will inevitably say, “We need bread for sandwiches,” and you will find yourself at White Hen, grabbing a loaf of balloon bread. Because that late-night turkey sandwich with soft white bread, cold turkey, mayo, stuffing, cranberry, mashed potatoes and maybe a little pepper... is one of this week's real treasure.

The week is scattered with fallen leaves, maybe a couple early snowflakes, and an odd warmth the Midwest gets in November when it wants to remind you that it still has a heart.

This is the week for thanking whoever you pray to for the straight F’s in life: Faith, Family, Friends, Food, and Football.

Don’t overthink it.

Don’t forget the dessert table and the annual battle between pecan and pumpkin. Someone always tries to sneak in a new recipe. Nobody wants the new recipe. Tradition wins every time.

This week isn’t about mountaintops or miracles. It is about the kids’ table, the flimsy folding chairs, and Aunt Tilly farting between bites like it’s part of the ritual. It’s the parades on TV, the first glimpse of Santa, and the feeling that the holidays are finally, officially rolling in.

But more than anything...

... this week is about remembering the ones who once sat at your Thanksgiving table. The ones who carved the turkey, told the jokes, said grace, or snored on the couch by halftime. Their memories keep them seated with you, year after year. Thanksgiving stacks up like leaves in the yard, one on top of another, forming a pile of years, faces, mistakes, miracles, and moments that become your family’s story.

Thanksgiving isn’t swimsuits and pool sides. It is thick sweaters, wool socks, and a fire that crackles louder than the conversation.

Loosen your belt and fart; nobody cares.

Just don’t bring up politics.

Tell jokes.

Remember mishaps.

Listen to laughter.

Say what you’re thankful for even if your voice cracks a bit.

... and before bed, don’t forget the cranberry salad you left outside to stay cold. And try, honestly try, to say “I love you” a shit ton this week. People need to hear it and you need to say it.

November 24th, 2025

 I don't have much of anything to chalk for you on a Monday morning. Fritz gave me the quote over the weekend, so Big George wanted to give me one for today.

I'm pretty sure he doesn't live his life by these words, but when he wakes up and sees his suggestion on The Morning Chalkboard, he will smile.

I couldn't leave Hazel out of the mix. Her contribution is in the Grabber section. I don't know what the hell this six-seven trend is, but I quoted that market many times in the trading pit.

Six bid at seven, five hundred up!

I do know Hazel is the only kid in her class that knows the hand signals from the bond room of the Chicago Board of Trade. Some kids learn TikTok dances. My daughter learned how to flash a bid across a room full of screaming grown men.

It is Thanksgiving Monday, the Bears won and astonishment is all around.

November 23rd, 2025

 I have been walking through a cemetery more than usual lately.

It is a tiny postage-stamp patch of ground tucked inside a forest, surrounded by million-dollar mansions that crowd close to the dead. The cemetery rolls over soft hills with narrow, winding roads. Trees outnumber the tombstones. A couple ponds sit still as glass. Only disturbed with an occasional curious mallard. Creeks trickle through, making a soft babble under the chilled breeze. Some of the people buried there have been resting here for a century. Others just got settled in the ground this year. The Irish rest beside Germans. The Jews beside Italians. Plenty of other Europeans, and a few Orientals mixed in too. Death doesn’t discriminate, it files us alphabetically by plot number and leaves the rest to the visitors to determine.

I was there yesterday under a dull November sky. Most of the trees were plain skeletons, bare branches clawing into the grey. The last drops of autumn still clung to a few stubborn twigs, little teardrops refusing to fall before the winter frost.

The grave that brings me back isn’t my Oldman’s or my Ma’s. It isn’t anyone with Shepley blood in their veins. It is the man who raised the woman who once loved me, the woman who made me a father three times over... My father-in-law.

A man who welcomed me into his family, handed me his daughter’s heart, and in return got his first grandchild. That connection never broke, even after the marriage did. That is why I have been visiting his graveyard more often. Love doesn’t end just because the paperwork changes.

It is also a damn fine excuse for a long walk and a cigar. I usually bring him a drink so we can share one more together. Yesterday it was Guinness. Other days it has been bourbon, and sometimes vodka. His preference when the living days still mattered.

I often leave a cheap thirty-nine-cent plastic comb. He insisted on keeping that comb-over neatly tucked when he walked this earth, so I figure he might need to keep it tidy in eternal rest as well.

Tucked tightly to his right is a famous Chicago hockey player. His stone is covered in weather-worn pucks left by the faithful. A shrine built out of vulcanized rubber and memories from the Madhouse on Madison.

On a recent visit I found the resting place of a dear friend’s family. His mother, gone just before the millennium. His father, a few years back. And his brother, the sibling whose time was far too short. Someone placed a little duck statue at the child’s stone. Childhood frozen in ceramic.

I brushed off their headstones, cleared the leaves, and had a Guinness with my buddy's father. Then I walked back across the rolling ground to finish my cigar beside my father-in-law.

There weren’t many visitors that afternoon. Those who were there became an unwilling audience to my trading pit voice drifting through the trees. I said a couple Hail Mary's out loud. When I finished an Our Father, a cold rush went through me, the kind that somehow carries security.

A strange joy only cemeteries can give.

I sang a little Sinatra. I even gave the Talking Heads a run. When I passed by a Jewish headstone, I sang Sunrise, Sunset from Fiddler on the Roof. I ended with The Parting Glass near an Irish grave.

Before I left, I told Mr. Bergmann I would be back in a couple days. Maybe with a Thanksgiving mimosa. Standing there, with cigar smoke still curling above the grass, I recited the little phrase from Looking Glass PopPop loved to repeat whenever a sleepy Shepkid flopped face-down on his belly. I left the last inch of the cigar at his stone so he could enjoy the smell with the Guinness seeping into the earth.

As I walked back to the car, the thought crossed my mind. This wouldn’t be a bad place for me to land someday. A place where the Shepkids could visit PopPop and JoJo, then stroll over and say hello to their Oldman. Maybe their mom would be close by too. At least she and I wouldn’t be fighting. The dead don’t bother with old arguments.

That reminded me of something my Oldman told me more than once: We spend so much of life fighting and hating, but in the end we all wind up together in heaven, where none of that garbage is f'ing allowed. Maybe we should practice loving each other now, so it feels natural when we get there.

Alright, you Chalkheads, go live your life with gusto today. Enjoy the Thanksgiving week ahead. Make the miles mean something before you sleep.

Lewis Carroll, from Through the Looking-Glass. 

“The time has come,” the Walrus said,

“to talk of many things:

Of shoes — and ships — and sealing-wax —

Of cabbages — and kings —

And why the sea is boiling hot —

And whether pigs have wings.”

November 22nd, 2025

 My son Fritz gave me the quote for today's Morning Chalkboard.

When he asked me what I thought about it, I replied, those five words are a reminder that the best things in life don't come from having everything. They come from making the most of what you already have.

Today is like another Columbus Day for my friends associated with the Chicago Family. A Chicago Mayor made the American President sixty-five years ago and another Chicago guy ended it.

Enjoy your Saturday before Thanksgiving. Just remember all the other jagoffs at the Jewels are under the same holiday stress that you are experiencing. Shop with kindness today.

November 21st, 2025

         It is the Friday before my favorite holiday. I love all four seasons, but it is autumn that holds my favorite spot. We are going through the New Moon phase of the month. A time to reload and gather yourself into order.

Go love someone....

November 20th, 2025

      Some mornings hit me with a blindsided block.

I woke up suddenly with a clogged nose and a jammed up left ear from sleeping hard on the same side all night. Walk into the kitchen to make some coffee and stare dumbfounded at that Chalkboard... and the words just won’t come.

Happens to all of us, even the bastard who has written a few thousand of these things.

“Risk is always better than regret.” That isn't philosophy, but the truth in life.

Risk is walking into the unknown with your chin up. Regret is walking away from the moment and then spending the next ten years wishing you had a do over. Every good thing I ever grabbed in this life came from stepping toward something instead of away from it. Jobs, opportunity, kids, love. Even the screw-ups taught me more than sitting safely on my hands ever did. My Oldman always told me that I would make a shit ton of mistakes in life. Make sure you learn from them the first time and pray to God it isn't an expensive lesson. The older you get the more expensive mistakes become.

The sky is nothing but gray again today. That heavy November lid that hangs over Chicagoland like an old drop cloth. Sunrise at 6:47 comes in a drab gray this morning with darkness coming quick at 4:26 this afternoon. I hate going to the grocery after work in the dark.

Tucked in the Grabber section of the Morning Chalkboard is the real anchor: amorem firmiter tene. Latin for hold fast to love. Not the easy, sweet kind, but the stubborn kind. The kind you stand your ground for. The kind you carry even when the world feels cold and cluttered.

So if you are starting discombobulated this morning, here is the way out:

Take the risk.

Make the move.

Step firmly into the day.

Regret has never done a damn thing for you.

November 19th, 2025

    Some mornings don’t really start fresh.

They carry the remnants of whatever rattled around in your head the night before. The worries, the hopes, the noise, the mishaps. The beat of last night didn’t vanish just because the clock flipped.

We don’t get clean slates...

....we get continuity.

I gotta go get another piece of chalk. This one isn't flowing as smoothly as I would like. Less than a month and I get to go over to Uncle Ira's and spin dreidels and eat sufganiyot. The festival of light will also ring in longer days. Albeit, we will be stuck with sunsets at 4:20 for a week or so, but the days will get longer around the last candle on the menorah being lit.

Mazel Tov you Chalkheads. Try to find astonishment on Humpday. A week from tomorrow is Gobble Gobble.

November 18th, 2025

 I was in high school when the song dropped that I chalked today.

It was the perfect anthem for a bunch of kids who thought Animal House was a lifestyle guide. Keggers in the forest preserve. Beer bongs that could empty a six-pack in one pull. Toga parties in the dead of winter. We partied in 1983 like it already was 1999, because back then thirty-something felt a lifetime away.

1999 showed up faster than expected, stayed shorter than a sparkler on the Fourth of July, and disappeared in the rearview mirror even quicker. I haven’t owned a keg tap in years and my toga is long gone. I actually had an Izod toga. My Gramma cut the alligator and tag off an old shirt and stitched them onto a sheet. She even ironed my custom toga for a homecoming party at Dear Old Cathedral.

God bless her… she never had a clue about the debauchery that toga survived.

Those kids from the early eighties grew up. Most lived to see the real 1999, and honestly, it was anticlimactic, like most things we build up in our heads, but the memories still have some juice left. I still have a beer bong, and there is a video floating around out there of me hammering one after a Sox game. Standing in the ruins of a tailgate like a middle-aged warrior reliving the glory days.

These days, partying like it’s 1999 is tough to pull off when your lights are out by 8:45. Prince is gone and my classmates have scattered, but the song still puts a little pep in my step when it pops up on the car radio.

I would like to go to one more kegger in the woods... toga, sunburn, solo cups, boom boxes and evading the local police. I will bring my beer bong and a keg of Old Style.

I sure hope heaven has toga parties. That will be a reunion worth showing up early for.

Alright Chalkheads, it’s raining as I chalk this. Grab your umbrella, square your shoulders, and stay brave.

November 17th, 2025

 I’m one of those golfers who says it’s better to be lucky than good. I got a job in the bond room because I was in the right place at the right time. I won the lottery when I met my wife and I picked up more than a couple girls by accident rather than on purpose.

Which reminds me of something the Oldman told me when I was eighteen or nineteen,

“Moose, all girls have sex. Some more than others.”

Big Don used a different word than sex, but you get the point and he was right.

Timing matters.

Luck helps, but hard work and integrity are what people remember.

I hate golf. I only go for the camaraderie, the cart girl, and the cigar. I should swap my golf score with my bowling score.

That job in the Ten-Year pit? Sure, I got it because I happened to walk by when a guy just got fired, but I kept it because I worked my ass off and showed integrity.

Did I win the lottery when I met my ex? I sure as hell did and I invested every bit of it into the Shepkids.

Here is another gem the Oldman taught me:

If a girl is generous enough, or stupid enough to think you are special and offers a little tenderness, make her feel like she made the right decision and keep her in your life somehow.

That is why most of my girlfriends are still my friends. Except for one, the lottery ticket. She thinks I’m a jagoff, but our children love me, and even her mother likes me.

That’s a win in my book.

Work hard, be honest, get lucky every once in a while and astonishing results follow.

Today is going to be a gorgeous autumn day. With the holidays closing in fast, I figured I’d give you Chalkheads a little heads-up on timing.

Rise and Shine, here is your Monday morning earworm, courtesy of Daft Punk:

We’re up all night ’til the sun

We’re up all night to get some

We’re up all night for good fun

We’re up all night to get lucky.