October 31st, 2025

 Every Midwesterner knows the feeling.

The one that hits you right around Halloween. You step outside and the air has that strange mix of warmth and warning. The sun still carries a little kindness, but the shadows are sharpening their teeth. You smell the leaves turning brittle, the first backyard firepit of the season, and the faint trace of winter waiting around the corner.

This is the final exhale before we hunker down. Tomorrow the clocks will fall back, and the afternoon will disappear faster than the CTA Christmas train in the chilly fog. The park benches will empty, the bikes will hang in garages, and everyone will start talking about soup.

But tonight, tonight belongs to the ghosts, the kids, the parents with beers in the stroller pouch and the people who know enough to stand on their porch a few minutes longer just to feel that last warm breath.

Raise your glass to the final ember of October. Enjoy it, Chalkheads. By morning, November will be on our doorstep and winter will be awakening.

Hanukkah and Christmas are just around the corner. Maybe the last holiday season celebrated in the five boroughs that mourn annually in September.

Tomorrow is rugby day in Chicago! Welcome home Ireland and New Zealand.......

October 30th, 2025

 I was a Snickers and Three Musketeers kid, and occasionally the Oldman would hand me a Peppermint Patty when he grabbed the papers at the White Hen. Then one afternoon in 1978, a new candy bar appeared, Whatchamacallit. It was crunchy, chewy, and completely different.

To this day, I will pick up a Whatchamacallit at a gas station, and suddenly I am twelve again, sitting in the back seat of the Dadillac with WGN quoting the weekly commodity prices.

That candy bar isn’t just sugar and crisped rice, it’s a time machine….

…unwrapping a memory from when everything felt new and the world still had that “just opened” smell.

I think I have a quote for a future Chalkboard.

“A candy bar is a good Time Machine.” —John Shepley, The Morning Chalkboard

Tomorrow is Halloween, a holiday built on sugar and nostalgia. So here is a thought for my fellow Chalkheads: What’s your favorite candy bar and what memory does it unwrap for you?

The sun is smiling brightly today. Go enjoy one of the last sunny afternoons that won’t be dark by five o’clock and don't let that candy bar you grab spoil your supper.

October 29th, 2025

 Growing up, I often heard the phrase, “He’s been around the block a few times.”

It wasn’t meant as an insult. It meant a guy who has seen a few things, lived a little and learned the hard way. Turns out, that is what growth really looks like. Not a steady climb up some shiny ladder, but a looping, twisting walk around the block of life. Revisiting old corners with new shoes and a different stride.

You run into familiar faces, familiar mistakes and familiar dreams. Each time seeing them with a bit more wisdom and a lot less ego. Setbacks and reruns aren’t failures, they are checkpoints. Each lap around the block adds another layer of understanding, even if it feels like déjà vu. Throw in that reoccurring dream that drags you through the same high school hallways of memory and maybe that is life reminding you that the lesson ain’t over yet.

We are closing in on the end of October, and Saturday brings the long-awaited rematch... Ireland versus New Zealand back to Chicago. Hard to believe it has been nine years since the Irish stunned the All Blacks on the lakefront. One thing I have noticed between Soldier Field lined for football or painted for rugby. After a match, rugby fans hug it out and buy each other beers. After a game, gridiron fans often shout until somebody bleeds.

It is hump day you Chalkheads. Let’s slide into the weekend with a pint of grace, a bit of grit, and a warm welcome for the international crowd invading our town. Bring on Ireland’s Call and the Kiwis' Haka.

October 28th, 2025

 Today’s quote doesn’t need a long explanation.

It hits like a clean punchline right in the chest, you are the common denominator. Every win, every screw-up, every second chance...

...you are in the middle of it.

That isn't judgment, it is accountability. It is a reminder that we steer the ship, whether it’s calm water or a squall off Lake Michigan.

And fittingly, today is National First Responder Day. The heroes who show up when the rest of us are staring at disaster. Police, medics, firefighters, they are the ones running toward the trouble while we are backing away. You don’t think much about them until you need them, and when you do, you damn well remember their faces. It is easy to forget that they have families waiting at home, praying tonight is just another shift and not another headline.

Say a prayer for them. Buy them a coffee if you are standing in line behind a uniform. Give the sign of the cross when you see the lights flashing and pull to the side of the road. Because they have a job to do.

If the day ever comes when it is you calling for help, remember that these men and women show up not because they must, but because that is who they are.

Chicago has always had their kind...

...gritty, loyal, and brave enough to face chaos.

God bless our First Responders. May every one of them make it home after their shift.

October 27th, 2025

   We live in a world that sells happiness by the ounce and bills it by the hour. You can drop a fortune chasing thrills that vanish faster than a weekend in October. The richest moments are the ones that stick to your ribs and don’t cost a damn thing.

I spent the weekend with the ShepKids, and it reminded me how true today's quote really is. There isn't a price tag on watching your children laugh until they hiccup or seeing that little spark of pride when they tell you a story that matters to them. Those are the kind of returns that don’t fit on a balance sheet.

When I look back at my own childhood, it wasn’t the vacations or the shiny toys that stuck. It was riding shotgun with the Oldman on a Saturday morning, having breakfast at the diner counter or listening to him hum Gershwin under his breath. I didn’t know it then, but those were the richest moments of my life.

Now, I’m the one behind the wheel. Different car, same lesson. My job isn’t to give the ShepKids the world. It’s to give them a world they will want to remember. A walk to the zoo, Sunday breakfast, silly dad quotes or trips to Parky's for hotdogs.

Cheap pleasures. Long dividends. The kind of wealth that builds quietly and lasts a lifetime. Because when the noise of the world fades and the lights dim, what is left isn’t the stuff we bought, but the laughter we earned.

Last Monday in October as the moon glides through a waxing crescent. Trick or Treat at the end of the week and New Zealand versus Ireland at Soldier Field on Saturday.

Make Monday mo' betta.........

October 26th, 2025

 There is something about a crisp Sunday morning that stirs up the imagination. For us Gen Xers, imagination often came with a dose of time travel. We grew up with Marty McFly, Bill and Ted, Josh Baskin, Phil Connors, and John Connor. A whole cast of characters who made us believe we could bend time if we only tried hard enough. We could be our own HG Wells if we wanted to.

When I think of imagination, I think of the Oldman. Saturday mornings, there were errands and diners, hardware stores and barbershops. After the chores, he’d point the Cadillac to nowhere in particular. We would wind up at a bakery, a butcher, a hotdog joint, a newspaper stand or an old antique shop off the beaten path.

Sometimes, we would make our way to Maxwell Street…

… a new toolbox in one hand, a pork chop sandwich in the other. The only fast food chain the Oldman tolerated was White Castle. I can still hear him hollering when I left grilled onions on his dashboard.

By the time we got home, the Oldman would nap, and I’d drift into my own little world. I used to imagine that when we drove under the Halsted viaduct south of Maxwell Street, we’d come out in 1932, maybe even 1922.

The “Dadillac” was our time machine, dropping us into a Chicago thick with soot, jazz and prohibition whispers. We’d look at each other dumbfounded, trying to figure out how to hide a twenty-foot car from the future. The Oldman would find work on the railroad, and I’d land on the floor of the Chicago Board of Trade. Him in the glory of steam and me shouting in the corn pit on the old trading floor. Which was actually a new trading floor at the time. Just a father and son, stuck in time, perfectly fine with it.

These days, my imagination has been traded in make-believe for what ifs.

What if Nixon beat Kennedy like he should’ve in ’60?

What if Ross Perot hadn’t split the ticket in ’92?

What if O.B. had the Irish flu on that September Tuesday?

What if I moved to New Orleans at the turn of the millennium?

Well, if Nixon won, men might still wear suits to the ballgame. If Perot stayed home, Monica Lewinsky wouldn’t have had to explain the cigar. If O.B. stayed home, a dad from Park Slope would have watched his kids grow up.

And if took the Illinois Central to NOLA, I wouldn’t have the Shepkids and I would have probably been trapped by Katrina.

So yeah, imagination still has its place, it just looks different now. Today, it is what keeps me grateful for where the road did take me. Time travel isn’t always backward. Sometimes it is standing in the kitchen on a Sunday morning, flipping pancakes for three imaginations left for me to nurture.

Be true to your team today. Cheer proud and loud. It is the last week of October…

…rock it with gusto and astonishment.

October 25th, 2025

    

“Look on my works, ye Mighty, and despair.” — Percy Bysshe Shelley

Many of you who walked through the halls at Dear Old Cathedral will probably recognize the line I used for today’s quote. It comes from Percy Bysshe Shelley’s Ozymandias. A poem about a traveler who comes upon a ruined statue in the middle of a desert. What was once a monument to a king’s greatness now lies in pieces, sand drifting through the cracks of time. The inscription boasts of power, of a man who thought his empire would never fade, but all that remains is silence and stone.

Shelley wrote Ozymandias as a reminder that no matter how grand our achievements or how grandiose our name may become, time will eventually level it all. The careers we build, the titles we earn, the collections we gsthered will all fade into dust. What outlives us isn’t our “works,” but the moments we shared and the people we lifted along the way. Humility, not pride, is what endures in memory.

As we head into the last week of October, take a moment to look around at what really matters. A week from today the clocks fall back, and we will start the wintering process…

…shorter days, longer nights, and that slow cold fade into another season.

Let’s use this week to soak up what is left of the light.

Sit outside a little longer.

Watch the leaves hold on just a day more.

Let the sunshine stretch across your afternoon, because soon enough, we will be looking on our own works and thinking if we used our time well.

Go put a smile on the sun today you Chalkheads.

October 24th, 2025

 In a world built on instant gratification, the beauty of waiting has become an endangered species. We want everything right now.

The package, the promotion, the apology, the miracle, but life, real life, still makes us wait. Waiting forces us to slow down, to look around, and to notice the things that rush quickly usually are blinding. It is not wasted time, but preparation. It is the stretching before the sprint. It is faith with a stopwatch.

I didn’t become a dad until I was forty years old. That was when I finally became a man. When that beautiful woman I once loved handed me my firstborn, George, everything started to click. All the waiting, all the screw-ups and second chances were worth every damn second.

I didn’t become an orphan until my fifties. My mom went first, just before I turned fifty. My Oldman followed four years later, and with him went the last bit of the generation that raised me. I remember kids in grade school losing their parents. I never thought I’d still have both of mine for so long. Waiting to feel that loss until later in life gave me a different kind of gratitude. It taught me to sit still, to breathe, to watch the sunlight move across the dining room wall.

Now I’m waiting for the next chapter...

... hopefully one that includes more laughter, a few wins, and maybe a Denny’s coupon or two through AARP. The sun I drew today has a crooked smile, and it is gonna be a high temperature of Momma Boy Otis, one of a kind.

Today is National Bologna Day, so tip your cap to the kid who sang about his Oscar Mayer bologna. Finish the week strong and lavish in the astonishment of what you have been patiently waiting for.

October 23rd, 2025

 “You can’t polish a turd.”

That is one of those blunt Midwestern truths that doesn’t need a second read to understand. You can dress something up, shine it, spray it, market it, but if it’s garbage underneath, it’s still garbage. Integrity is about the inside matching the outside. Whether it’s a person, a product, or a promise, you either build it right from the start or you don’t bother.

Don't be a turd today.

On this day in 2001, Apple introduced the iPod. Before that moment, music lived in milk crates, CD towers, and glove compartments. We lugged around albums, tapes and CDs like we were packing for war. We listened to albums in reverse to hear hidden messages and we made mix tapes for our girlfriend.

Then the iPod showed up.

A pocket-sized jukebox with a click wheel that made us feel like a DJ and a curator of our own life’s soundtrack.

For me, it was a wild leap in just fifteen years. I went from crate after crate of albums in 1986, to a slick little CD tower in the ’90s, to 5,000 songs sitting quietly in my front pocket by 2001.

I could mow the lawn to Springsteen, take the CTA to work with The Clash, make love with Barry White in the background, drive with Johnny Cash while stuck on the Ike, and fall asleep to Coltrane and Miles…

…all without lifting a record needle.

It is Thursday, I put a half-ass smile on the sun and my cankles feel pretty good....

Gusto Baby!

October 22nd, 2025

 For in the dew of little things the heart finds its morning and is refreshed. Kahlil Gibran

The sky is going dark tonight. The new moon slips out of sight, hiding in plain view above the rooftops. Most people won’t even notice it is gone...

...but the farmers, the fishermen, and the dreamers do.

They know that darkness doesn’t mean absence, it means beginning. The new moon is the start of another cycle, a clean slate written in black ink.

Gibran had a way of reminding us that the big truths in life are found in small things: the dew, the stars and the quiet act of caring. That is what the moonless night is about. A pause before the glow builds back again. The heart’s own reset button, a monthly do over.

We live in a world that celebrates noise, speed, and constant exposure. The new moon asks us to step back, shut up, and start again. After the shine fades, renewal will always follow.

The same way dew gathers in the dark, your spirit rebuilds itself in the quiet hours. The new moon doesn’t announce its arrival; it just lets the light come back when it’s ready.

It is Wednesday and we have the new moon. Bundle up and spread astonishment.

October 21st, 2025

 Yesterday marked forty-eight years since Lynyrd Skynyrd’s plane went down. Taking half the band and leaving behind a message that outlived them all: “Be a simple kind of man.”

Ronnie Van Zant once said those words came from his gramma’s advice; to be patient, stay honest, and live by your own measure.

Good advice then, maybe better now.

We have made life a hell of a lot more complicated since 1977. I went to the doctor and the bank last week and noticed how big everything looked. Not because they added space, but because the steel file cabinets are all gone. Our lives used to be kept in drawers, folders, and manila envelopes.

Now it all floats in the clouds, guarded by passwords and a few caffeine-soaked nerds who have never seen sunlight. Yesterday, one of those basement dwellers figured out the password and hacked the internet. The poor bastard has never seen female genitalia, but he knows your social security number, your blood type, and your sophomore transcripts.

We lost the cloud for a few hours, and the world panicked like a toddler without a pacifier. Maybe Gramma Van Zant was right all along, be a simple kind of man, because the more we hand our lives to machines, the dumber we get.

Keep your word.

Know who you are.

Do your job and do it well.

That is how simple men and women built this country before the cloud stored our memories.

Finally, the sunset today...

...the last one past six o’clock until next March.

The weather corner has sperm swimming under the clouds, my way of saying it is going to be a windy day.

Tuesday morning, perfect for being in a daydream, humming some Skynyrd, and remembering to keep it simple.

October 20th, 2025

    It Is that time of year when the morning air feels like it has a little memory in it.

The mist rolls off the Des Plaines river like an old story trying to be retold, and even the lions roar from the zoo sounds more like groans on an early Monday morning. The days shorten, but the meaning grows deeper. That is autumn, the great balancer.

Keats called it the season of mists and mellow fruitfulness. Not because everything is dying, but because everything has been earned. The farmers have brought in the crop. The rest of us are starting to count our blessings and our bruises.

It is not the time for fireworks or beach parties. It is the time for slow coffee, rugby on Saturday, football on Sunday, and that quiet walk around the block, trying to remember the smell of burnt leaves in the distant air.

Thanksgiving is thirty-eight days away, but it isn’t just a date, it’s a destination. A reminder that gratitude isn’t found in the turkey or the pie; it is found in the people who still sit at the table.

Mardi Gras is one hundred and twenty days off, the other end of the see-saw. When we will trade sweaters for beads, roasts for revelry, and we settle our debts with a dance before Lent resets the meter.

Two of my favorite holidays.

So this morning, take your coffee to the window and breathe in the cool mist. Remember what you have harvested this year….

…the work you put in, the people that you love and the lessons that came with a bruise or two.

Because autumn isn’t about what is ending, but about what has been earned.

Kick the crap out of Monday and start a good week. We are well into the backend of October.

October 19th, 2025

 Today’s quote could have come from an old soul somewhere between Steinbeck and a South Side bartender. It reminded me of something my Oldman practiced his whole life.

My Oldman knew everyone.

The banker, the lady at the dry cleaner, the cook at the diner, the overnight guy at the White Hen, most of the cops in the neighborhood, and the morning CTA guy who took our tokens. Don Shepley was always kind to the working man.

One of the men I thought about this morning was Mr. Shapiro. Bill Shapiro, my dad’s go-to salesman at the Big and Tall Shop. From the late 1960s through the early 1990s, Mr. Shapiro measured my dad’s waist and inseam, picked out his trousers and sport coats, and had his suits tailored just right.

My Oldman was a fine dresser. A mechanical engineer who spent most of his time in a draftsman’s office before finally getting his own office at the end of his career. He wore a suit to work every day; wing-tipped shoes, a square handkerchief in the pocket, cufflinks on his monogrammed shirts, and silk ties that glowed without shouting. On dress-down days, he would wear pressed khakis, a blue shirt, and a navy blazer... still with the square handkerchief, of course.

When he went to inspect railroad cars in the yards, he would show up in freshly pressed bib overalls and well-polished shit-kickers. And yes, there was still a handkerchief squared up in that pocket. The man had standards.

I remember one weekend when I was in eighth grade. I was coming up to Chicago to visit. He called my mom and told her to send me with slacks, a tie, a sport coat, and church shoes. Trouble was, nothing I had fit. My Oldman had bought us tickets to see Do Black Patent Leather Shoes Really Reflect Up? at the Candlelight Dinner Theatre down on Harlem Avenue.

When I got off the train at Union Station, the first thing he asked was, “You got your sport coat and slacks?” I told him I did, but they were too small. He came unglued, and we drove straight to Karoll’s Red Hanger, where Bill Shapiro was working at the time. Mr. Shapiro changed shops often, but always made sure my dad knew where to find him.

Looking back, I’m guessing Mr. Shapiro was gay. Though I didn’t know what gay was back then. Most men of his generation were still closeted. He was Mr. Brady gay, not Freddie Mercury gay. Back then, gay men carried themselves like British aristocrats with proper etiquette, soft voices, sharp suits. It wasn’t until disco and The Village People that the closet door swung open. Or at least that was around the time I noticed a difference.

Mr. Shapiro fitted me in a brown tweed sport coat, a tan V-neck sweater, a brown knit tie, and light brown trousers. It screamed 1979 Catholic schoolboy and he nailed it. The perfect look to attend a play about Catholic school life.

My dad wore a navy suit that night. He made sure I had a pressed square handkerchief in my new sport coat pocket. I worried we would be overdressed, but when we arrived, everyone looked sharp. After the show, we drove to White Castle and grabbed a sack of sliders. Sitting in his Cadillac at 11:30 at night, both of us in our Sunday best, eating sliders under the glow of the parking lot lights...

...that was the best.

They tore that dinner theater down in the late 1990s and replaced it with a Portillo’s and a Krispy Kreme. Maybe that is another reason that I hate both those chains. Mr. Shapiro passed around the same time. My dad and I went to his wake, both wearing suits we had bought from him.

Happy Sunday, Chalkheads. Go make friends with a stranger today. You might be surprised how astonishing that can be.

October 18th, 2025

 I take a shit ton of grief for being an open book.

Most guys my age are told to keep their pie hole shut, let life roll on quietly, and stop making a public spectacle of your thoughts.

But these Chalkboards, this thing I have built called Chalkhead Nation, it is proof that running my mouth has done more good than harm. It has helped me find my tribe. It has given me a voice in a world that has gotten too damn quiet.

Last night, I was on my balcony overlooking what I lovingly call the Divorced Dad District of Riverside, Illinois. Two Manhattans deep, thinking about life’s stages, and I was about to pour a third until I heard, “Dad, you promised to make me popcorn tonight.”

That was George, my daily anchor. My reminder that no matter how rough the wind blows, I still have something solid that keeps me grounded.

I put on Bob Seger and sat there listening to Against the Wind. I started thinking about this current stage that I am in, the Riverside years.

It is where the next act of my life began after the curtain dropped on my marriage. It is where I brought the ShepKids into the light and tried to balance fatherhood, the loss of my parents and the last stretch of my career.

Somewhere along the way, I stopped auditioning new characters and friendships faded. I got quiet and somehow became an introvert who only jumps through hoops if it’s for the ShepKids or Futures International.

That is my current cast right now.

I have dated a few times since the divorce; women who have never married, women who lost someone, and women who have walked through hell like me. Most of them moved on to a successful chapter. Maybe my purpose was to be that stepping stone?

The truth is, I have never been fully there. My mind drifts to work or the ShepKids or whatever is next on the agenda. I have realized something hard: I don’t have the strength to hold a woman’s heart the way it deserves to be held. Maybe it is cowardice, maybe it is self-preservation, but it’s my truth. For now, Hazel can tug at my heart, George steadies it and Fritz is the glue that keeps our dysfunctional family together.

And yeah, maybe that knocks me out of the dating pool.

So be it, I will take peace and purpose over pretending. My hindsight might thank me someday for knowing my limits.

The last few weeks, I have been helping rebuild a family member’s life. It’s been heavy, but there’s a weird beauty in crisis; sometimes when the shit hits the fan, positive things grab the mop and start cleaning it up. I even managed to co-parent with someone I once thought impossible to deal with. Turns out two stubborn mules can pull in the same direction when it really matters.

I’m getting older, no doubt about it, but the fire is still there. I have lost some players along the way, benched a few I probably shouldn’t have, and picked up one or two late-round draft picks that shocked the hell out of me.

That is life, the roster is always changing.

Maybe I do talk too much. Homeboy, I never shut up.

But if one Chalkhead out there reads this and realizes they are not alone...

...that there is still gas in the tank and still wind to run against. Then my job here is done.

So, on this Sweetest Day, raise a glass, hug your people, and don’t be afraid to be an open book. The world needs more honesty, not less. Let’s keep running against the wind, together

October 17th, 2025

 “In the garden, I see, west purple shower bells and tea orange birds and river cousins dressed in green.”

Beautiful, isn’t it?

Read it again slowly.

It sounds like a poem pulled from some dusty anthology or maybe something you’d find in the margins of an old college notebook, but it’s not.

It is a lyric from a soulful 1970's song that most of us have heard a hundred times. The funny part is, we have sung along to it for years, never realizing how poetic it really is.

Life is like that.

We hear things all the time, but we don’t always listen. We hear our friends’ words, our children’s laughter, our parents’ advice, our partner’s sighs. Yet half the time, we let them roll off like background music. We hum along without catching the lyrics.

Friendship, marriage, parenthood, they all have a soundtrack. Some songs are loud and joyful. Others are soft and a little broken. And sometimes, like this one, they are so layered that you don’t understand them until you finally stop and listen. That is when you realize the message was there all along, waiting for you to pay attention to it.

We live in a noisy world.

There is always another notification, another headline, another reason to rush past what matters. The older that I get, the more I believe that the good stuff; the truth, the heart, the meaning always hides in the quiet parts of the song.

We are seventy-six days away from a new year. Seventy-six days to start listening instead of just hearing. To pick up the phone when someone crosses your mind. To notice the color of the sky instead of complaining about the weather. To listen when your kids talk, even if it’s about nothing.

Because one day, you will wish you could hear that voice again...

...that laugh, that tone, that melody that once filled your kitchen, your car, your life. Today we are doing something that we will cherish tomorrow.

So today, slow down and listen.

Really listen.

The garden, the birds, the traffic jams, the B-side, the friends, the neighbors, the colleagues, the family.

They have been singing to you all along. Time to listen to the lyrics because life doesn't have the words inside the album cover.

It is Friday... I don't know about you, but I would like a steak, medium rare, a bourbon that coats the back of my throat peacefully and a kiss that doesn't bite back...

Gusto and astonishment this weekend!

October 16th, 2025

 It was on this day five years ago that my trading firm packed up our office in the Loop and moved out to Oak Brook. Six months before that, the trading floor itself shut down because of Covid.

Those final months downtown, the summer of 2020, were silent. The sidewalks were barren, the beer gardens empty, restaurants shuttered, and both ballparks played to empty seats. I left a city that didn’t look at all like the one I walked into back in the 1980s.

I will never work on a trading floor again. I will never walk over to the Berghoff for a beer and a carved sandwich. I will never wander through Marshall Field’s to look at the Christmas windows.

But luckily, those memories are still in my heart, and that is where they will stay.

Today is National Liqueur Day. Pour yourself a Frangelico after dinner and think about what you carry inside your heart. The things that truly belong to you; your people, your places, your moments will never fade. They will always come back to life, one memory at a time.