March 12th, 2026

 I chalked a quote from Alex Dumbass this morning. Some problems in life can’t be fixed with noise.

You can’t argue problems away.

You can’t negotiate with them.

You can’t shout them into submission.

You just have to wait it out. It takes time and silence to navigate the problems in the world.

Time lets the truth surface and silence lets the dust settle.

Farmers understand this better than most people. A farmer can’t rush rain, he can’t hurry a seed and he can’t bargain with the wind.

He plants.

He waits.

He watches the sky.

…And sometimes the sky answers in ways nobody expected.

This morning the weather folks are talking again about the possible return of El Niño later this year. The Pacific Ocean warming that can shift the rainfall and put major moves in the growing season.

Weather predictions are a lot like life predictions, but a little more forgiving. They look smart on paper until the clouds move the other way.

The truth is markets move, weather shifts and every year changes. Most of the time the best move isn’t panic, but patience and silence. Because the loudest voices are rarely the wisest ones.

Sometimes the smartest man in the room is the one leaning against the wall, saying nothing, waiting for the picture to become clear.

Farmers know that and traders should too…

…. time and silence.

Two remedies the world doesn’t use nearly enough.

March 11th, 2026

 Some people walk in the rain, others just get wet.

Some call it gabagool, nobody calls it capicola. Some put mutzadel on their gabagool sangweech.

Me?

I’m in the school of walking in the rain and prefer roast beef with provolone, a pickle and a slice of tomato.

I have lost a couple umbrellas to the wind whipping across a bridge along the Chicago River. The kind of wind that turns an umbrella inside out and sends it tumbling down Wacker Drive like a wounded bird.

Clothes dry off eventually and a good raincoat doesnt turn into tinsel like an umbrella will.

The banker never wears a Mack in the pouring rain, very strange.

March 10th, 2026

 The walls are built up, stone by stone. That line has been rattling around in my head all morning.

Most of us have wanted our life to change overnight. New habits, new attitudes and new results, but that’s not how anything real gets built.

A wall isn’t just dropped into place all at once. A mason lays one stone, then another, then another. Most of the time it doesn’t even look like the job is getting finished. He is just stacking rocks in the dirt.

Then one day you step back and realize something solid has been built.

Faith works like that.

Families work like that.

Friendship works like that.

Character works like that.

You go to Mass. You give structure and make examples for your kids. You show up when a friend needs help. You go to work with a fever. You take the next step even when nobody is around watching.

Stone by stone.

That is why Opening Day matters to me. Not because it’s just baseball, but because every season starts the same way. It starts from scratch, fresh grass and the belief that what you build everyday can turn into something worth cheering for by October.

Championships aren’t won on Opening Day. They are built stone by stone with every pitch, every out, every inning and every game.

Same goes for life...

... Wherever you are this morning, keep stacking stones.

March 9th, 2026

 The first work day after the time change has me blocked up with nothing to chalk about.

It is National Meatball Day and that alone makes a Monday mo betta’. I love them in a bowl with pasta and I love them in a sandwich.

Wrapped in a Turano roll with a gentle amount of sauce. Sprinkle on some giardiniera and melt a slice of mozzarella over the top and you have yourself a delicious sangwheech.

It’s going to be a gorgeous afternoon as we officially rolled into Saint Patrick season over the weekend. I see there might be snow flurries flying for the Southside parade.

Get up and go, enjoy the smile on the sun…

March 8th, 2026

 We have had this date circled since early November when the sunset was at 4:30 in the afternoon. Cocktail season on the balcony has officially started.

I could use that hour of sleep after a parade day that involved a dozen pints of Guinness and several shots of the Tullamore D.E.W..

It was great seeing old friends and meeting new ones. The best part of the day was seeing a Saint Cletus football player with his mom and his girlfriend.

Enjoy the longer day and make sure to change all the clocks around the house.

March 7th, 2026

 Every year the Westside Irish parade rolls in front of the same pubs. The same bagpipe bands playing the same familiar tunes. The same politicians running for office, the same public-school band and the same floats gliding across Madison Street.

But if you look closely, it’s never the same parade.

I started going to the Forest Park Saint Patrick's Day Parade back in the 1990s. Back when it was new and I was young. Back when the sidewalks were packed shoulder to shoulder and the bars were packed by noon. Back when my Old Man was still around.

When we would drive past the Jewish cemeteries in Forest Park, my dad would break into song, loud and proud. Belting out “Tradition!” from Fiddler on the Roof. Not a singer in the technical sense, but he didn’t care. He sang it like it mattered. I keep with the tradition for the Shepkids, but my go to song is "Sunrise, Sunset."

Now when I go to the parade, the streets look familiar but the faces are different. Parents who once stood beside me are gone. Friends who shared beers along the route have drifted off with time.

Twenty-five years ago, my new girlfriend joined me for our first parade. She brought me a green carnation to mark the occasion. The next year her mom and dad joined us and then several years later we started bringing our children.

Those days are gone, but the parade still comes.

The pipes still play and the flags still wave. That is the thing about tradition. It isn’t permanent at all. It is a relay race. People carry it for a while, then hand it off to the next group standing along the curb.

Today I’ll stand there again, remembering the ones who used to stand beside me. My eyes will be wet when the bagpipes start up. I will hug and shake hands of many old friends and familiar faces...

... and somewhere in the back of my mind I’ will hear my dad singing: “Tradition!”

The morning starts out wet and as the wind picks up the temperatures will drop. I'll wear my kilt so the grown-up single Irish dancers have a warm place for their hands.

Six Nations this morning with Scotland and France. Followed by the English playing the Italians. Congratulations to the Irish beating Wales yesterday afternoon.

Let's get our Irish on and enjoy some gusto and astonishment.

March 6th, 2026

 Ten years ago today my mom called from Indianapolis and said,

“I’m sick, Pumpkinhead.”

Sixty days later she went up to heaven.

My mom was the only person who ever called me that term of endearment. Rightfully so, since she gave birth to a big-headed son who came into the world gregarious and truculent.

I have never really grieved the loss of my mother because she never really left me. Throughout my adult life my mom lived one hundred and seventy miles down I-65. A straight shot through cornfields and truck stops, the kind of drive you can do with muscle memory. The most important thing I have learned these last ten years is that heaven is much closer than Indianapolis, Indiana.

My mom leaves me dimes and shows up occasionally at my bedside at 2:22 in the morning. That is her angel number, symbolic of the 222 mile post on I-65. Whenever we drove past that stretch of Hoosier highway, she would tell me she loved me and lean over to kiss my forehead.

Most of those trips I would cringe and tell her to stop. I was too grown up, too cool, too busy being a tough guy. Today I would give anything for one more of those embarrassing smooches.

Every year since her passing I celebrate what I call the Sixty Days of Cecilia. From March 6th, when she told me the grave news, until May 6th when she died.

This year I’m giving up sweets, which I actually began on Ash Wednesday. I’m also giving up cigars and maybe the biggest sacrifice of all, Chicago food.

That last one will be the hardest.

Hot dogs dragged through the garden. Pizza cut in squares. Italian beefs dripping down my wrist. Gyros wrapped in foil smothered in tzatziki. Pizza puffs that burn the roof of your mouth and Maxwell Street polishes with grilled onions.

Chicago food isn’t just food. It is memory, it is a way of life. It is as comforting as my mommy's embrace.

Through the years I have given up booze, sex, red meat, and bread. Sixty days has a funny way of reminding a man what he leans on and what he can live without.

It is hard to believe how quickly these ten years have passed.

My mom hasn’t been around to watch me blossom into fatherhood or see me take a second swing at bachelorhood. Then again, if heaven really is closer than Indianapolis, she has probably had a front-row seat the entire time

She has seen every time I raised my voice at the Shepkids and every time I’ve had a little Jumbo love sleepover.

So I raise my parting glass to Cecilia Marie and honor her these next sixty days in prayer, sacrifice, and memory.

Because a mother doesn’t really leave. Sometimes she just moves a little closer to heaven and a little deeper into your life.

March 5th, 2026

 There is a funny thing about courage.

Most people think courage belongs to the brave guy. The tough guy that never seems scared. The one who walks into a hard situation like he owns the joint. Some people are just wired that way.

The real test comes for the rest of us.

The runner or broker who feels the knot in their stomach before they walk onto the trading floor. The school counselors who have to swallow hard before making the tough call, saying the difficult thing, or standing their ground when it would be easier to keep quiet.

That is where the quote comes in.

“The courage of a coward is greater than all else.”

Because when a scared man finds the nerve to stand up and fight, that isn't natural courage, but an earned courage that comes out of nowhere.

It is the kind of courage that shows up at 4:30 in the morning when the alarm goes off and you’d love to stay in bed, but you need to get out to the barn. It is the courage that keeps a father moving when the bills are stacked on the kitchen table. It is the courage that makes a man admit he was wrong or take responsibility when nobody else is willing to.

That kind of courage isn’t flashy. It isn't Tom Cruise or Bruce Willis.

It is more like absinthe in a Sazerac. It isn’t the whole drink. It is just a rinse in the glass. That small touch changes the character of this gorgeous cocktail. I had to sneak that in because it is National Absinthe Day.

Most days we are not heroes. We are just regular people trying to do the next right thing even when we are scared.

And that, believe it or not, might be the bravest thing there is for the single mom, the tired dad, the over worked nurse or the doubting pastor.

Go put your pants on, one leg at a time and leave your cape in the box under the bed.

You Chalkheads are all courageous to someone in your life.

March 4th, 2026

 Happy 189th Birthday, Chicago. I chalked a William Blake quote for Wednesday, March 4th.

I tossed and turned last night thinking about something my Oldman told me when I was a kid growing up at 220 South Lombard.

He said once you step outside that front door, the world doesn’t care who you are.

At the time it sounded harsh, but the older I got, the more I understood what he meant. The world isn’t cruel, It’s just busy. It keeps moving whether you’re ready or not.

That is something that I wrestle with now raising the Shepkids.

They carry anxiety and labels. They carry the weight of divorce and the confusion of growing up in a different world than the one I knew. Sometimes I want to shake them and say what my father said to me: nobody out there gives a shit, but Blake reminds me of something different.

The real work in life isn’t convincing the world you matter. The real work is learning how to see the world properly and seeing the meaning in small things. Finding purpose in ordinary effort while holding something infinite in the palm of your hand.

That lesson isn’t easy to pass down. Because raising kids means watching them struggle with truths you learned the hard way. It means realizing that grit, humility, and responsibility aren’t lectures. They are discoveries each person must make on their own.

Parenting, it turns out, is harder than anything my parents ever warned me about, but maybe that’s the point.

You raise them, you guide them, and you hope that one day they look at a grain of sand, a wildflower, or a hard day’s work and finally understand why I’ve been pissed off at them most of the time.

March 3rd, 2026

 March usually doesn’t knock, but rather It pushes the door wide open. Letting the fridgid air of winter out and the fresh breeze of spring in .

The wind comes in loud, sharp, and unapologetic. It rattles bedroom windows and it bends naked tree branches. March reminds us that winter never leaves quietly and beneath that departure the daffodils are being awoken.

This morning brings us the full moon of March, the Worm moon. At 5:04 Chicago time a lunar eclipse begins. It peaks around 5:30 and finishes at 6am.

Today is National Anthem Day. A moment where we are supposed to stand a little straighter and remember who we are and remember who paid the price for us to be here.

Like the March wind, our anthem can feel uncomfortable. It calls you to attention and demands respect.

We live in a time where comfort is king. Where silence is easier than conviction. Where it’s simpler to sit than to stand, but growth doesn’t come from still air.

The wind doesn’t apologize for blowing. The daffodil doesn’t complain about being shaken awake. Let the anthem remind you.

Let the wind strengthen your roots instead of testing your patience.

March is here and the madness is loud. The season is changing whether we are ready or not.

Stand up and be stirred. Be proud of yourself and the country you live in.

March 2nd, 2026

 Always be quick on your feet…

First Monday of March, let’s get it on!

March 1st, 2026

  16,919... that is how many days have passed since November 4, 1979. The day Iranian students stormed the American embassy in Tehran and the world shifted. I was in eighth grade when this happened.

History books remember the hostage crisis. News anchors counted the 444 days. Politicians used leverage to get the hostages released.

I remember Omar.

My dad worked with a mechanical engineer from Iran in the 1970’s named Omar. My dad always said he was probably the finest engineer he ever met. Omar was Persian, proud of his heritage, and a strong Catholic. He came to our house often for dinner. He laughed easily and told stories with my Oldman. He loved his country, both the one he was born in and the one he chose.

Then November of 1979 arrived.

Overnight, Omar wasn’t the best engineer in the room anymore, he was Iranian. The revolution that toppled the Shah didn’t just change Tehran. It changed the temperature around every Iranian in America. Suspicion replaced respect and distance replaced fellowship.

Omar’s comfort level evaporated as the 1980’s began. His career stalled and his marriage collapsed. The weight of being a Christian from Iran in that moment pressed down hard. He tried to outrun it the wrong way and eventually lost his battle with alcohol.

My Oldman never turned his back on Omar. Omar was his friend who came to our home and broke bread. Omar was a colleague that made my Oldman stronger at his job.

When Omar died, hardly anyone from the railroad industry showed up at the wake. My dad was heartbroken and furious. Furious that a man who gave so much of himself could be reduced to a headline and easily forgotten.

The regime born 16,919 days ago may still stand as the politics grind on. What remains for me is the stardust and the memory of a gifted engineer who sat at our table.

I will remember the lesson in loyalty of my father, and the reminder that geopolitics always lands on the wrong shoulders.

Regimes rise and fall. Headlines will always flare and fade, but the measure of a man is who will stand together when the room gets quiet.

If the world shifts again this weekend, may it do more than redraw alliances. May it restore the dignity of men like Omar. Men who were better than the moment that swallowed them.

…And may we never confuse a flag with a soul.

The lyric I used today is from a song that I associate with Omar. Omar told me the song was composed by a Hoosier, Hoagy Carmichael. Omar and my Oldman also shared a passion for jazz and old standards.

When I’m done chalking here, I will add Iran’s future to my prayers.

March has arrived with historic events and the promise of change. The sun will smile over Tehran and gusto and astonishment will become a reality.

February 28th, 2026

 The constant through my life has been friendship. Not money or romance, but a solid flow of friends.

I have been blessed with great people who showed up when the weather turned, who didn’t flinch when things got hard, who stayed seated at the table long after the meal was over.

Love on the other hand, has come and gone just like yesterday’s weather. One afternoon, warm enough to fool you into thinking winter had surrendered. The next morning, gray skies, wind off the lake and the kind of cold that creeps into your bones and reminds you it is still February.

That’s life, warm fronts and cold snaps that open windows and slam doors.

Today’s grabber section pits Hammond, Indiana against Arlington Heights, Illinois. Two towns, two states with civic chest-thumpers fighting over who gets to host the Chicago Bears.

I could give two shits where the Monsters of the Midway play their mediocre football. The Bears aren’t my friend. They are the toxic relationship in my life. I keep showing up in my old Payton jersey and they keep disappointing. I swear I’m done, then September rolls around and there I am again, like a fool waiting for an apology that never comes.

That isn’t friendship, it is an addiction with nostalgia attached.

Today is the last day of February and if we are being honest, it has been a horrible month. Gray, heavy, and expensive. The kind of month that sets a tone you didn’t ask for in 2026.

The good news is the calendar flips tonight. Winter will loosen its teeth and the sun climbs over the lake. We might not see it when clouds get in the way, but it is there.

We get to choose whether we carry February into March or leave it on the nail where it hung. I say flip it before you go to bed tonight .

Let’s find some decency in March. Some gusto, some astonishment and some smiling suns breaking through the cloud deck.

Friendship is love without the wings. It doesn’t float off. It doesn’t disappear with the weather. It stays up on the stage or in the shadow behind the curtain. Friendship plows through the snow and answers the phone…

…and that is more than enough for me.

February 27th, 2026

      So far this morning I have let the shit show of life keep me from gusto and astonishment. Fortunately I can see the sun rising through the fog.

Let's get this month finished and move into spring.

February 26th, 2026

 I was searching for a quote for today’s Chalkboard and came across the classic from Dylan Thomas. He wrote the full poem as his father was dying.

When I first read it as a young man, I thought it meant to finish life with a kegger and a mosh pit, loud, reckless with my fists in the air.

The closer I get to my own final day, the more I realize it’s not about noise, but about defying decay.

“Do not go gentle into that good night” isn’t a command to rage at the world, but a refusal to drift. A refusal to soften into irrelevance. It’s about staying engaged, both mentally, spiritually, and physically. Even when the body slows and the world feels upside down.

That lines up with my whole gusto and astonishment theory. Keep searching, stay curious and don’t coast.

Not to go out in fury, but to finish knowing you showed up.

In the grabber section I threw in that line from Apocalypse Now, “Charlie don’t surf.” War all around, chaos everywhere and what does he say? Grab a surfboard.

It might be absurd, but there’s something there. The world may crumble and noise may surround you. Decay may knock at the door.

Do your thing anyway.

Stay sharp.

Stay engaged.

Refuse to drift.

Grab a surfboard.

Create gusto and search for astonishment.

Put a smile on the sun.

That’s the rage I'm searching for before the lights go out.

February 25th, 2026

 The first thing I thought about when I chalked this quote was sports radio. I can’t listen to sports radio.

The only show I can stomach is during football season when Dan Hampton and Ed O'Bradovich do their pre- and post-game Bears show on WGN.

Two former Bears who failed before they ever succeeded.

Mr. OB was a defensive end on the 1963 World Champion team and Hampton was on the Super Bowl XX team. They played in seasons were losing outnumbered winning. They took their lumps and got up to give lumps back. One got chewed out by George Halas while the other got screamed at by Mike Ditka. That is why they know what the hell they are talking about. They paid rent in sweat and bruises and have every right to talk about the future team from Hammond Indiana.

I can’t stand these whiny little pukes who never played the game. Mealy-mouthed critics dissecting the “kingdom of sports” like they built it. High-pitched bitching and moaning devoted to criticizing, nitpicking and second-guess...

...rarely congratulating the teams they cover.

Sure, they are successful and popular with the fanbase and advertisers. Just not for me.

If you never lined up across from a man trying to take your head off, maybe ease up on the sermon.

Failure earns a voice, effort earns an opinion.

And as for the grabber section this morning. It is National Clam Chowder Day. I’ll take mine red over white. Manhattan over New England any chance I can. Problem is, around here, red chowder is harder to find than a winning football season.

February 24th, 2026

 I woke up this morning and realized I don’t have plenty of time, but I have enough time if I use it deliberately.

The numbers in the grabber aren’t random. 2,245 is how many days we’ve spent in the 2020s. 1,407 is how many remain until 2030. It isn't morbid, It’s just math.

At 30, I thought faith meant optimism. Filled with big prayers, big dreams and believing everything would somehow work out.

Faith at 30 is hopeful. Faith at 60 should be grounded.

Grounded faith isn’t supposed to be loud. It is showing up for your family and friends even when you are tired. It is choosing restraint over reaction. It is believing in God not because life is easy, but because you have buried parents, weathered storms, made mistakes, and still stand.

Grounded faith says that we know who we are. I know who I am and I’m going to use the time I’ve been given on purpose.

I need enough time to nurture, enough to grow stronger and enough to leave people better than I found them.

Enough, if I’m deliberate.

Enough to find gusto and astonishment.

February 23rd, 2026

 I woke up early Sunday and heard the lions roaring across the river. My balcony sits about a quarter of a mile from the lion grotto at Brookfield Zoo.

The sound is pure power. It reminds you that there are teeth in the world that can rip your head off. I’m safe because they are zoo lions. If they were wild along the banks of the DesPlaines, I would be dead before sunrise.

The irony here is the lions aren’t the ones caged, I am.

Caged by routine.

Caged by comfort.

Caged by the steady hum of a predictable life.

I have never lived in a jungle. Standing in a trading pit during a fast market is insanity, but it isn’t a jungle. Taking the Lake Street home at three o’clock in the morning is a risky move. Still not the jungle.

Today is Tootsie Roll Day. I never have been a big fan of candy that hurts your jaw when eating.

Let’s get this last week of February safely in the books. It has a forecast with a winter bite to it. Still not the jungle.

Especially when you have a remote start on your car.

February 22nd, 2026

 The proud oak looks powerful with its thick trunk and deep roots, but when the storm hits hard enough, that same pride snaps it in half. The bamboo bows to the storm and takes the wind. It gives a little so it doesn’t lose everything.

In life, you don’t resist reality. You adjust to it and you keep moving.

Yesterday was rugby day and today is all about Olympic hockey. Two teams stacked with professional players meet for the gold early this morning.

This is the last week of February. Weather is not expected to be brutal as we slide into March.

Bend but don’t break this week.

February 21st, 2026

 Every morning I try to knock out a hundred smile-ups. Smile-ups are push-ups for your face.

I am working on earning those crinkled crow’s feet near my eyes. The kind that old, happy men wear like medals. I am also trying to undo the Shepley frown I inherited from my grumpy Oldman. Some things get passed down whether you ask for them or not. My dad handed down a big can and a pissed off smirk.

One of my new disciplines for 2026 is to have a smile when I pull up to a red light.

It keeps me from cursing the fact that I’m stuck at this F’ing intersection. It also throws the other drivers off if they glance over at the handsome prick in the Ford Flex. Maybe the smile spreads, maybe it doesn’t, but it is better than scowling at brake lights.

It is a cold and cloudy Saturday. The Six Nations are on the television and the Olympics are wrapping up.

England versus Ireland is the early match followed by Wales versus Scotland.

Saturday is rugby day, so find someone to ruck and scrum with today… at the pub, on the pitch, or under the sheets. Keep your face loose enough to smile while you do it.