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.

February 20th, 2026

   Finishing the week with the same theme I’ve been working lately. Life isn’t meant to be hoarded. Love isn’t meant to be stored. Life and love are both meant to be spent.

Perfect quote for the nod in the grabber section this morning. The USA women’s hockey team gave their life away. In training, in sacrifice, in playing for the USA on the front of their sweater instead of the name on the back.

Happy Friday Chalkheads, give it away, give it away, give it away now…

February 19th, 2026

  I had a dream twenty minutes before I started chalking. Let me make this very clear, I was sound asleep.

In the dream, my mom caught me rubbing one off.

“John Stephen Shepley! What is going on in here?”

I wasn’t worried about getting caught nearly as much as I was upset that I was a kid again, living in my mom’s house. I was worried about not making it to work today. I was worried about all the things I own as an adult, where everything was and who was taking care of my stuff. Most of all, I was concerned that the ShepKids didn’t have an Oldman because he was back in high school, in trouble with their Gramma.

I sure was relieved when I woke up and realized my ma didn’t bust me sleeping with Farrah Fawcett.

I started chalking the quote and thinking about that dream. It made me think about my age and the milestone I’m lifting this summer, especially one that starts with a six handle. I have been auditing my life more. Reflecting on how I got here.

At 30, you think you have time.

At 40, you think you are building.

At 50, you realize the clock is real.

At 60, you start asking: Did I waste spins on a merry-go-round?

I don’t fear the big 6-0. I fear unfinished business.

I am stepping off the ride and looking at the park map. I don’t have to impress anyone anymore. I just need to be honest with myself.

My mom busting me with my schwantz in my hand made me realize something simple: I’m not late for the show. I’m wide awake and everything I want is all around me.

Today is Chocolate Mint Ice Cream Day. It is going to be a good day... unless that is what you gave up for Lent.

This last week of warm temperatures was just what we needed to get over the hump and into spring...

...And that, right there, is astonishing.

February 18th, 2026

 I looked at this quote and I first thought it meant how we exhaust ourselves, but realized it means how we invest in ourselves. Life isn't a savings account, but more a checking account.

Most people spare themselves. They spare the effort, the risk, the vulnerability, the hard conversations and the sacrifice.

Life isn't meant to be hoarded... You can't feel alive by protecting your comfort. You feel alive by exploring yourself.

You feel alive by spending your time on something meaningful. Being alive is spending your talent on what matters. It is spending your love even when love isn't returned immediately. Courage gets your blood moving when it would be easier to stay quiet.

Today is the day to truly come alive. We have a new moon that symbolizes a fresh start. Feria quarta cinerum is that reminder that we are dust and our time here is limited. Comfort isn't the goal, legacy is.

The question I asked myself this morning: Where am I still sparing myself?

That will be the place that I need to start spending myself....

February 17th, 2026

       Can you guess what movie we watched last night?

February 16th, 2026

 What you don’t see still shapes you. Habits, character, faith, resentment, love and fear. You can’t hold them in your hand or measure them with a yardstick, but you can see where they have walked.

Habits determine outcomes and character determines direction. Faith steadies a man when the wind picks up. Resentment poisons swiftly while love builds quietly. Fear shrinks a person before he ever takes that first step. These forces are invisible, but the tracks they leave are unmistakable.

Here is the hard truth: it cuts both ways. Unspoken bitterness leaves footprints. Neglect and excuses also leave footprints. Even silence can leave a mark. You don’t get to opt out of the impact left behind. Whether you intend to or not, you are pressing something into the ground behind you.

I chalked a bright sun on the board this morning. Sunlight creates shadows, but shadows disappear when the light moves. The shade from the sun shifts by the minute, footprints don’t. The impressions you leave through your habits, your character, your love, your faith... those can last decades.

That is the difference between a moment and a legacy.

Today is Presidents Day. My favorites are Andrew Jackson, Teddy Roosevelt and Ronald Reagan. Different eras with different styles and different controversies.

Not one of them was invisible. They believed in something, acted on it, and left trails the country still walk on today... for better or worse.

The sun will move.

The shadows will fade, but what you press into the earth will remain after you are done breathing.

Enjoy this gorgeous gift of Monday February 16th, 2026.

Today is Lundi Gras, tomorrow is Mardi Gras and for the Catlicks, Ash Wednesday follows on Humpday.

Laissez les bons temps rouler...

February 15th, 2026

 I usually do laundry on Saturday morning. Sometimes Sunday if I push it, but this week, for reasons I can’t explain, I did it on Tuesday afternoon.

Two big loads with a mix of my clothes and Fritz’s. George handles his own laundry. Hazel hasn’t been around much, so there wasn’t anything of hers in the basket. Just mine and Fritz’s. Washed, dried, folded, put away before dinnertime.

The next day was when I had to take Fritz to the hospital.

Now who gives a crap about Jumbo doing laundry outside of his routine!?!?

That is when it hit me.

They say pregnant women start nesting before they give birth. Getting the house ready. Preparing without fully knowing why.

I’m thinking by divine intervention, that is why I got the laundry done before my whole schedule shifted. Before the hospital visit and before bringing a patient home for the long weekend.

Another small mystery in the long story of my faith.

Yesterday was Saint Valentine’s Day. I saw a shit ton of boys at the grocery store grabbing flowers like they were buying insurance. I had a romantic evening of my own with a cigar and a glass of bourbon. Smoke rising slowly and elegantly under the brim of my cap. Bourbon stinging the back of my throat like a French kiss with a rough tongue. I climbed into bed with my book and just as I settled under the clean sheets, I farted without apology.

That was when I appreciated being alone. No “pardon me.” No performance of being the first man to ever fart in bed. Just the peace of a novel, Downey fresh bedding and WDCB playing blues on my nightstand radio.

Today is Sunday Funday. The sun is smiling and we are flirting with sixty degrees in February. What is the over-under on middle-aged white men wearing shorts today? They will be on the walking path, in the beer aisle, maybe even holding court at the tavern.

Go find some astonishment today.

Chase it with a little gusto.

Three more weeks and we move the clocks forward.

February 14th, 2026

 It is already Saint Valentine’s Day and Fat Tuesday waits just around the bend. Winter is loosening its grip, even if it refuses to admit it. The light lingers a little longer. The cold still bites, but it doesn’t own the day the way it did in January. We are in that in-between season, not quite thawed, not quite frozen.

And here comes Shakespeare.

“Speak low, if you speak love,” from Much Ado About Nothing. Fitting, isn’t it? Because that play isn’t about starry-eyed romance. It is about guarded people with sharp tongues and wounded pride. Benedick and Beatrice don’t trust love. They mock it. They circle it like two fighters who have been hit before. And yet, somehow, they walk toward it anyway.

Here is the truth: I’m not against love. I’m against illusion.

I am weary of the version of romance that gets packaged and sold like it is a guarantee. Life taught me better than that. Love isn’t violins and restaurant reservations.

It is complicated.

It is sacrifice.

It is disappointment.

It is timing that doesn’t line up. It is people doing their best and still coming up short.

But I do love.

I love my family and my friends. The surprise phone calls and shared meals and showing up. I love my work and the career I have had. Decades of mornings, markets, mistakes, wins, and lessons. I love where I live. The streets I know by heart, the seasons that mark time whether I ask them to or not.

I love sitting at the counter in a good diner. Coffee poured without asking. Strong and black like George McGinnis. I love the radio humming in the kitchen before the sun is fully up.

Maybe I don’t believe in fireworks anymore, but I believe in loyalty. I believe in routine. I believe in praying. I believe in the kind of affection that grows roots instead of wings.

Winter makes a man reflective. Saint Valentine’s Day can make him defensive. Maybe the point isn’t to shout love from rooftops. Maybe it’s to speak it low. To recognize it in the ordinary. To honor it in the steady things that haven’t left.

Spring will come the way it always does...

...not dramatically, but gradually.

...And maybe love does the same.