Friday, September 5, 2025

September 5th, 2025

       If I could pull 1978 John Shepley aside… if I could sit with 1984 John Shepley, talk some sense into 1992 John Shepley, buy a beer for 2004 John Shepley or take a long walk with 2016 John Shepley, I’d only say one thing...

... Work harder.
Easy roads are a mirage. They are a crock of shit. Every shortcut has a toll booth at the end.
Make yourself stronger, John. Push yourself harder, Shep. Put more passion into it, Jumbo. Don’t settle for second best, because second best turns into second place.
I spent too much time praying for breaks instead of creating them. Waiting for doors to open instead of kicking them in. I took the easier route more than I should have... and now I am paying for it. That is why I’m working harder now.
I have one of those fancy trading desks that goes up and down with a switch. I left mine standing and unplugged it. I am standing today because I don’t want to be lying in a bed tomorrow with a stranger wiping my ass.
I’m taking my father-in-law’s advice too, ordering a medium-rare strip today, so I’m not eating gruel in a nursing home later. I never scored a try in my twenties, but I will in my sixties. I finally finished James Joyce's Ulysses this year and maybe I will complete my Twilight Zone marathon.
I am closer to my funeral than my baptism, and I promise you, Chalkheads… I’m going to hit every pothole and keep driving along.
It is the first Friday of September. Go find a football game. Go find a bonfire. Go find a friend.
And like Don Shepley hammered home: “You can judge a man by the way he finishes a job.”
Let's finish strong!
Today is leg day. Push yourself and don’t forget the gusto.




Thursday, September 4, 2025

September 4th, 2025

 I might come off like a jag off this morning, but I am taking a tough love stance towards someone that I love dearly. If today's Chalkboard can heal one regret, fanfuckingtastic!

I have known my cousin since we were toddlers. Our dads, my Oldman and Uncle Charlie... were thick as thieves, running side by side through life.
My cousin got me my first job on the trading floor. That wasn’t just a paycheck, that was a door opening to a career that has lasted nearly forty years. I owe him for that. I’ll never forget it.
BUTT gratitude doesn’t erase truth.
My cousin, the birthday boy has walked away from his only sibling. Ghosted her. Ghosted her family. Ghosted memories that should be shared. Once, they were tight... laughter loud, history deep, stitched together by the love of family. But years have slipped away, and silence has settled in.
I have seen this movie before. Back in the late ’80s, my Oldman and Uncle Charlie had a blow-up. Six, maybe nine months, they didn’t speak. Later, my dad told me it was one of the saddest stretches of his life. When Uncle Charlie died in 1992, the regret crushed him even more. You don’t get back the time you throw away. You don’t get a do-over.
That’s why today’s chalkboard carries this quote:
"I am never afraid to start again. Restart is always better than regret.”
Cousin, give yourself the best birthday present you can, heal this wound. Pull your head out of your stubborn ass, make the call, and fix this while you still can. Do it for your sister. Do it for the family. Do it for yourself.
And to the rest of you Chalkheads, if this hits close to home:
Every year you don’t make the call, the clock gets louder. Someday it will stop. Don’t wait for the funeral to wish you’d picked up the phone. Life’s too damn short to let pride run the show. Swallow it, make the call, fix the wound. Be the one who ties the knot, not the one who leaves it frayed.
Because regret?
Regret is the heaviest thing you’ll ever carry.




Wednesday, September 3, 2025

September 3rd, 2025

 When I first told my ex-wife that I loved her, I promised her something simple.

That I would work hard to love her more today than I did yesterday. I stole the idea from the Spiral Starecase song, but I meant every word, and for most of that marriage, I lived up to it.
Then life shifted.
My energy turned more towards fatherhood. I put everything I had into being a good dad, trying to be better today than I was yesterday. That is still true today and it always will be.
Now, as the working years have started to wind down, I have found myself doubling down again. I am working harder today than I did yesterday. I am writing more consciously, more intentionally, leaving pieces of myself behind in chalk. I am loving God more today than I did yesterday, this country I call home, and the gift of my life, even when it has not been easy.
More than yesterday…
This is how I am going to finish this somabitch: by working harder, loving harder, praying harder, and trying, in my own small way, to bring us all together.
I want to promote my faith, my family, and my friends... louder today than I did yesterday. I want tomorrow to be more astonishing than today. If I can get the world around me to see that, to feel that, then maybe my legacy will lean more toward the positive than the negative.
It is supposed to rain today. Maybe, if we are lucky, a little August rain has lingered. Just enough for one more smell, one more reminder that even the smallest things carry meaning.
Because at the end of the day, the goal hasn’t changed.
Be better than yesterday.
And tomorrow?
Better still.




Tuesday, September 2, 2025

September 2nd, 2025

 There is a Talking Heads song that is carved into the soundtrack of the ’80s. This Must Be the Place (Naive Melody).

A song so tied to the movie Wall Street that I still see Charlie Sheen whenever David Byrne belts out those gorgeous lyrics.
For me, it is more than nostalgia. Every time I hear it, I also hear the voice of the late Lin Brehmer from WXRT. His iconic sign-off echoes in my head: “Take nothing for granted. It’s great to be alive.” Lin understood what that song stood for. That home isn’t just a place, it’s a feeling. It’s the people, the small gestures, the fleeting comforts that make us feel like we belong.
The last night I ever slept under my Oldman’s roof, he left a towel and washcloth folded on the guest bed. On top sat his old Grundig Yacht Boy radio. On the nightstand, a perfect cup of tea... splash of milk, rounded teaspoon of sugar. Just the way I drank it.
I turned on the Grundig, and there it was:
“Home is where I want to be…
Pick me up and turn me round…
I feel numb, born with a weak heart.”
I showered in that creaky 1920s tub and fell asleep for the last time with my Oldman just down the hall. I haven’t really had a home since. Just landing pads along the way, but that night still holds me.
Today, I bet half of Chalkhead Nation will listen to that song. Because it is more than music... it’s comfort.
Like a bowl of soup, an old Champion sweatshirt, or the smell of Arm & Hammer detergent on a towel at your dad's house.
While we’re all here sharing this life for just a minute or two, love each other until your hearts stop. Feet on the ground. Head in the sky.
In the Grabber Section today, Noli rumoribus credere/Do not believe rumors.
Believe in each other.




Monday, September 1, 2025

September 1st, 2025

“All the months are crude experiments,” Virginia Woolf said and maybe she was onto something.
Think about it… the calendar starts us in the dead of winter, cold and dark, like life before the spark. Then comes spring, full of bloom and rebirth, teasing us with hope and second chances. Summer follows, wide open and loud, stretching out long days where freedom and warmth make us believe the season might last forever. Maybe all of those months, all of those seasons, are just the opening act.
Maybe their only purpose is to prepare us for this moment, the first of the “Ber” months, September.
September brings clarity. It doesn’t rush in, it just arrives with its cooler mornings, sharper skies, and a reminder that change is the one thing we can always count on. It gives us a proper farewell handshake with the longness of summer days, then slowly walks us toward autumn’s front porch. There is comfort in that transition… in knowing that it is okay to pause, breathe, and watch the leaves ignite in color before drifting to the ground.
I think back to the few falls I spent in Indiana, the smell of burning leaves floating down the block, the soft crackle of smoke hanging in the air. The sound of rakes dragging across lawns. Sweatshirts pulled out of the bottom drawer or better yet, that new sweatshirt with the name of your favorite college. The smell of burning leaves only lives in my autumnal memory. Nobody lives at 6130 Indianola that I know or love.
Maybe life, just like Virginia’s September, is a crude experiment, as well. There are no blueprints, no instructions, no guarantees. We stumble, we adjust and we learn as we go.
So, you magnificent Chalkheads, grab your favorite sweater, sip your first pumpkin latte and let the sun put a smile on YOUR face today. Go find the first astonishing treasure this new month has waiting for you.




Sunday, August 31, 2025

A Farwell to Summer (Chalkboard Bonus)

 

The Last Evening of August

There wasn’t a breeze on the last evening of August.
The air hung still, heavy with the usual late summer fatigue. The kind that makes you feel like the whole world has been holding its breath for weeks and is finally about to exhale into September. Bats glitched across the fading sky, their quick, erratic movements cutting black strokes against the pale orange wash as the sun settled into another month.

The cicadas screeched softly from the tree line. Not the manic roar of July, but something quieter, wearier, as if even they understood summer was reaching its close. Above them, the moon hung half-lit in the southern sky, its borrowed light pulling at shadows like a slow tide.

 The sun has slowly melted into Monday, while the constellation Scorpius crawled ahead in the first-quarter glow. Its curve bending toward Antares. That red heart burning stubborn and low on the horizon. A reminder, maybe, that some things burn brightest right before they fade.

Lincoln Avenue and the Quiet Glow

The last of the dog walkers drifted home down Lincoln Avenue. Their shadows stretched long under the soft hum of the gas lamps, that old Riverside glow pooling in front yards where annuals leaned like tired sentries. There wasn’t the flash of lightning bugs anywhere, no tiny bursts of electricity to illuminate summer’s final bow. The stage was closing without fanfare, and nobody seemed to notice.

The moon crept toward Antares, slow and deliberate, like it had nowhere else to be. I sat back and let Charlie Parker’s horn spill from the speakers, sharp one second, soft the next. Cutting across the stale air like a memory you’re not ready to unpack. My Avo burned lazy between my fingers, its smoke curling up into a ceiling of stillness, while the espresso and Licor 43 blended vanilla and citrus into the edges of my thoughts.

An Unused Season

August and summer were the subjects scaling through my mind, each one taking turns on the balance beam of regret. It wasn’t a bad summer, not exactly, but it was an unused one. A season that somehow slipped away while I was busy catching up on work, running numbers, chasing markets, grinding through another set of days at my trading desk.

I spent more time watching the green of the corn belt than the blue of the lake. More hours staring at soybean spreads than sunsets…. and when I wasn’t buried in the churn of my career, I was helpless with the nurturing of family, stuck between wanting to do more and not knowing how to fix what was fraying.

Then, in the distance, fireworks cracked against the dark. Not mine. Some other town’s celebration carried on through the breeze, too far to see, but close enough to hear. That is summer in a nutshell, isn’t it? Somebody else’s joy, miles away, drifting just out of reach.

Rebirth, Regret, and GoldBond Powder

Daylight gave way to darkness, and with it, the season gave way to its clamor. I thought about autumn the way I always do, not as death, but as rebirth. A chance to reset, to take inventory, to sharpen the edges before the cold sets in.

One less summer to live.
One less summer to forgive.

That is the math that keeps hitting harder every year. As the smoke from my stogie curled across my face, I wondered if I’d spent this season wisely or wasted it altogether. No margaritas on the beach. No music on the stage. The rituals I used to chase slipped right past me, swallowed by workdays and quiet nights that stacked into months.

And yet, there were moments. Little ones. Enough to hold onto.

The Ice Cream Stand with George

Picking George up after his therapy sessions became my favorite part of the summer. No plans. No agenda. Just a dad and his son at the ice cream stand. He always ordered soft-serve, and somehow, without fail, he’d finish his cone before I was halfway through mine.

Then came the grin. That scheming little grin.
Always trying to finagle my last bite, but I never gave in. Not once. That was our dance. That was ours, only ours.

Hotdogs, French fries and Fritz

With Fritz, it was the occasional trip to our hotdog stand. A ritual, small but steady. Parky’s, where the smell of grilled onions hangs in the air and the umbrellas over the tables have their own kind of nostalgia baked into the fabric. Something I once shared with my father. Something I now share with my son.

We’d sit there and talk, and I’d listen, really listen. As he tried on his voice, trying to balance who he has been and who he wants to be. You can hear it in your kids when they are starting to figure things out. It isn’t loud, it isn’t dramatic. It’s a shift, a subtle settling, and if you are paying attention, it sounds like growing.

Hazel and the Roar

My daughter, though… Hazel didn’t spend much time with her dad this summer. That part stings. Her little squeaky voice, the one that used to light up rooms, has shifted into something new… a sparky, sarcastic roar. Maybe part of me loves it, because it has strength. It has fire. It is her owning her edges, but I want her to have that roar when she’s twenty-two, not twelve. I want to buy her time before the world forces her to sharpen her teeth.

Farewell to a Boring Summer

The stogie burned down to its butt.
The espresso cooled.
The liquor slipped into the last quiet traces of spicey content.

And above me, the moon settled into the silent branches, indifferent as always.

Farewell, boring summer of 2025. One less summer to powder the nooks with GoldBond. One less summer to worry about sunscreen. One less summer of mediocre baseball in Bridgeport. The White Sox mailed it in again, and maybe so did I.

The Polar Bear ice cream shop will board up soon.
The umbrellas at Parky’s will fold away until spring.
Hazel will have one less summer to be embarrassed by her gregarious father.

What Comes Next

I look forward to fall. To the soft rain of autumn teardrops and the quiet dark that comes to claim the streets earlier each night. Another full moon is coming. Another scoreless period will run out of time. Another season will turn, whether I am ready or not.

Maybe that is the thing about summer?
It doesn’t end when the calendar flips.
It ends when you realize how much of it you let slip away.

 

August 31st, 2025

 Today’s quote comes from one of the most famous of Billy Shakes’ 154 sonnets, Sonnet 18.

The one that opens with, “Shall I compare thee to a summer’s day?” The line that I chalked, “Summer’s lease hath all too short a date,” lands like a quiet reminder, that summer is fleeting, and so are we.
The Summer of 2025 has slipped into memory now. We will never live these days again except in the stories we carry forward. Everyone thinks Sonnet 18 is a love poem, and maybe it is, but beneath it lies something deeper...
... the truth that youth and beauty will fade, that time builds against us, and that we need to grasp the moments while they are here. We must paint them in wonder and keep them alive not just in life, but in legacy.
For me, Labor Day’s legacy will always be tied to a childhood memory. Trying to stay up all night with my mommy, watching the Jerry Lewis Telethon, seeing the tote board climb with every donation. That was my marker that summer was over and the school uniform was waiting to wear.
Tomorrow, we turn the calendar to the “Ber” months, September through December. The stretch of the year where the air cools, the sweaters come out, and the anticipation builds for Hanukkah, Christmas, and the promise of a new year. These months bring coziness and comfort. Warm drinks by the fire, raging bonfires in backyards, and quiet evenings under heavy blankets.
This last week of August pulled out our school colors, filling stadiums and fields with cheers that bring back fond memories of seasons past. Take time to walk beneath the tired leaves before they flash their quick brilliance and let go. Notice the angle of the sun today, how it drapes itself differently across your shoulders than it did in July, already preparing to join the birds on their southern journey.
Summer may have ended, but autumn arrives carrying its own kind of grandeur. The kind Billy Shakes knew how to capture, and the kind we keep alive by remembering.
Sunday-Funday has a smile on the sun and a memory to create.




Saturday, August 30, 2025

August 30th, 2025

 I quote a man who defended his country against the brutality of a devil hiding behind a swastika. For Winston Churchill, success wasn’t a final destination where you could rest and relax. Instead, success created a greater need for sustained, relentless effort to maintain and build upon it.

That is a mantra worth carrying as we push through life’s victories and setbacks.
I have stood at a trading desk so busy my head was spinning, and I’ve stood there on quiet days where my thoughts and worries had all the room they wanted. I’ve had weeks where one Shepkid shines and another one completely falls apart. That’s life, the ups and downs, the ebbs and flows. Some days the road is smooth and other days you blow an axle or flatten a tire.
The trick is remembering there are good days behind you and better ones ahead, even when you are standing in the middle of a bad one.
The weather girl here at The Morning Chalkboard has dialed up something rare for August 30th, a mild kickoff to the season. Most football games this time of year call for sunscreen, sunglasses, and short sleeves. Not in 2025. Today, you can leave the SPF in the drawer and let the breeze do its work.
So, to whatever team stirs your heart... whether if it was under the Friday night lights, on the college gridiron, the pro stage, or the rugby pitch... good luck today. Sports have a way of reminding us who we are and where we belong.
Success, after all, isn’t where you stop. It’s where you dig deeper. It’s where you lean in.
Go Team. Always.




Friday, August 29, 2025

August 29th, 2025

    When this Chalkboard project is all said and done, it won’t just be a collection of quotes and scribbles. It will be a map. A record of where John Shepley stood when life threw him a curveball and how he carried the weight.

One day... George, Fritz, and Hazel will look back and see the path... every climb, every stumble, every hard day survived will be written right here in chalk.

Generations before us had photo albums, letters, and stories passed around the dining room table. We have smartphone cameras and blogs. The ShepKids are the first generation to inherit a living timeline. A chance to scroll through their family’s story and see the fingerprints in real time. This board isn’t just about weather reports or moon phases; it’s proof that we were here, we stood our ground, we watched our shadows, we gazed at the stars, we witnessed time together and we kept moving.
Life will never be easy and you don’t want it to be. If life feels easy, it means something is wrong. Struggle shapes you, pressure sharpens you and the storms don't ask for permission.
The mark that you leave behind isn’t about the size of the load. It is about the way you shoulder it, the way you stand back up, the way you keep walking even when wind across the Chicago River bridge cuts you sideways.
Resilience
Dignity
Character.
That is the inheritance.
When the ShepKids read the Morning Chalkboard years from now, I hope they understand one thing:
Legacy isn’t built by what you bear. It’s built by how you bear it…
... and who is watching when you do.




Thursday, August 28, 2025

August 28th, 2025

  I wanted to talk about an issue that I am having with a Shepkid and school. I was going to ask for advice and bitch and moan about the situation.

Then another mentally unstable person got its hands on a gun. Taking its agenda and guns to a Catholic school where this monster shot up a church while the students were attending the first mass of the school year.
It hit me hard because I went to a baker's dozen "First Day of School Mass" through my school years. Kindergarten through senior year in high school.
Suddenly the issues at Highlands Middle School became petty compared to those at Annunciation.
My Shepkids sat at the dinner table last night. Two kids in Minnesota did not.
Fade to black