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...
Just a typical Chicago guy juggling fatherhood and bachelorhood. I’m an old trading floor broker who drives around in Chet the Ford Lemon and lives by the river. Most of these stories are life lessons meant to make you laugh, cry, and think. The “Chalkboard” is a daily post scribbled on the blackboard in my kitchen ... it has become my morning ritual, a bit of therapy and a small win to start the day. All Chalkheads are welcome to ride along.
Friday, September 5, 2025
September 5th, 2025
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!
Wednesday, September 3, 2025
September 3rd, 2025
When I first told my ex-wife that I loved her, I promised her something simple.
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).
Monday, September 1, 2025
September 1st, 2025
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.
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.
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.
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.