June 8th, 2026

  Most people think bravery happens on battlefields, in burning buildings, or during headlines that make the five o’clock news.

The truth is, most bravery happens on ordinary Monday mornings.

A father getting out of bed before sunrise and heading to work. A mother worrying about her children long after they have become adults. A husband sitting beside a hospital bed. A wife holding a family together during difficult times. A son carrying memories of his parents who are now in heaven.

Love is what gives courage its purpose.

Without affection, bravery becomes recklessness. Without something to care about, there is nothing worth sacrificing for.

Eighty-two years ago, those young men climbed into landing craft and crossed the English Channel. They were scared, but fear took a back seat because they loved something more than they feared.

They loved their families, their hometowns, and the hope that future generations would live in freedom.

The same principle applies today on a much different scale.

The dad coaching Little League after a long day at work. The woman checking on an elderly relative who can’t get around. The parent helping a child navigate a difficult school year. The friend who answers the phone when someone is struggling.

None of these people will receive medals. Yet each is fighting a battle on behalf of someone they love.

As I get older, I have become convinced that the things worth fighting for are remarkably simple: faith, family, friendship, community, and country.

The older I get, the less impressed I am by people who boast about themselves. I am more impressed by people who quietly carry responsibility.

Because courage is not measured by how loudly a person talks. It is measured by what they are willing to protect.

… and every brave man or woman I have ever known had one thing in common, they loved something more than themselves.

Have a good Monday, Chalkheads. Make it count.

June 7th, 2026

 Sunday’s quote is from Khalil Gibran.

It is simple, but there is a lot packed into it. Gibran isn’t saying life and death are identical. He’s saying they belong to the same journey. A river doesn’t end when it reaches the sea, it becomes part of something larger. The river’s shape changes, but the water continues.

For me, It’s simple, I can’t control the current. I can only swim downstream and hope the ocean forgives me when I arrive.

I know I chalked a cloudy day with rain later, but the sunrise suggests otherwise. The orange glow came quickly over the lake. Reflecting softly off the bottom of the whispering cloudscape.

Off to find gusto and astonishment on this 7th day of June.

June 6th, 2026

    Today’s quote comes from Tolstoy’s War and Peace. The grabber section points to June 6th, the anniversary of the Normandy invasion.

Sometimes I wonder what the spirits and ghosts of those young men who died on a beach in France eighty-two years ago would think if they could see us now.

For the last twenty-five years, it feels like we have been fighting a different kind of battle. Maybe it started on Wednesday September 12th, 2001. The day afterwards….

Somewhere along the line, too many Americans began seeing each other as enemies instead of neighbors. Some of us love America and some of us don’t.

Next month we celebrate 250 years since a collection of farmers, merchants, laborers, and dreamers told King George to go ‘F’ himself and pound some sand. Two hundred and fifty years of victories and defeats, prosperity and hardship, good decisions and bad ones.

Eighty-two years after D-Day, and I’m living in the Divorced Dad District.

I’m trying to raise three kids who will love each other, love life, love their faith, and love their country.

Eighty-two years later, I still worry about bills, but I have a solid job.

Eighty-two years and I’m in a heavily taxed state, but my neighborhood is safe and my neighbors are friendly.

Eighty-two years later and my church isn’t as crowded as it once was, and my parents aren’t sitting in the pew with me anymore, but the Gospel remains unchanged.

Eighty-two years later and we still have a country worth fighting for. A country that needs our support. A nation that needs appreciation.

None of us will be asked to jump from a landing craft while nazis fire machine guns from a bluff above us. Our duty is different. We honor those who fell by building something worthy of their sacrifice.

This morning I will buy gasoline that costs more than I want to pay. I will buy groceries that thin out my wallet a little more than I’d like.

On the other hand, I will make breakfast for people who love me.

Later, I will have a hot dog with people who love me.

Tonight I will break bread and give thanks with people who love me.

All because a bunch of kids stormed a beach on the other side of the ocean.

So go get the gusto and find some astonishment today, Chalkheads.

Show the spirits and ghosts of June 6th, 1944, how grateful you are for the opportunity of June 6th, 2026.

Live a life worthy of the gift they left behind.

June 5th, 2026

 I looked at the quote that I chalked and saw that the Grabber section points out that it is National Donut Day.

It reminds me of something my Father-in-Law often said before a good hearty meal…

"I would rather enjoy this steak today than have to eat gruel in the future.”

What he was saying is to enjoy life to its fullest, take care of yourself and go out on your terms.

… And that is what my Oldman through marriage did. He never ended up in a nursing home. He fell in his kitchen making dinner in late October and went to heaven in early November.

Now I’m not going out and eating a dozen donuts today, but I’m going to enjoy the gusto life brings me.

The first weekend of June. Perfect for a glass of German wine, a Cuban cigar and Gershwin’s Rhapsody in Blue.

I’d like to be doing that on the front porch of 220 South Lombard with my dad, but we only had a brief instant together.

Maybe that is why these small pleasures matter.

The cigar burns down, the music ends and the wine glass empties. The people we love leave sooner than we'd like.

So enjoy the donut.

Just don't forget to savor the day that comes with it.

June 3rd, 2026

I put a smile on the sun today. That alone should lead you Chalkheads to gusto and astonishment.

Today’s quote comes from a Persian poet, scientist and scholar from over one thousand years ago.

I think what Omar is telling us is….

…Quit waiting for the next thing. Summer is upon us. The coffee is hot, the sun is rising over the lake and Wednesday is here for a moment.

Christmas sounds far away when I put 205 days in the Grabber section. It will be here in a moment.

The shadows are short today, but they’ll start getting longer in three weeks….

… Eat some fruit, call a friend, change the sheets, pet a dog and drink whiskey!

June 2nd, 2026

 I remember the first time I had Rocky Road ice cream.

I was probably ten or eleven years old, and right away I thought there was too much crap going on. Too many textures and too many flavors competing against each other.

I came from a family that kept ice cream simple. One flavor in the bowl and maybe one topping on top.

My mom was a chocolate ice cream person. Her mom, my Gramma in Indianapolis, was strictly vanilla. The Oldman loved New York Cherry or Pralines and Cream. I became a mint chocolate chip guy, followed closely by butter pecan.

Let us take this discussion a step further. The battle between soft serve, traditional ice cream and gelato.

When I do soft serve, I do the combination twist, vanilla and chocolate swirled together with a chocolate dip top. In our neighborhood we have the little hole-in-the-wall in Oak Park, Polar Bear in North Riverside and Highland Queen west of Mannheim Road toward Hinsdale.

When I’m feeling nostalgic for ice cream, I drive up to Petersen’s in Oak Park or Margie’s Candies in the city.

Recently, I was introduced to a Boston Cream shake.

I never seemed interested in one because I dislike almost everything associated with Boston. Outside of Larry Bird and Marky Mark, Boston blows. My hatred with Boston has shortchanged me out of this delicacy well into my post-middle age years.

Think of being involved in a threesome, but instead of a blonde and a redhead, it is a milkshake with a hot fudge sundae plopped right on top.

You need a straw for the shake and a spoon for the sundae. The Chalkheads that are priests are expecting to hear a confession now.

Gelato, however, is the Cadillac of the creamery world. My go-to gelato is pistachio. Whenever I have gelato, I’m usually with an Italian.

Nothing pairs better with gelato than an espresso, very adult stuff. Gelato requires a refined palate and enough patience to slow down and enjoy what life has brought you. Don’t rush a gelato…

Today may be National Rocky Road Day, but the chalkboard also says sunshine and 76 degrees. That sounds pretty close to perfect.

Grab someone you love and go get some ice cream. Soft serve, traditional or gelato. A bowl, a cone, a malted or a sundae. It doesn’t matter, just treat yourself.

Go grab the Boston cream shake, but leave my dirty mind out of it.

The older I get, the more I realize life doesn’t need nearly as much Rocky Road as we think it does. Most days are better when they are kept simple.

A little sunshine.

A little conversation. Someone you care about sitting across from you, and something cold melting faster than you can eat it.

There is nothing but astonishment and gusto when ice cream is involved.

June 1st, 2026

   

The older I get, the more I realize losing my parents isn't something that happened the one time.

It has happened over and over again.

It happened when my car made a strange noise and I reached for the phone before remembering my Oldman isn't there to tell me what he thinks it might be. It happened when life throws a problem at me and I find myself wanting to hear my mom’s voice for just five minutes.

It happens on bad days. Days when I am fucking tired. Days when being an adult feels like a lousy deal. Days when I just want to walk into my parent’s home and get into my old bed.

When we are young, we think losing our parents is about funerals. We think grief is crying, prayer cards, flowers, and tuna casseroles.

The truth is grief sneaks up years later. It arrives when we need advice. When we need reassurance. When we need someone to listen.

We come into this world naked and confused, handed to two people who somehow know exactly what to do. They spend years teaching us how to walk, talk, work, love, pray, drive, and survive. Then one day they are gone and we are expected to continue the journey without them.

Nobody warned us about that part. Nobody warned us that one of the hardest parts of growing older is realizing our emergency contacts are disappearing.

Friends move.

Families drift apart.

People get busy.

The phone gets quieter and the text messages get shorter.

We have never been more connected and yet so many of us have never felt more alone.

I still talk to those people who have gone up to heaven. My parents, old friends that left too soon, mentors who shared their wisdom and relatives that I miss spending the holidays with.

Most days it helps, but every now and then I wish one of them would answer back. Not with some profound wisdom or even taking the liberty of bullshitting me.

Just enough to say, "I'm listening." Or maybe, "You're doing better than you think."

Or maybe the words every tired son still wants to hear: "It's going to be alright, this too shall pass"

Maybe that is why we need each other. Not to solve every problem. Not to carry every burden. Just to remind one another that none of us are walking this road alone. Even on the days it feels that way.

I put the Chicago baseball club’s records in the Grabber section. I am blessed to have seen my White Sox win the final game of the 2005 season. My mom was a Cub fan. She passed in May of 2016. The beginning of the season when the Cubs won their last game. My Oldman was a Saint Louis Browns fan. He was a miserable son of a bitch during every baseball season.

We have one less day to find astonishment and Gusto. Go get it and enjoy June you magnificent Chalkheads.

May 30th, 2026

 “It's called survival and only the strong can survive, It's called survival in order to stay alive.”

Grandmaster Flash wasn’t talking about comfort, luxury or convenience. They were talking about making it through another day when life wasn’t interested in making things easy.

Most people spend part of their lives surviving.

Surviving layoffs, breakups, funerals, doctor appointments, empty bank accounts, sleepless nights, and phone calls we never wanted to receive.

We survive raising children without an instruction manual and watching our parents grow old.

We survive becoming the age we once thought was ancient.

Survival never is celebrated. People cheer victories, applaud championships and admire the success stories.

Before every victory came a season of survival. Before the harvest came the drought. Before the sunrise came the darkness. Before the comeback came the stubborn refusal to quit.

In the grabber section on today’s chalkboard is the Latin phrase “frusta ut ubera tauri.” Many Catholic school kids have heard it during the survival years of catechism. It means as useful as tits on a bull.

Life is full of things like that. Grudges can be that way. Excuses can be that way. Worrying about things we cannot control can be that way.

So can spending too much time trying to impress people who have already made up their minds about us.

The trick isn’t collecting more baggage. The trick is figuring out what is useful and what belongs at the curb on garbage day.

This Saturday morning, maybe the goal isn’t greatness. Maybe the goal is simply to keep moving forward.

To show up.

To do the work.

To say a prayer.

To make the coffee.

To call someone you love.

… and if that’s all you accomplish today, don’t dismiss it.

Sometimes what looks ordinary from the outside is actually survival.

… and survival is how every good story stays alive long enough to reach the next chapter.

Gusto, astonishment and JumboLove

May 28th, 2026

 The quote I chalked today is from Rudyard Kipling.

It is timeless because most people overreact to both victory and defeat. They let success make them arrogant and failure make them quit. Kipling’s point is that both are temporary and that both can lie to you.

Triumph tells you: You are untouchable.

Disaster tells you: You are finished.

Most of the time neither one is true.

Like Don Shepley always reminded me…

…The same world that gives you a standing ovation will quickly turn around and kick you in the ass.

Today is National Hamburger Day.

My best memories of a hamburger are with my Oldman.

The Wabash Inn hamburger served with a tulip. The Gossage Grill hamburger served with hashbrowns and a cup of black coffee. Goldyburgers with a hot bowl of their great soups and a cold bottle of Old Style.

Though the best hamburger in my humble opinion will always be at the BillyGoat. My first visit was with my father when I was too short to climb a bar stool.

Since then…. I have brought my buddies, third dates, out of town friends and the Shepkids.

Enjoy your favorite hamburger today…

May 27th, 2026

 The backyard was full of conversation and laughter on Sunday afternoon.

The grill was stacked with hamburgers, sausage and hotdogs. Plates filled with potato salad, chips and beans. George and Fritz carrying on conversations that probably started when they were toddlers. Hazel keeping her distance from her grouchy Oldman. My ex-wife and I sitting in the same yard where we dated, were newlyweds, became parents and finally, former spouses. We were just trying to navigate modern family life without making it weird.

And honestly, it wasn’t weird, it was good.

Then “Linger” by The Cranberries came on the radio, and something shifted in me for a moment.

Not regret, I want to make that clear.

I do not regret my marriage, my divorce, or the road that followed afterward. Regret is a heavy chain, and I have carried enough weight through the years.

I did think about the “what ifs.”

What if we tried a little harder?

What if we listened better instead of waiting for our turn to talk?

What if we gave each other a little more grace over the years?

Years when life was heavy, money was tight and exhaustion became part of the wallpaper.

Maybe things would have turned out differently or maybe they wouldn’t have.

That is the thing about getting older. You eventually realize that life isn’t a movie script waiting for a rewrite. Events happen despite our plans, our wants, and our intentions. Human beings like to think they are holding the steering wheel all the time. Life is learning how to ride through storms we didn’t see coming.

Where does faith come into the “What ifs?” I don’t go to God with the same prayers I once did. When I was younger, I mostly wanted comfort, relief, rescue, and guidance to an easier road.

Now I think differently. I don’t believe God’s main goal is my comfort. I think His goal is to make me good, more patient, more forgiving and less selfish. God has taught me to be more aware of other people’s burdens. More capable of carrying suffering without becoming cruel.

That does not mean life becomes painless. It means pain might have purpose.

The Sunday cookout over Memorial Day weekend was not about sadness. It was about gratitude. Gratitude for the people still sitting in the backyard of my life. Gratitude for the memories that still ache a little when certain songs come on, and gratitude for the hard roads that didn’t destroy us, even when we thought they might.

Because sometimes the best families are not the perfect ones. Sometimes they are just the ones that keep showing up anyway.

May 26th, 2026

   For the last two and a half years or so, I have been spending time at Bronswood Cemetery. It has become part of my routine to stop by for a visit.

That probably sounds strange to some people. Most folks think cemeteries are only for burials, final farewells and flowers. Places to visit out of obligation once or twice a year before hurrying back to the noise of everyday living.

Bronswood has become something different for me.

My father-in-law, PopPop Bergmann, is buried there. I like stopping by with a cigar, a couple shots of bourbon from my flask and whatever thoughts are rattling around in my head that week.

Sometimes I talk to him about the Shepkid. Sometimes I talk about work. Sometimes I talk to him about his daughter. Sometimes I talk about God. Sometimes I just sit there quietly and let the wind and the trees do most of the talking.

Not far from Mr. Bergmann rests Stan Mikita. If you grew up a Blackhawks fan in Chicago, you know exactly who Stan the Man was. One of the greats. A legend resting quietly just a grave away from regular people who loved each other and fought with each other. People who struggled and carried on just like the rest of us.

Bronswood itself feels alive in a strange and peaceful way. The cemetery rolls gently across hills lined with enormous old trees that have probably watched generations come and go. Some headstones date back to the 1800s, weathered and softened by time, while others bear dates from the 2020s. Still carrying that fresh grief of families learning how to move forward without someone they loved. Walking through reminds me that grief is not new and neither is love.

The seasons change the cemetery the way Antonio Vivaldi might have imagined. Autumn covers the grounds in burnt orange and gold. Winter strips everything bare and quiet. Spring arrives carefully, bringing green life back to the hillsides, and summer settles in heavy and warm beneath the shade of the old trees. The cemetery never really stays the same, yet somehow it always remains familiar.

That is one thing cemeteries can teach us quickly. In the end, all the titles disappear. The hockey legend, the labor lawyer, the banker, the mother, the neighbor down the block, the grandfather, the brother gone too soon and the father-in-law.

Eventually we all rest shoulder to shoulder.

I think about how short life can be and how quickly people become memories.

Bronswood has become important to me because it has taught me that cemeteries are not only for mourning.

Sometimes they are for maintenance. Maintenance of memory, maintenance of family and maintenance of the soul.

The older I get, the more I realize that I want to end up there someday. Not because it is fancy or expensive. Truth be told, I have never really lived in an expensive house or a high-end neighborhood during my life.

I want the Shepkids to have one place where the family can gather.

One place where they can visit their grandparents, their mother and their father.

A quiet piece of ground where they can come and think about life, talk to God, remember where they came from and maybe sit long enough to hear their own thoughts.

That idea means more to me now than it once did. Life humbles us that way.

Maybe part of growing older is understanding that even after divorce, disappointment and mistakes, family still matters. Maybe more than ever.

Because someday the Shepkids will walk those paths without us. I hope when they do, Bronswood gives them the same thing it has given me… Perspective.

The grabber section chalks out that we are approaching the second full moon of the month, a Blue Moon.

Don’t let that blue moon catch you standing alone without a dream in your heart...

May 25th, 2026

 “Uncommon valor was a common virtue.”

Admiral Chester Nimitz on the Marines at Iwo Jima

There are certain days in America that should always make us stand up tall.

Memorial Day is one of them.

Not because of a mattress sales at Tempur-Pedic or backyard beers at Uncle Ray’s or because today is the unofficial start of summer.

Because somewhere beneath all the noise and sunshine are rows and rows of white stones, folded flags and gold star families that never got their sons and daughters back.

The quote on today’s Chalkboard was about Iwo Jima. Young Americans climbing into hell on a black sand island because somebody had to do it.

Farm boys and factory workers. Kids from ethnic Chicago neighborhoods and small rural Indiana towns. Catholic boys carrying rosaries. Jews who had blood in the fight. Poor whites from coal country who could barely read. Black kids fighting for a country that didn’t always fight for them. Immigrants trying to become Americans by shedding blood for America.

Most of them were barely old enough to shave, but they were brave enough to fight for this country.

Yet when the moment came, courage became ordinary.

That is the meaning of the quote I chalked down this morning.

Not that valor was rare, but that it became expected.

Today, before the bratwursts hit the grill and before the first pitch at Comiskey, take a minute and remember somebody who never got the chance to grow old.

Somebody whose mother received a knock at the door. Somebody who left behind a baseball glove, a high school sweetheart, a future that barely began.

Freedom always costs somebody something.

Enjoy the cookout.

Laugh with your family.

Sit in the sunshine….

… But remember why you can.

May 24th, 2026

 My gramma brought her transistor radio out to the front porch so we could listen to the race.

We had ham sandwiches on white bread with bread and butter pickles and ice tea. What was unusual, my gramma always made us sit at the table for meals. They all started and ended in prayer.

This was the only time she let me bring my lunch to the porch.

Oh and I forgot to mention…

The ham was carved from last night’s supper. The bread was baked in my gramma’s oven and someone in the family made the pickles. All homemade and never any snacks.

The race was a fight between Danny Ongais and Al Unser. My favorite drivers, AJ Foyt and Johnny Rutherford were never a threat. Unser won the race and my gramma scolded me for saying I hated the Unser family.

I never felt at home in Indiana, but I sure would love one more afternoon on that front porch on Indianola Avenue in Broad Ripple.

Sunday Funday and I have two growlers of BuckleDown for the race and the family cookout.

“Gentlemen, start your engines….”

May 23rd, 2026

 Soft rain woke me up this morning. Backyard birds singing to each other before most people even poured their first cup of coffee.

Memorial Day weekend has arrived for 2026.

Another Indy 500 winner will be added to the Borg-Warner Trophy and summer officially begins. A summer filled with weddings, birthdays, funerals, hot afternoons and warm evenings. Days that will soon become faded memories from the summer we celebrated the semi-quincentennial. 250 years of stirring the American gumbo pot.

Labor Day is 107 days away.

One hundred and seven days to enjoy a summer that will mark beginnings, milestones, victories, defeats and unforeseen endings.

107 days of not putting it off until tomorrow. 107 days of not waiting for a better day because today is the better day.

Plant the flower.

Try the new Thai joint.

Take the drive.

107 days of making love, making friends and making goals. 107 days of dancing awkwardly and singing off-key. 107 days to pick up a wiffle ball bat, play catch in the alley and sit in a beer garden under string lights listening to John Prine songs.

This weekend is the beginning of the Summer of ’26.

And just like the summers of ’76, ’86 and ’96…

…it will become a distant memory sooner than we planned.

So take chances. Take the road trip for the pork tenderloin sandwich. Go to the street festival filled with people who don’t look like you.

Put the smile on the sun and look down at your shadow lying underneath your ass. Because before you know it, that shadow will be stretching long down the sidewalk.

These next 107 days should be filled with gusto, astonishment and high-pitched laughter.

May 22nd, 2026

 Yesterday I listened to the CBS jingle on Chicago’s WBBM radio for the final time.

One hundred years of affiliation and history gone with the flip of a corporate switch. Maybe that is just how business works now, but it still feels like somebody tore down an old neighborhood tavern to build a parking garage.

Morning radio today doesn’t sound like it used to. It used to keep you company. Voices had personality. DJs sounded like regular people drinking burnt studio coffee at 4:30 in the morning while telling you about traffic on the Ike and whether the Sox bullpen blew another one. Now half of it feels like noise designed by a committee.

The quote on the board this morning says pain is God’s megaphone to rouse a deaf world. Maybe that is why losing little traditions hits harder as you get older. They remind you time keeps moving whether you’re ready or not.

As for the grabber section… today belongs to the cooler.

National Cooler Day deserves more respect than it gets. I still have a cooler from the 1989 Bluesfest, back before I was handed the persona of Jumbo. Back then I was still just “Shep,” and somewhere along the way I scrawled that name across the lid with a Sharpie that never fully faded.

That cooler has survived lakefront parties, tailgates, road trips, picnics, heartbreaks, and enough cold Old Style cans to fill Comiskey Park.

The handle squeaks now, the plastic is worn, but like an old Chicago bartender, it still shows up and does its job without asking for applause.

Funny how objects become witnesses to our lives.

Today is another reminder that the old stuff mattered.

Old radios.

Old songs.

Old Sox fans.

Old coolers.

Old Arb Clerks.

Old voices.

May your cooler be filled with ice, gusto and astonishment.