July 5th, 2026

     I was able to grill some chicken, vegetables, hot dogs and burgers between the raindrops for the Fourth. The typical staples that seem to find their way onto America's birthday menu every year.

   Throw in some ribs, bratwursts, corn on the cob, ice cream, watermelon and apple pie, and you have the Top Ten of Americana backyard parties.

   In Chicagoland, the celebration usually spills through the garage and into the alley, where kids wave sparklers, dads light M-80s and roman candles, and the smell of charcoal hangs down the block.

  I went with a Shakespeare quote this morning because sometimes tragedy can become comedy.

My biggest Fourth of July food memory doesn't include any of those traditional foods.

      Sometime in the late 1970s, we had spaghetti for America's birthday. We didn't have spaghetti because our family was Italian American. We had spaghetti because of an accident.

   My Oldman and Uncle Charlie went shopping together on July 3rd. They bought everything you would expect for a Fourth of July cookout and packed it neatly into our big Coleman cooler on the back porch.

       There was just one problem. Neither one of them put any ice in it.

  The cooler sat in the summer sun the rest of the afternoon and all night long. On the morning of the Fourth, my Oldman walked outside expecting to drain melted ice water and see if he needed to add more ice.

       There wasn't any water shooting out of the spout on the bottom of the cooler. When he opened the lid, he was hit with the smell of spoiled meat.

   Every burger, every hot dog, every brat and every package of chicken had gone bad.

Embarrassed, he walked back into the house and called Uncle Charlie. Each brother thought the other one had taken care of the ice. Now they had a backyard party to save.

   The first order of business was figuring out what could be salvaged and what had to be thrown away. The whole time my dad was cleaning out the cooler, his wife was giving him the full "money doesn't grow on trees" speech. It was a speech I heard dozens of times growing up. Only this time, it wasn't coming from my Oldman.

    He was getting it from my Step Monster. She threatened to take her kids and head to a friend's cookout instead. The pressure was on.

   My dad wasn't just expecting Uncle Charlie and my cousins. Two of his railroad buddies were bringing their families over that afternoon.

   When my Oldman was frustrated, he usually disappeared to the basement to cool off and that was exactly what he did.

    I could hear him on the phone in the laundry room, working on Plan B with Uncle Charlie. Somehow these two German, English/Irish guys decided that the answer to their Fourth of July disaster was an Italian dinner. They each headed to different grocery stores on a national holiday and somehow pieced together enough ingredients for a spaghetti feast.

   The other two families coming to Oak Park that afternoon were Jewish and Irish. I guarantee they weren't expecting pasta on the Fourth of July.

   When my dad explained how he forgot to ice the cooler, his railroad buddies busted his balls all afternoon. Honestly, they busted his balls for serving spaghetti on the Fourth for the rest of his life.

     Looking back, I don't remember missing the burgers or the ribs. I remember the laughter.

I remember everyone giving my Oldman grief. I remember Uncle Charlie walking through the door carrying another armful of groceries.

  Funny how the mistakes become the memories that last the longest. That celebration in 1978 became one of the greatest Fourth of July memories my cousins, my stepbrothers and I ever shared.

   Two of my mentors made a mistake and instead of wallowing in it, they didn't panic. They adapted, they laughed, and they created the best Fourth of July party of my childhood.

    Maybe that is America in a nutshell. Things don't always go according to plan. Sometimes they fall apart completely, but you gather the people you love, figure out Plan B, laugh it off, and somehow the story turns out even better than the one you planned.

    That pasta supper is another reason this has always been one of my favorite holidays.

        Parades, fireworks, Uncle Sam, patriotic music...

                             ...and spaghetti.

      It is Sunday Funday, you Chalkheads. Finish this rainy Fourth of July weekend with gusto and astonishment.  

 

July 4th, 2026

 

   Today's Morning Chalkboard has all three of my favorite holidays written on it. The Fourth of July, Thanksgiving and Mardi Gras.

      Those might seem like an odd combination when you think about it. One celebrates the birth of a nation, one celebrates gratitude and one celebrates joy before sacrifice.

       If I had to pick three holidays that best describe how I try to live my life, those would probably be them.

    The Fourth reminds me that freedom is never free. It belongs to people willing to be bold enough to defend it.

   Thanksgiving reminds me that no matter how much life has given and taken away, it has always left me with something worth giving thanks for.

   Mardi Gras reminds me that laughter, good food, good music, cigars, and one more round of Sazeracs are not distractions from life. They are part of the reason we are here.

         Maybe that is why today's quote spoke to me… "Freedom lies in being bold..."

Not just politically, but personally.

Have the courage to say what you believe.
Have the courage to forgive.
Have the courage to love.
Have the courage to push through.
Have the courage to laugh hysterically and cry when your heart is full.

       Freedom, Gratitude and Celebration are a pretty good recipe for a life well lived.

   So today, you Chalkheads, celebrate the positives that these past 250 years have accomplished. Never forget that our country has always been, and always will be, a work in progress. Built on liberty, justice, and the pursuit of happiness.

                And remember... all Sox and Cub fans are created equal.

Bonus feature: Color Strong

 
    One of the strangest lessons my Oldman ever taught me involved a Polish sausage from Jim's Original.
    I was about twenty-five years old, and we were driving to Maxwell Street for lunch. He decided it was time for another one of his fatherly tests. My Oldman was always testing me. Sometimes I would pass the exam, but most of the time I would get his ‘You gotta be shitting me?” smirk.
    He looked over and said, "You've got one extra Polish sausage. If you want to get into heaven, you've got to give it away."
              "Okay. That’s easy enough…."
     "You have two choices. A black man wearing a White Sox hat or a white man wearing a Cubs hat."
       I didn't hesitate.
                 "The Sox fan."
      He looked at me for a second.
              "Why didn't you pick the white guy, son?"
    "Because he's a  f’ing Cubs fan dad!"
     The Oldman started laughing.
               "You passed."
     It had nothing to do with baseball. It had everything to do with what he wanted to know about the son he had raised. He wanted to know if I saw race before I saw a person.
       My father had a phrase he used that I have never forgotten. He didn't like the expression color blind. He would say, "That's nonsense. Everybody can see color."
      His point wasn't that race didn't exist. His point was that it shouldn't be the thing that decides how you treat someone. He called it being color strong.
        "Sure, that man's Black," he'd say. " It is pretty obvious, So what?"
   That was his entire philosophy. Recognize the differences, respect the differences and move on. Judge people by the things that actually matter.
        Their character, their honesty and whether they would help you change a flat tire in February on the side of Roosevelt Road. Whether they would buy the next round at Comiskey.
        Or, in Chicago...
                    …Whether they rooted for the White Sox or the Cubs.
   If I walked up to that Sox fan outside Jim's Original, I wouldn't have given two shits about the color of his skin. I would have handed him the Polish sausage and before long we would be arguing about whether the Sox needed another left-handed bat or if the bullpen was going to blow another ninth inning lead.
    That was the way my dad looked at the world. He had a gruff way about him, and Lord knows he wasn't politically correct, but underneath all of that bluntness was a simple belief…
          …every person deserved to be judged by who they were, not what they looked like.
    I think that is a lesson worth remembering. Forget being color blind and be Color Strong.
         If you are a Cubs fan, we may have to have a different conversation. We may call Chicago home and eat our hotdogs with mustard, but we will never agree when it comes to baseball…
       Gusto and astonishment, you gorgeous Chalkheads.

July 3rd, 2026

 

    Over the last couple days, more than fifty thousand Americans became casualties in a field in Pennsylvania.

   Beginning on July 1st and ending on July 3rd, 1863, the Battle of Gettysburg became the turning point of the Civil War.

   Roughly 23,000 Union soldiers and 28,000 Confederate soldiers were killed, wounded, captured or missing during just three days of fighting. More than fifty thousand casualties in one place, all in the name of what America would become.

        Could you imagine the media coverage if something like that happened in 2026?

    Growing up during the tail end of Vietnam, we played war almost as often as we played baseball and smear the queer.

             Every kid seemed to have a favorite war.

   We had older cousins, brothers, young uncles and neighborhood kids who fought in Vietnam. We had older uncles and men down the block who served in Korea. We had grandfathers and church ushers who fought in the Second World War.

    I even knew a great-uncle who fought in what he called the Great War. I knew it as World War I and could never understand why he refused to call it that.

     He died when I was in fourth grade, and somehow, I ended up with his mess kit and his helmet.

     I still have the utensils he carried while fighting in Europe. The helmet, with its unmistakable shape from a war fought fifty years before I was born, eventually became a prop for the Cathedral High School drama department.

      If I had to pick my favorite war to study, it has always been the Civil War.

   The Battle of Gettysburg sparked a lifelong fascination with the period when our country was most deeply divided. It made me want to understand how a nation could become so divided and somehow find its way back together.

    That fascination was fueled even more by a history teacher at Dear Old Cathedral named Daniel "Doc" Wellman.

Doc stood about five feet tall and nearly five feet wide. He had a thick beard, a receding hairline with long hair hanging over his collar and looked like he could have stepped out of the 1860s himself.

    He loved two things with all his heart, American history and Indiana Hoosier basketball. By the time I left his classroom, I loved Abe Lincoln and Robert Knight.

      The ShepKids, on the other hand, don't know many details about the wars America has fought. Their knowledge of wars mostly begins and ends with George Lucas and Luke Skywalker... maybe followed by the time Martians attacked Earth in the 1990s.

  "Dad... were you ever in danger when the extraterrestrials invaded the world?"

              "Are you serious, son?"

 "Yeah. I think it was 1996."

            "You've got to be shitting me."

I saw an opening and couldn't resist.

         "Yes, son. Terrifying time. I fought off three of those slimy bastards downtown between State and Wabash. I was walking to catch the CTA when they tried to suck my heart right out of my body."

There sat my sixteen-year-old, completely mesmerized.

           "Really, Dad?"

    "No, son. I just took the liberty of bullshitting you. Get your alien invasions straight. The war between Earth and Mars happened about five hundred years before I was born."

        Sometimes I feel sorry for this generation. Not because they are bad kids.

    Because they don't know what a nazi or an Imperial Japanese soldier was. They don't know a Yankee from a Johnny Reb, or a Redcoat from a Founding Father.

       But they do know the Force is with them and that the Men in Black are protecting Earth from monsters from another galaxy.

     Over the next couple of days, we will wave flags, sing patriotic songs and celebrate the birth of a nation that turns 250 years old this weekend.

     It truly is an honor to live in a country where so many men and women have sacrificed to preserve this republic.

      I don't want the ShepKids to grow up with a favorite war the way many of us did, pretending to defend the neighborhood White Hen Pantry and the parish rectory from Germans and the 1^st Alabama infantry regiment.

      I just want them to have a better appreciation for the history that made this country possible. I have a feeling Doc Wellman would remind me that if we don't pass that history along, somebody else will replace it with something less important and incorrect.

    So put on that Spirit of '76, you gorgeous Chalkheads, and celebrate the red, white and blue.

 Baseball, hot dogs, apple pie and Chevrolet.

      Valley Forge. Antietam. Gettysburg. Iwo Jima.

           Gusto, astonishment... and a sun with a smile.

July 2nd, 2026

 

      There comes a point in a man's life when he stops asking himself, "How do I get ahead?" and starts asking, "How do I finish my way?"

               I think that is where I am now.

  Not because I suddenly became the valedictorian. Lord knows I have spent almost sixty years making enough mistakes to fill a library of books. I have trusted the wrong people, argued when silence would have been stronger, chased things that didn't matter, and held on to things I should have let go of years earlier.

     Maybe that is what sixty is supposed to be. Not the decade when you finally know everything, but the decade where you finally know what isn't worth knowing.

     When I was younger, I wanted people to notice me. I wanted to win the argument, get the attention, make the money, have the bigger house, tell the better story.

   Now I would rather have a strong cup of coffee before sunrise, listen to the Sox game on the radio, have a healthy conversation with one of the ShepKids, and find peace in my daydream on an ordinary Tuesday.

      That sounds boring to some people, but to me, it sounds like wealth.

  I have learned that the strongest people I know don't announce what they are building. They simply keep showing up. They don't post every workout, every accomplishment, every sacrifice. They don't need applause to keep moving forward. The work is enough.

         I want to be that kind of man.

   I want to spend less time explaining my plans and more time living them. Less time reacting to every foolish comment and more time protecting my peace. Not because I don't care, but because my energy has become too valuable to waste on things that don't deserve it.

       I have noticed something else.

  The older that I get, the smaller my circle has become, but the richer my life feels. I don't need to know everybody. I just want to know the people who make me better and the people I can make better in return.

   I still want to learn something new every day. I still want to read books that smell used. I still want to discover a new piece of jazz, a Shakespeare quote I somehow missed or another lesson hidden inside an old baseball box score.

       Growth doesn't stop because your hair turns gray or falls out. If anything, it becomes more intentional. The competition has changed, as well. I don't measure myself against my colleagues, other classmates, other altar boys or other fathers anymore. I measure myself against the man I was yesterday.

Was I more patient?

Did I listen better?

Did I forgive a little quicker?

Did I make a stranger's day brighter?

        Those are the scoreboards that matter after sixty. I have also learned that peace isn't something you stumble upon. It is something you stop giving away. You stop giving it away to anger, to regret and to the people who only bring chaos. It is time to stop proving yourself to people who were never going to understand you anyway.

      Life has a funny way of finally sanding off the rough pieces. It might take decades, a few broken hearts, some funerals, a divorce, children, disappointments, laughter, and a thousand ordinary wake ups before you finally understand what is happening here.

        The truth is... I don't want the rest of my life to be louder. I want it to have a better sense of caring for the peace of mind that has always been a day away.

If these next couple decades teach me anything, I pray they teach me to become less interested in being impressive and more interested in being dependable.

To my children.

To my faith.

To my friends.

To my colleagues.

To my neighbors.

To myself.

      When my time finally comes, I hope nobody remembers me because I had all the answers.

I hope they remember that I showed up on time. That I worked my fat ass off. That I found joy in simple things. That I loved deeply, laughed often, forgave eventually, and never stopped believing tomorrow was worth getting up early to see.

Gusto and astonishment, Chalkheads.

Gusto and astonishment.

July 1st, 2026

 

    My twenty-year-old self would have never imagined this. He was busy doing the Super Bowl Shuffle and watching MTV.

    1986 John Shepley would have never believed that becoming a father mattered more than becoming successful. He would have never realized that losing love was a bigger lesson in life than finding it.

   Twenty-year-old me would have never comprehended how a ballgame on the radio or a sunrise over the lake would someday mean more than a kegger with a bunch of horny Catholic girls. The extraordinary has a funny way of giving way to the ordinary, and somewhere along the line I learned that the ordinary was what mattered the most.

    I think that is why Robert Frost's words hit home today, "The afternoon knows what the morning never suspected." 

   When we were young, we thought we were writing the story. As we got older, we realize life has been writing us all along. Every joy, every mistake, every heartbreak, every sunrise, every goodbye, every child, every friend, every loss has quietly introduced us to the person we were becoming.

    I put the number of days in the Grabber section because that is how many days it has been since I met my parents up in Edgewater on the north side of Chicago.

    All I know is this…

             … life keeps revealing who we are with every passing day.

   Gusto and astonishment, you gorgeous Chalkheads.

   Gusto and astonishment.

June 30th, 2026

 
       For the past week or so, I have been writing the same sunset on the chalkboard every morning, 8:30 p.m.
      That is today’s sunset again here in Chicagoland. Around the middle of June, into the beginning of July, the sun hangs on longer than any other time of the year. It almost feels like summer slows everything down for a second, but it doesn't hold.
      Six months from now, I'll be chalking 4:20 p.m. for ten or twelve sunsets in December. The sun slips away before most of us even get home.
              How do you like that contrast?
     The longest evenings, the shortest afternoons, both predictable, both temporary…
                    ... And that's the point, right?
       The calendar is always moving, and the 4th of July is upon us. One of my favorite holidays, and a proper summertime marker with that flag snapping in the heat.
       Thanksgiving, well, that is my favorite holiday. Bigger than Christmas, bigger than Mardi Gras. I used it as a marker in the grabber section this morning to show you Chalkheads how quickly the turkey will roast.
       But those sunrise and sunset times, those numbers I chalk without thinking, are telling a quieter truth. Whether the day stretches late or cuts off early, don't wish them away. Don't curse the heat. Because someday you will miss it. Don't resent the cold because it has its place too.
        The hard part, the honest part is this…
                …we don't get one more day, we get one less, and that is not meant to be gloomy. It is meant to sharpen our gratitude and help us appreciate what we have today.
      So, enjoy the late light now, welcome the early dark later, give thanks in both seasons. The clock keeps moving, but that's not a threat, it's a gift.

June 29th, 2026

        It is the last Monday in June of 2026.

    This week, the United States of America prepares to celebrate the 250th anniversary of the beginning of our independence.

    I am running a little late this morning because I have been watching Wimbledon. I am pulling for Serena Williams to do well as she begins her remarkable comeback at the young age of forty-four. Chris Evert is on my prayer list. She won’t be in the booth during this year's fortnight as she continues her battle with ovarian cancer.

    You might ask yourself, "Why is Jumbo so interested in a tennis tournament?"

    Well, back in the late 1970s and early 1980s, we got this brand-new cable station called HBO. Every summer they televised Wimbledon, and I was hooked. I had managed to pirate HBO through my old Pong game, which somehow made it even more exciting.

    Wimbledon became part of my summers. It was the era of Jimmy Connors, John McEnroe, Chris Evert, Martina Navratilova, and later Boris Becker battling on Centre Court. Those were great summers.

    The Cubs and the White Sox both head into July above .500. Around Chicago, that's enough to put a little extra bounce in your step.

          Finally, this week is officially a Gold Bond Action Alert.

   Powder up those nooks and crannies, stay hydrated, and don't let this heat get the best of you Chalkheads.

    Happy Monday.

June 28th, 2026

 

   There were only two times I ever went to dinner alone with my dad and the Step Monster, his wife after my ma.

 The first time was my twenty-first birthday at La Majada in Oak Park. It turned out to be pretty anticlimactic after spending years waiting to drink legally.

  The whole meal I was anxious because my softball buddies were waiting for me at the tavern that sponsored our team. I wolfed down my enchiladas and slammed the first two legal drinks of my life. A couple of La Majada margaritas and then I got the hell out of there.

    The second time was a few years later. Same restaurant, same enchiladas and the same margaritas.

     This time there wasn't a birthday or a celebration. My Oldman and the Step Monster wanted to talk to me about something serious. The way they looked, I thought they were going to tell me the dog died or they were selling the house in Oak Park.

     Instead, they told me the Step Monster's oldest son officially came out of the closet. They were worried because I was the conservative Catholic in the family and they thought I would become unglued over the news.

         I honestly couldn't have given two shits.

             Hell, I knew my stepbrother was gay when we were kids.

  Both of them were floored by how little I cared. Ironically, as the years passed, it turned out the Step Monster had a much harder time accepting her son's sexuality than anyone else and she considered herself a big liberal.

         That memory brings me to this weekend.

  Pride Month reaches its grand finale with the parade through Boystown. The music, the flamboyance, the politicians and the pageantry.

                              ...and I still don't give two shits.

   If you are attracted to the same sex, have at it. Fall in love. Get your heart broken. Fight over money. Argue about whose turn it is to do the dishes. Experience all the same joys and misery that us breeders have.

   As long as you are happy and love is involved, good for you. Be gay and be proud.

       It doesn't bother me one bit that June is your month.

  To me, June is the beginning of summer. It is when baseball settles into the meat of the season. It is Ella and Louis singing Porgy and Bess. It is my grandma's rose garden blooming. It is the one month of the year when my shadow falls directly beneath my big booty.

     What I don't need is the loudest, most extreme part of the gay community shoved in my face.

             Then again...

      I don't need the loudest extreme conservatives shoving their bullshit in my face either or the loudest far left liberals shoving theirs.

    When you see me, you don't see my Catholicism or my Republican politics hanging off my sleeve. Because I don't wear them that way.

      Sure, I have a Reagan/Bush '84 t-shirt. I have an "eracism" shirt. I even have a Lynyrd Skynyrd concert shirt with the Confederate flag.

I have another one that says:

Race: Human
Birthplace: Earth
Politics: Freedom
Religion: Love.

       Hell, I still own the Confederate flag that hung in my bedroom when I was a teenager. I also have the Pride flag that I flew from my balcony overlooking the Divorced Dad District a couple years ago.

      In other words...

       You probably wouldn't have a clue what I'm all about. I am a gumbo pot of JumboLove. I don't care if you are Black or Puerto Rican. Jewish or Lutheran. Straight or gay. Republican or Democrat. Trump or Obama. Bush or Clinton.

         I don't hate you more because you are different than me and I don't love you any less either.

   I have another twenty to twenty-five years left on this planet, I would like to go out believing the Beatles had it right.

                  "And in the end, the love you take is equal to the love you make."

 So, enjoy your Pride weekend, my gay and lesbian friends.

      … And if your community ever decides to add a couple more letters to the acronym...

                      Make it JBL.

                       Because JumboLove is for everyone.

June 27th, 2026

 

 In almost sixty years of existence, I can't recall waking up, checking the score of last night's ballgame, and seeing the White Sox won 22-1.

    Nope, I didn't watch the game. I don't get the cable network they play on.

 Instead, I finally got around to my annual June tradition, one that started with the Oldman back in the early 1990s.

    On a warm Saturday afternoon in June, I mowed the lawn at 220 South Lombard. When I finished, my dad pulled a chilled bottle of Liebfraumilch from his ice bucket and poured me a glass. That sweet German wine was Don Shepley's favorite on hot summer days.

   We sat in the shade on the deck he had built with some of his railroad retirement money and listened to the radio.

   Most Saturdays he listened to the old radio shows on WNIB, but that afternoon the jazz station was playing George Gershwin. Rhapsody in Blue drifted through the speakers while my Oldman and I guzzled cheap sweet white wine together. Funny how a song and a bottle of wine can become part of a man's calendar over thirty years later.

   Ever since then, I have bought one bottle of Liebfraumilch every June. It is the only time all year that I drink that stuff.

  Last night I sat on my balcony overlooking the Divorced Dad District, put on Rhapsody in Blue, polished off my annual bottle, and was sound asleep by 8:30.

        So, I have a pretty good excuse for not listening to the Sox game on the radio last night.

  Even so, this morning feels special. I have woken up before with the White Sox in first place on June 27th.

    The most magical season I remember was 1977, when both the Cubs and the Sox spent most of the summer sitting in first place, only to melt in late August and finish in third.

   That summer I went to Comiskey with the altar boys, our associate pastor, and a couple of dads. The Sox beat the Indians 18-2. For nearly fifty years, that was my personal definition of an ass-kicking.

  Now it is 2026, and the Sox are up a game in first place. It has been twenty-one years since that magical World Series championship. A championship shared by a Board of Trade guy and an Augustinian priest.

     Years later, I'm no longer standing in a trading pit in Chicago. I'm standing behind a trading desk in the suburbs.

     Years later, that priest isn't living in a rectory anymore. He is living in the Vatican.

             …And yes, I know "if" is a dangerous word.

     But IF the White Sox somehow pull off another magical season, maybe Pope Leo and I will find ourselves at another World Series game at Comiskey.

        A guy is allowed to wake up and daydream on the last Saturday of June.

 I have been around long enough to know the baseball gods have a way of putting everything back into its proper alignment. That won't stop me from feeling just a little special today.

       I root for the same baseball team as the Pope. That means the man doing Saint Peter's job understands gusto. He knows the astonishing feeling of watching a scoreboard explode.

      And if anybody asks...

          Please don't tell them you saw me on my balcony drinking cheap German wine while listening to that song from the old United Airlines commercial.

    I've got to take the liberty of bullshiting and come up with a better story when people ask me where I was the night the White Sox beat the Royals 22-1.

       Okay, Chalkheads...

            Go get 23 hits and score 22 runs today.

     In other words...

               … go have yourself a big win on this beautiful Saturday.

June 26th, 2026

  

     I don't think there is a person alive who has truly loved someone that hasn't wondered at some point if it was worth the bullshit.

    When we are young, we think love is about finding the perfect fit. As the years pile up behind us, we realize love is just as much about discovering who WE really are. It introduces us to the best parts of ourselves and, unfortunately, to some of the worst.

          Nobody walks away from falling in love without scars.

     Some people lose a spouse to death. Others lose someone to distance, divorce, betrayal, or simply the slow drift that happens when two people stop running in the same direction. The ending is different, but the ache has the same rhythm. Empty chairs at the kitchen table. Favorite songs that suddenly become difficult to hear. Driving past places that once meant everything and now forces you to take a detour.

     C.S. Lewis wrote, "To love at all is to be vulnerable." He wasn't warning us to avoid love. He was reminding us that the price of opening our heart is that someday it may break and it probably will.

     I have spent enough years on this earth to know that heartbreak isn't a punishment. It is a tuition bill.

     Love teaches lessons that success never can. It teaches patience, forgiveness and humility. It teaches that people are wonderfully imperfect, including the person staring back at you in the bathroom mirror every morning.

     Looking back, I can see mistakes that I couldn't see while I was making them. There were moments I should have listened instead of trying to solve the problem. Times I should have put down my pride before it became more important than peace. Days when I assumed there would always be another tomorrow to say what needed to be said.

           That doesn't mean I regret loving someone. Not for a single minute.

    Because even though love can leave you with an empty side of the bed or a quiet house after the kids have gone home. It also leaves you with memories that become part of who you are. It teaches you how deeply your heart is capable of caring. It gives you stories that still make you smile in the middle of a melancholy day.

     The goal isn't to avoid getting hurt. The goal is to become the kind of person who learns from the hurt without allowing it to harden your heart. Bitterness is easy and growth is difficult. One builds walls while the other builds character.

     If you have loved and lost someone, don't waste that pain. Let it make you kinder. Let it make you more patient with the next person who crosses your path. Let it remind you to hug your kids a little longer, call your parents while you still can, and tell the people you care about exactly how much they mean to you.

          Love doesn't always last forever, but the lessons often do...

                                       … And maybe that is one of God's quiet miracles.

      He doesn't promise that every love story will have a happy ending, but He does promise that none of the love we give away is ever truly wasted.

      It changes us, it prepares us and it reminds us that a broken heart is still proof that, at least one time in our lives, we had the courage to put it on the line of scrimmage.

            Happy Birthday Terese, the three best gifts we ever had come from love.

June 24th, 2026

 

   My plan was simple.

      Hang a blackboard in the kitchen at the new place. Just like the one in the kitchen the Shepkids had looked at for most of their lives.

      At the time of the separation, I wanted some things to remain familiar between the split homes. It was going to be hard enough on an eleven-year-old, an eight-year-old, and a four-year-old.

    What I didn't plan on was that blackboard, originally meant for schedules and logistics in a divorced family, turning into the Morning Chalkboard.

    Over time it became a daily ritual. A form of therapy for me. Somehow it became therapeutic for a growing collection of friends, acquaintances, and strangers who would eventually become known as Chalkheads. I still make schedules and plans, but instead of organizing life for three kids, it feels like I'm trying to give a little boost to thousands of people every morning.

    People who need to know life is tough sometimes. People who need to know that they aren't the only ones carrying a burden.

    Over the years I have used quotes from Shakespeare to Bowie. I have told stories about dumb things that I have done through my life. I have snuck hidden messages onto the board and shared lessons that usually arrived after making a mistake that taught me a valuable lesson.

   Back in August of 2017, I never imagined there would someday be more than three thousand chalkboards sitting in the archives.

    I have written about planets and our relationship with the stars, the moon, and the sun. The sun gets most of the attention. Every morning I write its arrival time and its departure time in the lower left corner.

    I think it's important to know where the sun is and where your shadow will fall. On the short days our shadows are long. On the long days our shadows are short. Somehow it all balances out over the course of a year.

              I still get a kick out of drawing a smile on the sun.

   I think about my friends when I'm doodling Sox and Cubs logos on Monday mornings. I feel a certain responsibility to make sure Chalkheads know when it's National Beer Day or National Donut Day.

       … and every National Fondue Day, I feel obligated to remind everyone about the time I burned my nipples with melted cheese during what was supposed to be a romantic fondue date.

             Some lessons deserve to be preserved for future generations.

    Chalkheads have watched the Shepkids grow up. They watched me learn how to navigate bachelorhood. We went through Covid together. They felt my sorrow when the Old Man died. They followed along as I went from a trading floor in Chicago to a trading desk in Oakbrook Terrace.

    Someday there might be a book that comes from all of these chalkboards.

           If not, that's okay too.

  I will be happy knowing that somewhere along the way I managed to heal a few wounds of my own and maybe helped heal a whole bunch of Chalkheads during the late 2010s, through the 2020s, and maybe into the 2030’s..

       Like today's quote says, none of this turned out according to my plan and maybe that was the point all along.

     The Chalkboard has always worked best when I stop trying to steer every detail and leave room for the mystery of my faith to do the heavy lifting.

     Today I am supposed to tell you that it's National Pralines Day.

    I fell in love with pralines on my first trip to Louisiana. They are good with an Abita and even better with a scoop of vanilla ice cream.

      We are closing in on the end of June already. I still need to drink my annual bottle of Liebfraumilch and listen to Rhapsody in Blue before the month is over. It would be nice to do that on the front porch in Oak Park, but a balcony in the Divorced Dad District will have to suffice.

      Go out there and be kind to each other, Chalkheads.

             Find that gusto.

         Swim in the astonishment that life offers when it refuses to follow the plan…

              … and if you get the chance today, grab a piece of chalk and put a smile on the sun.

                              Deus Vult.