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.

June 23rd, 2026

   We just started summer over this last weekend, but I felt that it was important to let you know when summer is over. So, I put the countdown to Labor Day in the Grabber section.

    When the Shepkids were toddlers and they would fall down, their mom and I would look at them and tell them to pop up. We would ask them, “What is the next thing we do when you fall down?” and they would answer us with tears on their red faces, “You get right back up!”

   Now one is an adult, another is nearly an adult, and their baby sister is about to become a teenager. I’m not sure they are prepared to get back up when they fall.

       I worry more and more that they won’t be able to rebound when I’m not around.

  We teach our kids how to read and tie their shoes, but we don’t spend nearly enough time teaching them how to handle it when they lose a job. How to survive a broken heart or recover when life doesn’t go according to plan.

   I was sitting in Ceres at the Board of Trade with a dear friend the week we found out George was on the autistic spectrum. At the same time, he had just learned that his college-age son was having some problems at school.

     He looked at me and said, “Jumbo, small kids, small problems. Big kids, big problems.”

                   Years later, those words proved to be wisdom.

   The other day I chalked about being a good father and a horrible husband. The truth is that fatherhood came easier to me. I knew how to hold a baby. I knew how to show up for soccer games. I knew how to make pancakes, change diapers, help with homework, and sit in an emergency rooms when life got scary.

       What I never figured out was how to guarantee that my kids wouldn’t get hurt.

Because eventually every child gets introduced to the same things the rest of us did.

Heartbreak.

Disappointment.

Failure.

Rejection.

The phone call you never wanted to receive.

The person you thought would stay forever who leaves anyway.

The job that disappears.

The friend who turns out not to be a friend.

      Nobody hands out an instruction manual for those days and that is what worries me as a father. Not whether my kids can read. Not whether they can drive. Not whether they can make a living.

      I worry whether they know how to get back up. Because sooner or later life knocks everybody on their ass. Every single one of us.

     It knocked me down when George was diagnosed. It knocked me down when my marriage ended. It knocked me down when my parents died. It knocks me down every time my daughter misses another day of being healthy. If I have learned anything in nearly sixty years, it’s that getting knocked down isn’t the test. The test is whether you decide to stay there.

    My friend in Ceres was right.

            Small kids, small problems.

            Big kids, big problems.

            … But the answer remains the same no matter how old you are.

   When you fall down, you pop back up. Maybe not today. Maybe not tomorrow, but eventually you wipe your face, catch your breath, and stand back up.

   Because life isn’t asking whether you fell. Life is asking what you did after you hit the ground.

         If you fell down yesterday, stand up today.

  Summer is already slipping away. We have only 76 days until Labor Day. Don’t waste a single one of them lying on the mat while gusto and astonishment is out there waiting.

June 22nd, 2026

 

      On Juneteenth, dozens of people were shot in Chicago and several ended up dying.

        It happened during a celebration, a day that was supposed to be about freedom, community, family, and progress. By the next morning, people had already moved on to the next headline.

         As a father and as a Chicago guy, I struggle with that.

     Not because I think one tragedy should receive more attention than another, but because I think we have developed a habit of ranking our grief. Some victims seem to receive endless coverage while others disappear into a statistic before the blood is dry on the pavement.

    A shooting at a grade school is horrifying. A shooting at a shopping mall is horrifying. A shooting at a church, a concert, a movie theater, or a parade is horrifying.

     So is a shooting at a neighborhood celebration on the South Side of Chicago. The pain does not become smaller because of the ZIP code.

    A mother is waiting for a child to come home, it doesn’t matter whether she lives in Beverly, Englewood, Bridgeport, Austin, Oak Park, or Naperville. The fear is the same. The phone call is the same. The grief is the same. The empty chair at the dinner table is the same.

    As Chicagoans, we sometimes develop a strange relationship with violence. We hear about another shooting and simply shrug our shoulders. We tell ourselves that it happened in a rough neighborhood. We tell ourselves that there were probably circumstances we do not understand. We tell ourselves that it is sad, but it is normal.

                 That might be the most dangerous thing of all.

    When violence becomes normal, we stop seeing the people involved. We stop seeing sons and daughters. We stop seeing fathers and mothers. We stop seeing dreams that will never be fulfilled and conversations that will never happen. We start seeing numbers. Thirty-five shot, five killed. Those are just numbers printed out on the front of the Sum Times.

     Unfortunately, every one of those numbers had a name. Every one of those names belongs to a family. Every one of those families will remember Juneteenth for the rest of their lives for reasons that have nothing to do with celebration. Juneteenth of 2026 became a death anniversary for five families.

    I am not interested in chalking this into a political argument. There are plenty of people who get paid to argue about politics. I am interested in reminding people that human suffering should not be ignored because it happens too often.

         If anything, repeated violence should demand more of our attention, not less.

   Chicago is one of the greatest cities in the world. It is a city of neighborhoods, churches, parks, taverns, corner stores, hot dog stands, softball fields, block parties, and families trying to build a good life. Most people get up every morning, go to work, pay their bills, raise their kids, and hope for something better tomorrow.

         Those people deserve peace.

         Those children deserve peace.

         Those parents deserve peace.

               … and the victims deserve to be remembered as more than a statistic buried beneath the next news cycle. A tragedy does not have to happen in our neighborhood for us to care about it. It only has to happen to another human being, another Chicagoan.

                That should be enough for someone to stand up and figure out what needs to be done.

      I am tired of turning on channel nine news and hearing that there was a mass shooting over the weekend and quickly talk about a traffic jam on the Kennedy and what movie Dean Richards viewed over the weekend.

June 21st, 2026

 

       I turned forty about a month before my oldest child, George, was born.

 Soon after, I realized something important. I wasn't really a man until I became a father. Before that, I was a selfish only child who spent the first forty years of his life doing more stupid things than smart things.

       Fatherhood came naturally to me. It was much easier than being a husband. I never minded changing stinky diapers. I got up in the middle of the night without complaint to warm a bottle and feed a baby.

           I also pulled a few stunts as a father that turned heads.

  Do you remember those blue plastic things you are supposed to stick in a baby's nose when they are congested? Your child can't breathe, there is snot everywhere, they are running a fever, and somehow you are supposed to clear their sinuses with a little piece of plastic that couldn't suck a marble through a garden hose.

         I couldn't do it. So, I improvised.

  I would put a towel on the floor, cradle the sick baby in my arms, put my mouth over their nose and mouth, and suck all that junk right out. Then I would spit those lovely phlegm treasures onto the towel.

   A couple rounds of that, and I would have a relieved baby sleeping peacefully in my arms while their mother looked at me like I had completely lost my mind.

           Years after my marriage failed, I realized part of the problem.

I wasn't a husband anymore.

I was only a father.

       I fell asleep more nights on the kids' bedroom floor after reading stories than I did next to my wife. I hugged and kissed my children but forgot to hug and kiss their mother.

              That realization took me years to understand.

      If I have any advice for you young guys who are about to get married and have children, it is this… Don't let the flame die.

   After children arrive, it is easy to make them the center of everything. Be the best father you can be, but make sure your children see that you are also a great husband.

     Children need to see their parents laugh together. They need to see them flirt. They need to see their father treat their mother with love and respect.

             Don't let them see only the arguments and disagreements.

  It is important for sons because it teaches them how to treat women. It is even more important for daughters because it teaches them what kind of man they should expect in their lives.

    You don't want your son growing up to be an assclown, and you certainly don't want your daughter attracted to one.

      Like the Oldman always said……

         "The two greatest gifts a man can receive in life are the love of a woman and the trust of a child."

       Happy Father's Day to all the dads who would do anything for the passion produced from their loins and continues to fill their hearts with love.

           Show them why you are the best that today proclaims you to be!

June 20th, 2026

 

    This summer marks the end of the decade when everything I do is still done as a man in his fifties.

       It was a quick decade.

  It started with a man standing at the end of a failed marriage, wondering what the hell just happened. It ends with a man getting ready to enter a decade where the Shepkids will become adults, his career will start heading toward the finish line, and the calendar will stop pretending that time moves slowly.

    If one thing stands out from my fifty-something years, it is that the world is ridiculous.

It has always been ridiculous, but it takes about fifty years of living to finally admit it.

   Everything seems to have some ridiculous attached to it. Start with the easy targets. The media, advertising, trends and fashion. The things people pretend are important because somebody on a screen told them they should be.

   Then move into the heavier stuff. Politics, religion, status, money and pride. The teams we pick. The sides we join. The flags we fly. The hills we decide to die on, even when most of those hills are nothing more than piles of crap that we made ourselves.

      The most ridiculous thing I have figured out is how we treat each other.

   How we love each other. How we hate each other. How fake we can be with each other. How quickly we decide who matters and who does not. How often we measure people by what they can do for us, what they look like, where they come from, what they believe, or whether they fit inside the little box we built in our own heads.

    I am not talking about family here. Blood is thicker than water, and family gets its own complicated chapter.

              I am talking about the pecking order.

   I am talking about users and abusers. I am talking about people who smile when they need something and disappear when they do not. I am talking about how foolish we are when we let things that do not really matter decide how we live, who we love, and who we refuse to forgive.

      That might be the most ridiculous part of all.

   The importance we give to things that do not matter.

      They matter for a minute. They matter to a few people. They matter in the moment when everybody is worked up and puffed up and acting like the world will stop spinning if they do not win the argument.

      But most of that bullshit has a short shelf life.

 Most of the things that keep us angry, worried, jealous, bitter, or afraid do not matter nearly as long as we think they will.

           Do you know what else has a short shelf life?

           Our time between our birth date and our death date.

             That little dash in the middle is not as long as we pretend it is.

   As I finish my fifty-something decade, I realize that most of the things that came along and mucked up my life were ridiculous. Not all of them. Some pain is real. Some loss is real. Some heartbreak leaves a mark that does not wash off, but a lot of the noise was ridiculous.

A lot of the anger was ridiculous.

A lot of the worry was ridiculous.

A lot of the people I tried to impress were ridiculous.

       That is why today’s Shakespeare quote fits my mood this morning:

                      “Better a witty fool than a foolish wit.”

     Shakespeare is saying it is better to be the guy who knows he is a fool and can still laugh at the world than the guy who thinks he is clever but has no wisdom at all.

     Maybe in my next decade, when I am sixty-something, I will finally know which man I am. The guy who realized he was the fool on the hill, or the guy too stubborn to realize it.

     Either way, I am starting to figure something out. Ridiculous things do not deserve front-row seats in our lives. Let’s figure out what is ridiculous and ban it from the room.

      Gusto is not ridiculous. Astonishment is not ridiculous. A good laugh is not ridiculous. Forgiveness is not ridiculous, and a sun with a smile on its face is not ridiculous.

    Those are the things that get us through the dash.

               Ignore the ridiculous crap today, Chalkheads.

           Be the witty fool, at least he knows enough to laugh.

June 19th, 2026

            Today’s quote is about leaving the past behind.

    Apparently, I decided to take that advice literally.

        It is not often that I wake up on my couch with my clothes and shoes still on. When I checked my messages, my bartender informed me that I had left with an open tab, and my neighbor downstairs sent me a picture of a cigar ash in the back hallway along with a note explaining that the hallway smelled like a casino.

   I never get a Thursday night off from the markets, so it turned into one of those nights where the walk to the local bar was 675 steps and the walk home somehow stretched to 913.

I’m sure I left quite an impression on my acquaintances. Hopefully they remember that I rarely go out on a school night. That still isn't much of an excuse for pounding down four, maybe five, Old Fashioneds.

       It is 3:30 on a Friday morning and I don’t have to stand at a trading desk today.

 It would have been nice to wake up next to someone who loves me and make a pot of coffee together, but instead I’m sitting alone with a cool breeze drifting through the window and a headache pounding behind my eyes.

      Yesterday I quit all my social media accounts.

 I had been on Facebook since 2008. Eighteen years with Mark Zuckerberg is longer than I was married to Terese.

      This morning I reached for my phone to check for likes and comments that no longer exist. I never thought of myself as an addictive person, but apparently, I had become pretty attached to posting my thoughts to a shit ton of strangers.

    At some point I started wondering why I was sharing my worries and anxieties with 1,679 people. The truth is that I probably never met 1,300 of them.

   The more I thought about it, the more it seemed like one more thing from the past that needed to be left behind. So today I must slink down to the bar, pay my tab, apologize if necessary, and find a way to deodorize the back hallway.

          After that?

                    Who knows.

    It is a national holiday. I don't have to work, I don't have Facebook and I don't have TikTok.

What I do have is a three-day weekend and a little more time to look for gusto and astonishment.

        Happy Friday, Chalkheads.

    Now if you will excuse me, I need a large glass of water and enough aspirin to make peace with yesterday's decisions.

June 17th, 2026

 The famous line by Captain Jean-Luc Picard when it was time to get your butt in gear…

“Make it so.”

Very proper, very Captain like.

I am not much of a Trekkie, but if you make me choose between Star Trek and Star Wars, I’m taking Star Trek.

I enjoyed the first couple of Star Wars movies, especially The Empire Strikes Back. That one had Lando Calrissian, played by Billy Dee Williams. The coolest soul brother in space. The same guy who played Gale Sayers and convinced America that Colt 45 malt liquor was a fine life choice.

As far as Star Trek goes, I am only interested in the original series and The Next Generation.

The thing I always found fascinating was the holodeck.

For you non Trekkies, a holodeck was a room sized virtual reality simulator. You could step inside and become part of any story, any place, any time. It was one of the most famous pieces of technology from The Next Generation era.

Back in the early 1990s, it seemed like pure fantasy. Now? Maybe not so much.

With virtual reality hardware getting better every year and artificial intelligence advancing at a pace that is frightening…

… the holodeck no longer feels impossible. It feels inevitable.

Someday I might be able to live out some of my own storylines.

I could spend an evening in a Havana nightclub listening to Tito Puente while smoking a Cuban cigar, wearing a linen suit and a Panama hat.

I could line up at center for the 1958 Baltimore Colts and snap the ball to Johnny Unitas.

I could attend Midnight Mass celebrated by Pope John Paul II with my family sitting beside me in the pew.

I might even hotwire the holodeck for an intimate evening in Paris with Julia Roberts and see where the night takes us.

Virtual reality and AI may never replace real life, but they sure have the potential to add a few exciting chapters to it.

The future is arriving faster than most of us expected. Maybe the real question isn’t whether we can build a holodeck. Maybe the question is what we will choose to do with it once we have one.

As for me, I already have a list.

Make it so……

June 16th, 2026

 I chalked this quote from Ralph Waldo Emerson. His point is that a minute of anger does not cost you a minute.

It usually costs the entire morning. It can cost a relationship, a night’s sleep, or simply the chance to enjoy something that is right there in front of you.

Every one of us has a list of people, events, disappointments, and struggles that could keep us angry all the way to the two-minute warning of life.

The problem with anger is it charges you interest. It steals the moment, it steals laughter, and it steals an ordinary Tuesday afternoon that we will never get back.

Forgiveness doesn’t mean the other person was right. It means you are no longer willing to let them control your happiness.

Life is too short and summer is too beautiful to stay pissed off.

Get out and enjoy the sun while it shines, and appreciate the clouds that arrived without an invitation.

Angry people have a hard time finding the gusto and astonishment that life brings. You Chalkheads on the other hand, sure as hell can find it.

It is Two for Tuesday…

…. Please don’t let it be the Eagles or Boston.

Deus Vult.

June 15th, 2026

 Monday morning already, and this week brings us into the second half of June.

The funny thing about life is that things never really calm down. There is always another calamity, another obligation, another worry, another shot to the groin lurking around the bend.

So stop waiting for everything to calm down.

Grab life by the throat and yell, “Bring it on, you somabitches!”

The Grabber section shows a couple of winning ball clubs here in town. Let’s not start kissing each other on the mouth just yet.

I’ve seen this scenario before, and most of the time it doesn’t end the way we wanted.

Still, that’s no reason to sit on the sidelines...

… Go toward the commotion, Chalkheads.

June 14th, 2026

     I have this theory that God has a whacked sense of humor.

Think about all the energy we spend hating each other while we are alive.

Blacks and Whites, Shep and Bergsy, Rome and Carthage, Tupac and Biggie, Polish and German. Irish and English. Democrat and Republican, Catholics and Protestants, Cub fans and Sox fans.

We spend our lives building fences, flying flags, choosing sides, and deciding who belongs on the other side of the Monon tracks.

Then God looks down from Heaven and says, "You knuckleheads have no idea what is coming."

Because if His plan is true, eternity is going to be one giant family reunion.

The Polish guy will be sitting next to the German guy eating sausages. My ex-wife and I drinking coffee together. The Irishman will be saving a barstool for an Englishman. The Southsider and the Northsider arguing about what team Harry Carey liked better. While they are both enjoying Old Styles with Ron Santo and Minnie Minoso.

The people who spent their entire lives avoiding each other are suddenly neighbors for eternity. That seems like the biggest prank phone call ever made.

Imagine getting up to Heaven and finding out God put your eternal cloud right next to the person you spent eighty years being pissed off with.

“Lord, there must be a mistake over here.”

“No mistake,” says Jesus. “Pull up a chair. You two are family now.”

Maybe that is why forgiveness matters so much.

Maybe God isn’t asking us to forgive because the other person deserves it. Maybe He is asking because eventually we are all going to be breaking bread together anyway.

The older I get, the more I suspect Heaven is not a place where God separates the people who annoyed us. It is a place where He finally teaches us to love each other…

…. And if that is true, God definitely has one heck of a sense of humor.

June 13th, 2026

         Today I chalked a line from the Ike Reilly song “Devil’s Valentine.”

What makes this lyric powerful is how it rejects both extremes.

Dreams give us hope, and fear is what keeps us up all night. In the middle is a pile of bills, a broken promise, an empty beer bottle, and a career that never quite panned out the way I imagined.

I will never be free of fear, and I will never fully realize those dreams. Most of life is lived on the road between fear and desire.

That is pretty much how I ended up in the Divorced Dad District.

I dreamt about a different life, and I had the fear of losing everything. Somewhere between stop signs, life happened.

I raise the ShepKids on dreams and fear, but they don’t know it.

Every morning, somewhere between a Hail Mary and an Our Father, I tell the devil to go fuck himself.

I chalk on this blackboard, I stand at a trading desk, I pay an overdue bill, I wonder what I’m missing out on, and I wait for another sunset.

Somewhere in between it all, I better figure things out before I become part of someone else's prayer.

One day we all become the name spoken after grace at dinner, the face in a photograph on a dresser, the person somebody misses when a song comes on the radio.

I’m not living a dream, but I’m not having a nightmare either. I’m just breathing in and out the life that was given to me by two people who left before I was ready to let them go.

I’m not sure I would have understood what Ike Reilly was talking about when I was twenty-five, but standing on the doorstep of sixty…

…it makes a lot more sense.

That is why I don’t worry too much about the story my pillow tells.

Okay, Chalkheads…

It is Saturday, and we are moving into the middle of June. This time of year brings long days and short shadows. Perfect for finding the gusto, astonishment, and smiling back at the sun.