August 25th, 2026

 Who in the hell decides what our potential is?

      Here is a question that starts showing up somewhere around sixty.

             Did I live up to my potential?

                   … And I have another question.

            Who the hell made the scale for living up to our potential??

   Who decides what our potential was supposed to look like in the first place?

       A bigger house? More money? The marriage that lasted? A corner office? Kids who never screwed up? A retirement account big enough that the financial planner kisses your ass when you see him?

      Because if that is the scoreboard, an awful lot of people are walking toward retirement convinced they somehow lost the game.

        Especially my generation, GenX.

   We were the kids who came home from school, let ourselves into the house, did our homework and made dinner for our single parent.

    We grew up having five television channels. We were worried the Soviets might blow us up before dinner. If you wanted to talk to somebody you had to call their house and risk getting their father on the phone.

     We watched factories close. We watched our neighborhoods change. We watched our parents work thirty years for the same company because there was supposed to be a pension waiting at the other end.

        Then some jagoff changed the playing field.

    Companies downsized, jobs moved overseas, and pensions disappeared. Technology showed up and told half the workforce that everything they had learned for twenty years was obsolete.

     Then came the dot-com crash, then September 11^th, then years of war and terrorism. Then 2008 knocked some of us back to square one. Then smartphones arrived and everybody became available twenty-four hours a day. Then a pandemic shut down the goddamn planet.

      That is one tough road trip to take, and somewhere along the way we made decisions.

    Some were decent and some were fucking lousy.

    We married the wrong person or stayed too long at the dead-end job. Maybe we ended up quitting the right job. We bought the wrong stock, or we didn't buy the right stock. We didn't call somebody back. We didn't show up for lunch, or we didn't tell somebody we loved them.

    Wait until Monday.

      Wait until January.

         Wait until the kids got older.

             Wait until things settled down.

         … And suddenly we are sixty fucking years old and things don’t settle down.

    That is the part nobody explained to us when we were thirty. Time doesn't announce itself when it leaves. There isn’t a guy standing by my bathroom door saying, “Jumbo, just so you know, you are never going to get 1997 back.”

      Procrastination is probably responsible for more unrealized potential than failure ever was. Failure at least means you swung the bat. Procrastination leaves the bat sitting on your shoulder.

        I think we have been looking at potential all wrong. Potential isn't one destination. It is a thousand different trajectories.

    At twenty-five your potential might have been to become a writer at the Sun-Times. At forty it might have been saving a marriage. At fifty it might have been becoming a better person. At sixty it might be repairing a friendship, writing the book, helping your kids find their way, mentoring somebody younger or finally becoming comfortable with the guy staring back in the bathroom mirror.

     We get fewer chances as we get older. That is just the mathematics of time, but fewer isn't none. Maybe potential was never about becoming everything we planned on. Maybe it was about becoming something useful with whatever remained in front of us.

   There is still another conversation, another opportunity, another sunrise, another idea, and another wrong that can still be made right.

      Potential doesn't have a time clock.  There is no foreman punching your card at sixty-five. There is no closing bell that rings and announces that whatever you were going to become, you are wearing it. At sixty, potential changes from accumulation to contribution.

      As long as you are here, the trajectory can still change.

   Maybe not dramatically. Maybe just a few degrees, but anybody who has ever looked at a map knows that a few degrees over enough distance can take you someplace completely different.

      Someday, when people talk about us, they probably won't spend much time discussing whether we maximized our potential. They will remember what we did with it. Because in the end, our potential isn't just part of our story. It becomes part of our legacy.

  

          It is Tuesday morning and it never looked so good. 

             I’m already in, in a daydream…

August 24th, 2026

          SIT DOWN AND WATCH THE DAMN GAME.

    Thirteen days ago, 40,000 people stood inside Comiskey Park and offered one another the sign of peace. A Catholic priest stood on the field as the White Sox celebrated Pope Leo XIV, a South Side kid and Sox fan who somehow wound up succeeding Saint Peter.

     People turned to strangers and said to each other, “Peace be with you” which received the reply, “And also with you.”

              I watched it and cried.

      Yesterday, in the same ballpark, a bunch of drunken jagoffs were tumbling over seats in the upper deck trying to beat the hell out of each other.

     There was another fight earlier in the week at Wrigley between Cubs and Sox fans.

        This isn't a new thing.

  Ballpark fights have been around forever, and Comiskey has had more than its share of notorious ones. We once had a father and son run onto the field and attack the opposing team's first-base coach.

          …And spare me the demographic explanations.

     White guys fight, Black guys fight, Hispanic guys fight, women fight, Cubs fans fight and Sox fans fight.

         The common denominator is assholes.

    Usually, a couple assclowns fortified with twelve-dollar beers, but I think there is something else going on.

    We have turned the ballpark into a three-hour carnival where apparently nobody can be left alone with a baseball game anymore.

     Music blasting, video boards flashing, contests, promotions, kiss cams, dancing and screaming. The billboards have statistics covering every square inch of available real estate.

        Silence is now considered a crisis.

    I want to go backward. Give me the organ. Give me Gene Honda. Give me a Dixieland band playing underneath the stands. Give me fireworks when a Sox player hits a home run.

          That is it.   

I do not need Grand Theft Auto music rattling the upper deck between pitches. I do not need some jackass dancing on the scoreboard. I do not need to know a hitter's launch angle, exit velocity and OPS against left-handed relief pitchers on Tuesdays after 8:15.

    I just want to watch the damn game. Bring back the Andy Frains standing at the end of the aisle. Hell, bring back a dress code. Not jackets, fedoras and ties. Just dress like you are going someplace where other human beings will be present.

   Grown men should not wear tank tops to a baseball game. Women should not dress like they are hooking after the game.

    Have a hot dog. Eat some Cracker Jack. Drink a couple beers. Buy the nachos and keep a scorecard.

    Talk baseball with the guy sitting next to you and when you get up to take a piss, wait until the play is over before climbing over twelve people.

            When did we stop doing that?

    There was an etiquette to going to a baseball game. You learned it from your Oldman, and he learned it from his.

     Baseball doesn't need constant stimulation. That is one of the reasons I love it. It has pauses, it breathes, it gives you time to think.

      That is what we are afraid of now.

   Thirteen days ago, 40,000 people at Comiskey Park stopped everything long enough to turn toward a stranger and wish him peace.

Think about that.

No politics.

No Cubs.

No Sox.

No race.

No bullshit.

     Just one human being looking another in the eye, Peace be with you.

  Instead of another video board, another promotion and another speaker blasting music into the upper deck, we ought to try a little more of that and if that doesn't work?

     Bring back the Andy Frains and sit down and watch the damn game.

Okay Chalkheads, sorry to bitch and moan on a Monday Morning….

      …. Play Ball!

Dear Old Cathedral for the Funeral Mass of Coach Tom O'Brien.

 

https://youtu.be/uYGid6k18zQ?si=AgU0xS-kat1AdGzv

August 23rd, 2026

 

        As a chubby little kid in the early 1970s, I was quite the inventor.

  Not because I was particularly brilliant. I just used the wrong words for things.

    Whenever I did something for the first time, instead of saying I got my first Wacky Pack or had my first Kayo, I would announce that I had invented it.

      This drove my Oldman absolutely crazy.

         “I invented Wacky Packs and KayO’s today.”

    “How the hell did you invent Wacky Packs Moose?”

       “When we drove over to White Hen.”

 Perfectly reasonable explanation if you were five-year-old me.

     I invented my First Communion. I invented Saturday morning cartoons. I invented shopping malls. I invented those new CTA cars with the windows that didn't open. I invented Elton John and the Beatles. 

    I invented popping a wheelie on my bike. Never before accomplished by a five-year-old kid on a Schwinn.

    I even invented mixing Cap'n Crunch Peanut-Butter with Honeycomb. Actually, I did come up with that one. 

    I invented putting a baseball card near the spokes, so my Schwinn sounded like a Kawasaki. Sorry to the millions of American kids who thought they came up with that one themselves. It was me.

            … And then there was ice cream.

    For the first few years of my life, as far as I knew there were two flavors, chocolate and vanilla. Then my world expanded.

Mint ice cream? Me.

New York cherry? Me again.

Pralines and cream? You guessed it. Another John Shepley invention.

    The best part was that I would announce these breakthroughs in front of my Oldman's work buddies. They would scratch their heads, look over at Dad and ask some variation of…

        “What the f**k is wrong with your kid?”

     Don Shepley had his answer ready.

     “My son is the next goddamn Einstein. Lord help us when he takes a jet somewhere when he gets older. He will have invented air travel. He already thinks he found the Illinois Central Railroad.”

     Thankfully, I grew out of my Thomas Edison phase before I heard the lyrics I chalked this morning. Otherwise, Blue Öyster Cult might owe me some royalties.

     Enjoy figuring that one out, Chalkheads. And enjoy the earworm when you do.

       Which brings me to today's other important subject. The Cuban sandwich.

     I didn't discover the Cubano until sometime in the last ten years or so and, for the record, I did not invent it, but whoever did deserves my respect.

    Pork, ham, Swiss cheese, pickles and mustard pressed together on Cuban bread until the whole magnificent creation is hot, crispy and gooey.

         That is what I call a pretty damn good samich.

   It is probably never going to become a staple on the Chicago food pyramid. Around here, the gyros, hot dog and Italian beef have pretty well staked out their territory, but every once in a while, even a Chicago guy needs to wander off the reservation.

    There is a Cuban joint on the other side of town, and I'm thinking today might be a good day to walk over and grab myself a Cubano.

        So go out there and have yourself a fanfuckingtastic Sunday Funday.

    Turn Blue Öyster Cult up to eleven on the volume knob.

      Grab yourself a Cuban sandwich and if you happen to try something today that you have never done before, feel free to tell everybody you invented it.

       Five-year-old Jumbo would understand completely.

August 22nd, 2026

 

   I rarely get political on the Chalkboard, and I don't intend to start today.

        Election Day is 72 days away, and something has been bothering me.

  Our political parties seem determined to stretch themselves farther and farther toward their respective edges. Somewhere in between are conservatives, moderates and liberals who don't recognize themselves in all the shouting anymore.

       Maybe fixing that is bigger than any one of us.

   My Oldman always told me the quiet guy in the crowd was usually the toughest guy in the room and the smartest as well.

The loud voices were usually mealy mouths who had never been punched in the nose or had never come up with an original thought of their own.

   That was my Oldman. A little rough around the edges, but there was some wisdom underneath it.

     Anybody can shout. Anybody can repeat somebody else's talking points. It takes considerably more strength to listen, think for yourself and occasionally admit the other guy might have a point. Not everything requires an argument.

       Certainly not one worth losing a friendship over.

  We have become awfully good at sorting one another into teams. Red or blue. Right or left. Us or them, but the person across the table is still your brother, your neighbor, your old friend, the guy you went to school with or the woman who brought a casserole over when your family needed one.

          Politics shouldn't erase that.

    So over the next 72 days, read, listen and think for yourself. Question your own side once in a while. Decide what you believe instead of borrowing somebody else's outrage.

    Then do your talking in two quiet places. A church pew and an election booth. Say what needs saying and pray in the first. Cast your vote in the second.

   Then walk out the door, shake somebody's hand, buy somebody a beer, listen to some music, watch a ballgame, call an old friend and get back to the considerably more important business of living.

      The election will come and go. Our lives won't wait for it.

  So reach for the gusto and astonishment, you gorgeous Chalkheads.

         There is still plenty of both out there for all of us…

August 21st, 2026

 

     By August 21, you can see what is happening just by looking at the clock.    

  Sunset has slipped all the way back to 7:41 PM. We are losing roughly two and a half minutes of daylight every day now. Look up towards the sun and look down at your shadow. It is getting longer.

 There are still summer nights left, but they are starting to become precious.

   That feels like a good Chalkboard thought…

    …We spend half the summer acting as though it will last forever, and the other half wondering where the hell it went.

      Maybe that is true about more than summer.

            Enjoy the day you are standing in.

August 20th, 2026

 

     There is something old school about radio.

   You don’t watch it. You can’t scroll through it, and you don’t have an algorithm reading your mind. You turn the dial, find the voice you know, and let that voice keep you company.

    I have a radio in every room of my home. I suppose that tells you something about me.

   For generations, Chicago has been one hell of a radio town. Ballgames, agriculture reports, weather, traffic, music, news and those comforting voices coming out of a speaker while we drove to work, sat on the back porch or fell asleep at night.

    Some of my earliest memories have a radio playing somewhere in the background.

    WLS-AM got me through the seventies before I discovered the FM dial. Before school in the morning there was Wally Phillips, who would play the Ellery Queen Minute Mystery. My mom and I would try to figure out the murderer before it was time to leave. Later there was Orion Samuelson giving us the grain and livestock prices. Funny how life works. Back then they were just numbers coming out of the radio. Eventually, those numbers became my livelihood.

     I listened to Indiana Pacer games with my Gramma. Sitting at the table playing Kings Corners and eating warm zucchini bread.

   I fondly remember sitting with my Oldman on a Saturday afternoon in the Dadilac, eating White Castles and listening to Jack Benny shows with Chuck Schaden.

   Sunday afternoons had their own soundtrack. I sat on the porch with Dad while Dick Buckley played jazz records. Those Sunday afternoons probably have something to do with why jazz still sounds like home to me.

      And sports?

     Give me the radio.

I'll take the baseball game on the radio over television any day, hockey too. A good radio announcer doesn't merely tell you what's happening. He paints the damn thing. You can see the runner taking his lead from first. You can hear the crowd building before the puck hits the back of the net. The best broadcasters make you feel as though you are sitting at the game without ever showing you a picture.

        Maybe that is what I love most about radio.

   It asks something of you. Television gives you the picture. The internet gives you everything at once. Radio gives you a voice, a few sounds and enough empty space to build the rest yourself. Your imagination has to participate.

    Mark Twain supposedly said, “The secret of getting ahead is getting started.”

    I don't know how many thousands of mornings in my life have gotten started the same way, with a radio playing somewhere nearby.

   From Wally Phillips and Ellery Queen before school, to Orion and Max covering the farmers, Pacers games with Gramma, jazz with Dad, baseball in the summertime and radios scattered around my home today. That little box has been keeping me company for most of my life.

     The voices change, the stations change and the people sitting beside us eventually change too.

        …But somehow you turn that dial, hear an old song or the crack of a bat, and for just a moment they are all sitting there with you again.

Television may give us pictures. The internet gives us everything, but radio leaves just enough room for your imagination and memories.

        

          What is your favorite radio memory Chalkheads?

August 19th, 2026

 

    Just after Thanksgiving in 2021, a little tabletop Christmas tree appeared in a window across the street.

   We were still feeling the effects of the Covid pandemic. The world had reopened, but things hadn't quite been put back where they belonged.

    The tree sat in a first floor window directly across from my balcony. The apartment is in one of those big courtyard buildings built just after the First World War. They are all over Chicagoland… brick walls, rows of windows, tiled foyers and generations of people who called them home for a short time.

     I never knew who lived there, but through Christmas and well into the winter of 2022, that little tree stayed lit.

        … and for reasons I didn't completely understand at the time, I began looking for it every day.

    It became a tiny beacon of reassurance from across the street. We were all trying to climb out of those strange pandemic years, but I was also trying to climb out of something of my own. Divorce had rearranged my life, and there were mornings when I was still trying to figure out exactly what the new arrangement was supposed to look like.

    Then I would look across the street and see that little tree glowing in the darkness.

    The tree returned after Thanksgiving in 2022 and then again the next year and the next. It greeted me on dark December afternoons when the sun disappeared before dinner and on bitter January mornings when Riverside was frozen solid.

          It became part of my winter.

   When I look back someday at the 2020s and remember how unsettling the beginning of this decade was, I suspect I will remember that little tabletop Christmas tree in the apartment window across the street.

     Yesterday, when I got home from work, I noticed something was different.

The curtains were gone and the windows were bare.

     Whoever had lived in that apartment for the last five years had moved away from the Divorced Dad District and I knew at once what that meant.

       The tree won't be coming back for Christmas this year.

   I thought about The Great Gatsby and that green light at the end of Daisy's dock. Gatsby could see it across the water, small and distant, and he filled that light with everything he hoped his life might someday become.

    My light across the way wasn't green. It was a little Christmas tree glowing through an apartment window.

    Unlike Gatsby, I was simply reassured by knowing it was there.

 Maybe that is the difference. Gatsby's green light pulled him toward a future he desperately wanted. My Christmas tree helped me through a present I was learning to accept.

    Still, there was something similar about them. A light in the distance can become much more than a light.

   We give ordinary things meaning because sometimes we need them to carry us through certain periods in our lives.

  It could be a song on the radio. A familiar conductor on the morning train into the city. The smell of rain on an August afternoon. A coffee cup that your mom used when you were a kid.

                  A tree in a stranger's window.

   They become landmarks in our lives without anybody ever deciding they should be. What bothers me most isn't that the tree is gone. It is that I never got to thank the person who put it there.

     I never figured out who lived in that apartment. They had no idea that someone across the street noticed their little tree year after year.

    They had no idea that on those cold mornings, somebody looked through the darkness and was glad to see it.

       That is the funny thing about our lives. We know the stories we carry inside ourselves, but we rarely know the part we are playing in somebody else's.

     You might be somebody's Christmas tree in the window and never know it. Someone new will move into that apartment before the end of the month. New curtains will go up and new furniture will appear. Maybe there will even be another Christmas tree someday, but it won't be the tree that carried me through the first half of the 2020s.

   That light belonged to a particular stretch of my life, and now both the person who put it there and the man who first needed to see it have moved on.

    Maybe that is what you are supposed to do with a beacon eventually. You stop needing it and you keep walking.

          Today is National Soft Serve Ice Cream Day.

   The Hole in the Wall in Oak Park brings back memories for me that stretch nearly forty years. Polar Bear here in the neighborhood is our go to joint, and Highland Queen always hits the spot when we are on the other side of Mannheim Road.

         Go get yourself a cone today.

           … And while you are enjoying it, remember that there are people walking around carrying stories you know absolutely nothing about.

      Maybe you are even part of one. There is no greater agony than bearing an untold story inside you.

              Tell your story, Chalkheads.

August 18th, 2026

 

     I often chalk about my Exile in Indy, and though I speak fondly of it many years later, the truth is, I never wanted to be there.

    Because of that, I probably kept myself from getting everything I could have out of my years in the Hoosier State.

             Time has a way of changing the view.

   The older I get, the less I remember how badly I wanted to leave and the more I remember the many dear people I met while I was there. People I still think about. People who helped shape me and guide me.

     The mentors, the neighbors, the coaches, the teachers... My friends.

  There is one of those people who, without either of us ever realizing it at the time, has been with me almost every day of my career.

  Especially after the trading pits closed and the shouting and hand signals of the trading floor were replaced by computer monitors and keyboards.

       Coach Tom O'Brien.

   Coach built athletes who went on to great heights. He mentored young men who became clergymen, service members, politicians, businessmen, coaches, fathers, and leaders. His legacy reached into all walks of life.

      For me, his legacy can be heard in the pounding of a keyboard at my trading desk.

          … And I mean pounding.

 The cacophony of my fingers beating on those poor keys has driven coworkers crazy for years.

    Once, a Millennial kid in the office asked me to take it easy.

       "You don't have to take out your aggression on the keyboard dude."

 Then he asked if I knew what the home row was and informed me that a person could actually type using more than four fingers.

   I explained that I learned how to type on a typewriter from the basketball coach at Dear Old Cathedral High School and I will continue doing it exactly the way I like.

     Then, loudly under my breath:

         "Mind your own business, you little jagoff."

    Of all the things I learned in Catholic school, two of the most useful things I carried into adulthood were my rosary and my typewriter skills.

      Prayer and work.

More than forty years ago, I never imagined Coach O'Brien's typing class would help carry me through the rest of my life, but it did.

     Every morning, I sit down and type this Chalkboard. Every workday, I sit at a trading desk and pound bids and offers into the market.

     I can do both because a basketball coach at Cathedral took the time to teach and mentor a sad kid with a Chicago accent.

     Coach O'Brien will rightfully be remembered for the great basketball players he coached and sent on to bigger stages. Names like Kenny Barlow and Scotty Hicks are part of his legacy.

     … But for every star athlete whose name people remember, there are thousands of guys like me.

    Kids who were not going to play college basketball. Kids who were not going to have their names in the newspaper. Kids sitting in a classroom who didn't yet have the slightest idea what direction life was going to take them.

      Coach taught us, pushed us, and expected something from us. Practice, practice, practice.

      We thought he was teaching us how to type. He was teaching us how to work.

      Coach O'Brien took his whistle up to heaven yesterday.

 The width of his legacy is wider than most because it cannot be measured simply in victories, championships or the athletes who went on to play college basketball.

   It is measured in lives, in families, in careers, in classrooms, capitol buildings, battleships, churches, homes and offices.

     And, apparently, on one loud keyboard at a commodity trading desk in Chicagoland.

       So one more time for Coach...

            Here come the Irish, the mighty, mighty Irish...

           Wherever we go, people want to know who we are, so we tell them...

  WE ARE THE IRISH! THE MIGHTY, MIGHTY IRISH!

  May your memory always be a blessing, Coach O'Brien.

          Thank you for pushing me during my Exile in Indy. I didn't appreciate everything about those years when I was living them. It took me a long time to understand how many good people were quietly pointing me in the right direction.

         Coach was one of them.

  Maybe that is why this morning's Chalkboard quote feels especially appropriate…

   The compass came before the clock because direction matters more than time.

    Chalkheads, most of us were fortunate enough to have somebody come into our lives who made our foundation a little stronger and pointed our compass in a better direction.

   Sometimes we do not recognize what they gave us until years later.

         We were all blessed that Coach Tom O'Brien came in our direction.

       Go Irish.

August 17th, 2026

    I have decided that I should be more curious about the future. Most of the time I only worry about it.

   I worry about the Shepkids becoming healthy and happy adults. I worry about the end of my career and what retirement will look like. I worry about my health and how comfortable the next twenty years will be.

     I need to replace some of that worrying with curiosity.

  Instead of worrying about how everything is going to turn out, maybe I should be curious to see how it does.

       Yesterday, I celebrated twenty years of being a parent.

  It was twenty years ago that the entire maternity ward heard me yell…

          “Terese, the baby has a penis! A penis! We have a baby boy!”

   A voice built for booming bids across a trading floor wasn't exactly what the nursing station found helpful.

   Though they did compliment me on the way I announced the arrival of George Edward Shepley into the world. Apparently, through all their years of delivering babies, nobody had ever quite phrased it that way.

    Twenty years later, I am curious to see how that baby boy will continue to grow and where his life takes him.

         I will tell you what I am not curious about.

       Everything Fox News, CNN and the BBC are talking about. I am not curious about any of that bullshit that I cannot control.

     Politics will continue to swing back and forth. Taxes will continue to eat at my wallet. Hatred will somehow continue to get top billing over love.

     The world will keep doing what the world does.

  Maybe I should spend less time worrying about all of that and more time being curious about the things happening right in front of me.

          Well… it is another Monday and I won’t mind if it is ordinary.

   The Sox have already won more games this year than they did in each of the last three seasons. I am curious to see how this ends up.

     School starts this week for my two redheads. Senior year and eighth grade. Two milestones that once seemed impossibly far away are suddenly here. I am curious to see how this year works out for them.

    Last week, I chalked about our last eight o'clock sunset. This week, I'm a tad sad that I have to chalk sunrises after six o'clock in the morning.

     For a morning person, that one stings a little more, but I suppose that is part of being curious. Getting another chance at seeing how the day plays out.

   The days get shorter, the kids get older, careers eventually wind down, and bodies change. Seasons turn whether we are ready for them or not.

    We can worry about what is waiting around the corner, or we can walk around the corner and see. Only the curious have something to find.

     Avoid the raindrops of mid-August and shake that tail.

          Be curious, Chalkheads. You might be astonished by what you find...