1,000 Straight Days of Painting
On this beautiful early autumn Sunday in the Blue Ridge Mountains, I took the easy walk downstairs, out through the courtyard, and into my semi-finished studio. I pulled up a photo on my phone that I'd taken last week, clipped it to a holder, and started mixing up some lights and darks on my palette.
I put some midtone touches on a small 5x7-inch canvas panel. Just a little study of a waterfall. Nothing particularly interesting or special about it. But this Sunday was the thousandth straight day I had put brush to canvas (or paper).
The streak started at the beginning of 2024, and I had no idea how long I'd go. My thinking was simple: I had started painting inconsistently during the 2020 pandemic. I'd gone in fits and starts but knew I had to log some serious time with a brush if I wanted to get anything out of this hobby — and I felt I owed it to myself to give it a try.
Here's where it intersected with a lot of thinking and learning I've done on habits, discipline, and learning.
There is a theory in the art world that every artist has at least a thousand ugly paintings in them. It's the artist's job to get through those paintings to some (hopefully) really good stuff.
The logic rests on three foundations, which I think apply to almost any pursuit:
1. A Quantifiable Learning Curve: Many are familiar with Malcolm Gladwell's "10,000 Hour" theory for achieving mastery, popularized in his 2008 bestseller Outliers. While the number of hours is oft-disputed, what's not in question is that being good at something takes time — lots of time — and deliberate practice. There are no shortcuts here. You have to do the work. Better to get that through your head now.
2. Liberation from Perfectionism: This is a big one with art. I've talked to so many people who've said some variation of the following: "I've tried it, but I wasn't very good!" After just doing it a few times? No kidding.
Despite how easy things may look in a YouTube video, I can assure you that it will be harder and take more missteps than you realize. Trying to get through "1,000 ugly paintings" essentially removes this mental hangup. The results are predetermined: it's not going to be a masterpiece. Realizing this is strangely freeing. Suddenly there's less pressure. Things that turn out well will feel great, but you won't beat yourself up about the stuff that is, to put it bluntly, bad. But that's the plan. Embrace it.
3. Muscle Memory: Just as a great golfer needs to make hundreds of thousands of swings to develop their best swing, you need time with a brush in your hand. You have to learn how it feels, how to make different brushstrokes, how to control the paint, and how to mix the colors you want to see. Again, there's no way around the reps here.
I also intentionally kept the commitment light. I didn't say I had to finish a piece every time I picked up the brush. Some days I would only have time to put a few strokes down. Some days I had to sneak a few in at a hotel while traveling. Other days I would finish several pieces in a longer studio session.
But just making the commitment to paint something every day is like the old gym advice to exercise for just five minutes (spoiler: you usually end up getting into a groove and going further). Sometimes it's just getting started that's hard.
As the streak grew — first hitting one year, then 500 days, then two years — there was a natural inclination to keep going. There is a habit-building method commonly attributed to Jerry Seinfeld: mark each successful day with a big X on a calendar, and before long you've created a chain you don't want to break.
But the truth is that it has not been that hard to keep it going. Certainly, there are days when it comes more smoothly, but I have been excited to get that work in each day. The feeling of creating, the feeling of getting better, and having tangible results from an effort you sink your heart and soul into is invigorating.
I'm not going to say I'm done with the ugly stage of my painting. I'm not selling my work, and I still don't share as much as I should. Some of what I create is frustratingly bad. But there are glimpses — there is more control, and I can feel the improvement.
I'm not sure how much longer I will insist on painting every day, but I don't expect to stop any time soon. That desire to "not break the chain" is strong, and we're almost to three full years.
I hope to keep writing more about the journey as well. I came to this pursuit later in life than many and am doing my best to catch up. If there is a similar thing you have been thinking of pursuing, please do it. It's not easy, but it is worth it.
Mark's 2025 Reads
Full list of the books I’m Reading in 2025
Below are the books I read in 2025. I have tried to divide them by how much I enjoyed them and how valuable I found them.
Highly Recommended:
Dying Every Day, James Romm
10x is Easier than 2x, Dan Sullivan
On the Shortness of Life, Seneca
The Gap and the Gain, Dan Sullivan
Bottom of the 33rd, Dan Barry
Black Snow, James Scott
Recommended:
Hombre, Elmore Leonard
Eight Men Out, Eliot Asinof
Kitchen Confidential, Anthony Bourdain
From Here to Eternity, James Jones
It’s Not All About Me, Robin Dreeke
Gone, Baby, Gone, Dennis Lehane
Days of Rage, Ryan Burroughs
The Next Conversation, Jefferson Fisher
It Still Moves, Amanda Petrusich
The Let Them Theory, Mel Robbins
Turn! Turn! Turn!, Richie Unterberger
Others:
Stolen Focus, Johann Hari
The Joy of Art, Carolyn Schlam
Phil, Alan Shipnuck
Israel, Noa Tishby
The Record Men, Rich Cohen
That Thin, Wild Mercury Sound, Daryl Sanders
The Grand Tour, Rich Kienzle
Tell to Win, Peter Guber
Previous Years’ Reads
For more, connect with me on GoodReads.
Mark's 2024 Reads
Running list of the books I’m Reading in 2023
Below are the books I read in 2024. I have tried to divide them by how much I enjoyed them and how valuable I found them.
Highly Recommended:
11.22.63, Stephen King
Composition of Outdoor Painting, Edgar Payne
Titan: The Life of John D. Rockefeller, Sr., Ron Chernow
Manhunt, James Swanson
The Last Picture Show, Larry McMurtry
Recommended:
Daily Rituals, Mason Currey
Oranges, John McPhee
Six Days of War, Michael Oren
Surely You Can’t Be Serious, David Zucker
Good to Great, Jim Collins
Cod, Mark Kurlansky
Pappyland, Wright Thompson
On Confidence, The School of Life
Mission at Nuremberg, Tim Townsend
In The Arena, Richard Nixon
An Ordinary Man, Richard Norton Smith
Death of an Angel, Don Davis
The Big Sleep, Raymond Chandler
Farewell My Lovely, Raymond Chandler
The Anatomy of Peace, The Arbinger Institute
Altamont, Joel Selvin
The High Window, Raymond Chandler
Others:
A Necessary Act, Tony Wirt
Nixon Agonistes, Garry Wills
Hot Dog Money, Guy Lawson
American Moonshot, Douglas Brinkley
A Concise History of Florida, James Clark
How to Talk to Anyone and Everyone, Mindnatic
Master of Change, Brad Stullberg
The Big Roads, Earl Swift
The West, Geoffrey C. Ward
Previous Years’ Reads
For more, connect with me on GoodReads.
Mark's 2023 Reads
Running list of the books I’m Reading in 2023
Below are the books I read in 2023. I have tried to divide them by how much I enjoyed them and how valuable I found them.
Highly Recommended:
Smart Brevity, Jim Vandehei
A Man in Full, Tom Wolfe
Excellent Advice for Living, Kevin Kelly
Recommended:
The Gatekeepers, Chris Whipple
The Final Days, Bob Woodward
His Very Best: Jimmy Carter, A Life, Jonathan Alter
One of Us, Tom Wicker
The Last Brahmin, Luke A. Nichter
The Making of the President: 1960, Theodore White
A World Lit Only by Fire, William Manchester
Urban Watercolor Sketching, Felix Scheinberger
Just Stay Away, Tony Wirt
The Civil War - An Illustrated History, Geoffrey Ward
TR: A Life, H.W. Brands
A Civil War, John Feinstein
How Successful People Win, John Maxwell
A Christmas Memory, Truman Capote
Others:
The Lost Peace, Robert Dallek
One Man Against the World, Tim Weiner
Eisenhower Declassified, James Scheer
Curtis LeMay: Strategist and Tactician, Warren Kozak
Case Closed, Gerald Posner
The Last Policeman, Ben Winters
Hannibal, Patrick Hunt
Death of a Busybody, George Bellairs
Endless Energy, Peter Hollins
Previous Years’ Reads
For more, connect with me on GoodReads.
Mark's 2022 Reads
Running list of the books I read in 2022.
Below are the books I read in 2022. I have tried to divide them by how much I enjoyed them and how valuable I found them.
Also, I read or listened to many of these books on Scribd, which is a monthly service offering a huge variety of digital books, audio books, and documents. It’s like Netflix for book lovers!
Use this link for a free sixty days of the service - it’s a great service.
Highly Recommended:
Competing Against Luck, Clayton M. Chritensen
The Big East, Dana O’Neil
No Country for Old Men, Cormac McCarthy
Four Thousand Weeks, Oliver Burkeman
Recommended:
How to Win Friends and Influence People, Dale Carnegie
It’s Better to Be Feared, Seth Wickersham
The Dynasty, Jeff Benedict
Not Fade Away, Laurence Shames
Building a StoryBrand, Donald Miller
Blood in the Garden, Chris Herring
Gulag: A History, Anne Applebaum
How to Watch Basketball Like a Genius, Nick Greene
The Splendid and the Vile, Erik Larson
The Arm, Jeff Passan
Fins, William Knoedsleder
Courage is Calling, Ryan Holiday
The Moon is Down, John Steinbeck
The Storm of War, Andrew Roberts
The Man Who Died Laughing, David Handler
The Coaching Habit, Michael Bungay Stanier
How The Hell Did This Happen?, P.J. O’Rourke
The First World War, Martin Gilbert
HBR Guide to Making Every Meeting Matter, Harvard Business Review
Hitler, the Germans, and the Final Solution, Ian Kershaw
Hitler’s Hangman, Robert Gerwarth
Rammer Jammer Yellow Hammer, Warren St. John
Saban, Monte Burke
13 Things Mentally Strong People Don’t Do, Amy Morin
Make it Stick, Peter C. Brown
The Age of Eisenhower, William I. Hitchcock
Contempt of Court, Mark Curriden
How Ike Led, Susan Eisenhower
The Best of Me, David Sedaris
Others:
The Best American Short Stories 2017, Meg Wolitzer (Editor)
Do Hard Things, Steve Magness
Boys Will Be Boys, Jeff Pearlman
Six Days of the Condor, James Grady
The Man Who Lived by Night, David Handler
The Man Who Would Be F. Scott Fitzgerald, David Handler
Take Your Eye off the Puck, Greg Wyshynski
Instant, Christopher Bonanos
False Start, Terry Pluto
The Postman Always Rings Twice, James M. Cain
Buried, Jeffery Dever
Overtime, John U. Bacon
The Last Temptation of Christ, Nikos Kazantzakis
The New Rules of Cheese, Anne Saxelby
Pontius Pilate, Ann Wroe
Playmakers, Mike Florio
The Invisible Bridge, Rick Perlstein
In The Garden of Beasts, Erik Larson
Previous Years’ Reads
For more, connect with me on GoodReads.
Mark's 2021 Reads
Running list of the books I read in 2021.
Below are the books I read in 2021. I have tried to divide them by how much I enjoyed them and how valuable I found them.
Also, I read or listened to many of these books on Scribd, which is a monthly service offering a huge variety of digital books, audio books, and documents. It’s like Netflix for book lovers!
Use this link for a free sixty days of the service - it’s a great service.
Highly Recommended:
The Bully Pulpit, Doris Kearns Goodwin
Steve Jobs, Walter Isaacson
The Win Without Pitching Manifesto, Blair Enns (*Read Twice)
Prisoners of Geography, Tim Marshall
The Spy Masters, Chris Whipple
Parkland, Vincent Bugliosi
The Devil in the Grove, Gilbert King
Parting the Waters, Taylor Branch
Recommended:
Authentic Gravitas, Rebecca Newton
Killers of the Flower Moon, David Grann
Mornings on Horseback, David McCullough
The Last Stand, Nathaniel Philbrick
Careless People, Sarah Churchwell
The Spy and the Traitor, Ben Macintyre
Eisenhower: A Life, Paul Johnson
Ike’s Bluff, Evan Thomas
How to Be a Great Boss, Gino Wickman
Sage Advice, Richard Borden
Make Time, Jake Knapp
Stony the Road, Henry Louis Gates, Jr.
Trump Revealed, Michael Kranish
Musonius Rufus: Lectures and Sayings
Clementine, Sonia Purnell
The Infinite Game, Simon Sinek
24 Hours in Ancient Rome, Philip Matyszak
The Great Gatsby, F. Scott Fitzgerald
The Almanack of Naval Ravikant, Eric Jorgenson
Accidental Presidents, Jared Cohen
Turtles All the Way Down, John Green
A Life in Parts, Bryan Cranson
Robin, Dave Itzkoff
Three-Ring Circus, Jeff Pearlman
Effortless, Greg McKeown
They Ask You Answer, Marcus Sheridan
Playing for Keeps, David Halberstam
Pillar of Fire, Taylor Branch
That Distant Land, Wendell Berry
The End is Always Near, Dan Carlin
The Year 1000, Valerie Hansen
Sharp, Josh Donald
The Best American Noir of the Century, James Ellroy (Editor)
Fanocracy, David Meerman Scott
The Devil in the White City, Erik Larson
Benjamin Franklin, Walter Isaacson
The Boys in the Boat, Daniel James Brown
The Wright Brothers, David McCullough
The Big Goodbye, Sam Wasson
Others:
Tanking to the Top, Yaron Weitzman
Legendary Self-Discipline, Peter Hollins
Life of a Klansman, Edward Ball
The Catalyst, Jonah Berger
Ten Innings at Wrigley, Kevin Cook
Digital Gold, Nathaniel Popper
Queen of Scots, John Guy
Smart Baseball, Keith Law
How to Build a Car, Adrian Newey
Murdered Midas, Charlotte Gray
Blockchain, Harvard Business Review
Making Time, Bob Clagett
The Last of the President’s Men, Bob Woodward
The Happiness Advantage, Shawn Achor
They Thought They Were Free, Milton Sanford Mayer
Previous Years’ Reads
For more, connect with me on GoodReads.
Mark's 2020 Reads
Below are the books I read in 2020. I have tried to divide them by how much I enjoyed them and how valuable I found them. Click to buy on Amazon via my referral link (price stays same for you but helps support the SportsBiz Book Exchange).
Also, I read or listened to many of these books on Scribd, which is a monthly service offering a huge variety of digital books, audio books, and documents. It’s like Netflix for book lovers!
Use this link for a free sixty days of the service - it’s a great service.
Highly Recommended:
Them: Why We Hate Each Other - And How to Heal, Ben Sasse
High Output Management, Andrew Grove
Richard Nixon: The Life, John Farrell
The Coddling of the American Mind, Greg Lukianoff & Jonathan Haidt
Principles: Life and Work, Ray Dalio
The Science of Self Learning, Peter Hollins
Leonardo da Vinci, Walter Isaacson
Recommended:
The Upside of Stress, Kelly McGonigal
The Design of Everyday Things, Donald Norman
The Inner Game of Tennis, Timothy Gallwey
Travels with Epicurus, Daniel Klein
Narrative of the Life of Frederick Douglass, Frederick Douglass
Dueling with Kings, Daniel Barbasi
The Death of Ivan Ilych, Leo Tolstoy
Two Americans, William Lee Miller
Fast Times: How Digital Winners Set Direction, Learn, And Adapt, Multiple Authors
The Cold War: A New History, John Lewis Gaddis
Gridiron Genius, Michael Lombardi
Seinfeldia: How a Show About Nothing Changed Everything, Jennifer Armstrong
Winning is Not a Strategy, Zac Logsdon
The Dichotomy of Leadership, Jocko Willink & Leif Babin
A Calendar of Wisdom, Leo Tolstoy
The Sun & The Moon & The Rolling Stones, Rich Cohen
The Code. The Evaluation. The Protocols, Jocko Willink
Machine Learning: The New AI, Ethem Alpaydin
So You’ve Been Publicly Shamed, Jon Ronson
The Tao of Charlie Munger, David Clark
Lou Gehrig: Pride of the Yankees, Paul Gallico
Chernobyl 01:23:40, Andrew Leatherbarrow
Worst. President. Ever, Robert Strauss
Hadrian and the Triumph of Rome, Anthony Everitt
The Happiness Equation, Neil Pasricha
Artificial Intelligence: The Insights You Need from Harvard Business Review
No Filter: The Inside Story of Instagram, Sarah Frier
Reconstruction: A Concise History, Allen Guelzo
Lives of the Stoics: The Art of Living from Zeno to Marcus Aurelius, Ryan Holiday
The Sharing Economy, Arun Sundararajan
The Great Gatsby, F. Scott Fitzgerald
The Castle on Sunset, Shawn Levy
Others:
Why We Make Things and Why It Matters, Peter Korn
Grace will Lead Us Home, Jennifer Berry Hawes
The Electric Kool-Aid Acid Test, Tom Wolfe
How Smart Machines Think, Sean Gerrish
When Things Fall Apart, Pema Chodron
Everybody Lies, Seth Stephens-Davidowitz
A Life Well Played, Arnold Palmer
Finite and Infinite Games, James Carse
Everybody Lies, Seth Stephens-Davidowitz
You Are Not A Rock, Mark Freeman
Previous Years’ Reads
For more, connect with me on GoodReads.
Sue Thaden (From Now On) Joins The Sports Leadership Podcast for Episode 43
Sue Thaden, who I have had the pleasure of knowing for several years, has done amazing work with her two companies - CRi, an IT staffing firm and From Now On, who builds mobile apps in the sports market. Sue joined us on Episode 43 to discuss her background as an entrepreneur and company founder for two successful companies.
She shares some great tips on hiring, developing your people, and keeping them engaged. Kevin and I really enjoyed this conversation and I’m sure you will too!
If you have not yet, please subscribe to the Sports Leadership Podcast on iTunes, Spotify, Stitcher, SoundCloud or Google Play.