Why Smart People Stay Stuck
A Hard Lesson I Learned This Week
Most people don’t need more learning—they need more reps.
I was reminded of that in the most unexpected place… a two-day oil painting class.
At one point, my instructor shared something her students often ask:
“What does it take to go from being a beginner to becoming a professional artist?”
Her answer was simple. Almost disarmingly so.
“Paint every day. Use a small 4x6 panel. Number each painting 1–100. When you reach 100, come back and we’ll review your progress together. And by the way—stop taking workshops if you’re not putting the daily practice into action.”
Ouch. (In the best way.)
That landed squarely on me.
For three years, I’ve faithfully attended monthly art workshops. I love them. I learn a lot. I leave inspired.
And then… I don’t paint.
Not because I don’t have time.
But because it feels uncomfortable.
I feel a little lost.
I don’t want to confront my own ineptness.
The blank canvas.
The messy paints.
The clean-up.
And especially that moment…
when what I create looks nothing like what I imagined.
It’s disappointing.
Seeing how child-like my efforts look.
Like this church spire that somehow turned into a cartoon top hat.
Painting at this level feels… exposing.
And I’d rather stay in the safety of learning than risk being bad.
Where in your life are you playing it safe to avoid looking bad?
So now, I’m on a mission: 100 paintings.
Not masterpieces.
Not frameable.
Not Instagram-worthy.
Just… paint.
Every day.
I’m letting go of “Is it good?” and replacing it with “Did I show up?”
What Actually Changed
Once I committed, I realized something important:
Motivation is overrated. Environment matters more.
So I made a few simple changes:
I stopped worrying about the mess
I pulled my supplies out where I could see them
I made it easy to begin
And one constraint changed everything:
Forty minutes.
That’s it.
Forty minutes gets me started.
Forty minutes keeps me consistent.
And consistency, it turns out, is where the path to mastery lives.
The Leadership Lesson
I see this all the time with my clients.
Brilliant, capable leaders—
reading, learning, attending workshops…
And still feeling stuck in some significant part of their life or work.
Not because they aren’t trying.
But because they haven’t turned insight into practice.
And more importantly…
They haven’t been honest about why they’re avoiding the practice.
So let me ask you:
Where are you “taking workshops”… but not painting?
Where are you avoiding the reps?
Maybe it’s asking your team for real feedback.
You want your meetings to be more engaging, more effective.
You’ve read the books. You’ve hired the coach.
But to improve, you’d have to ask:
“What’s not working?”
And then… listen.
You might hear:
“You talk too much.”
“You don’t really listen.”
“These meetings feel repetitive.”
That could sting.
So instead… you stay where you are.
Your Version of the Challenge
Pick one area where you are stuck - this is not just for corporate leaders - maybe it’s around your health or your spiritual life. Maybe you are seeing a counselor but not taking significant action on a key issue that’s holding you back.
One area,
Not five. Not someday.
One.
Make it small.
Make it daily.
Make it just uncomfortable enough that you might avoid it.
And then… do it anyway.
Because here’s what I’m learning:
You don’t become who you want to be by thinking about it.
Or reading about it.
Or even understanding it.
You become that person… by practicing.
The life you want isn’t built in grand gestures—it’s painted, one small stroke at a time.
A Longer View
My daughter Julia recently sent me a quote she saw next to a Matisse drawing.
After fifty years of work, he wrote:
“For a year now I’ve been making an enormous effort in drawing. I say effort but that’s a mistake, because what occurred is a floraison (flowering) after fifty years of effort.”
A flowering.
Not instant. Not dramatic.
But something that emerges… after years of showing up.
A Gentle Challenge
Pick your “painting.”
Make it small.
Make it daily.
Make it uncomfortable.
And begin.
You don’t need more information.
You need a canvas.
A year from now, you won’t wish you had learned more.
You’ll wish you had started sooner.
If this hits close to home, you’re exactly who I write for. Join me for practical, honest insights on growth, leadership, and the inner work that actually creates change.
Painting and learning new skills offer a great example. Thanks for sharing your challenges and the opportunities that arise from repetition and commitment to our goals and desires.