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Home - Classy Problems: Confessions of a Recovering Control Freak
Classy Problems

Classy Problems: Confessions of a Recovering Control Freak

Dan T. RogersBy Dan T. RogersNovember 3, 20256 Mins Read
Classy Problems: Confessions of a Recovering Control Freak
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Photo Credit:  «Depositphotos.com»

Classy Problems is a daily post of thinking in motion by Dan T. Rogers. Each post stands alone as a thought-provoking piece, yet together, they create a puzzle of ideas. They invite you to see things from a different angle, rethink what you thought you knew, and explore what’s beyond your current understanding.

Classy isn’t just a read: it’s a practice. Read, listen, and join us for Classy Problems Live, a 15-minute, live virtual conversation held Monday through Thursday at 12:15p PT, where we gather to reflect on the Classy Problems post of the day. No need to prep. Just connect, explore, and reflect. 

Classy Problems Black Crown

Join Then Contribute

I wanted to contribute.
To add value.
To make an impact.
I jumped ahead.
Tried to contribute
before I had joined.
Before I had entered.
Before I had aligned.
I wasn’t a part of.
I was apart from.
Looking in from the outside,
trying to change the inside.
Contribution without joining
is an intrusion
like breaking and entering
is a crime.
To contribute, I have to enter.
To enter, I have to notice where I am.
What’s already in motion.
What’s already being held.
Not to conform.
To connect.
To know what’s needed,
I need to understand.
Understanding joining is my choice.
Contribution is the next choice.
Not the first.
The loop of contributing without joining
is the loop of looking to control without connection.
What helps me connect is asking:
Have I entered?
Do I know what’s happening here
before trying to change it?
Joining precedes contributing.
If I haven’t entered,
I’m not a part of,
I’m apart from.

Classy Problems Black Crown

Prisoner or Participant?

Sometimes I didn’t join.
Not really.
I showed up.
Went through the motions.
Did the job.
I didn’t enter.
I didn’t align.
I didn’t opt in.
Then I wondered
why it felt like I was being held hostage.
Why the work felt like a burden.
Why I was resentful.
Why every ask felt like a demand.
It felt like I’d been taken prisoner.
No one locked the door.
Ironically, I never walked through it.
I didn’t join and still expected to contribute.
Still wanted to have a say.
Still wanted impact
without membership.
That’s the loop
of being apart from
while pretending to be a part of.
Of performing without participating.
Of resisting while expecting to belong.
When I skip the step of joining,
the work becomes chore.
The expectations feel unfair.
The experience feels forced.
Even when I was the one who stayed silent.
What frees me is asking,
Did I choose this?
Did I join with intention
or did I show up and expect it to work?
If I didn’t join,
I can’t be surprised that I don’t feel connected.
That it feels like performance.
That contribution feels like compliance.
Joining isn’t surrender.
It’s alignment.
It’s the act of saying:
“I’m here. I’m in. Here we go.”
Unless they took me prisoner,
I made a choice.

Classy Problems Black Crown

Willingness vs. Resistance

Willingness looks like yes.
Not yes, but.
Not yes, if.
Not yes, after.
Just yes.
Everything else is a version of resistance
dressed up in reasonable language.
I told myself I was open.
I was being smart.
Cautious. Strategic.
I wasn’t being willing.
I was negotiating.
I didn’t say no.
I didn’t say yes, either.
I said yes, but not yet .
Yes, once it’s clear.
Yes, if it’s safe.
Yes, after they go first.
That’s not willingness.
That’s conditional compliance.
The loop of yes, but.
Hiding in discernment.
It’s fear impersonating wisdom.
Willingness is not agreement.
It’s not certainty.
It’s not liking it.
It’s saying:
I’m in. I’ll go. Here we go.
Even when it’s unclear.
Even when it’s uncomfortable.
Even when I don’t feel ready.
How I find my willingness is asking:
Am I willing?
Or trying to sound like I am.
Willingness sounds like yes.
Everything else is resistance
with and without the polite tone.

Classy Problems Black Crown

Confessions of a Recovering Control Freak

I used to call myself a control freak.
Said it like it was a strength.
Something to brag about.
Evidence that I cared.
That I was dialed in.
That I took things seriously.
“You don’t get it. I’m a control freak.”
Like it explained my excellence.
Like it excused my exhaustion.
People would say things.
Let go.
Turn it over.
Let go and let…
You know the rest.
Those phrases brought relief.
They did not provide release.
They’re trying to solve the wrong problem.
The problem isn’t that I held on too tightly.
The problem is I believed it was mine to hold.
If I ever had control
Real, actual, full control
I wouldn’t let go.
Not ever.
I might give you an afternoon off.
I’d still be running the show.
That’s the lie I had to face.
thebossissupergenerous.
Held back most of the control.
Kept almost all of it.
We’re not suffering from control.
We’re suffering from the delusion of it.
A delusion is a lie I tell myself.
What I needed to let go of
isn’t the control.
It was the lie that I had it.
That’s the only thing I have to turn over.
That’s what puts things
back in proper order.

Classy Problems Black Crown

Understanding Demonstration

I used to think wisdom could be shared,
loaned, or even stolen.
It can’t.
I thought it could be taught.
That I could explain it.
Pass it on.
I confused transmission with transformation.
Wisdom can’t be shared.
It can only be demonstrated.
Lived.
It must be earned.
I don’t make the rules.
I notice the patterns
And offer you a consideration.
Information is data, processed.
Knowledge is information, transmitted.
Understanding is knowledge, translated.
Through my own experience.
Through reflection.
Through trying. Failing.
Mistakes at full speed.
Wisdom is understanding applied.
Classy problems show up
when I try to borrow wisdom
I haven’t earned.
When I speak truth
I haven’t lived.
When I use answers
I haven’t questioned.
The paradox cuts both ways.
You have to earn yours.
I have to earn mine.
Wisdom is understanding
applied.

Classy Problems Black Crown

My Dream, Our Nightmare

It was like waking up from a dream.
Except I hadn’t been sleeping.
I was awake.
I found myself in an argument.
I found myself already in it.
It wasn’t going well.
Despite my best efforts.
Not my best self.
My best pushes.
My points. My logic. My tone.
Nothing was landing.
Then I came to.
Not all the way.
Not enough to end it.
Enough to see I was trying
to use words to fix something
that was only asking for space.
A space for love to take hold.
That’s when I stopped talking.
I hadn’t given in.
I had given up.
It was time to align up.
I’d been trying to push
in a universe that prefers pull.
Trying to win.
To be right.
To be heard.
To be understood.
I’m still in it.
Haven’t mastered it.
Haven’t perfected it.
Haven’t outgrown it.
Still resisting the urge
to prove, to defend,
to drop one perfect sentence.
I am attempting to demonstrate
that truth doesn’t require more.
It doesn’t require more firepower. More positioning. More me.
It needs space.
To be seen, felt, to be lived.
On purpose.
My purpose is to make that demonstration.
However imperfectly.
With love.
Even when I’m frustrated.
Especially when I’m frustrated.
That’s what Intentional Demonstration
means to me.
Right now. Mid-argument.
There’s an opportunity to be the truth
instead of trying to deliver it.

Classy Problems Black Crown

What a To Do

I caught myself thinking.
That’s not true.
I caught myself feeling like I was thinking
When I was spinning, looping really.
Replaying the same loops.
Fixing conversations that already happened.
Planning arguments like victory celebrations.
It felt like problem-solving,
Or at least like I was preparing.
Preparing for what?
It was problem-stalling.
I wasn’t creating space.
I was filling it.
With noise.
With urgency.
With control.
With me.
Then I paused.
Not because I had the answer.
Because I didn’t.
No answer is an answer.
For a moment,
I let the thought be a thought.
I noticed.
What was here.
What I was feeling.
What I was afraid to feel.
In that pause was enuf enough space
for awareness. For insight. For clarity.
Space that blurs certainty.
Leaving room for something more honest
than me by myself.
That’s what Intentional Thinking is for me.
It’s choosing to think on purpose, on purpose.
To make space for what I can’t see
In the sea of ‘figure it out’.
Turns out it’s easier to figure out what not to do,
then what to do.


Want more from us? OPT IN to our daily email and join our Classy Problems community. It’s where we abandon certainty in the pursuit of clarity, one interaction at a time.



Graffiti Classy Problems NEW

Classy Problems is a daily post of thinking in motion by Dan T. Rogers. Each post stands alone as a thought-provoking piece, yet together, they create a puzzle of ideas. They invite you to see things from a different angle, rethink what you thought you knew, and explore what’s beyond your current understanding.

What is a classy problem? A classy problem is when we’ve been afforded the opportunity to figure out what to do. Time to figure it out. Time to practice. Time to discern. When faced with the time to figure out a classy problem, it is more effective to focus on what NOT to do than trying to figure out what to do. In a word: restraint. JOIN US in exploring the distinction between what to do and what not to do in the pursuit of clarity.

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Meet Dan T. Rogers, visionary leader of WORKP2P, Point to Point Transportation, BEATS WORKING podcast, Classy Problems, and The Intentional Course. This former burrito roller turned CEO has dedicated his life to creating systems to help people figure out what they want and how to get it.

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