Explore by Date
Classy Problems is built with layers of meaning and designed to be revisited. Like lasagna that tastes better the next day. These posts reveal new patterns, questions, and insights each time you return to them.
Browse the archive. Discover what might be worth reheating.
July 11, 2026
Mine the Gap
It’s easy to treat the gap like a to-do list item.
A problem to solve.
An inefficiency to address.
I thought my job was to close it.
Fast. Clean. Correctly.
The faster I tried to close it,
the less I understood it.
The more I missed.
I noticed I was skipping something.
Something valuable.
Something alive.
I paused for a moment.
Stayed in the discomfort.
Named what was here.
Noticed what I preferred.
Let the difference between those two things
be the work.
That’s when it became evident.
The gap isn't something to fix.
It's something to mine.
Not for certainty.
For clarity on how I could contribute.
Now, when I notice the gap,
I don’t close the gap.
I make it mine.
I remind ... >>>
A problem to solve.
An inefficiency to address.
I thought my job was to close it.
Fast. Clean. Correctly.
The faster I tried to close it,
the less I understood it.
The more I missed.
I noticed I was skipping something.
Something valuable.
Something alive.
I paused for a moment.
Stayed in the discomfort.
Named what was here.
Noticed what I preferred.
Let the difference between those two things
be the work.
That’s when it became evident.
The gap isn't something to fix.
It's something to mine.
Not for certainty.
For clarity on how I could contribute.
Now, when I notice the gap,
I don’t close the gap.
I make it mine.
I remind ... >>>
July 10, 2026
If I Am Being Honest
I tell myself I’m being honest.
I believe it.
I even feel self-righteous about it.
Until later.
When something doesn’t add up.
When someone reflects something back.
When I feel the tension I talked my way around.
If I’m being honest, I’m not always sure if I’m being honest.
What I do know is when I’m consciously being dishonest.
The lie. The avoidance. The performance.
Hard to admit in a post.
Easy to see in my intentional review.
What's harder to see and easier to admit,
is when I am unconsciously dishonest.
When I am oblivious to it.
It’s not truth.
It’s perception posing as truth.
I’ll push it with conviction.
Call it clarity.
Claim it as obvious.
It’s not.
It’s ... >>>
I believe it.
I even feel self-righteous about it.
Until later.
When something doesn’t add up.
When someone reflects something back.
When I feel the tension I talked my way around.
If I’m being honest, I’m not always sure if I’m being honest.
What I do know is when I’m consciously being dishonest.
The lie. The avoidance. The performance.
Hard to admit in a post.
Easy to see in my intentional review.
What's harder to see and easier to admit,
is when I am unconsciously dishonest.
When I am oblivious to it.
It’s not truth.
It’s perception posing as truth.
I’ll push it with conviction.
Call it clarity.
Claim it as obvious.
It’s not.
It’s ... >>>
July 9, 2026
Winning the Wrong Game
I’ve had several conversations recently
that were a reminder that
what I notice,
doesn’t tell me something
about what I’m looking at.
It tells me something
about me.
The frame doesn’t explain the picture.
It reveals the framer.
What I’ve been hearing feels familiar.
Different people.
Different details.
Same arc.
Work hard.
Sacrifice.
Achieve.
Arrive.
Then, somewhere near the top,
realize how incomplete it feels.
Despite the success.
The comfort.
The proof
The view.
They are all real.
They feel great.
They don’t feel complete.
That’s what makes it disorienting.
Disappointing.
Getting there and feeling how little “there” there is.
I can relate.
More than 30 years ago,
I found my own version of that mountaintop.
I had enough success to believe I had found the answer.
It worked for a while.
That’s the ... >>>
that were a reminder that
what I notice,
doesn’t tell me something
about what I’m looking at.
It tells me something
about me.
The frame doesn’t explain the picture.
It reveals the framer.
What I’ve been hearing feels familiar.
Different people.
Different details.
Same arc.
Work hard.
Sacrifice.
Achieve.
Arrive.
Then, somewhere near the top,
realize how incomplete it feels.
Despite the success.
The comfort.
The proof
The view.
They are all real.
They feel great.
They don’t feel complete.
That’s what makes it disorienting.
Disappointing.
Getting there and feeling how little “there” there is.
I can relate.
More than 30 years ago,
I found my own version of that mountaintop.
I had enough success to believe I had found the answer.
It worked for a while.
That’s the ... >>>
July 8, 2026
Comforting a Symptom
When I’m cold,
a heated blanket feels like an answer.
It might even be an answer.
The warmth is real.
The relief is real.
For a moment.
In the moment,
it can feel like fulfillment.
That’s what makes it a classy problem.
Comfort helps.
It softens my edge.
Quiets my symptom.
Changes my experience.
If I stay there long enough,
something changes.
I adjust.
What first felt like an answer becomes normal.
Once it becomes normal,
it stops feeling like fulfillment.
That’s the problem.
What felt like fulfillment was relief.
Real relief.
I’m grateful for it.
Grateful that something stopped the hurt.
Grateful that something helped.
Grateful that the discomfort eased.
Relief and fulfillment are not the same thing.
That’s where I get confused.
I mistake comfort for ... >>>
a heated blanket feels like an answer.
It might even be an answer.
The warmth is real.
The relief is real.
For a moment.
In the moment,
it can feel like fulfillment.
That’s what makes it a classy problem.
Comfort helps.
It softens my edge.
Quiets my symptom.
Changes my experience.
If I stay there long enough,
something changes.
I adjust.
What first felt like an answer becomes normal.
Once it becomes normal,
it stops feeling like fulfillment.
That’s the problem.
What felt like fulfillment was relief.
Real relief.
I’m grateful for it.
Grateful that something stopped the hurt.
Grateful that something helped.
Grateful that the discomfort eased.
Relief and fulfillment are not the same thing.
That’s where I get confused.
I mistake comfort for ... >>>
July 7, 2026
Answering the Wrong Question
I spend time trying to fix what I am feeling.
Discomfort.
Restlessness.
Confusion.
Urgency.
I want relief.
That part was honest.
I am missing that I am asking the wrong question.
It keeps my attention inside the experience
instead of helping me see the situation.
How do I make this stop?
How do I get past this?
How do I feel better?
Those questions can produce answers.
They also keep me aimed at the symptom.
That’s a classy problem.
A better question doesn’t provide a better answer.
It provides a better line of sight.
What is this showing me?
What kind of moment am I in?
What is indicated that I can’t see from inside my urgency?
The moment I ask ... >>>
Discomfort.
Restlessness.
Confusion.
Urgency.
I want relief.
That part was honest.
I am missing that I am asking the wrong question.
It keeps my attention inside the experience
instead of helping me see the situation.
How do I make this stop?
How do I get past this?
How do I feel better?
Those questions can produce answers.
They also keep me aimed at the symptom.
That’s a classy problem.
A better question doesn’t provide a better answer.
It provides a better line of sight.
What is this showing me?
What kind of moment am I in?
What is indicated that I can’t see from inside my urgency?
The moment I ask ... >>>
July 6, 2026
The Hunter and the Decider
I think about AI in a simple way.
What would I do
if I had 1,000 years
and 1,000 people to do it with?
That’s the impact.
Scale.
Not intelligence.
Capacity.
The system can hunt.
Endlessly.
Data.
Information.
Knowledge.
It gathers faster than I can ask.
What used to take effort now shows up.
Organized.
Connected.
Ready to use.
We used to be the hunters.
Searching.
Collecting.
Piecing things together.
That was the work.
Now it isn’t.
AI hunts better.
It finds patterns.
Builds relationships.
Delivers answers to what and how.
Up through knowledge.
That part collapsed.
Understanding didn’t.
Understanding is internal.
It’s translation.
Why this matters.
What fits.
The system can gather.
It can’t decide.
It can’t carry consequence.
It can’t live with the outcome.
That part stayed with me.
The work split.
We are the deciders ... >>>
What would I do
if I had 1,000 years
and 1,000 people to do it with?
That’s the impact.
Scale.
Not intelligence.
Capacity.
The system can hunt.
Endlessly.
Data.
Information.
Knowledge.
It gathers faster than I can ask.
What used to take effort now shows up.
Organized.
Connected.
Ready to use.
We used to be the hunters.
Searching.
Collecting.
Piecing things together.
That was the work.
Now it isn’t.
AI hunts better.
It finds patterns.
Builds relationships.
Delivers answers to what and how.
Up through knowledge.
That part collapsed.
Understanding didn’t.
Understanding is internal.
It’s translation.
Why this matters.
What fits.
The system can gather.
It can’t decide.
It can’t carry consequence.
It can’t live with the outcome.
That part stayed with me.
The work split.
We are the deciders ... >>>