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Home - Classy Problems: The Story of Why
Classy Problems

Classy Problems: The Story of Why

Dan T. RogersBy Dan T. RogersFebruary 10, 20255 Mins Read
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Welcome to the Classy Problems weekly mash-up for Monday, January 20, 2025 – Sunday, January 26, 2025

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 Problems Black Crown

January 20 – The Story of Why

Opinions reflect how we process information and reveal our preferences. They are the ‘story of why’ justifying our feelings and impacting our interactions.

They serve as valuable reference points for me — but not so much for everyone else. My opinions don’t matter outside of my own head.

Sharing an opinion, however, is an act of courage. It is my willingness to take a stand. It can be an invitation to join or a demand to separate. Opinions have the power to bring together and divide — both of which have their time and place.

Are you sharing your opinions as invitations or demands?

Classy Problems Black Crown

January 21 – Silent Driver

An assumption is the silent driver of our actions and expectations. It is an unspoken belief we accept without verification, how we anticipate outcomes, and guides our behaviors influencing interactions without conscious thought.

They are all of the components that are necessary but choose not to address — details we have chosen to make irrelevant.

While assumptions can simplify decisions, they can disconnect us from a shared reality, misalign our actions, and often emerge during conflict.

Assumptions are not to be avoided but examined. When examined, they evolve from disconnect and misalignment into clarity and connection.

What details are irrelevant and which ones should be examined?

Classy Problems Black Crown

January 22 – The Proper Use of Hoarding

When we keep anything to ourselves, it invariably diminishes its value. Ironically, when we give with no strings attached, more often than not, the joy we experience in sharing is amplified by the recipient.

It seems the thing we should be hoarding is giving. When we give, we become the beneficiary of our own giving.

That’s worth hoarding.

What are you currently hoarding that could increase in value if shared?

Classy Problems Black Crown

January 23 – The Strength of Sameness

Sameness is where connection begins. By choosing to focus on what is shared, we create alignment and clarity that transcend individual differences. It’s not about dismissing uniqueness but grounding it in the context of what binds us together.

Connection thrives not in separation but in the spaces where we recognize our shared humanity and align with what we hold in common.

There is an opportunity to build a bridge through sameness without creating a barrier of difference.

How can focusing on shared connections create clarity and alignment in your next interaction?

Classy Problems Black Crown

January 24 – How Precious

We define precious as the uniqueness of convenience.

The uniqueness over-inflates the importance of a perceived difference. Convenience minimizes the greater quantity of sameness.

Preciousness magnifies detail and distinction without acknowledging a larger context or environment that surrounds it.

It distracts in its attention to what is not the same over what is.

Focusing on sameness places uniqueness in context and reconnects it to the broader patterns that matter and design constraints that must ultimately be aligned to.

What convenient distractions are you over-inflating?

Classy Problems Black Crown

January 25 – Words Matter

The more complex life gets, the classier the problems become, and the more precise we need to be with our words – yet it seems we’re doing the opposite.

It’s incredible that more people can now contribute their voices. But the classy problem is that ‘tech’ is granting us unearned wisdom in the form of ‘communication reach’ with the byproduct of scaling our imprecision.

Remember that viral post from last month? Neither does anyone else. If we were together, would we talk about it? Or is it just easier (one of the qualities of unearned wisdom) to share, like, troll, and move on?

Words inform. Words define. Words matter.

Words INFORM us of what we perceive to be true.

Words DEFINE our best articulation of our thoughts, feelings, and actions.

Words MATTER. They determine the outcome between clarity and confusion, understanding and frustration, alignment and chaos – with one another and ourselves.

Are you making your words matter, or are they a matter of words?

Classy Problems Black Crown

January 26 – Precious Planning is Over-Planning

Precious planning prioritizes perceived differences over the clarity of sameness.

It’s a distraction that complicates decision-making by inflating uniqueness instead of identifying shared patterns.

When we focus on sameness, we amplify connection allowing plans to align with reality rather than preferences.

Precious planning creates the illusion of novelty and control, leading to overproduction and terminal uniqueness.

Effective planning lies in focusing on what connects us, not what separates us.

Are your plans grounded in sameness, or are they swimming in preciousness?


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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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