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The Art of Choosing: Why People Decide Differently

Benny Obayi

Academic | Researcher | Project Management Specialist

© 2026 All Rights Reserved

May 10, 2025
The Art of Choosing: Why People Decide Differently

“We don’t see things as they are. We see them as we are.”
– Anaïs Nin

🌱 Every Decision Tells a Story

Have you ever found yourself baffled by someone else’s choices?

Maybe it was a friend who stubbornly clung to one issue in a debate, ignoring every other factor; or a colleague who couldn’t move forward with a project because it didn’t check every single box; or someone who made a choice you considered "flawed"—but somehow, it worked for them.

At first glance, these behaviours can seem irrational, frustrating, even reckless. But underneath, a simple truth often explains the difference: we don’t all decide the same way.

Behind every decision lies a hidden framework—a mental map that helps us weigh options, prioritize, and accept trade-offs. Some maps are rigid and absolute. Others are flexible and strategic. Understanding these patterns doesn't just explain human behaviour. It builds empathy. It strengthens leadership. It turns conflict into collaboration.

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The wise mind is able to hold multiple perspectives and still choose decisively.

 

In a world increasingly polarized by differences—in careers, relationships, politics—grasping how people choose is no longer optional. It’s essential.

 

Let’s dive into it.

🔍The Three Major Decision-Making Styles

1. 🎯 Single-Issue Decision-Makers: "If It Doesn’t Have X, I’m Out"

 

This one thing matters most—without it, the rest is meaningless.

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Single-issue decision-makers see life through a keyhole. They focus on one defining factor and reject anything that doesn’t align with it. It could be a moral principle, a lifestyle preference, or a deeply rooted value.

 

While this can bring clarity and strong personal identity, it can also create blind spots—causing people to dismiss nuanced, complex realities.

Daniel Kahneman in Thinking, Fast and Slow, explains that we often fall into anchoring bias—overweighing one piece of information at the expense of others.

2. 📋 Checklist Decision-Makers: "All Boxes Must Be Ticked"

 

It’s not perfect if it’s missing even one thing I value.

Checklist decision-makers treat decisions like contract negotiations: every term must be satisfied. Their intentions are thorough and idealistic, but this style can backfire by creating analysis paralysis—an inability to move forward because perfection seems just out of reach.

 

In The Paradox of Choice, Barry Schwartz describes how maximizers—those who seek the “best” rather than a “good enough” solution—often experience regret, dissatisfaction, and anxiety.

Checklist thinkers reflect a mindset shaped by control and high standards—but life rarely checks every box.

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3. 🥇Priority-List Decision-Makers: "These Are My Must-Haves"


I can live without some things—as long as my top values are honored.

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Priority-list decision-makers live in the real world. They know that every choice involves trade-offs. They carefully rank their priorities and move forward when the most critical ones are satisfied—even if a few lower-priority needs aren’t.

Herbert Simon called this bounded rationality: humans can’t make perfect decisions because of time, knowledge, and complexity constraints. Instead, we "satisfice"—we make the best possible choice given the circumstances.

Unlike checklist or single-issue thinkers, priority-list thinkers exhibit flexibility without losing integrity. Yet, they often face criticism from others who see them as inconsistent or compromising.

🤝 Where Conflict Begins: Misreading Each Other’s Framework

The biggest fights aren’t about what we want. They’re about how we decide what matters.

 

To a single-issue thinker, the priority-lister seems unprincipled.

To a checklist thinker, the priority-lister looks like they’re settling.

To the priority-lister, both others seem rigid and disconnected from reality.

🧩 Imagine three friends are planning a holiday trip.

One says, “I don’t care where we go, as long as it has a beach.” That’s a single-issue decision maker—everything hinges on one non-negotiable.
the second pulls out a list: “The place must have hiking trails, nightlife, Wi-Fi, vegetarian food, and under $150 a night.” That’s the checklist thinker, trying to tick every box.
The third friend suggests, “Let’s agree on our top three priorities—like affordability, safety, and warm weather. If we get those, we can compromise on the rest.” That’s the priority-list leader, focused on what matters most.

Now imagine these three trying to choose a destination without understanding their different styles—conflict is almost guaranteed.

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But when the styles are recognized, respected, and balanced, the group can move from tension to teamwork.

 

We clash not over what we want—but over how we decide what matters.

 Why We Double Down (Even When We Should Rethink)

Ever notice how once we make up our minds, we suddenly start “finding” evidence to back it up everywhere? It's like the world bends to fit what we already believe.

 

In the scenario of the three friends, each decides a destination is the best vacation spot, and suddenly every travel blog, photo, social media post, news article, and friend's story seem to prove each one was right.

 

That’s not a coincidence—it’s what we naturally do. We cling to choices that make us feel secure, even if they’re not the smartest or most up to date.


And when someone questions that choice? We often don’t calmly explain why we made the choice—we defend ourselves, sometimes irrationally or even aggressively.
Why?

 

Because admitting we might be wrong about how we made a decision, or how we judged someone's decision feels uncomfortable—like tugging at a loose thread that might unravel everything.

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So instead of re-evaluating, we dig in deeper.
We find new justifications, rewrite the past in our minds, and sometimes even shut out people who challenge us.

It’s not always about stubbornness. It’s about protecting our sense of self.

 

Then, that’s the way we see meaning in the choices we make.
To some people, choosing to compromise feels like being wise and mature.
To others, it feels like weakness or betrayal.

We’re not just picking actions. We’re defending identity.


That’s why a simple disagreement—over a political choice, a vacation, or even what brand of coffee to buy—can suddenly feel like a personal attack. Because to us, it is personal.


Two people can look at the same choice and see two completely different things—because they’re not just looking at the facts. They’re looking through their own stories.
 - Their decision making framework

 

The trick isn’t to erase those stories—it’s to recognize them. When we do, we stop fighting the person and start understanding the perspective.

🧠Making Room for Each Other’s Brains

We don’t all approach decisions the same way—and that’s not a flaw. It’s actually part of what makes working (and living) with others both challenging and beautiful.


Here are a few ways to lead and live better in a world full of different decision styles.

 Start with Curiosity, Not Criticism
Before jumping to conclusions about someone’s choice, try asking: “What was most important to you when you made that call?” 
That one question can shift the whole conversation from tension to understanding.

 

🪞 Know How You Decide
Sometimes the hardest person to figure out is ourselves.
Do you go with your gut? Do you overanalyze? Do you dig your heels in once you’ve chosen? Knowing your own default style helps you explain yourself—and adjust when needed.

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🤷 Compromise Isn’t Weakness
Making a trade-off doesn’t mean giving in or selling out. Sometimes, it means growing up. 
Maturity shows up when we realize we can’t have it all—and that’s okay.

👥 Mix Up the Mindsets
The best teams don’t think alike—they think together.
When necessary, get a big-picture thinker, a detail-lover, a gut-feeler, and a logic-checker in the same room. That’s how smarter decisions get made.

❤️ Understanding How Others Decide Is Its Own Kind of Leadership

In a world that’s quick to argue and slow to listen, pausing to ask how someone made a choice might be the most powerful thing you do.

 

Because behind every decision is a story—a fear, a hope, a habit, or a personal rule they may not even realize they’re following. And the same goes for everyone.

 

When we start paying attention to how people decide—not just what they decide—we create space for connection instead of conflict.

 

When we judge someone’s decision without understanding their process, we’re not exposing their weakness—we’re exposing our own impatience.

 

So next time you hit a disagreement, ask yourself:
What if I understood their “why” before pushing mine?

That simple shift doesn’t just make you a better teammate, partner, or leader.
It makes you a better human.

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May 6, 2025
Unstuck: When Digging Deeper Isn’t the Way Out

“If you find yourself in a hole, stop digging.”
— Will Rogers

 

This saying may sound like common sense, but in truth, it offers a profound lesson. It speaks to that critical moment of self-awareness—not one that calls for more effort in the wrong direction, but one that demands the courage to pause, to reflect, and to change course.

 

In life, our “holes” are rarely physical. They’re often mental, ideological, or emotional—deep trenches we dig with our own beliefs, opinions, and assumptions.

 

And even when we sense that we’re stuck, many of us just keep digging.

The Hole We Keep Digging

We’ve all been there—clinging to an idea or belief that once gave us identity, direction, or certainty. But over time, something shifts. A new fact emerges. The belief no longer fits. And yet… we keep defending it.

We rationalize. We quote selectively and cite unrelated evidence. We surround ourselves with others who affirm us. What we don’t realize is—we’re not protecting the truth anymore. We’re protecting our ego.

 

I’ve seen this play out countless times. In conversations, I often see instances of people presented with clear, compelling counter-evidence, but instead of re-evaluating, they resist. They deflect. Over time, the falsehood becomes a kind of armor “their truth”. And eventually, they go beyond defense: they become evangelists for the belief. Aggressive. Dismissive. Even hostile to dissent; attacking those who challenge it.

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But this isn’t intellectual strength.


It’s fear—dressed up as conviction.

The Courage to Rethink

This is where the dialectical method becomes powerful—a model of growth that invites us to move through ideas with honesty. It begins with a thesis, the belief or idea you currently hold; followed by an antithesis, an opposing idea or fact that directly challenges it; and culminates in a synthesis, a new perspective that either integrates truths from both sides or transcends them entirely.

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When your initial belief or idea—your thesis—is directly confronted by a valid opposing idea or fact —antithesis— that’s not the time to dig in or build walls around your thinking. It’s a signal, not of defeat, but of opportunity—an invitation to pause and consider that there may be more to it. In that tension lies the chance to pursue a new perspective —synthesis— A more honest, refined, and balanced perspective that neither blindly defends the old nor impulsively embraces the new, but instead seeks understanding that transcends both. This process isn’t a sign of weakness—it’s a quiet act of courage. Rethinking doesn’t mean betraying your values; it means placing truth above pride. It’s the shift from clinging to certainty to reaching for clarity from defending your ego to allowing your mind, and heart, to grow.

When Beliefs Become Battlefields

Some people don’t just cling to a flawed view—they build entire fortresses around it.

 

They:
🧠 Invent explanations to protect it.
🚫 Label dissenters as enemies.
🕹️ Manipulate systems to validate it.
📢 Spread it as unchallengeable truth.

 

Over time…
🧱 The belief becomes more than just a belief.
🪪 It becomes an identity.

 

And the deeper it roots, the harder it becomes to step back. What could have been a private moment of growth becomes a public crusade. A chance to evolve becomes a mission to convert.

 

But here’s the truth: the longer you stay trapped in a faulty idea, the deeper the hole becomes.

And at some point, it’s not about being right anymore.

🕊️It’s about being free.

It’s Okay to be Wrong

There is profound freedom in saying, “I used to think differently.” It shows you're not chained to the past.

There is quiet strength in admitting, “I’ve learned something new.” It means your mind is still open.

And there is real courage in declaring, “I’m growing;” because, growth means choosing evolution over ego.


We need more people who are willing to unlearn, to listen, and to rise above outdated convictions.

 

And here’s something we often overlook:
When someone we dislike changes their mind and starts doing what we’ve long advocated, it’s not a sign of hypocrisy. It’s a sign of strength.

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Too often, our ego tempts us to vilify the change rather than welcome it. It wants to gloat. To mock. To dismiss their shift as too little, too late. We say, “Now they’re doing what we said all along!” as if change somehow invalidates their worth or it’s a weakness to evolve.

 

Yet the real power lies not in holding a position forever, but in the willingness to evolve—even when it means adopting a truth once rejected.

Let’s not punish people for growing.

Let’s not shame them for changing.
Let’s not let our resentment blind us to their progress.

Growth isn’t about how long you’ve believed something. It’s about how bravely you’re willing to leave it behind.

Find the Ladder, Not a Better Shovel

So, what do you do when you realize the belief you’ve been defending no longer serves you?

You don’t dig deeper.

You don’t justify it with new excuses.
You don’t silence those who challenge it.

 

Instead:

🛑 Put the shovel down.
Ask better questions.
🔥 Embrace the discomfort of change.
🧗 Climb out—and choose a better path.

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Growth doesn’t come from proving the old you was right. It comes from making room for the new you to emerge.

🧭 Reflection

“The mark of an educated mind is to be able to entertain a thought without accepting it.”
— Aristotle

 

🧠 Challenge your thoughts.
🤝 Welcome the ones that challenge you.
🔄 When the facts change, let your mind follow.

 

Because your greatest strength is not in loyalty to the past—It’s in your openness to the future.

If you’re stuck in a hole, stop digging,— then, figure out how to climb out🪜

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