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September 21, 2025 17 mins
I’ve been thinking a lot lately about how easy it is to stumble into trouble—not because we're incapable, but because we just don’t take a moment to truly think before we act.
It’s crazy how often folly doesn't announce itself as a disaster; it shows up disguised as a simple favor, a great opportunity, or just a "harmless choice". I’ve realized that making a bad choice isn't the problem; the real problem is making a choice without thinking.
I used to rush into things, especially when I felt pressure to be "supportive" or a "team player." I’m reflecting on how easy it is to casually vouch for someone or make a promise, thinking it's "just a formality" or "just a reference". We forget that our words can actually become chains that bind our future, often carrying legal or reputational weight we never imagined.
The antidote I keep coming back to is the simplest one: the discipline of questioning, or what the sources call the Socratic Method. It's essentially forcing yourself to create a pause between impulse and action.
It shifts the conversation from "Do I want to help?" to much more practical and difficult questions:
1. What am I really promising here? Not just the surface commitment, but the full implications. If I cosign, I'm accepting full financial responsibility.
2. What happens if circumstances change? (Because life is unpredictable, and that job or relationship might crumble).
3. What will this cost me? This goes beyond money—it includes trust, self-respect, and reputation.
It feels a little rebellious, honestly, to demand time to think in a world that constantly pushes us to click without reading and commit without considering. But the ability to pause and ask good questions isn't just wisdom; it's survival. And when you make fewer promises but keep them all because they were carefully considered, your word gains genuine weight.
I’m trying to choose wisdom while there’s still time.
What’s one question you rely on to protect yourself from committing to something you shouldn’t? How do you carve out that "pause" in a high-pressure moment? I’d genuinely love to hear your tools for avoiding folly.


James Henderson is the founder of Misa.solutions, a veteran-owned company bringing the Socratic Method into modern education through AI-powered tutoring. With a passion for helping K–12 students, homeschoolers, and educators move beyond memorization, he focuses on building curiosity, wisdom, and critical thinking for the next generation of learners.
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Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
Welcome to the deep dive. Today, we're digging into an
ancient defense strategy for a very modern problem. Folly. We
often assume folly means, you know, a lack of intelligence,
but if we look closely at our sources, well that's
not really it at all.

Speaker 2 (00:16):
No, it's not about being stupid. It's about making choices
without thinking. Yeah, it's passive, passive, Okay, it's the absence
of calculation, and it often comes disguise, doesn't it as friendship,
maybe a simple opportunity, even just common courtesy.

Speaker 1 (00:30):
Right, which is why I can catch even really bright
people off guard exactly.

Speaker 2 (00:34):
Folly doesn't, you know, announce itself like some big disaster.
It kind of sneaks in as a harmless favor.

Speaker 1 (00:39):
We saw that devastating pattern in the story of Jake.
He was nineteen intelligent. Ye, a friend asks him to
co sign a car Loan, says it's just a formality. Jake,
wanting to help, he signed.

Speaker 2 (00:51):
And then what happened six months later?

Speaker 1 (00:52):
The fringe is vanished, gone, leaving Jake holding what was it,
twenty five thousand dollars in.

Speaker 2 (00:57):
Debt, twenty five thousand dollars. His credit was obliterated, his
education plans completely derailed. It took him seven years, seven
years of really crushing effort to dig himself out.

Speaker 1 (01:08):
Okay, but wait the Jake story. I mean, most of
us know or think we know, you shouldn't co sign
huge loans like that. What's the real insight here? Is
it just that we ignore obvious risks?

Speaker 2 (01:20):
Well, see, that's the crucial part. It's not just ignoring
the risk. He never actually calculated the risk, he admitted later,
I never even thought to ask what would happen if
something went wrong?

Speaker 1 (01:29):
Ah? Okay, So the folly isn't ignoring the danger, it's
failing to even consider.

Speaker 2 (01:33):
It, precisely, failing to calculate it at all. That failure
to pause to question, that is the essence of modern vulnerability,
especially today.

Speaker 1 (01:41):
That's really the mission for this deep dive. Then, in
a culture that's practically designed to make us, you know,
click without reading sign without understanding, the ability to pause
in question isn't just some abstract wisdom. It's like survival.

Speaker 2 (01:53):
It is survival. And we're using the Socratic method, that
practice of asking thoughtful questions before acting as the the
active defense.

Speaker 1 (02:01):
Okay, let's unpack this let's start where I think most
people get tripped up when our words become chains exactly.

Speaker 2 (02:08):
And you know, we live in a culture that well,
it treats words pretty cheaply, doesn't it.

Speaker 1 (02:13):
Yeah, Like promises don't mean much sometimes.

Speaker 2 (02:16):
Right, we make these promises, give these sort of informal assurances.
But the enduring principles we're looking at, they remind us
that careless commitments they do bind.

Speaker 1 (02:26):
Our future legally, financially.

Speaker 2 (02:28):
Reputationally too. They become chains, sometimes invisible ones.

Speaker 1 (02:32):
At first, let's think about Sarah. She was just trying
to be helpful, right, promised a coworker should be a
reference for a business loan.

Speaker 2 (02:40):
Yeah, barely knew the guy, but thought, what's the harm?
It's just a reference.

Speaker 1 (02:44):
But that casual word that.

Speaker 2 (02:46):
Yes, it became a chain. When the business inevitably failed
and worse, trod was uncovered, Sarah got subpoened.

Speaker 1 (02:54):
Wow, just for being a reference, Just for.

Speaker 2 (02:56):
Being a reference. Her integrity was suddenly questioned, her professional
reputation dragged right into court proceedings. She learned the really
hard way that vouching for someone means you're basically lending
them your reputation, and she.

Speaker 1 (03:09):
Gave that asset away without really stopping to question.

Speaker 2 (03:11):
The cost, without a second thought.

Speaker 1 (03:13):
Okay, that sounds great in theory, but let's be real.
You're say twenty two, your friend is standing right there
looking you in the eye, asking, come on, don't you
trust me?

Speaker 2 (03:24):
How do you actually pull off that Socratic pause? Then
it's awkward.

Speaker 1 (03:28):
It is awkward. That's the friction, isn't it. Wisdom is
often socially uncomfortable. The Socratic method forces us to kind
of transform that discomfort into necessary clarity. The moment you
feel that pressure.

Speaker 2 (03:39):
That's the signal.

Speaker 1 (03:40):
That's the signal to ask, first, Okay, wait, what am
I really promising here? You have to look beyond the
surface label.

Speaker 2 (03:46):
So not just helping but right.

Speaker 1 (03:47):
If you co sign, you're not just helping out. You
are accepting full financial responsibility, full stop. If you vouch
for someone, you're lending your actual character, your good name.

Speaker 2 (03:56):
Okay, first question? What else?

Speaker 1 (03:58):
Then you got to ask? Can I actually deliver this?
And be honest? Hope is not a strategy here.

Speaker 2 (04:04):
If the commitment needs resources, you don't truly possess time, money,
maybe specific skills. You're basically just setting yourself up for failure.
And maybe taking someone else down with you.

Speaker 1 (04:16):
And crucially, I imagine what happens if circumstances change.

Speaker 2 (04:20):
Oh, absolutely crucial. Can this promise you're making survive a
job loss, a relationship breakdown, a health crisis? Yours are
theirs because life happens. Life happens. If the promise only works,
if everything stays absolutely perfect, Well that's a really weak foundation,
isn't it.

Speaker 1 (04:37):
It's terrifying how easily this happens.

Speaker 2 (04:39):
It is. And look the statistics we found in our sources,
Well they're kind of a horror show. Actually, the number
one reason for financial derailment among young adults, it often
isn't student debt or credit cards. Surprisingly, no, what is it? Then?
It's obligations they took on for other people. They co signing,
co signing, informal business partnerships, lending money they couldn't aff

(05:00):
to lose. They were literally ruined by trying to be
nice because they failed to question the commitment deeply enough.

Speaker 1 (05:06):
Okay, So the practical takeaway here is recognize the pressure points.

Speaker 2 (05:10):
Yes, legitimate requests can usually withstand scrutiny, manipulation often can't.
So when someone hits you with I need an answer
right now, that urgency itself is a red flag, and
you flip it. You flip it, you shift that urgency
back onto them and question it. Okay, I understand it's
urgent for you, But why can't this wait for proper consideration?

(05:32):
On my end? Just asking that simple question gives you
back control. That pause, That pause is everything.

Speaker 1 (05:38):
Okay. So if carelessness with our words, our money, our
commitments chains us, we also have to talk about carelessness
with our time.

Speaker 2 (05:47):
Ah. Yes, the folly of laziness.

Speaker 1 (05:49):
Which is maybe even more insidious.

Speaker 2 (05:51):
It's certainly seductive, isn't it, Because laziness promises comfort now.
It whispers things like, ah, you can do it tomorrow,
don't worry, your natural ability will care you through.

Speaker 1 (06:00):
That sounds familiar. We looked at the example of Tom Right.

Speaker 2 (06:02):
Tom, talented guy, charming, intelligent by all accounts, coasted on it,
completely coasted, figured his raw aability was enough so we
never really buckled down and enveloped discipline. He was brilliant, sure,
but totally sporadic, and the result, the consequence was frankly devastating.
By thirty five, he found himself unemployed, fundamentally unskilled, despite

(06:25):
his intellect, watching peers who were maybe less naturally gifted
but way more disciplined, advanced right past him. Gosch he
had this realization, he said, he felt like the grasshopper
in the fable when winter came. His intelligence had actually
become his biggest liability because it allowed him to avoid
the hard work for so long.

Speaker 1 (06:43):
So to counter that whisper of do it tomorrow, we
need to apply these Socratic questions to our own excuses.

Speaker 2 (06:50):
Yes, rigorously, Yeah, you have to ask ourselves, Okay, what
really happens if I wait too long to prepare and
don't be vague, be specific, very specific? What job do
I want in five years? Skills? Does it require? What
specific crisis could destroy my savings if I don't build
that buffer.

Speaker 1 (07:04):
Now and challenge the myth of sporadic brilliance.

Speaker 2 (07:07):
Exactly, ask why is steady, maybe even boring effort actually
better than sporadic brilliance. The answer lies in compounding, like interest,
but for effort. Precisely, the person who writes just two
hundred words every single day produces infinitely more over time
than the person waiting for that perfect bolt of inspiration
that might never come.

Speaker 1 (07:27):
And maybe the hardest question, what am I really avoiding
by choosing comfort? Right now?

Speaker 2 (07:32):
Uh? Huh? That usually gets to the heart of it.
It's typically the difficult conversation, the boring but necessary task,
the hard work that's actually required for genuine transformation.

Speaker 1 (07:44):
We saw that incredible example with Jennifer the surgeon.

Speaker 2 (07:46):
Oh yeah, powerful story. Her turning point came when her
mentor challenged her reliance on just her natural talent. The
question wasn't about her grades or test scores.

Speaker 1 (07:56):
No, it's much heavier, much heavier.

Speaker 2 (07:58):
The mentor asked, what happens, Jennifer when you're holding someone's
life in your hands and your natural ability just isn't
enough when someone's child is dying on your table and
you need skills you never bothered to develop because you
are too lazy to practice practice practice.

Speaker 1 (08:12):
Wow, I mean, how do you even respond to that?

Speaker 2 (08:14):
You don't really? That question apparently just completely rewired her
priorities on the spot because it injected a specific, visceral,
terrifying consequence directly into her daily decision making process about
practice versus coasting.

Speaker 1 (08:29):
And this isn't just individual, is it? This failure to
be diligent, this choosing comfort?

Speaker 2 (08:34):
No, it absolutely has collective costs when excellence isn't demanded,
when we all sort of choose individual comfort over rigor, systems.

Speaker 1 (08:42):
Decay, our shared resources, our.

Speaker 2 (08:44):
Educational standards, our economies, our civic institutions. They all decline
bit by bit because everyone kind of assumes someone else
will do the hard discipline, supervised work.

Speaker 1 (08:55):
That makes perfect sense. Laziness isn't just a personal failing
in that view, it's almost like a fill of citizenship,
a failure to contribute to the whole.

Speaker 2 (09:03):
That's a good way to put it.

Speaker 1 (09:04):
Okay, let's sift here slightly. Let's talk about the poison
of deceit and conflict. These sort of internal follies.

Speaker 2 (09:10):
Right, Lying, deceit, gossip, stirring up trouble. These are actions
that can destroy trust, community, and reputation faster than almost
any external crisis. A single lie can just fracture years
of built.

Speaker 1 (09:23):
Up trust, and the socratic method here helps us dissect
why we even do it. We looked at Maria's story.

Speaker 2 (09:30):
Maria, Yes, yeah, she exaggerated her qualifications. Okay, let's be honest.
She lied to landed a dream job. She told herself.
It was just a little embellishment, you know, just to
get her foot in the door.

Speaker 1 (09:40):
A common rationalization, very common.

Speaker 2 (09:43):
But that short term win getting the job, it immediately
became this long term trap. She described it as a
two year prison of anxiety.

Speaker 1 (09:51):
Constantly afraid of being found out, every.

Speaker 2 (09:53):
Single day, living in fear of exposure. And when the
truth inevitably did emerge, she didn't just lose the job,
She damned that's your entire career prospects in that specific industry.
Her insight was chilling. The lie got her in the door, yes,
but it locked her in a prison where she couldn't
even breathe freely.

Speaker 1 (10:10):
That's a huge, huge cost for what seemed like a
small lie at the time. So the key Socratic question
here has to be what does lying really accomplish exactly?

Speaker 2 (10:19):
You have to weigh that trade off honestly, short term
avoidance maybe versus long term anxiety, stress, and the high
probability of eventual ruin.

Speaker 1 (10:27):
And we also need to ask, maybe even more fundamentally,
is this action truly honest?

Speaker 2 (10:33):
Yeah, not just technically true, but honest, Like, would you
be perfectly comfortable if everyone involved knew the absolute full story,
the context, your motivations. If the answer is no, then
you're probably lying to yourself first and foremost, and that
self deception is where it starts.

Speaker 1 (10:51):
This applies to creating conflict too, doesn't it. We had
David's example.

Speaker 2 (10:55):
David the reformed workplace troublemaker. Yeah, he had admitted very
candidly that he used to create drama, gossips, stir things
up because deep down it made him feel important. It
put his ego right at the center of the office narrative.

Speaker 1 (11:08):
Wow, that's some self awareness.

Speaker 2 (11:10):
It took socratic questioning, probably some hard feedback too, for
him to see that he was essentially destroying his workface
environment just to feed his own need for significance. He
was manufacturing a lie of his own importance through conflict.

Speaker 1 (11:22):
That level of self examination is so critical, especially when
we face temptation.

Speaker 2 (11:27):
Oh absolutely, because every temptation is like this carefully wrapped package,
isn't it, promising immediate pleasure, seemingly without consequence.

Speaker 1 (11:36):
Yeah, Temptation is the master salesman, the ultimate trader, always
offering to trade your long term well being for what
a five minute dopamine hit.

Speaker 2 (11:44):
Exactly. We need those sharp Socratic questions to just strip
away that seductive disguise.

Speaker 1 (11:50):
So what's the first question when facing temptation?

Speaker 2 (11:52):
Yep, you have to start with the honest calculation. Okay, really,
what will this choice cost me? And calculate the full price?
Not just mine, no, rarely just money, think self, respect, trust,
yours and others, future opportunities, relationships. You have to realize
that every yes to a harmful temptation is simultaneously a

(12:13):
no to something essential, something valuable. You're giving up that's powerful.

Speaker 1 (12:16):
And what about how it affects others?

Speaker 2 (12:18):
Crucial question? Am I treating others with respect? In this
temptation so often involves dehumanizing people, turning spouses, partners, friends,
colleagues into mere objects for our gratification.

Speaker 1 (12:30):
If you're violating someone else's dignity, then the choice.

Speaker 2 (12:33):
Is inherently destructive, not just to them, but ultimately to
your own character.

Speaker 1 (12:37):
Kevin's story was just brutal on this point.

Speaker 2 (12:39):
Yeah, Kevin's story is maybe the most painful illustration. He
started what he called an emotional affair, seemed harmless at first,
you know, just messages, conversation, the classic slippery slope, and
he admitted he completely failed to ask himself the critical
Socratic questions early on questions like hang on, what I
hope my wife having these exact conversations with someone else,

(13:02):
or even just where is this realistically heading?

Speaker 1 (13:05):
By the time he recognized the danger, it was too late.

Speaker 2 (13:08):
The trust was shattered. He said something haunting that maybe
fifteen minutes of hard, honest questioning at the beginning could
have saved him and his family five years of devastating
pain insecurity and rebuilding.

Speaker 1 (13:21):
Fifteen minutes of thought versus five years of pain. Wow. Okay,
that brings us naturally to our final segment. This idea
of viewing correction not as punishment but as light.

Speaker 2 (13:30):
Exactly the enduring principles we've been drawing on often describe
instruction and correction using metaphors of a lamp or light,
something that illuminates the path forward, not something that beats
you down.

Speaker 1 (13:43):
And the Socratic method fits perfectly here, doesn't it. It
turns potentially painful criticism into well accelerated discovery.

Speaker 2 (13:51):
Instantly, think about traditional correction. It feels like a personal attack.
You're wrong, that's bad.

Speaker 1 (13:56):
Yeah, puts you immediately on the defensive right.

Speaker 2 (13:59):
But Socratic correction reframes it completely. It transforms it into
a dialogue. Okay, help me understand, walk me through your
thinking here or interesting approach? What if we looked at
it another way?

Speaker 1 (14:10):
What might we be missing that totally changes how we
receive feedback. We talked about Anna the designer.

Speaker 2 (14:14):
Yeah, Anna, she used to be just devastated by criticism
of her work, felt.

Speaker 1 (14:19):
Personal until her mentor shifted tactics exactly.

Speaker 2 (14:23):
The mentor stopped saying your design is bad and started
asking socratic questions instead, things like, Okay, Anna, what response
are you hoping to create in the user with this design?
Does this visual actually achieve that specific goal? What might
work even better to solve the user's problem?

Speaker 1 (14:40):
So it reframed the feedback away from you failed to
let's solve this problem together.

Speaker 2 (14:45):
Precisely, it immediately shifted the focus away from her ego
and onto the shared intended goal. It became collaborative problem solving,
not personal rejection.

Speaker 1 (14:55):
And we can use this ourselves when we have to
give feedback.

Speaker 2 (14:58):
Absolutely, it's a much more effective and frankly, more respectful
way to guide others. Instead of the blunt judgment that's wrong,
Try asking help me understand your process? Or what other
options did you consider before landing on this one.

Speaker 1 (15:11):
It preserves dignity.

Speaker 2 (15:13):
It preserves dignity, and it promotes genuine growth because people
rarely resist discoveries. They feel they've made themselves, even with guidance.

Speaker 1 (15:20):
Okay, so let's try and synthesize this. We started with
the core idea, folly is essentially failing to question.

Speaker 2 (15:26):
Right and the traps the forms of folly, they're remarkably
consistent throughout history, even if the technology changes. It's still
the casual promise that ends in bankruptcy, the procrastination that
leads to failure, the temptation that spirals into addiction.

Speaker 1 (15:41):
The patterns are ancient.

Speaker 2 (15:42):
The patterns are ancient, and the defense, while simple in concept,
requires immense conscious effort. It's created that pause, that space
between the impulse and the.

Speaker 1 (15:53):
Action, between feeling and choosing.

Speaker 2 (15:55):
Exactly and every question we learned to ask ourselves consistently,
what am I really committing to? What happens if I wait?
Is is truly honest? What will this ultimately cost me?
How else could I look at this feedback? Each one
is like a tool for survival in a complex world.

Speaker 1 (16:10):
So here's the core takeaway for you listening right now
these questions. This socratic approach. They aren't meant to be
restrictions on your freedom.

Speaker 2 (16:18):
Quite the opposite. They are arguably the only path to
genuine sustainable freedom. Think about it. The person enslaved by
debt they didn't foresee, or consumed by the anxiety of
maintaining a lie, they aren't truly free, are they?

Speaker 1 (16:31):
No, they're trapped.

Speaker 2 (16:31):
They're trapped. The person who thinks before acting, who questions
before committing, who learns proactively from correction, that person is
the one who is truly liberated.

Speaker 1 (16:42):
Perhaps we should encourage you to view this kind of
questioning as maybe a quiet act of rebellion.

Speaker 2 (16:47):
I like that, a rebellion against a culture that often
encourages clicking, signing green, choosing all without deep consideration.

Speaker 1 (16:54):
So the challenge is this, choose wisdom, question thoroughly, especially
the next time you face attempt, opportunity, or feel that
internal or external pressure to act without thinking.

Speaker 2 (17:04):
Your willingness to pause and think critically, that's your greatest strength.
Use it. Choose wisely, question thoroughly,
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