This Question’s Been Wrecking Me Lately

Last night, my cat was asleep on my chest. My wife was reading beside me, and I had this book open that's been messing with my head for weeks.

I picked it up because someone mentioned Socrates had this way of asking questions that would completely unravel people's certainty. I figured there might be something useful there for business.

I was not prepared for how much this would f*ck with my thinking.

Farnsworth opens with this idea that most of us think we know things when we're really just carrying around unexamined beliefs. Socrates had this annoying habit of asking simple questions like "What is courage?"

Seems easy until you try to define it. Then you realize you've been using the word without understanding it.

That hit me hard because I started thinking about all the business terms I throw around.

> Freedom

> Success

> Growth

> Scale

Do I know what these mean to me? Or am I just repeating what I've heard other entrepreneurs say?

So I started asking myself the same types of questions Socrates would ask:

> What does freedom actually mean to me?

> Why did I start this business?

> What am I optimizing for, really?

The answers weren't what I expected.

I realized I don't want to be the richest person on earth. I want to chill with my wife on a random Wednesday. I want to travel without checking calendars. I want businesses that challenge me without owning me.

There's this quote in the book that stopped me cold: "We are not seeking to know what virtue is, but to become virtuous; not what courage is, but to become courageous."

Translation for entrepreneurs:

We're not trying to define success - we're trying to live successfully.

Most of us never ask ourselves what "living successfully" looks like personally. We just copy what other successful people do and hope it works.

That's backwards.

I've been thinking about why so many entrepreneurs burn out. We say we want freedom and time, then we build businesses that enslave us. We grind 80-hour weeks for "freedom" while being less free than employees.

Farnsworth talks about how Socrates would expose these contradictions by simply asking: "How do you know that's true?"

So I asked myself: How do I know the way I'm building my business is actually getting me what I want?

Uncomfortable question. Even more uncomfortable answer.

Now I'm asking different questions in business meetings. Instead of stating opinions, I ask things like "What assumptions are we making here?" or "How do we know this will work?" or "What would have to be true for this to fail?"

It's uncomfortable. People don't like having their ideas questioned.

Farnsworth writes: "The Socratic method is not about winning arguments. It's about testing ideas until you find ones that can withstand scrutiny."

That's exactly what we need in business. And in building personal brands.

If you're building a personal brand, you're literally building your identity in public.

- Whose identity are you building?

- Are you positioning yourself as who you think you should be?

- Or who you actually are?

Most personal brands feel fake because they're built on unexamined assumptions about what "authority" or "success" looks like.

The Socratic thing flips this by starting with questions.

What do I actually believe? Why do I believe it? What evidence supports this belief?

Then build from there.

So here are the questions I'm sitting with right now:

Am I building businesses or am I building a life?

What does generational wealth actually mean beyond just money?

How do I create freedom without falling into new forms of slavery?

I don't have clean answers yet. And that's the point.

The questions are more valuable than premature conclusions.

If you picked up "The Socratic Method" and applied it to your business, what would you discover?

What beliefs about success are you carrying around unexamined? What definitions of freedom, wealth, or impact have you inherited from others? What assumptions about your market, your audience, or yourself need testing?

The book costs $15. The questions it raises are worth millions.

Because the right questions don't just change your business. They change your life.

My cat just woke up and now she's meowing at me like I've personally offended her by existing.

Socrates would probably ask: "What is the nature of a cat's cry? Is it communication or manipulation?"

I'm asking: "What does she want now?"

Some questions are more practical than others.

—Wiz

P.S. If you’re ready to build a brand that earns trust at scale, I’ve got two paths for you:

→ Utopia: Learn the frameworks and run it yourself

→ Mogul Media: Let my team do it for you

Just reply to this email and I’ll help you pick the one that fits.