The Question That Changed Everything

This week, I started reading a book called Fax Club.

It’s about a group of 100 strangers who agreed to answer one question each week, sent out anonymously over the internet. No introductions. No small talk. Just one prompt, and the honest responses that followed.

Week by week, something fascinating happened: through the simple act of answering one thoughtful question at a time, these strangers started showing up more fully, not just for the exercise, but for themselves and for each other.

This didn't surprise me as I've always thought that it's the answers that matter. Human answers, with real thought and depth of feeling, can only come from a lifetime of experiences.

And these days, questions are cheap. ChatGPT can give me 100 questions at the push of a button

But lately, I’ve been wondering if I've got this backwards. Maybe asking better questions is important.

Or, better yet, maybe we only need one great question?

The Case for One Great Question

Most of us are constantly trying to figure things out. Our next career move, the right strategy for our business, how to be more productive, more creative, more in control.

So we binge on answers. Podcasts. Books. Courses. Feeds.

But answers are context-dependent. They solve for a moment. They don’t always apply to your life now.

What if instead of hunting down another insight, you chose one question and stayed with it?

For the last three months, that’s exactly what I’ve done. I've stopped trying to outsmart myself. And I've started asking myself a single question. Not to force an answer. Just to see what it would reveal.

It’s been more useful than anything I’ve read all year.

The Question That Changed How I Think

The question is this:

What if I trusted my ability to think clearly?

It first surfaced during a week of minor-but-constant indecision. I was stuck in a loop, making choices, then immediately second-guessing them. Not because of new evidence, but because of an old habit: distrusting my own gut.

That’s when the question arrived. Not as a solution, but as a provocation.

I wrote it down.

Then I kept looking at it. Couldn't stop thinking about it.

And slowly, it started to shift things. It changed how I think through problems, and in how I approach each day.

What Shifted When I Took This Question Seriously

When I let this question shape my thinking, a few things started to happen.

1. I made decisions faster.

Not impulsively but just with less self-editing. I stopped outsourcing my judgement to five extra browser tabs or three more people. When I trusted that I could think clearly, the noise started to fall away. I didn’t need to make perfect choices, just honest ones.

2. I showed up more fully in conversations.

I stopped hedging. I stopped performing nuance for the sake of sounding smart. I trusted that I could listen well and speak clearly and that was enough. (This is kind of important to me in my new role as a Do Radio show presenter.) It means I have better conversations.

3. I took more ownership.

I stopped deferring to imaginary experts. You know these guys: the ones who always seem to have more context, better instincts, stronger opinions. That subtle belief that someone else always knows better? It lost some of its power.

All from one question.

Not All Questions Are Worth Your Time

Here’s the catch though: not every question is worth it.

Some questions are great. Others are just anxiety in disguise.

You know the ones:

“Why do I always mess this up?”

“What’s wrong with me?”

“Why haven’t I figured this out by now?”

They don’t create insight. They create judgement. They trap you in shame and call it curiosity.

But clarity questions are different.

They don’t try to diagnose you. They try to open you.

Here are a few I’ve seen others use well:

“What would this look like if it were simple?”

“What am I pretending not to know?”

“What would I do if I had enough time?”

“What’s the tradeoff I’m avoiding here?”

They’re not magic. But they are mirrors. They reflect back what you already know.

Carry, Don’t Chase

When you find a question that resonates, don’t rush to answer it. Just carry it.

Put it at the top of your journal. On your notes app. In the back of your mind as you walk through your day.

The best questions aren’t urgent. They don’t demand a clever answer. They invite you to live with them and to keep noticing how they shape your choices, your conversations and your priorities.

And over time, they reveal something deeper about who you are when you stop overthinking and start trusting yourself.

So, What’s Your Question?

Fax Club reminded me of something simple and true: questions are how we get to know ourselves.

Not by answering them all at once, but by staying in conversation with them long enough for something real to shift.

So as you head into your weekend, try this:

What’s one question you’ve been avoiding that might change everything?

Write it down.

Sit with it.

Let it follow you around for a while.

You don’t need to force an answer. Just pay attention to what it stirs in you.

Because sometimes, the most powerful thing isn’t knowing what to do next. It’s knowing what to ask.

Until next time,

Jon "Quiz Master" Kaye

Choosing to live a more meaningful life

P.S.

Got a great question for me? Hit reply. I'd love to hear it.

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