3 Questions That Will Change Your Life

Welcome to Refusing to Settle! My weekly newsletter where life-changing frameworks and uncomfortable truths collide to build the 2.0 You.

🎉 My Best Journal 2.0 is finally LIVE! 

The exact system I’ve used for 4,000+ days to coach myself, find clarity, and reinvent when life got messy.

It’s a journaling system that will change your life and help you grow more in 1 month than most people do in an entire year. If you’ve ever wanted to journal but didn’t know where to start, this was built for you.

Get My Best Journal Now!

P.S. It’s a launch special: 50% off for a limited time. Don’t miss out!

What’s on deck today:

• 3 hard-hitting questions that change everything
• The “rocking chair test”
• One question that could’ve saved me 4 years in the wrong relationship
• How to be 3X happier (according to research)

Missed last week? — Catch up on the archive here​

You don’t need more advice.

You need better questions.

That’s the one truth nobody told me when I was lost, bingeing self-help videos and drowning in “hacks.”

Nothing changed. Until I started asking myself questions that hurt to answer.

I spent $20K on a coach who basically did nothing but ask me questions for 12 months.

Questions that made me squirm.

Questions I didn’t want to answer.

And those questions changed everything.

Today, I’m giving you the exact 3 questions that rewired my brain.

Take these seriously, and I believe you can compress 1 year of growth into 1 hour.

Fair warning: these aren’t gentle. But if you’re ready to stop bullsh**ting yourself, let’s go.

Question 1

When I was 22, stuck in a job I hated, I asked myself one question that changed everything.

Turns out, Jeff Bezos asked himself the exact same one.

Bezos was making $1 million a year on Wall Street when he had the crazy idea to sell books online. Everyone thought he was insane. But he had a secret weapon: the “regret minimization framework.”

He imagined himself at 80 and asked: “what would I regret not doing?”

That same question led me to start posting drum covers. Eight years of “failure” later, a band discovered those videos and I toured the world.

“At the end of my life, when I’m 80 years old in a rocking chair… would I regret not doing _____?”

This question eliminates your fear of failure because it shifts focus from “what if I fail?” to “what if I never try?”

Because regret lasts way longer than failure ever will.

Question 2

Ever notice how some days you feel unstoppable, and others you feel like you’re swimming upstream in molasses?

There’s actually a reason for that.

When you’re using your natural strengths, everything feels lighter.

You’d think the next question is:

“What are my strengths?”

But most people get stuck there. It feels vague, abstract.

Inside My Best Journal, we give you the same two strengths assessments used in Martin Seligman’s positive psychology research, the ones linked to a 3X boost in life satisfaction.

You’ll know your top strengths within 10 minutes.

I write these in the front cover of my journal.

Here’s a better question:

“What consistently makes me lose track of time?”

That’s your strengths in action.

And don’t just guess here. I recommend you track it this week.

Keep a casual log in your phone of the moments that make you feel electric:

• What made you forget to check your phone?
• When did you feel completely in the zone?
• What rabbit hole did you go down “just for fun”?
• What are you always giving advice on, without even realizing it?
• What conversations left you more energized after than before?
• What were you doing the last time you thought, “I could do this all day”?

Think of it like a food journal for your soul.

I did this a few years ago and realized every time I was teaching, creating, or riffing on ideas, I was in flow.

Here’s what’s wild: you probably undervalue what you’re naturally good at. If you’re great with people, you assume everyone is. Meanwhile, someone with social anxiety sees that as a superpower.

Stop undervaluing your talent. Know your strengths, use them often.

Question 3

This next question is going to hurt…

But it might save you years.

In my 20s, I found myself trapped in a long-term relationship that was slowly killing my soul. We had a friend group, routines, inside jokes, families had met. From the outside, it looked perfect.

But I knew. Deep down, I fucking knew after year one it wasn’t right.

Then another year passed. Then another. Four years of my life, gone.

She felt it too. We both knew we wanted different things, but instead of being honest, we spent four years trying to change each other. Fighting the same fights. Having the same conversations. It wasn’t love anymore—it was habit.

This question would have saved me:

“What am I pretending not to know?”

I was pretending not to know she wasn’t the person for me. And she was pretending I wasn’t the person for her.

You know that sinking feeling in your stomach when you’re lying to yourself? That voice that whispers the truth you don’t want to hear?

That’s your gift, call it intuition, gut instincts. It’s usually right about yourself. Problem is, the truth hurts. So we pretend we can’t hear it.

Remember being a kid? You’d plug your ears and go “LA LA LA” when you didn’t want to hear something.

We’re still doing it as adults. We emotionally plug our ears to block intuition through:

• Escape: video games, doom scrolling, getting lost in other people’s drama
• Numb: alcohol, partying, food, exercise
• Run: staying so busy you never have to think

Heavy right?

This is the hardest question on the list.

But it’s where all your breakthroughs are, I promise.

So… what are you pretending not to know?

The job that’s slowly draining your soul… even though the money’s good?

The business you built that no longer fits who you’ve become?

The habit that’s quietly destroying your confidence?

The dream you keep postponing… because you’re waiting to feel “ready”?

I knew after year one.

I wasted four pretending I didn’t.

Try this: Set a timer for 10 minutes. Write down what you’re pretending not to know. I promise your answers are in there.

Updates

My Best Journal 2.0 — We officially launched! This is the complete framework to coach yourself, create the 2.0 version of you, and genuinely change your life. Click here to get the launch special (50% off) for a limited time. If these questions hit you, you’ll love what’s inside.

YouTube — Latest video dropped: “3 Journaling Systems to Change Your Life”. Took the Bronco out to the desert and had some fun filming this for you.

What I’m listening to — A Day to Remember’s latest album. Got some bangers on this one. Takes me back to Warped Tour days ✌️

See you next Saturday,

CK