Why I'm addicted to impossible questions (and you should be too)


I spent 3 hours last night thinking about how to get 10 million YouTube subscribers in 24 hours.

Crazy, right? Probably impossible.

But here’s the thing - I’m addicted to impossible questions. They’re like mental CrossFit for entrepreneurs.

Most people call me an overthinker. They’re not wrong. But what they see as a weakness, I’ve turned into my secret weapon.

Let me explain…

Last week, I was sipping coffee (probably my 5th cup), when this random thought hit me: “How could someone stack 1000 Bitcoin starting from zero?”

Instead of dismissing it as impossible, I let my mind run wild. That’s when something interesting happened.

The Beauty of Impossible Questions

Here’s why I love playing this game: Impossible questions force your brain into solution mode. They bypass all the normal “that won’t work” filters we usually have.

Think about it. When you ask, “How can I make an extra $100 this week?” your brain gives you boring answers: - Sell some stuff - Drive for Uber - Do some freelancing.

Yawn.

But ask, “How can I make $1 million this month?” and suddenly your brain goes into overdrive: - What if I created a viral marketing stunt? - Could I leverage celebrity connections? - Is there a gap in the supplement market I could exploit?

The Liver King Effect

Speaking of supplements… Let’s talk about the Liver King for a second.

This dude built a $100+ million supplement empire while walking around shirtless, eating raw organs. Sounds impossible, right?

But break it down: - Outrageous personal brand ✓ - Solid product margins ✓ - Proven market demand ✓ - Low startup costs ✓

Suddenly, the impossible starts looking… possible?

Why This Matters For You

Here’s where it gets interesting. After years of being a “professional overthinker” (yes, that’s going on my business card), I’ve noticed something:

The best business ideas often come from asking seemingly impossible questions.

Remember that YouTube question I mentioned earlier? Here’s where my brain went:

  1. Drop flyers from helicopters (probably illegal, definitely attention-grabbing)
  2. Partner with 1000 creators simultaneously (logistics nightmare, but imagine the reach)
  3. Create the world’s biggest treasure hunt (now we’re talking)

Are these ideas practical? Maybe not. Are they better than “post consistently and use good thumbnails”? Hell yes.

The Six Degrees of Possibility

You know that game “Six Degrees of Kevin Bacon”? Where you connect any actor to Kevin Bacon in six moves or less?

I’ve started playing a similar game with impossible goals. I call it “Six Steps to Impossible.”

Here’s how it works:

  1. Start with an impossible goal
  2. Break it into ridiculous sub-goals
  3. Keep breaking it down until something feels doable
  4. Find the most practical starting point
  5. Identify potential shortcuts
  6. Take the first actual step

Real Talk: Why This Actually Works

Remember when I mentioned my background in copywriting? Specifically in the health industry?

That’s not just a random detail. It’s proof that sometimes the “impossible” is closer than we think.

Want to build a supplement empire? Well:

  • I know the industry ✓
  • I can write converting copy ✓
  • I understand marketing ✓
  • Startup costs are manageable ✓

Suddenly, that “impossible” goal looks more like a game of connect-the-dots.

The Overthinker’s Advantage

Most people will tell you to stop overthinking. I’m telling you to overthink harder - but with purpose.

Because here’s the truth: Every major innovation started with someone asking an “impossible” question:

  • What if we could fit 1000 songs in our pocket? (Thanks, iPod)
  • What if we could order anything to our door in one click? (Hey, Amazon)
  • What if we could sleep on strangers’ couches worldwide? (Looking at you, Airbnb)

Your Turn

Here’s your homework (yes, I’m that guy now):

  1. Think of the most ridiculous, impossible goal you can
  2. Give yourself 10 minutes to brainstorm ways to achieve it
  3. Find the most practical first step
  4. Actually, take that step

Remember: The point isn’t to achieve the impossible overnight. It’s to train your brain to find creative solutions.

Because sometimes, the path to success starts with an impossible question.

Keep overthinking (strategically),

Chris “Professional Impossible Question Asker” Reck

P.S. Here are more ways I can help you make your Dent!

#1: Want To Ask Me A Question?: Dent Makers is a coaching group with monthly calls and a community designed to help you make your DENT on social media. ​​Join Here​

#2: Check out my ​YouTube channel , where I share more tips and tricks for making your Dent. I also have interviews with other Dent makers on the channel.

#3: ​Follow me on X ​And ​LinkedIn ​. I share deep dives into the strategies I use to make my own dent and more tips and tricks!

Meet your host

Chris Reck

A seasoned YouTube creator with over a decade of experience crafting impactful digital content. For the past 10 years, I’ve dedicated myself to helping others carve out their unique space online through Dent Makers, a vibrant community dedicated to empowering aspiring experts, creators, and entrepreneurs.


113 Cherry St #92768, Seattle, WA 98104-2205
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