Are You Asking the Right Questions? Lessons from “The Road Less Stupid”

STOP! Are You Paying the “Dumb Tax” Without Even Realising? Here’s How I’m Fixing It—And How You Can Too!

Hello everyone, on my relentless mission to run beyond Day 4,292, clock 40,075km (yep, that’s a lap of the world, barefoot!), and—most critically—raise £1,000,000 to save children’s lives. Every day counts. Every step matters. But today, let’s talk about something I’ve discovered is even more valuable than miles or money: the art of asking the right questions.

Why Your Questions Are Costing You More Than You Think

Have you ever made a split-second decision, only to regret it much later? Congratulations, you’ve paid what Keith Cunningham (author of “The Road Less Stupid”) calls the “dumb tax”. My ears pricked up when I heard this—because it stings to know how much we lose not from what we do, but how we think!

Cunningham, rumoured to be the “rich dad” behind “Rich Dad, Poor Dad”, says that avoiding costly mistakes isn’t about working harder or just ploughing ahead. It’s about thinking smarter.

My Realisation—and What I’m Doing About It

Here’s the kicker: Most mistakes (and lost money, energy, time) happen because we ask the wrong questions or rush in emotionally. The solution? Take proper thinking time. Ask better questions. Doesn't matter if it's business, family, or—yes—even this crazy running challenge I’m on.

Cunningham suggests wearing FOUR HATS when making decisions:

1. The Creator/Artist (big ideas, creativity)

2. The Operative/Technician (getting things done)

3. The Founder/CEO (strategy, blueprint)

4. The Investor/Board (reducing risk)

Each ‘hat’ asks different questions. Digging into this, I started to really see the holes in my old approach.

My Secret Weapon—AI “Keith Cunningham”!

Now, here’s where my journey takes a 21st-century twist—I built a custom ChatGPT to act as Keith Cunningham for my thinking time! Whenever a decision looms (big run, charity plan, or life choice) I run it through “Keith” and get bombarded with the right, deep, specific questions.

You wouldn’t believe how much this has helped cut down bad calls, stress, and—yep—dumb tax.

Takeaway for You: How to Pay Less Dumb Tax—In Life and Business

Here’s what you can do right now:

• Slow down. Don’t dive in emotionally.

• Frame your challenge using ALL FOUR HATS. Think like a creator, operative, founder, and investor.

• Use AI tools. Custom prompts or chatbots can ask what you forget.

• Go deeper. Don’t settle for surface answers.

It’s not about never making mistakes—it’s about massively reducing them. Imagine your future self thanking you for not just running hard, but running smart.