You’re probably making a mistake right now. Don't worry, everyone is. Most business owners spend their entire day sprinting toward "the next big thing" while completely ignoring the landmines buried right under their feet. We’ve been conditioned to believe that success is about being the smartest person in the room, but Keith Cunningham, the mind behind The Road Less Stupid, argues something way more practical. He thinks you don't need to be a genius. You just need to stop being an idiot.
It sounds harsh. It’s supposed to be.
We live in a culture that worships "the hustle." We want more leads, more revenue, and more complexity. But more complexity usually just leads to more expensive mistakes. If you look at the math of failure, it’s rarely a lack of opportunity that kills a company; it’s the pursuit of "great" ideas that weren't actually vetted. Most of us are playing a game where we try to win by making incredible plays, but in reality, business is often more like amateur tennis. In amateur tennis, you don't win by hitting winners. You win by not hitting the ball into the net.
Why "Thinking Time" is the most expensive thing you're missing
Keith Cunningham has this concept he calls "Thinking Time." It’s basically the core of The Road Less Stupid. Honestly, it sounds almost too simple to work, which is why most people ignore it. You sit down with a pen, a pad of paper, and a specific, high-quality question. No phone. No laptop. No "quick check" of Slack. Just you and the problem.
Most of us "think" while we’re driving or in the shower. That’s not thinking; that’s ruminating. Real Thinking Time is an active process. It’s about asking yourself the hard stuff, like "If I were a competitor trying to put myself out of business, what would I do?" or "What is the one thing I'm ignoring right now that could bankrupt me in six months?"
It’s uncomfortable.
If you’re doing it right, you’ll probably feel a bit of a pit in your stomach. We avoid these questions because the answers require work. They require us to admit that our "brilliant" new marketing campaign is actually a distraction from the fact that our churn rate is skyrocketing. We’d rather focus on the shiny new thing than fix the leaky bucket.
Cunningham often references his own massive financial loss—losing $100 million in the early 90s—as the catalyst for this philosophy. He didn’t lose that money because he was lazy. He lost it because he was "smart" and arrogant. He thought he knew what he was doing, so he stopped asking the "stupid" questions. He stopped looking for the "tax" he was about to pay for his ignorance.
The "Dumb Tax" is real and you're probably paying it
Every mistake has a price tag.
Cunningham calls this the "Dumb Tax." You pay it every time you hire the wrong person because you were in a rush. You pay it when you sign a lease on an office you don't need. You pay it when you launch a product without testing the demand first. The goal isn't to be perfect, but to lower the frequency and the magnitude of these taxes.
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Think about it this way:
If you have $100,000 and you lose 50%, you now have $50,000. Simple math. But to get back to where you started, you don't just need a 50% gain. You need a 100% gain. Losses hurt twice as much as gains help. This is why avoiding the "stupid" is mathematically superior to seeking the "brilliant."
The questions that actually matter
Most people ask low-level questions. "How do I get more followers?" is a low-level question. It doesn't lead to a transformative answer.
Better questions include:
- What must be true for this project to succeed?
- What are the assumptions I'm making that I haven't verified?
- If I could only do one thing this week to move the needle, what would it be?
- What would this look like if it were easy? (A classic Tim Ferriss-ism that fits perfectly here).
I once saw a business owner who was obsessed with SEO. They spent thousands a month on backlink strategies. During a "Thinking Time" session, they realized their checkout page had a bug where the "Buy" button didn't work on Safari. All that traffic was useless. They were paying a massive Dumb Tax because they were focused on the wrong end of the funnel. They were trying to be "smart" with SEO instead of "not stupid" with their website functionality.
Business is a game of logic, not just passion
We’re told to follow our passion. Passion is great for getting started, but it’s terrible for making decisions. Passion blinds you. It makes you overlook the fact that your margins are thinning or that your best employee is about to quit. The Road Less Stupid is essentially a plea for more logic and less emotion in the boardroom.
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Cunningham distinguishes between "Optimism" and "Reality." Optimism is what you tell your investors. Reality is what your bank statement says.
When you look at the work of Charlie Munger, the late vice-chairman of Berkshire Hathaway, you see a similar pattern. Munger was a huge advocate of "Inversion." Instead of thinking about how to make a business successful, he would think about all the ways a business could fail, and then he would systematically avoid those things. It’s the same logic. You don't need to be a grandmaster; you just need to avoid the blunders.
Implementation: How to actually do this without feeling like a fraud
You don't need a mahogany desk and a leather-bound journal to start this. You just need 30 minutes.
Pick a time when your brain is actually awake. For most people, that’s first thing in the morning before the emails start pouring in. Take a blank sheet of paper. Write one question at the top.
Example: "What is the biggest risk to my revenue over the next 90 days?"
Then, sit there. Don't get up. Don't check your phone. Write down every single thing that comes to mind, no matter how small or scary. Maybe it's that your main supplier is in a politically unstable region. Maybe it's that your lead developer is burnt out. Maybe it's that your biggest client is unhappy.
Once you have the list, you don't need a 50-page strategy document. You just need a plan to mitigate the biggest risk. That’s it. That’s the "road less stupid." It’s just a series of small, logical corrections that keep you from crashing into a wall.
Why complexity is the enemy
Small businesses often try to act like big businesses. They create complex hierarchies and 10-step approval processes. This is usually just a way to avoid making a decision. Cunningham argues for simplicity. If you can't explain your business model to a 10-year-old, you probably don't understand it well enough to avoid the Dumb Tax.
Complexity hides problems. Simplicity exposes them.
When things get complicated, we tend to rely on "hope" as a strategy. "I hope the market turns around." "I hope this new hire works out." Hope is not a strategy. It's a symptom of a lack of thinking.
Actionable Steps for the Next 7 Days
If you want to stop paying the Dumb Tax and start finding the The Road Less Stupid, you can't just read about it. You have to change your schedule. Knowledge isn't power; only the application of knowledge is power.
Schedule two 30-minute blocks of Thinking Time this week. Put them in your calendar as "Critical Meeting." If someone asks to meet during that time, tell them you're booked. You are. You’re meeting with the most important person in your business: the person responsible for the decisions.
Identify your "Single Point of Failure." Look at your business and ask: "If this one person or this one tool disappeared tomorrow, would we be out of business?" If the answer is yes, your next 30-minute Thinking Time session should be focused entirely on how to create redundancy.
Audit your last three "big" mistakes. Honestly. Write them down. What was the assumption you made that turned out to be wrong? Was it a "stupid" mistake (avoidable) or a "noble" failure (unforeseeable)? Most of the time, it's the former. Recognize the pattern so you don't repeat it.
Kill a "Zombie Project." We all have them. Projects that are half-finished, sucking up resources, and unlikely to ever produce a real ROI. Be "not stupid" and cut your losses. Reallocate those resources to something that actually works.
Focus on the "Who," not the "How." When you have a problem, stop asking "How do I fix this?" and start asking "Who is the best person to fix this?" Smart people try to do everything themselves. Successful people find the right people to do the things they aren't great at.
Business doesn't have to be a constant state of crisis. It feels like a crisis because we're constantly reacting to the "Dumb Tax" we just triggered. By shifting your focus from "how do I be brilliant" to "how do I avoid the obvious mistakes," you create a level of stability that most of your competitors will never have. They'll keep chasing the shiny objects. You'll keep staying on the road that actually leads somewhere.