“Be less sh*t.”
A friend of mine says it, and it’s stuck with me. It’s blunt, it’s a bit rude and it’s hard to argue with. It’s also the best summary I know of Keith J. Cunningham’s The Road Less Stupid, which I read in 2022 and gave five stars.
Cunningham is a businessman who made a fortune, lost it, and built it back. That’s the kind of person I’ll listen to about mistakes. He’s paid for his lessons the expensive way, so you don’t have to.
His big idea fits in one line, and it’s the line from the book that’s in my guide. “I don’t need to do more smart things. I just need to do fewer dumb things.”
The dumb tax
For me it’s all about the dumb tax. That’s his name for the price you pay when you make a mistake you could have avoided. The hire you rushed. The deal you didn’t read properly. The problem you could see coming and decided to ignore. Nobody sends you an invoice marked “dumb tax”, but you pay it all the same, in money and in stress.
Think about what one wrong decision really costs. The wrong hire costs you their wages, and the hours you spend managing them, and the customers they upset along the way. The rushed decision costs you the decision, and then the clean-up. It’s rarely one bill. It keeps arriving.
What I like is how ordinary the lessons are. There’s nothing clever about them. Most businesses that struggle can point to a handful of dumb things, done over and over, until the tax adds up to something serious.
If you could stop the two or three most expensive mistakes in your business, how much smart stuff would you even need?
Thinking time
Cunningham’s answer is something he calls Thinking Time. He sits on his own with a pad and a question, and thinks. No phone, no meetings. He writes down whatever comes and stays with the question long enough to get past the obvious first answer.
The questions do a lot of the work. He’ll ask what the real problem is, what he’s missing, and what he might be pretending not to know. That last one is uncomfortable. It’s meant to be.
The subtitle calls it advice from the chairman of the board, and that’s how it reads. Short chapters, each one a lesson he might give you across the table if you’d asked him to sit on your board. You can dip in anywhere and come away with something to think about.
You don’t need anything fancy to try it. Take one decision you’ve been putting off, or one problem that keeps coming back. Give it half an hour with a pen, a blank page and no phone. Write the question at the top and keep writing until you’ve gone past the first answer that pops into your head. The second and third answers are usually where the good stuff is.
You might think a book about slowing down sits oddly with the man who wrote Done Beats Perfect. I don’t think it does. For the record, done beats perfect doesn’t mean any old junk will do. It means doing things to the best of your ability, and actually doing them.
Cunningham wants you to spend a bit of time on the decisions that matter, so the things you get done are the right things. I can get behind that. A quiet hour before a big decision is a lot cheaper than the dumb tax afterwards.
His lessons cover the stuff every business owner runs into sooner or later. People, money, and the gap between what you think is happening and what’s really happening. Who you hire matters. Who you keep on when you shouldn’t matters too. He’s honest about getting plenty of it wrong along the way.
So this is what I take from it. Get rid of the things you’re bad at. Learn from them. Make fewer mistakes, and pay less dumb tax. It’s an important lesson for all of us, and I’m very much included in that “all of us”.
If you run a business and you’ve ever looked back at a decision and winced, this is your book. It’s one of four on focus and fewer mistakes in my free guide, 50 Books That Shaped Me, if you want the others.
Be less sh*t. It’s a good motto. Cunningham just gives you a way to actually do it.




