Thinking Time: The Highest-Value Meeting You’ll Ever Have… With Yourself
If you’ve never read The Road Less Stupid by Keith Cunningham, here’s the gist of one of its most powerful ideas: thinking time.
Sounds obvious, right?
“Oh yes Rob, I think all the time.”
No. You don’t.
You react all the time. You decide all the time. You firefight all the time.
But actual thinking — calm, structured, uninterrupted consideration of a single question that could move your business forward — is rare.
Cunningham’s take is brutally simple:
– The dumbest decisions you’ve ever made came from rushing in without enough thinking.
– The smartest, most profitable moves came from clear, deliberate thought.
– Therefore, if you want more smart decisions, you need more deliberate thinking.
Groundbreaking? Not really. Life-changing? Absolutely — if you actually do it.
How to Do “Thinking Time” Properly
This is not “sit in your chair and stare at your inbox until inspiration strikes.”
It’s a deliberate, structured meeting with yourself. Here’s how:
- Pick a Great Question. This is key. Don’t ask “How can we make more money?” — it’s too vague. Ask something pointed:
– “What are the top three reasons our best customers buy from us?”
– “What’s the single bottleneck that slows our delivery process?”- “What’s the single bottleneck that slows our delivery process?”
– “If we could only do three marketing activities next quarter, which would we choose and why?” - Pick a Great Location. Your desk is usually the worst place for thinking — it’s the epicentre of distraction. Go somewhere you can’t hear your email ping or see that pile of ‘urgent’ paperwork.
- Set a Timer. 45 minutes is plenty. Any longer and your brain wanders to lunch. Any shorter and you’ll skim the surface instead of diving deep.
- Write, Don’t Type. There’s something about pen on paper that slows your brain just enough to think clearly. Plus, you can’t click over to check LinkedIn.
- Review Your Notes. Don’t just admire your genius. Decide: What action will I take from this? What decision is now clear?
Why You Won’t Do This
Because it feels “unproductive”. You’ll convince yourself you’re too busy. You’ll say you’ll start “next week” (the same week you start your new diet, of course).
And that’s why most business owners run in circles — they never pause long enough to choose the right direction.
One Final Nudge
Book it in your diary like a meeting with your most important client — because that’s exactly who it is: future you.
A single 45-minute thinking session could save you months of wasted work.
Or, as Cunningham would say, “It’s about doing the road less stupid — because smart is a lot less painful than fixing dumb.”
