I have a buddy named Dave.
Dave has owned a landscaping company for 31 years. He knows every soil type in his county. He can look at a yard and tell you what it needs before you finish your sentence.
The man is not short on knowledge. He is one of the sharpest operators I know.
But last month, his biggest competitor — a kid half his age — launched a social media campaign that blew up. New customers started calling that guy instead. Dave's phone got quieter.
So Dave did what he has always done. He sat down at the kitchen table with a yellow legal pad. Wrote "NEW MARKETING IDEAS" at the top.
And stared at it.
For 45 minutes.
He Googled "marketing ideas for landscapers." Got the same list he has seen a hundred times. Start a blog. Post on social media. Ask for referrals.
Thanks, internet.
He asked his wife. She said, "What about one of those TikTok things?"
He asked his buddy at the supply yard. "Just keep doing what you have always done, Dave. You will be fine."
He was not fine. Dave called me that night. Told me he felt stuck. Told me he felt like the business was slipping away and he did not know how to fight back.
I knew exactly what was wrong. And it had nothing to do with creativity.
Here Is What I Told Dave to Look For
I said, "Dave, you are making the same four mistakes everybody makes. Let me show you."
1. The Blank Page Trap.
Starting with nothing and expecting brilliance. No framework. No structure. Just you versus an empty page. The page usually wins.
2. Generic Google Advice.
Searching for ideas online gives you the same recycled list every competitor already read. If everybody is reading the same article, nobody has an edge.
3. Asking the Wrong People.
Your wife loves you. Your buddy at the supply yard loves you. Neither one understands your business the way you do. Their advice is kind. It is almost always useless.
4. Defaulting to What Worked Before.
"Just keep doing what you have always done" is comfortable. It is also how businesses go invisible. The world moved. Your playbook did not.
The Real Problem
Dave does not have a creativity problem. He has a structure problem.
His brain is full of 31 years of knowledge about his customers, his market, and his craft. That is an incredible asset. But he has no way to pull it out, organize it, and turn it into something new.
That is what brainstorming actually is.
It is not sitting in silence hoping lightning strikes. It is feeding the right inputs into a system that does the heavy lifting for you.
Think of it like this: Dave has a garage full of every tool a landscaper could need. But he has been trying to dig a trench with his bare hands. The tools are right there. He just was not using them.
That system exists now. It was not around when Dave started his business. But it is here today.
Tomorrow
I am going to hand you the exact prompt I gave Dave.
You plug in your business. Your challenge. Your situation. And you walk away with 20+ ideas you have never considered — organized by how fast you can act on them.
No blank pages. No generic Google lists. No asking your wife about TikTok.
Ideas built around your business. Not someone else's template.
Dave figured it out. Tomorrow, you will too.
Hit reply and tell me: When was the last time you sat down to brainstorm and came up empty? What were you trying to figure out?
Stay in Win Mode!
Ps: WinMode is geared to the mature reader, often near or in their retirement years. The planning or lack of it can be overwhelming and quite consequential if you do not do it. We have created a tool for you to start exploring the numbers (for real) so you are not left surprised. Try the free Mortgage Calculator.
Pss: Feel free to pass this on to a friend.
They can subscribe here: WinModeAI.com or enjoy the archive of past publications