For the final lesson in the series I saved my favorite; one I talk about often. If you look closely, everyone’s playing checkers while pretending to play chess. They talk about “long-term thinking” but really mean next quarter’s numbers. I used to be that person, head buried in daily operations, thinking I was crushing it. I was not. Nor are you if this describes you.
Tomorrow is important but having the discipline to look 5, 10, even 15 years out is transformative. Not the safe, incremental stuff. I’m talking about the big, scary changes that make people uncomfortable. Sort of like seeing AI hit in a big way when you run a tech business, if you don’t see an immediate need to change, you are not paying attention. Your business has something like that (probably also AI). Find it. Now.
Too many businesses “Focus on what’s working now,”. This is exactly how you become extinct.
Want to know the hardest part? It’s not predicting the future – it’s sacrificing short-term wins for long-term gains. Try explaining to your team why you’re investing in something that won’t pay off for years while your competitors are banking quick wins. It’s not fun. But here’s the thing: by the time something becomes obvious, you’re already too late.
I see too many founders stuck in this cycle of reactive decision-making. Something changes in the market, and suddenly everyone’s scrambling to catch up. But by then, the real opportunities are gone. The money’s been made. The positions have been taken.
I wish I had learned earlier that my job isn’t to react to the future – it’s to actively shape it. That means making bets that look wrong to everyone else. It means being comfortable with uncertainty. And most importantly, it means being willing to redefine yourself over and over again. (and then over and over again after that).
But let’s be real – you can’t do this alone. The future’s too big, too complex for any one person to figure out. That’s why I’ve built teams of people who think differently than me, who challenge my assumptions, who bring perspectives I’d never consider. Because the best way to predict the future is to surround yourself with people who are already living in it.
The day-to-day stuff feels more urgent. I get it. It’s tangible. Measurable. But here’s the truth: while you’re optimizing for today, someone else is redesigning tomorrow. And by the time you notice, they’ll be years ahead of you.
So here’s my challenge: take one hour this week. Just one. Shut off your notifications, close your email, and think about where your industry will be in 10 years. Not where you hope it’ll be – where it’s actually heading. Then ask yourself: are you building for that future, or are you just managing the present?
Because at the end of the day, embracing the future isn’t just about survival – it’s about staying useful for your clients and your community by extension. And the only way to stay useful is to start building for tomorrow while everyone else is stuck on today.
