The Perfect Time to Start Doesn’t Exist — Here’s What Successful Investors Do Instead

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If you’re waiting for the economy, the market, or your confidence to all line up perfectly before you invest, you’re going to be waiting forever.

In this episode, I break down exactly how overcoming fear of investing really works, and why the people who win financially are the ones who move before they feel fully ready without gambling everything.

I start by talking about a pattern I’ve been seeing everywhere: people are frozen. They’re standing in a shaky boat, gripping the sides, hoping the waves calm down instead of simply stepping onto the dock, reassessing, and getting into a better boat. That same fear of doing anything different shows up in marriages, health, careers, and especially investing. If you do nothing and hope it all works out, it almost never does.

I share one of my favorite quotes from Will Rogers: “Even if you’re on the right track, you’ll get run over if you just sit there.” Then I dive into what I’ve learned from coach Bill Belichick in his book The Art of Winning. He makes a powerful point: you’re not born confident, and you can’t just talk yourself into confidence with affirmations and visualization. Real confidence is built through repetition and practice. He used that approach with the New England Patriots, leaning into what they repeatedly practiced the passing game with Tom Brady rather than overthinking and trying to be “tricky” when it mattered most.

I connect that directly to money and investing. I tell my own story of going from a shy, introverted kid who hated speaking in front of even two people, to someone who now presents, records this podcast, and gets feedback from people like Shannon, who told me she was completely drawn into my story. That transformation didn’t come from magically waking up confident it came from doing it again and again.

Then I share a real conversation I had with a guy who had just been laid off. He had time, he had money freed up from his 401(k), he had a slow season in his new business coming up which made it one of the best times for him to make a strategic move. And yet he was completely paralyzed by uncertainty, waiting for a crystal ball to tell him exactly what to do. That’s what analysis paralysis looks like in real time: wanting guidance, but refusing to act on it.

I compare that mindset to sitting in your driveway waiting for every traffic light between you and your destination to turn green before you’ll even start the car. Life and markets don’t work that way. The lights change while you’re on the road. The waves keep coming whether you’re in a crappy boat or a better one. The investors who win don’t ignore risk they take thoughtful, guided action with imperfect information.

I also talk about how even someone like Warren Buffett doesn’t sit on the sidelines doing nothing. He’s cautious, he keeps cash ready, he’s picky, but he still invests. He doesn’t live on “hopium” and neither should you. The difference between people who create real passive income and those who just dream about it is simple: they take the first step, learn from mistakes, and keep moving.

If you’re tired of spinning in your head, scared of losing money, or waiting for the “perfect time,” this episode is your wake-up call. I’ll show you how successful investors build investing confidence through calculated action, how to avoid letting fear quietly drain your future, and why having the right mentors and community around you changes everything.