354. The Hardest Lesson I’ve Learned About Opportunity

I want to let you in on something that hit me hard recently: If you’re “playing it cool” in life, chances are… you’re actually just playing yourself.

In this solo episode, I’m breaking down a moment that made me reflect deeply — a missed opportunity on a Brooklyn street that left me with instant regret. I’m sharing it because I know I’m not the only one who’s ever let fear get dressed up in confidence.

We convince ourselves we’re being smooth. That we’re in control. But deep down, we’re just scared — scared of looking dumb, getting rejected, or not living up to the version of ourselves we’re trying to project.

I dive into:

• Why “playing it cool” is costing you the life you want

• What fear looks like when it’s wearing designer clothing

• The hard truth about opportunities: they don’t wait for you to be ready

• Why it’s better to live with a “no” than a “never know”

• How to start acting like the version of yourself you’re trying to become

If you’ve been sitting on an idea, holding back your voice, or missing shots you know you were meant to take — this one’s for you.

Let them see you try. Let God see you try. You're not here to play it cool — you're here to play it real.

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Let’s stop letting fear call the shots. Appreciate you for tuning in.

– Matt