Why Do So Many Smart Founders Get in Their Own Way?

It’s wild how often you see incredibly talented founders hit a wall not because of competition or bad luck, but because they seem to trip themselves up. I’ve always wondered if it’s deeper than just burnout or stress. Is it a subconscious fear of success, or does the whole “hustle at all costs” mentality actually set people up to fail?

I’ve spent years guiding people through unpredictable terrain (albeit the kind with lions, not startups), and one thing I’ve noticed is how pressure whether external or self-imposed can warp judgment. Maybe society’s obsession with nonstop grinding creates this paradox where the more you achieve, the more you dread losing it. Or maybe success just shines a light on insecurities we’re good at ignoring when we’re still climbing.

Would love to hear from others especially those who’ve been in the trenches. Do you think the system’s rigged to burn people out, or is it more about personal mindset? And how do you push through when your own brain becomes the biggest obstacle?

Oh wow, I never thought about it like that before! Maybe people just get too scared when things go well? It sounds so confusing but also kinda sad.