Hi Dreamer,

Here’s the uncomfortable truth: no one chases a dream without carrying a suitcase full of fear. You think you’re the only one? You’re not. Everyone who has ever built something from scratch—everyone who has dared to say, “I want more”—has stared down that same terror of failure. It whispers the same poisonous things: “You’re not special. You’re not enough. This will never work.”

And you know what? Those whispers love to sound practical. They dress up like good advice, like a friend warning you to be careful, like a backup plan that quietly mutates into a full-blown exit strategy. Suddenly, your dream isn’t a dream anymore. It’s a phase. A cautionary tale. Something you “tried” before you got realistic.

But listen to me: backup plans aren’t the problem. Backup plans are fine. They’re the sturdy little boats you build while still flying your kite high into the sky. They don’t need to become anchors.

The real danger here isn’t failure. It’s the fear of failure. It’s how seductive it becomes to let that fear chip away at you, to let it convince you that playing small and staying safe is somehow nobler than risking it all for something you love.

You will feel like a failure. You will feel humiliated. You will scroll through social media and want to scream "FUCK EVERYBODY" at the top of your lungs. And that's not just okay — it's a sign you're alive, you're fighting, you're creating something that matters.

You’re not torn between being a dreamer and being practical. You’re torn between faith and fear. You’re scared to let yourself believe this could work. You’re scared of what it will mean if it doesn’t. But here’s the thing: risking everything doesn’t mean losing everything. Even failure—yes, even the big, scary failure you’re so afraid of—will give you something. Experience. Growth. A story worth telling. Proof that you tried. And in a world where so many people never even let themselves dream, that counts for a lot.

So go ahead. Build a parachute if you need one. Polish up your resume. Explore other opportunities that excite you. But don’t you dare let fear write the end of this story. Keep showing up for your dream. Keep fighting for it. You say you’re a risk-taker? Prove it. Risk failure. Risk humiliation. Risk it all to find out what’s on the other side of your fear.

Because here’s what I promise you: whether your startup takes off or crashes down, you’ll be stronger, wiser, and braver for having chased it. And if you ever do find yourself starting over, you won’t be back at square one. You’ll be at square two, armed with everything you’ve learned. You’ll have momentum. You’ll know you’re the kind of person who goes after what they want, no matter how terrified they are.

You’re not torn. You’re alive. You're also probably an idiot. And this—this messy, uncertain, exhilarating hustle? This is where all the good stuff happens. So lean in. Keep going. And remember: you’re not alone. There are so many of us out here, stubbornly chasing our dreams, failing and rising and failing again. You’re in good company. Keep the faith.

Maddy