Hey Fearless Friend!

Today on Stay Fearless or Die Trying😀 

• I've been pouring energy into the Chief Swag Officer Instagram lately, and I’d love for you to follow along. Check it out here!

• What’s been happening in Connecticut has literally changed my life. I’ve been building community for years but I never would’ve thought that my tiny hometown would be what would put me on the map. THANK YOU!

• That means…events are starting monthly in CT and will be servicing all areas from Tolland to Fairfield. More to come on Monday!

• Shop The Connecticut Hat Collection, designed and made right here in CT. Grab your favorite and help support this growing community.

We’ve all heard it before…

“You won’t be able to make money doing that.” “You need to choose a real career—don’t waste your time on a hobby.”

And then, like clockwork… “Your stuff is so cute! Do you ever sell it?” “You should do this full-time!”

The amount of people that still ask me how I have a side-hustle…none of this is a side-hustle: it’s all full-time and been in the works for 10+ years!

Cue the confusion. The doubt. The low-key excitement you’re trying to talk yourself out of.

But the question stands:
Are you ready to go full-time?
And better yet—what does that even mean?

Let’s Be Honest: It’s Not Just About Quitting Your Job

If you’re growing a side hustle, passion project, or small business on the side, I want you to know this:

You don’t have to have it all figured out to start taking it seriously.
You don’t need 100,000 followers.
You don’t need a fancy investor or a perfect plan.

But you do need a shift in mindset:
You’re not “just dabbling.” You’re building something real.

That doesn’t mean you also need to be extremely cringe, either. I see so many content creators say the more cringe you can be, the better! That may be true if you want to go viral, but if you want to build a career with longevity like I have, it’s way more important that you find the need in the market you’re serving, understand your customer, and do a slow burn.

The most successful founders became successful after 40-years-old: think the founder of Spanx, even Michelle Obama, or Michelle Grant (my friend who started LIVELY and sold it for $1B!)

That shift—mentally treating your side hustle like it matters—is the first step toward turning it into your main hustle.

What Most People Don’t See:

What people don’t see when they tell you, “You should do this full-time,” is the hard part:

• There might not be anyone in your corner at first.
  

• All the decisions come down to you.
  

• Some months feel amazing; others feel like you’re shouting into the void.

Going full-time means being your own boss and your own safety net. It means trusting yourself when no one else really gets it yet.

But it also means freedom. Flexibility. Ownership.
It means waking up knowing you’re building your dream—not someone else’s.

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Is It Time to Take the Leap?

There’s no formula, but here are a few signs you might be closer than you think:

• You’re consistently making money—even if it’s small, it’s steady.
  

• You’re more excited about your side hustle than your day job.
  

• You’re turning down opportunities because you’re out of time.
  

• You’re thinking about your business 24/7—it won’t leave your brain.

And maybe most importantly:
You’re tired of waiting for “someday.”

A Real-World Roadmap to Going All In:

I don’t believe in overnight success. But I do believe in intentional transition.

Here’s how to get started:

1. Run Your Numbers
Know your monthly bills and figure out how much income your hustle needs to generate. A savings cushion (3–6 months) makes everything less panic-y.

2. Build Full-Time Habits Now
Start showing up consistently before you make the leap. This helps you test your systems and stamina—plus it builds momentum.

3. Write Down a Plan
Doesn’t need to be fancy. Who’s your customer? Where do they find you? What’s your goal this month? Treat it like it matters—because it does.

4. Get a Support Crew
Even if it’s one person who believes in you. You’ll need someone to hype you up when you hit a wall (because, spoiler: you will hit a wall).

5. Expect Fear, but Move Anyway
You’ll never feel 100% ready. The people who make it happen don’t wait for the fear to go away—they just start anyway.

Here's What I Know for Sure:

No one ever built something great without getting uncomfortable.
No one ever made magic without making messes first.
And no one ever figured it all out before they took the first step.

You can build something powerful out of your passion.
You can take your “cute hobby” and turn it into a business.
You can go full-time—even if it looks different than you imagined.

So if you’ve been waiting for a sign?
This is it.

Newsletters I Read Weekly:

Stay Fearless or Die Trying,

Alexa Curtis 💌

P.S.
Are you building a side hustle right now? Or thinking about taking the leap soon? Reply and tell me what you’re working on—I’d love to cheer you on (or even feature you in an upcoming issue). And as always: forward this to a friend who needs to hear it today and get free swag!