The Awkward Ask: Talking About Your Offer Without Cringing

Telling friends and family about your side hustle doesn’t have to feel cringey. Here’s how to make the ask naturally — and build confidence as you go.

September 24, 2025 • Estimated Reading Time: 3 minutes

Everything You Need To Start Strong (Without Overwhelm)

Simple shifts turn awkward asks into confident, natural conversations.

Hey there fellow side hustler!

Let’s be honest: telling people about your new side hustle can feel… awkward.
Your palms get sweaty, your voice tightens, and suddenly you’re second-guessing everything you say.

💭 “What if they think I’m being pushy?”
💭 “What if they roll their eyes or just say no?”
💭 “What if I sound like I don’t believe in it myself?”

That’s normal. Almost every new side hustler feels this way. The good news? Talking about your offer doesn’t have to feel like begging or bragging. With a few simple shifts, it can feel natural — even confidence-building.

🛠️ Three Ways to Make the Ask Less Awkward

1. Share, Don’t Sell

Instead of: “Would you buy this from me?”
Try: “I just launched this new thing — here’s why I made it and who it’s for. Do you know anyone who might find it helpful?”
This way, you’re inviting them into your story, not putting them on the spot.

2. Frame It as Practice

Think of your first conversations as rehearsals. You’re not trying to close a deal at every turn — you’re practicing how to talk about your offer out loud. With every repeat, it feels less cringey and more natural.

You don’t have to be great to start, but you do have to start to be great.

— Zig Ziglar

3. Make It About Them

Instead of focusing on your nerves, focus on their needs. How might your offer save them time, ease stress, or create a result they want? That shift takes the pressure off you and makes the conversation about service.

📌 Trust The Process

Here’s the truth: your first few asks will feel clunky. That’s okay. Every confident seller you admire today had their own “awkward phase.” The only way out is through — and every attempt builds your confidence.

🧩 Tool Tip

If you freeze up, write a short “conversation starter” script in your phone notes.
Example:

“Hey! I just launched something new I’m excited about. It helps [specific group] with [specific problem]. Happy to share details if you know anyone who might be interested!”

A simple script can take the pressure off when your nerves kick in.

✅ Your Next Step

This week, tell one friend or family member about your offer using one of the approaches above. Keep it light, keep it short, and remind yourself: this is practice, not a performance.

✨ With each ask, you’re not just spreading the word — you’re building your confidence as a founder.

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