Isn't That Rich Podcast

Let’s be honest, putting a price on something you love to do can feel… weird. Maybe even a little cringey. You’ve probably had that moment where someone asks, “What do you charge?” and your stomach does a little flip. Because even though you’re good at what you do, it’s still personal. It’s your art, your hobby, your passion project—and now, it’s your business.

Welcome to the world of the side hustle!

In this episode of the Isn’t That Rich podcast, we (Ashley McVicker, Jill Franks, and Jared Gravette) sat down to talk through the emotional rollercoaster of pricing your personal work. Whether you're just starting your side gig or you’ve been at it for a while but still haven’t nailed your pricing strategy, this one’s for you.

When Passion Meets Pricing: Why It Feels So Personal

The biggest hurdle? Feeling like you're not allowed to charge for something that brings you joy.

Take Jill, for instance. Her glamping business started as a sweet sleepover setup for her granddaughters, and before she knew it, other moms were sliding into her DMs asking if she’d recreate the magic for their kids too. But charging for it? That felt strange at first. "Why would anyone pay me for something they could technically do themselves?" she wondered.

Or Jared,our in-house photographer, who's been behind the lens since high school. Even now, he still sometimes questions whether his work is “good enough” to deserve a price tag. It’s the creative equivalent of body dysmorphia: you’re critical of your own talent, assuming others will be too.

And Ashley? She's a self-taught makeup artist who’s been obsessed with YouTube tutorials since forever. She’s great at what she does, but struggles with impostor syndrome because she’s not professionally certified. “Why would someone pay me to do their makeup when they could just do it themselves?” she asked, before watching two high school girls light up after seeing themselves all glammed up.

That moment right there? That’s the value. But we don’t always see it that way, especially when it feels so personal.

What You’re Really Charging For

If you’re in a creative or service-based business, chances are you’ve struggled with this question: How do I charge for something that doesn’t feel like work?

Here’s the reality: It may be fun, but it’s not free. Your work takes time, skill, money, and effort.

Jill’s glamping setups? They involve hauling tents, furniture, air mattresses, and decorations. It’s physical labor, travel, and setup/tear-down. Her starting rate is $450, which might feel high for a kid’s party, but not when you consider the literal sweat equity that goes into it.

Ashley’s makeup sessions? They involve high-quality products, tools, and time, not to mention the emotional labor of helping someone feel beautiful on a big day. One bottle of foundation can cost $60. And those $5 fake lashes from Walgreens? Don’t discount the years of trial and error it took to figure out which ones actually work.

Jared’s photography? It’s not just two hours of snapping photos. It’s editing, uploading, file management, and hours of behind-the-scenes work that no one sees. Plus, years of practice to get the perfect lighting, angle, and vibe.

So what are you really charging for? Your time, your tools, your taste, and your talent.

Tools to Help You Set Confident Prices

Now that we’ve worked through the emotional side, let’s get practical. Here are some tools and tips we use to set pricing that feels good and fair:

1. Identify Your Ideal Customer

Don’t try to be everything to everyone. Think about who you actually want to work with. Who appreciates what you do and is happy to pay for it? This helps shape your pricing and keeps you from burning out on clients who don’t value your time.

2. Use ChatGPT for Market Research

Seriously, this tool is magic. Ask it things like, “What does a photographer with 5 years of experience in the Midwest typically charge for wedding photos?” or “How much should a freelance makeup artist charge for homecoming makeup in Southern Illinois?” You'll get a realistic range to work with, and you won’t have to awkwardly message your competitors pretending to be a potential client just to see what they charge.

3. Create Tiered Packages

Offer a base package, then add upgrades. For Jill’s tents, you can just rent the setup, or you can go all out with themed décor, extra beds, and more. Ashley might charge one rate for basic makeup, then offer lashes or travel as an add-on. Jared might charge per hour or per event, with extras for editing or longer sessions.

Tiered pricing makes it easier for people to choose what they want and it gives you flexibility.

4. Use Invoicing Tools

Use tools like Square, Autobooks (Jill’s go-to), Honeybook, or even PayPal. These help you build pricing menus, send professional invoices, and accept credit card payments. Once it’s in writing, it feels more official, and there’s less back-and-forth when someone asks, “How much would this cost?”

Friends, Family, and the Discount Dilemma

Let’s just say it: friends and family should be your biggest supporters, not your biggest moochers. But when you’re starting out, they’re usually your first clients, which can put you in a tough spot.

Our advice? Create a simple policy and stick to it. Maybe you offer a set friends and family discount (like 10–15%), or maybe you don’t discount at all, and that’s okay too.

The truth is, your cousin shouldn’t expect free wedding photography. Your best friend shouldn’t assume free makeup. And if they do get a discount? Make it clear that it’s a one-time offer or part of your official pricing structure.

Getting Paid: How to Accept Money Like a Pro

Whether you’re collecting cash, Venmo, PayPal, or using something more official like Autobooks or Square, the most important thing is to separate your side hustle money from your personal money.

Jill set up a separate bank account for her glamping business so she could keep better track of earnings. Jared uses PayPal. Ashley? She accepts everything from checks to cash to Venmo (and gets tipped pretty well, too).

Make it easy for people to pay you—and track those payments. Trust us, your accountant will thank you.

Building Confidence Through Experience

Sometimes, the best confidence boost is a glowing review, a heartfelt thank-you message, or the simple joy of seeing someone love what you created.

Jill once got a rave review from a band that stayed in one of her tents at a festival, they loved the hangover kit, the fan, the thoughtful touches she added. Jared has companies who come back and hire him again and again for video content. Ashley’s favorite moments are watching high school girls light up when they see themselves in the mirror with lashes on for the first time.

Those moments matter. They prove your work is worth something. That you are worth something.

Final Thoughts: Know Your Worth

Here’s the thing, if someone says no to your price, that’s okay. They’re not your person.

What’s not okay is continuing to undersell yourself just to make someone else more comfortable.

Charge what your time is worth. Use tools to help you stay organized. Know your value. And never be afraid to change your prices as you grow.

Your work is personal—but it’s also powerful. Own that.