Ep: 14 Confidence Is a Scam (and It’s Keeping You Broke) with Chelsea Quint

Oct 30

**"If you’re waiting to feel confident before you sell, you’ll be waiting forever."**

Chelsea Quint

Listen, I’ve said it before and I’ll keep saying it: selling is not sleazy, manipulative, or icky. It’s service. It’s art. And apparently, according to my guest this week, it’s love.

I sat down with Chelsea Quint, a messaging strategist and sales coach who has spent nearly a decade helping service providers, coaches, and creatives stop feeling gross about sales and start seeing it as the most intimate and impactful part of their business.

And y’all, this conversation went everywhere. We started by talking about staying up too late, Blink-182 concerts, and garden carrots (yes, literal carrots). But by the end, we had drawn a straight line between gardening, nervous system capacity, and why most of you are sabotaging your sales without realizing it.

What You’ll Hear in This Episode

How gardening (and patience) might be the metaphor your business desperately needs
Why so many of us “dig up our seeds” and ruin what’s growing
The real difference between data and information when you’re making marketing decisions
Why “confidence” isn’t the goal — capacity is
The psychology of selling as an act of love (and how to reframe the ick)
Why hiring out your sales is a terrible idea for most service providers
What “playing business” looks like and how to stop doing it
Why you don’t need a team to scale — you need systems and productized offers

When We’re Digging Up Our Seeds

At one point, Chelsea hit me with this line that stopped me in my tracks:

“You’re trying to dig up your seeds to make them prove they’ve sprouted.”

If you’ve ever refreshed your analytics dashboard every 15 minutes after posting something you swear was gold… that’s you, friend.

Chelsea broke down the difference between data and information. Data is that one lonely click you’re staring at. Information is the trend you see over time when you zoom out.

In business, we don’t give our seeds time to grow because we’re impatient and want proof. But growth doesn’t happen while you’re hovering over it. The carrot doesn’t sprout faster just because you keep checking.

The Art of Selling (and Why I Fell in Love with It)

Somewhere between comparing gardening to business and laughing about cringey internet content, I told Chelsea the story of the first time I realized I actually loved selling.

I used to be a photographer charging $75 per session. I was undercharging, over-delivering, and terrified to talk about money. So, I changed my approach. I created an experience — wine, cheesecake, music, and framed sample prints.

When I walked out of that in-home session with a $2,700 check, I realized:
I hadn’t “sold” anyone anything.
I’d just helped a family make a meaningful choice.

And that’s what sales actually is. It’s service. It’s empathy. It’s guiding someone toward what will genuinely make their life better.

Chelsea’s Take: Sales Is About Love

Chelsea put it perfectly:

“Sales is about love — love for the product and love for the people you’re selling to.”

If you’re not in love with the transformation your service provides, you’re going to struggle to sell it.

We talked about how so many service providers think they have a sales problem when what they actually have is an offer problem. You don’t need more scripts, you need more belief in what you’re selling.

And stop waiting to feel “confident” — Chelsea says that’s not even the point. You need capacity. The capacity to handle rejection, to stay grounded when someone says no, and to keep showing up even when it feels cringey.

On Being Cringe (and Why I Don’t Care Anymore)

We got real about how “being cringe” is often just the bridge between where you are and where you want to go.

No one dies from being cringe. You can’t flex the muscle of visibility if you never post, never pitch, and never say the thing that might ruffle feathers.

Chelsea and I have both been “cringey” online for over a decade. You know what that’s gotten us? Freedom, consistency, and businesses that actually pay the bills.

Stop Playing Business

We wrapped by calling out one of the most common traps I see service providers fall into — playing business.

You don’t need to build a fake mini-corporation. You’re not Google. You’re not H&R Block. You don’t need departments, you need direction.

Stop hiring for ego. Stop mimicking billion-dollar companies. Build the business that fits your actual goals and life.

You can make wildly profitable money as a team of one — if you know how to sell and if your offer is productized and simple to deliver.

Chapters

00:00 — Late nights, burlesque shows, and Blink-182 hangovers
06:30 — When business feels like screaming into the void
08:45 — Gardening metaphors and the “digging up seeds” syndrome
15:00 — Data vs information: why you’re analyzing too soon
18:00 — Bending time and using art to slow down
22:00 — Sales, storytelling, and art as creative connection
31:00 — My $2,700 photography sale story
36:00 — Chelsea on sales as love
41:00 — Capacity vs confidence
44:00 — Being cringe and visible online
53:00 — Selling as service, not manipulation
1:00:00 — Stop playing business and build what fits you

Resources & Mentions

The Lazy Business Podcast with Jessica Ely

About the Guest

Chelsea Quint is a sales and messaging strategist who helps service providers and founders sell more effectively without selling their souls. Her work blends buyer psychology, storytelling, and nervous system science to help you fall in love with selling.

Connect with Chelsea Quint:

Interested in Being on the Show or Working with Emylee?

Are you a service provider with a bold perspective to share? Apply to be a guest.

Ready to transform your service into a productized, scalable offer? Apply for Sold Out Services.

If you’d like to see a library of all published episodes in a gallery with easy-to-find links to all listening platforms be sure to check out the Sell The Damn Service Episode Library.

Emylee Williams