Now What, Y'all Podcast

Oops! I Almost Built Another Business I Didn’t Even Want


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Hey friends —Okay, I need you to channel your inner Britney Spears for a second because this week’s episode is called “Oops! I Almost Did It Again.”

If you’ve been around here for a while, you know I’ve been borderline obsessive about protecting my time and energy. But that obsession didn’t come from nowhere — it came from burning out so hard that “I don’t give a s**t” became my new life anthem.

So when I tell you that I almost said yes to starting a brand new business venture — even after swearing I was done — you might be thinking, “What the hell, Heather?”Let me explain.

Let’s rewind to 2023.I was just about out of the day-to-day of RSG Sales. You’d think that would feel like freedom, right? But instead, I panicked. I thought, “If I’m not building something new, then who am I?”

So I started a podcast called Boundaries, Business, and Boobs. (Yes, that was actually the title.) I convinced myself it would lead to a mastermind or coaching program… because apparently I didn’t know how to not be busy.

Spoiler alert: I never actually grew the show. I just stayed busy pretending to have purpose.

Then came 2024 — one of the hardest years of my life. I dropped everything and went into survival mode. That year broke me open in ways I didn’t see coming.

Fast forward to early 2025. I started this Substack — Now What, Y’all. It felt different. Real. Creative, but not performative. It’s the first thing in a long time that actually fit.

It even led to this book I’m writing. So yeah — things were finally feeling right.

Until the “shoulds” came back knocking.

Somewhere between book writing and newsletter drafts, I started thinking:“If I have a community and a book, then obviously I should build a mastermind or big event, right?”

That’s what everyone online says, after all.You have to leverage your audience.You have to scale.You have to monetize.

So when a friend suggested we start a mastermind for 7-figure women entrepreneurs — one we both wished existed — it sounded tempting.We talked about it. She even figured out how to start sooner.

And for two whole weeks, I didn’t mention it to Josh.Because deep down, my body already knew — I didn’t want to do it.

When I finally told him, he said, “You should do it. It’s a great opportunity.”And y’all… I burst into tears.

Because in that moment, I realized something: I didn’t want to say it out loud because saying it out loud made it real.

That’s when it hit me: my body knew before my brain did.This wasn’t fear or self-sabotage — it was truth.I could feel it in my gut, my chest, my whole being.

Britney started singing in my head again — but this time it was,“Oops, I almost did it again.”

That, right there, is growth.

Not because the old patterns disappear, but because you catch yourself before you say yes to something that drains you.

Growth is realizing that not every great opportunity is your opportunity.

I’ve aged out of hustle culture.I want ease. Sustainability. Meaning.

Old me would’ve said yes immediately.I would’ve built the thing, resented the thing, and then had to unwind the thing.

But current me?Waited two weeks.Cried instead of committing.And finally listened.

This isn’t laziness. It’s wisdom.The right opportunities make you come alive.The wrong ones make you nauseous before you even start.

So here’s where I’m at:I’m finishing the book.I’m writing this newsletter.I’m recording this podcast.

And I’m building a community — slowly, intentionally — around ease and meaning, not urgency and scale.

A place where the structure supports the life I want, not the other way around.

So let me ask you, friend:What are you sitting on right now that looks perfect on paper but makes you want to throw up in reality?

What “should” keeps circling back that you can’t quite bring yourself to commit to — because your body already knows it’s a no?

The question isn’t whether the opportunity is good.It’s whether it’s good for you.

Your body knows.Your tears know.Your avoidance knows.

Are you listening?

So that’s my Britney moment of the week — the one where I almost fell back into old patterns, but caught myself just in time.

And honestly? That feels like real freedom.

Thanks for being here while I figure this next season out — one honest “no” at a time.

If this episode hit home, would you forward it to a friend who might need the same reminder?Sometimes, permission is contagious.

Until next time —xx, Heather



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Now What, Y'all PodcastBy Heather Roberts