When Your Husband Treats Dinner with His Friend Like a Hostage Negotiation
Jo Rawald • March 2, 2025
Stop Letting Old Baggage Run Your Business
This past Saturday, I had to practically shove my husband out the door and, that’s
when it hit me. This is exactly what too many entrepreneurs do with their businesses.
My husband, Brett, had just come home at 4:30pm from a 5-day instructor trip (he’s a 787 Instructor Pilot for American Airlines, which sounds fancy, but basically means he’s been stuck in a flight simulator for almost a week straight). Normally after a trip like that, Brett comes home, unpacks & repacks his suitcase, and immediately becomes one with our couch - remote in hand, fully committed to doing absolutely nothing.
But this time was different.
One of Brett’s best friends, Derek, happened to be in Miami (a half-hour drive from us), and Brett really wanted to meet up for dinner at 6:30pm and a couple of beers before Derek headed home.
Sounds simple enough, right?
Except Brett was circling the conversation with me like he was about to ask permission to go on a bachelor party weekend in Vegas - not wings and beer with an old buddy. We’re talking nervous energy and all kinds of “only if you’re okay with it” disclaimers.
Why? Baggage.
You see, this is Brett’s baggage talking. His second wife, bless her heart (yes, that’s a Southern-term for “that Bitch”), had a whole rulebook for him. No beers with the guys. No hanging out without her. No female friends on Facebook. Basically, if she wasn’t involved, it wasn’t happening.
Me? I’m the opposite. I practically tossed Brett’s shoes at him, handed him his car keys, and told him to go have fun. I love my husband but, I did not sign up to be his one-woman entertainment committee. That’s way too much pressure for any spouse.
So what does any of this have to do with your business? Everything.
Because I see entrepreneurs do this all the time. You drag around someone else’s rules - old baggage from a micromanaging boss, a controlling former business partner, or some Instagram “expert” who declared that if you are not posting 3 times a day, your business is basically doomed.
Let me say this loud and clear. You get to build your business your way.
Want to work 3 days a week and take August off? Do it.
Want to sell your offers like you are telling your bestie about a killer Nordstrom sale? Yes, please.
Want to raise your prices without explaining yourself? Absolutely.
Want to sell your offers like you are telling your bestie about a killer Nordstrom sale? Yes, please.
Want to raise your prices without explaining yourself? Absolutely.
Business isn’t supposed to feel like a never-ending list of “shoulds” and “musts.” You started this thing for freedom - not to recreate the corporate cubicle in your living room.
That’s exactly why I made you something, The Entrepreneur Permission Slip, because sometimes, seeing it in black and white helps you believe it.
It’s your reminder
that you are the CEO, the CFO, the Head of Vibes, and the Chief Decision Maker all rolled into one. So who exactly are you waiting on?
Go ahead - download it, print it, sign it, and stick it where you will see it every single day. And while you're at it, write your top 3 business goals right on it. Because when you stare at your goals every day, they stop being “someday” dreams and start being “get it done already” plans.
And if you are ready for more tools, strategies, or just a real talk session about building your business on your terms, you know where to find me.
Explore my free resources, book a quick call, or just hang out on my site and see what speaks to you.
Whatever you decide, I’m cheering you on every step of the way.
Talk soon,
P.S. If you’ve ever had to unlearn someone else’s “rules” in business, I want to hear about it. Hit reply or drop me a DM. I guarantee you are not alone.
I went to a networking event yesterday at Rosie’s Bar & Grill in Wilton Manors. Tropical-chic to the max. You know the kind of place - upscale casual, strong cocktails, mandatory valet. Now usually, I’m all about valet. But not yesterday. I wasn’t there to sip martinis or hang around all night. I could only stay for 20-minutes. That means - I was on a serious 20-minute mission: say hi, shake hands, peace out. Then, get back in my car to jump on a Zoom meeting! I certainly wasn’t about to drop $20 just to park my car for 20 minutes. No way! I pulled into the valet area, looked the guy dead in the eye, and said, “I’ll be in and out faster than your last relationship. Can I just park it right here?” And bless his heart - he said yes. Honestly, that should’ve been my win for the night. But then I met Sean Gac-Guerrier. Sean’s the Marketing Director at Excel Title, Inc. We started talking about dogs - and **cue the angels singing. We clicked instantly. Not two strangers meeting, more like two childhood friends who hadn’t seen each other in a decade! Sean showed me a photo of his dog, Dottie. I pulled out pics of my girl, Adelaide. Then he pulled out a photo of Dottie that stopped me in my tracks. Sean had a photo of what Dottie would look like as a human. Not a cartoon. Not a filter. I’m talking AI-generated, fully humanized, real-world, cardigan-wearing, intelligent-and-intimidating Dottie. I was mesmerized! It was as if Pixar and the FBI teamed up to design her. I looked at Adelaide’s pic… then looked back at Sean… and blurted out, “I need to humanize my dog!!” And I did. I went home, found the exact AI prompt, uploaded Adelaide’s photo, answered a few fun questions about her personality, and style - then… BOOM. Human Adelaide was born. Tall, lean, cozy-chic, with that unmistakable “don’t-mess-with-me-but-I’ll-still-hug-you” vibe. She looked like she ran Homeland Security and still had time for tacos and espresso martinis on a rooftop. Honestly? I stared at the image for like five minutes. Because it wasn’t just about making something cute. It was about seeing something familiar - something you know - come to life in a new way. Here’s the AI Prompt if you want to try it yourself:
Your business is not a side dish. It’s the main course—and it deserves to be treated like one. In this no-BS blog, I’m calling out “leftover” business strategies that leave women entrepreneurs stuck, stressed, and scaling in all the wrong ways. Discover how to build a business that’s bold, sustainable, and built to outlast trends using my BAMBOO Framework.
Too many women are stuck in the hustle—working nonstop, solving the same problems, and barely seeing the return.
You didn’t start your business to burn out. You started it to break free.
If you’re ready to ditch the stress and build a business that actually pays you back, this is your moment.
Join me LIVE in South Florida at Brains, Brilliance & Bold Moves—where I’ll show you how to scale smart, simplify your systems, and make way more money doing less.
🍷 Dinner, wine, and your profit breakthrough: www.jorawald.com/Brains-Brilliance-and-Bold-Moves
If your business feels like a tornado of to-do lists, dropped balls, and duct-taped systems… it’s not just exhausting—it’s expensive.
Chaos costs you time, clarity, and cold hard cash.
This blog is your wake-up call:
🛠️ Simplify your operations
💸 Stop bleeding profit
📈 Build a business that works for you
Read it. Apply it. Start making smart money moves →
👉 https://siteeditor.thryv.com/home/site/c8e9f361/blog/if-your-business-feels-like-a-hot-mess-its-costing-you-money#preview
You’re not charging too much. You’re not “bad at sales.”
You’re just leaving money on the table—and this blog breaks down exactly how to stop.
If you’re underpricing, over-delivering, or relying on guesswork to grow… you’re leaking profit.
Let’s fix that.
I’m giving you the tools to:
💰 Price like a pro
📊 Package for profit
🎯 Sell with strategy
Read it, bookmark it, share it with your business BFFs →
👉 www.jorawald.com/youre-leaving-money-on-the-table-lets-fix-that
The right clients are watching—but do they actually know what you do?
If your messaging is vague, cute, or confusing, you’re basically invisible.
This blog is your wake-up call to get crystal clear, magnetic, and straight-up undeniable.
You’ll learn how to:
🧲 Attract the right people (without chasing)
📢 Clarify your offer
👑 Show up as the go-to expert in your space
Because your next client isn’t on the fence—they’re just unsure if you are the answer. Fix that here →
👉 www.jorawald.com/the-right-clients-should-be-coming-to-you-theyre-watching-but-do-they-know-what-you-do
One Zoom call. That’s all it took to blow up how I coach—and rebuild it into something way more powerful.
If you’re overcomplicating your client process, trying to “do it all,” or feel like coaching is starting to drain you… this blog is your game-changer.
Inside, I break down:
🔥 The shift that simplified everything
🎯 How I get faster results (without burning out)
💡 What most coaches get totally wrong
If you’re a coach or service provider who’s doing the most and getting the least—read this NOW.
👉 www.jorawald.com/this-one-zoom-call-changed-how-i-coached-forever
If your business isn’t making money… it’s not a business. It’s an expensive, exhausting hobby.
This blog is for the women out here grinding, posting, perfecting—but still not profiting.
It’s time to change that.
Inside, I cover:
💰 Why profit has to come first
🛠️ What to fix if your sales are flat
🎯 How to stop playing business and start running one
This one’s a tough-love truth bomb—with the strategy to back it up.
👉 www.jorawald.com/if-your-business-isnt-making-money-you-have-an-exhausting-hobby
They’re dyeing rivers green for attention—and you’re still “hoping” someone sees your post?
Nope. Not in this business.
Visibility isn’t optional. If you're not making waves, you're not getting paid.
This blog dives into why playing small is costing you BIG and how to show up like a brand that actually wants to win.
Inside, I break down:
🌊 Visibility vs. volume
🎯 Making moves that matter
💡 Building brand authority (without gimmicks)
Your audience is watching—what are you showing them?
👉 www.jorawald.com/they-re-dyeing-rivers-green-what-are-you-doing
Sometimes the best business lessons don’t come from a boardroom—they show up at the dog park.
This blog unpacks a real-life moment with my pup that exposed something big:
Too many women entrepreneurs are overthinking, under-trusting, and second-guessing their own power.
Here’s what I realized (and what you need to hear):
🐾 Your instincts are an asset
🧠 Overanalyzing kills momentum
👑 Leadership starts with self-trust
Don’t miss this one—it’s a mindset reset wrapped in fur.
👉 www.jorawald.com/the-lesson-i-didnt-expect-at-the-dog-park