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124. Business Nightmares: The Mistakes That Still Haunt Us Today 🎃

We’re serving up something spooky this week on Hustled Up — and no, it’s not ghosts or goblins. It’s the business mistakes that still haunt us to this day. 👀 From hiring horror stories to client communication gone wrong, we’re getting raw, real, and a little vulnerable about the lessons we’ve learned (the hard way).


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This episode is part therapy session, part masterclass in boundaries, and totally relatable for any entrepreneur who’s ever said, “I’ll never make that mistake again.”


💀 The Business Nightmares That Made Us Who We Are

We kicked things off with our biggest and earliest nightmare: hiring without intention. Back when we started our business, our hiring process was basically, “If you can walk, you’re hired.” We heavily blurred the lines between boss and bestie — which made it nearly impossible to discipline, set boundaries, or be respected as leaders. Lesson learned:

Be friendly, not friends. Setting expectations and boundaries from the start isn’t harsh — it’s what keeps your culture healthy and your leadership respected.

Next up was one of the most common mistakes we see other business owners make too: rehiring someone you fired. We get it — you want to believe people can change. But sometimes, it’s better for everyone if that change happens somewhere else.


Then we dove into a scheduling nightmare that still gives us chills: forgetting to add a client to the calendar for her biweekly cleaning. 😱 That single slip-up taught us the value of systems, task lists, and doing things in real time. And, most importantly, it reminded us that sometimes being generous (like offering a free makeup cleaning) can still backfire.


🧼 Protect Yourself: Deposits, Policies & Boundaries



This moment deserves its own spotlight: collect payment methods and deposits up front.


We once sent a cleaner to a deep cleaning, only for the client to turn them away at the door. No payment, no compensation, just wasted time and gas. That experience instantly changed how we run our business. Now, every booking requires:


  • A non-refundable deposit (50% up front)

  • A credit card or bank account on file

  • Clear terms and conditions that protect both us and our team


Since implementing those systems, we haven’t had a single issue with lock-outs and the late cancellations are significantly less. The best part? Clients don’t even blink when it’s presented confidently. Boundaries aren’t scary — they’re smart.


📞 Communication Is Everything

One of our most haunting lessons came from a miscommunication with a client about oven pricing. We learned (the hard way) that tone gets lost in text. A message you think is kind and professional can be read as cold or defensive. Now, when a conversation starts to feel tense, we always move it to a phone call or voice memo. It saves relationships, clears misunderstandings, and keeps things human.


🪞 What We’ve Learned (and What We’d Tell Our Past Selves)

  • Set expectations from day one.

  • Don’t let guilt make your business policies optional.

  • Protect your calendar and your cash flow with systems.

  • Mistakes don’t define you — how you respond to them does.

  • When in doubt, call instead of text.


We’ve made plenty of mistakes, but each one shaped us into better leaders. And if our horror stories can save you a few sleepless nights, it’s totally worth it!


💭 Homework for Our Hustlers

  1. Audit your policies. Do you have deposits and cards on file for all new clients?

  2. Check your boundaries. Are you being a boss or a bestie?

  3. Create your “parking lot.” A place to drop tasks that can’t be done right away (we use a to-do channel in our Discord server!)

  4. Give yourself grace. You’d forgive your best friend for a mistake — do the same for yourself.



🎧 Listen below!


🧡 Join the Conversation

What business nightmares still haunt you? We’d love to hear your stories (anonymously, if you’d prefer!) for a potential Part Two. Drop a 👻 on our latest post or DM us on Instagram @HustleHavenLLC to share your story!

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