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161. Would We Do It Again? Eight Years of Business Decisions, Mistakes & Lessons

Writer: Holly Silva
Holly Silva
6 days ago
3 min read

Eight years into entrepreneurship, we’ve made a LOT of decisions. Some were brilliant. Some changed the entire trajectory of our business. And some make us look back and think, what in the actual heck were we doing?! 😂


So for this episode of Hustled Up, we decided to put ourselves on the spot with a game of “Would We Do It Again?”


We’re looking back at some of the biggest decisions we’ve made since starting Chores & More in 2018 and asking ourselves one simple question: knowing everything we know now, would we make the same choice? And whew. Hindsight is a beautiful thing.



💗 Would We Do It Again?

We’re revisiting decisions from nearly every stage of building our business — from those scrappy early days when we were figuring everything out as we went, to becoming employers, building a team, expanding our services, creating additional brands, and becoming the business owners we are today.


We get into questions like:

  • Would we go into business with our best friend again?

  • Would we keep the name Chores & More?

  • Would we choose the same branding?

  • Would we price our services the way we did when we first started?

  • Would we hire our first employee when we did?

  • Would we hire friends or family?

  • Would we join a coaching program again?

  • Would we move into an office?

  • Would we offer so many different services?

  • Would we have put policies and boundaries in place sooner?

  • Would we fire employees—or clients—sooner?

  • Would we start the Hustled Up podcast again?

  • Would we launch The Hustle Haven the same way?

  • And the BIG one: knowing everything we know now, would we start Chores & More all over again?


Some of those answers came to us immediately. Others were a whole lot more complicated.


✨ The Mistakes Were Part of It, Too

One of the biggest things this conversation reminded us of is that building a business isn’t about somehow making every decision correctly the first time. We’ve underpriced ourselves. We’ve struggled to set boundaries. We’ve kept employees longer than we should have. We’ve learned leadership lessons the hard way. We’ve gone through seasons where money was terrifyingly tight, systems basically didn’t exist, and we were figuring things out in real time.


Would we want to relive every one of those moments? Absolutely freaking not. 😂

But those experiences also gave us thicker skin, better systems, stronger boundaries, and a much clearer understanding of the kind of business — and business owners — we wanted to become.


Sometimes the decision you’d never make again is also the decision that taught you the lesson you needed most.


🎧 Play Along With Us!

Whether you own a business or not, there’s a little something in this episode for everyone. Think about the decisions that got you where you are today. What would you do exactly the same? What would you change? And what would you NEVER freaking do again?


Come hang out with us for a funny, reflective, occasionally unhinged trip through eight years of entrepreneurship — and all the lessons we picked up along the way.


🎙️ LISTEN TO EPISODE 161



💗 CONNECT WITH US


Have a topic you want us to cover — or want to tell us about the business decision you'd never make again? Email us at hustleduppodcast@gmail.com. ♡


Don't forget to rate, review & subscribe to Hustled Up wherever you listen! 💗

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