5 Entrepreneur Mistakes I Made So You Don't Have To
Nobody hands you a manual when you start a business. You figure it out as you go — and if you're like most women entrepreneurs, you pay for a few of those lessons in time, money, and more than a little sanity.
This episode is Cara's most honest look at the mistakes she made over 10 years of running a business: the client she let take over everything (and what losing 60% of her income overnight taught her), the shiny object problem she still fights today, and why the to-do list was never supposed to clear in the first place. These are the lessons she wishes someone had handed her at the start — and now she's handing them to you.
These lessons come straight from what Cara teaches inside Chaos Detox — because building a business that works long-term requires more than hustle. It requires knowing which lessons are yours to learn and which ones you can borrow from someone who already paid the tuition.
In this episode, you'll learn:
Why trying to serve every client leads straight to burnout
How to build a client filtering system before you ever get on a discovery call
The 4-question marketing checklist that helps you stop copying everyone else
5 questions to gut-check shiny object syndrome before you click buy (00:07:00)
What a biz bestie with "no expectations of leverage" actually means
Why the to-do list never ends — and the real skill that changes how you work (00:11:31)
The theme day planning method for protecting your highest-priority work (00:12:30)
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Want to read the original blog post that inspired this episode?
CLICK HERE → 5 Tough Lessons I Learned The Hard Way As An Entrepreneur
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Full Episode Transcript
(53) 5 Entrepreneur Mistakes I Made So You Don't Have To
[00:00:00] Nobody hands you a manual. When you start a business. You just jump in with a dream and a vision, and then you probably spend the next several years learning the hard way. What you wish someone had just told you on day one, welcome to Ditch the Chaos. I'm Cara Chace, and this is your space to figure out how to run your life and business without running yourself into the ground.
[00:00:21] Today I am sharing five lessons from my own entrepreneurship journey, the ones that cost me the most and taught me the most. So maybe you can skip a few of the hard parts.
[00:00:32] When you have no entrepreneurial background, meaning you didn't have a family business or learn anything about business growing up.
[00:00:39] You go in thinking the skill you're good at is the business. Before I started my business in 2015, I knew I was a fantastic digital marketer. What I didn't know was that being great at the thing you do and being great at running a business are two completely different skill sets. I started my business because I'd spent a few [00:01:00] years managing social media for the metal band Megadeth and Dave Mustaine, and I knew I had a knack for digital marketing and wanted to help other people in their businesses with it. What I didn't have was any framework for things like client management or knowing when to walk away from work or gut checking the next shiny thing landing in my inbox.
[00:01:20] So I learned slowly. Expensively. And today I wanna save you some of that grief. So here are five lessons that changed how I run my business.
[00:01:31] Lesson number one is not everyone is your client, and that's okay. This is the one that hits hardest when you're first starting out. When you're brand new to a service-based business, you just take the work, any work because bills exist and momentum matters and you just need to get going.
[00:01:48] And I completely understand that phase I lived it. But here's what happens when you try to serve everyone, you end up burning out and watering down everything that makes you good at what you [00:02:00] do. The clients who aren't a fit or constantly ask for more than what's in their contract, drain you in ways that the great clients don't.
[00:02:08] Sometimes you don't find out a client is a bad fit until you're already knee deep in their project, and that's just reality. What matters is what you do when you do figure that out. I had to learn this in the most expensive way possible.
[00:02:23] I let one client I had towards the beginning of my business take over almost all my time. And when I finally recognized it wasn't working and I needed to let them go, I lost 60% of my income overnight. That was a very uncomfortable lesson, but it forced me to get clear on what I really want to be doing, who I wanna be doing it for, and how to build a system that filtered for good fit clients before I ever got on a discovery call with someone.
[00:02:51] After that client, I niched my services down to only what I loved doing. Not everything I could do, just what I actually [00:03:00] wanted to be doing every day. I required potential clients to fill out an application before booking a discovery call, which filtered out most bad fit clients before we even talked.
[00:03:11] And I gave myself a 60 day window. If red flags showed up after onboarding, I had two months to try and correct them or make a decision to let that client go, and that clarity made everything easier. The other piece of this was paying attention to my favorite clients, figuring out what made them such a good fit, and weaving that into my marketing, so I was attracting more of them.
[00:03:35] The clients who were wrong for you will find somebody else. The ones who are right for you are worth holding out for. And remember that when you make the hard decision to let go of a bad fit client, it creates room for a better one to fill that space, okay?
[00:03:50] On a lesson. Number two, you don't have to build your business or market your business the way everyone else says you have to. This one is about [00:04:00] permission. Permission you probably didn't realize You need to give yourself. There's really only one thing you actually have to do in your business, and that's market what you're offering because if no one knows you exist, none of the rest of it matters.
[00:04:13] But how you do it is entirely up to you. I was building a digital marketing agency in 2015, which was genuinely the wild west of social media. There weren't a lot of proven courses, very few scheduling apps, none of the infrastructure that exists now. We were all figuring it out in real time, and what I learned then still holds.
[00:04:35] There is no one size fits all approach to business and marketing. What works for the influencer you follow, or the buzzy mastermind program you're considering may have nothing to do with what works for your business, your personality, or your audience. I've wasted a lot of money signing up for programs and courses that turned out to be a bad fit for me for many reasons.
[00:04:58] I'm never gonna be the person who [00:05:00] spends hours every day in my Instagram dms selling and pushing, but there's more courses than I can count that will tell you that's the way you have to do it. It's crucial to experiment and find out what works the best for you. Some of the best, most creative ideas I ever executed came from outside my industry, entirely, not from watching what everyone else in my space was doing.
[00:05:22] The echo chamber is real and it will keep you stuck, and it will make you a poor carbon copy of everyone else if you let it. So here's the checklist I use when I'm building out marketing strategies that you can ask yourself.
[00:05:36] First, do you enjoy the platform you're marketing on? Because if you hate it and you're only on it because everyone else is, you won't show up consistently and consistency is everything. Second, is your ideal audience really there? It doesn't matter how much you love the platform, if the people you want to serve aren't on it.
[00:05:55] Third, is your brand voice and visual identity clear and [00:06:00] consistent,
[00:06:00] or are you just jumping on trends hoping something will go viral. And fourth, do you have a system for batching your content so you're not starting from scratch every single week or however often you try and batch your marketing if you're struggling with that last one, the batching part. I wanna tell you about something I use called Marketing Magic App. It's an AI powered tool that merges your brand with all the marketing assets you need to create, and it genuinely makes the whole process faster. We're talking, drafting a sales page in two minutes, a marketing email in under a minute, all the social posts you could ever need, everything. I'm an affiliate for it because I love it, and I think it's worth your time to check out. There's a free trial, and I mean truly free. There's no credit card required, no timer counting down until you get charged, so you can take it for a spin and see what it can do for your business.
[00:06:50] I will drop the link in the show notes if you feel like this would make your life easier. The takeaway from lesson two is. Stay true to how you actually want to [00:07:00] show up to market your business. That's the version of the business that's going to last. Okay, onto lesson number three. Shiny object syndrome is real.
[00:07:10] Have your own system for gut checking yourself. This one might be the one that I personally struggle with the most. If you're an online entrepreneur, you see a near constant stream of opportunities that look like the answer to everything. Ad targeting has gotten uncanny and it knows what you're thinking about before you do, and you're probably in that echo chamber with peers who are all on the same email lists, all seeing the same offers, all being tempted by the same things.
[00:07:39] The latest course, the newest app, the AI prompt bundle, the program that promises to solve the thing you've been trying to solve for the last two years, and that dopamine hit when you find something new. It feels like you've solved it. It feels like momentum. It feels like relief, but it usually isn't.
[00:07:58] Most of the time we don't need the [00:08:00] new thing. We need to follow through on what we already have. I'm gonna say that again. You probably don't need a new thing. You need to follow through on what you already have and know. So I built myself a gut check system. Five questions I ask before I buy anything. A course program, a subscription.
[00:08:20] Truly anything first, do I already have a solution available? Most of the time the answer is yes. The problem isn't the tool. The problem is that I'm not using the tool I already have. Second, am I avoiding something? If the urge to try something new, hits right when I should be doing something hard, that's not a coincidence.
[00:08:41] It's avoidance. It's like when I was in college and my apartment was never cleaner than during finals week. It's the same energy. Third, would my future self or future business be doing this? If I'm growing into a new version or an upleveled version of my business, I have to stop doing work that serves the old one.[00:09:00]
[00:09:00] Staying busy with familiar tasks feels productive, and it's often just comfortable. Fourth, will this actually save me time and money? Not hypothetically, but in reality, can I draw a direct line between the cost now and the benefit later? If I can't, it's worth reconsidering. Fifth, am I spending more time planning than doing.
[00:09:22] Planning feels like progress. It has all the vibes of productivity without the vulnerability of executing, putting yourself out there and finding out if it works. Running every shiny object through those five questions takes about five minutes, and it will save you a lot of money and a lot of distraction.
[00:09:39] My biz bestie is also built into my system. We've been doing this together for 10 years now, and she knows my blind spots. I made her an official roadblock. If I wanna try something new, I have to sleep on it and talk to her before I click. By having that external check has saved me probably thousands of dollars and dozens of rabbit [00:10:00] holes.
[00:10:00] Which leads me to lesson four, find a peer with no expectations of leverage. Running a business from home as a solopreneur is lonely in a way that people who haven't done it don't fully understand.
[00:10:14] You are the one making all the decisions all day with no one to gut check you in real time. No coworkers to bounce ideas off of no one who sees the inside of what you're building. Having someone to talk to matters, but the type of relationship matters just as much as having the relationship itself.
[00:10:31] What I'm talking about is a peer, not a mentor, not a coach, not someone in a networking group who's looking to make connections. A peer who genuinely cares about your success and has nothing to gain or lose from it. No leverage, no hidden agenda. Those relationships don't feel transactional because they aren't.
[00:10:51] They feel like someone who knows how you think and can see the things you can't see about yourself. My relationship with my biz bestie has been that [00:11:00] since 2015. We've seen each other through every major pivot, every income rollercoaster, every moment when we were convinced the new direction was the answer.
[00:11:09] We've been a mirror, a roadblock and a cheerleader for each other depending on what was needed at the time. And you can't manufacture that kind of relationship. You can't force it. My honest advice is to stay open to it and be patient with how it unfolds. The right person usually shows up when you stop trying to force it and start just being genuine about where you are.
[00:11:31] Lesson number five, you'll never get through your to-do list. Prioritizing is the skill you need. This one is the one I wish someone had told me before. I spent years feeling like I was failing at productivity. The to-do list never ends. Ask any adult, any professional, any parent, any entrepreneur, the list does not disappear.
[00:11:52] And that's not a failure. It's just the nature of being alive, especially when you're running a business. But here's where it gets tricky for [00:12:00] solopreneurs. When the list feels overwhelming, we tend to gravitate towards the stuff that's easy to check off. The emails, the small admin tasks, the creating the next reel, the things that make us feel like we're moving, and the stuff that would really move the needle, the things that require focus and decisions, those keep getting pushed.
[00:12:21] The skill you need to build isn't getting through everything. The skill is knowing what actually matters and making sure that gets protected and done.
[00:12:30] What works for me is the theme day planning method. It's flexible time blocking, or it's also called task batching. It gives you a real chunk of time with a single focus, so you can get into that flow state instead of constantly context switching.
[00:12:45] This is a foundational piece of what I teach inside my course. Chaos Detox. It's learning how to build your own planning frameworks that flex with your life, not someone else's ideal schedule or template. I'll drop the link in the show notes if you wanna go [00:13:00] deeper on that. And boundaries with protecting your priorities aren't just for work.
[00:13:04] This is the piece people miss if you're running on empty because you've deprioritized your own health. Relationships, sleep. You don't have a productivity problem. You have a priorities problem. No planning system will fix the problem of running on empty all the time. When I help women figure out their real priorities, I use a few questions to cut through the noise.
[00:13:26] Is this essential for my health? Is this essential for my relationships? Is this going to move the needle in my business? Is this something I actually want in my life for my own growth and wellbeing? Anything that doesn't land in one of those categories gets real scrutiny because your time is not infinite and the way you spend it is a choice, even if it doesn't feel like one in the moment. So let's bring this home. Here are the five lessons for entrepreneurship that I learned the hard way.
[00:13:55] Number one, not everyone is your client, and that's okay. Number [00:14:00] two, you don't have to build your business the way everyone else says you have to. Number three, shiny object syndrome is real. Have a system for gut checking yourself. Number four, find a peer with no expectations of leverage.
[00:14:14] And number five, you will never get through your to-do list. Prioritizing is the skill. so Let me give you something concrete to do with these lessons this week with your reset and reclaim action step. Pick one of these five lessons and ask yourself honestly if it's something you need to work on.
[00:14:32] Maybe you've got a client who's not quite right for you and you've been avoiding the conversation. Maybe you keep signing up for things and not following through. Maybe you haven't found your biz bestie yet, and you're navigating all of this alone. Just decide what's most important for you to learn right now and ask, what's one small thing I can do this week that moves me in the right direction of learning this lesson?
[00:14:54] That's it. Just start there.
[00:14:56] And if what came up for you most is lesson number five about how the to-do [00:15:00] list never ends, and you feel like you're constantly putting out fires and totally overwhelmed instead of running your business. That's exactly what Chaos Detox is built to help you with.
[00:15:09] It teaches you the lifelong skill of planning your priorities around your real life and your real energy, not someone else's perfect system. Check it out at carachace.com/chaos-detox.
[00:15:22] If this resonated, come join the Productivity Rebellion. It's my free monthly guide for women in business who are tired of holding everything together with duct tape and coffee. One email a month. Zero overwhelm. It's like tucking into your favorite magazine on Sunday morning. Sign up at Cara Chace.com/productivity-rebellion.
[00:15:41] That's it for this week, and thanks for listening. If this helped, please leave a review. It helps other women entrepreneurs find the show. I'm Cara Chace reminding you to keep questioning the rules and making your own. See you next week.
