Building a Success Mindset When You Hate Being Bad at Things
Most productivity advice skips straight to the system — the template, the framework, the five-step plan. What it leaves out is the part that actually derails most high-achievers: being bad at something new, and having to stay in it anyway.
This episode gets into the real mechanics of building a success mindset for women entrepreneurs — not the Instagram-quote version, but the kind that holds up when your confidence wobbles, a habit falls apart for the third time, and you're already running on empty. Cara shares six strategies pulled from real beginner experiences (triathlons, rock climbing, building a website after telling the drummer for Iron Maiden she could do it) and what each one taught her about learning something hard in the middle of a busy life.
These lessons come straight from what Cara teaches inside Chaos Detox — because building a weekly planning method that actually survives contact with your real life requires the same muscle as any other skill worth developing: the willingness to be bad at it first.
In this episode, you'll learn:
Why the discomfort of learning something new isn't a warning sign for high-achievers
How to build momentum when staring at how far you still have to go feels demoralizing
The confidence reset Cara uses when a skill or habit starts to slip (00:04:15)
What two questions to ask before restarting a dropped habit (00:06:18)
Why copying someone else's system almost always falls apart — and what to do instead (00:05:17)
The "Watch One, Do One, Teach One" framework and the third level most people never reach (00:07:48)
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Want to read the original blog post that inspired this episode?
CLICK HERE → Success Mindset: How to Build New Skills as an Entrepreneur
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Full Episode Transcript
Building a Success Mindset When You Hate Being Bad at Things
[00:00:00] If you are the type of person who would rather not do something at all than do it badly, this one's for you. 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. Today I'm walking you through what building a real success mindset actually requires.
[00:00:21] Not the Instagram quote version, but the kind that holds up when you're exhausted and starting something new and every instinct is telling you to stop.
[00:00:30] I want to start with a confession today. Practice is genuinely hard for me. If I'm not naturally good at something, I just don't wanna do it. Sitting in the discomfort of being a beginner of not having a clue what I'm doing is deeply irritating to me. And if you've taken the strengths finder personality assessment, my number one strength is competition.
[00:00:53] I don't even remember numbers two and three because they didn't win. And yes, I do see the irony in that completely. [00:01:00] So when I say I've had to learn how to be a beginner and sit with that being uncomfortableness, I mean, I've had to work at this in a very real way. Here's the thing, though, I'm not afraid of new things.
[00:01:12] I'm not afraid of change. I've gone from being a senior special agent to a social media manager for a worldwide metal band, to running a Pinterest marketing agency, to business coaching. When I decide to pivot, and it needs to happen, I'm already three steps in before I finish the thought. I get it done.
[00:01:31] But personal changes, lifestyle relationships, learning something that requires me to be genuinely bad at it for a while. That's a totally different animal to me. And I've been a real beginner more times than I can count. Learning to run training for two triathlons, rock climbing, meditation, becoming a mom, and then thinking I had it figured out, and then having a second kid and realizing, no, absolutely not.
[00:01:56] I did not have this parenting thing figured out. I designed a [00:02:00] website after I told the drummer for Iron Maiden that I could do it. Having never built a website before, I've learned how to do watercolors. I'm learning how to eat in a way that heals my body instead of punishing it. And some of those are things that I've accomplished.
[00:02:14] They're done and some are still in progress. And all of them have added something to my life that I'm glad I didn't quit, even when everything in me wanted to, and every single one of them taught me something that I now use and how I run my business and plan my week. So let's talk about what building new skills and a real success mindset actually requires, because nobody tells you any of this.
[00:02:40] The discomfort you feel when you're bad at something new isn't a warning sign for high achievers especially, that resistance is just your brain recognizing unfamiliar territory. It's not a signal to stop.
[00:02:54] The women who build sustainable businesses aren't the ones who skip discomfort. [00:03:00] They're the ones who learn to move through it without burning everything else down in the process. So here's how to do that first. Celebrate step one.
[00:03:08] I was more excited the first time I ran a mile without stopping as an adult in my twenties than I was when I crossed the finish line of an Olympic distance triathlon. That first mile was a glimpse into what I could actually do if I didn't quit, and it mattered more than the finish line months later because it was the moment that I believed I could get there.
[00:03:31] When you're building something new, your brain genuinely needs evidence of progress to stay in the game, not as a feel good tip, as a neurological reality. Staring at how far you still have to go is so demoralizing. Focusing on that first small step in the first win is what keeps you moving. this works for business skills the same way it works for physical ones.
[00:03:53] The first time you meditate for 15 minutes straight, or the first blog post you publish, or the first podcast [00:04:00] interview you land. Those are not small achievements. They're proof of concept. Write them down, celebrate them out loud, and give your brain something to come back to when things get hard. Next, go back to what you know when things get wobbly.
[00:04:15] I learned this one from rock climbing. When I was pushing harder climbs and hitting a wall, I was frustrated. My muscles were giving out. I was ready to walk away. I'd step back and run some easy climbs. I was reminding myself I'm not at square one. I've built real skills and I can get better.
[00:04:34] For entrepreneurs managing burnout, this matters in a specific way. Burnout doesn't just drain your energy, it erases your memory of your own accomplishments. You forget what you've already built. You forget what you know how to do. So when confidence gets shaky and a new skill or habit starts to slip, go back to a step where you were last successful at it and practice there for a while, then move forward.
[00:04:59] Again. [00:05:00] It's not regression. That's how you stay in it long enough to get better. Next, consider getting a coach or a mentor. There is nothing like someone who can show you the way, get you out of your own head and help you see what you can't see from inside. The problem.
[00:05:17] I learned this from triathlon training and starting a business. Running a business can be super isolating. You're surrounded by noise, everyone else's results, everyone else's methods, everyone else's systems, while flying completely solo on the decisions that actually matter.
[00:05:34] A good mentor can help you cut through that, and the right person isn't the one who hands you their blueprint. They help you figure out what your version looks like. Your weekly planning approach, your time management system, your goal setting strategy, that distinction matters because copying someone else's system is how you end up with one that works great for their life, but falls apart in yours.
[00:05:57] Next, strengthen your foundation [00:06:00] before you build higher runners. Call these base building weeks, the long, slow miles that don't feel impressive, but makes the hard weeks possible. Those base building weeks aren't wasted. They're infrastructure that everything else builds on. Productivity habits can work the same way.
[00:06:18] I've built a meal batching habit on Sundays for months, and then dropped it completely and never gone back. When that happens, I've learned to ask myself two questions. Was this actually a habit I'd mastered or was I white knuckling it? And is the reason I started it still true for me.
[00:06:36] Usually what I need isn't to restart the behavior from scratch. It's to revisit the purpose, adjust the routine a little if my life has shifted and recommit. Those moments when a habit falls apart, feel discouraging, but they're actually really useful data.
[00:06:52] They show you where the foundation is still soft or what needs to be tweaked, and that's exactly where to focus. When you build more.
[00:06:59] [00:07:00] Next, at some point you have to realize you've gotta jump. There's no tip that I can really give you for this one. Same as there's no tip that could have helped you jump off the high dive when you are eight years old.
[00:07:10] You just have to do it. Staying in the foundation building phase is useful. It keeps you from quitting. It keeps you building, but it won't get you where you want to go. At some point, you have to try the harder climb, the longer run, publishing the thing before you feel ready, and if it doesn't land, you try again, and the attempt can teach you more than another week of preparation ever could.
[00:07:34] Finally. Watch one, do one, teach one. This framework comes from medical training traditionally, but it maps perfectly into any skill you're trying to build. First, watch or listen to how the thing is done.
[00:07:48] Find someone doing it well and learn from them before you start. Second, do the thing. Then do it again and again until it becomes second nature and you know it inside and out, and [00:08:00] third, know it well enough to teach it.
[00:08:02] That third level is where real mastery lives, because explaining something to somebody else forces you to understand it more deeply than just doing it yourself ever requires. This applies to time management, weekly planning, business operations, self-care routines, anything you're trying to make sustainable, you're not done When you can do the thing you're done.
[00:08:25] When you understand why it works well enough to walk another exhausted entrepreneur through it on her worst Monday. That's where things start to feel manageable. Not in the perfect template or the newest app, but in knowing your own patterns well enough to trust what to do next.
[00:08:43] Here's your reset and reclaim action step for the week. Pick one skill or habit you've been putting off because you don't want to be bad at it. Just do step one, not the whole thing, just the first step. Run one mile. Open the blank document. Set a 15 minute [00:09:00] timer. And then write it down and actually acknowledge that you did it.
[00:09:03] That's the whole assignment. Your brain needs that first data point more than it needs a perfect plan . If this episode resonated, I'd love to have you join the Productivity Rebellion. It's my free monthly guide for women who refuse to choose between success and sanity. Once a month, you'll get one productivity strategy that actually fits your real chaotic life.
[00:09:25] Behind the scenes stories from my month, not Instagram. Perfect advice and the chance to ask me anything. I answer subscriber questions right here on the show. Think of it as your monthly reset for when you're tired of holding everything together with duct tape and coffee. You can sign up for free at carachace.com/productivity-rebellion.
[00:09:45] And PS. If you're ready to stop white knuckling your way through every week, check out Chaos Detox. It's my weekly planning method built for high capacity woman. Learn more at carachace.com/chaos-detox.
[00:09:59] Thanks for [00:10:00] listening. If this helped leave a review, it helps other women entrepreneurs find the show.
[00:10:05] I'm Cara Chace reminding you to keep questioning the rules and making your own.
