#ActuallyICan

Growing Pains: Why Business Growth Feels Uncomfortable (And What To Do About It)

business growth,grow your business, how to grow your business, fear of success, embracing discomfort, overcoming self doubt

Ever felt like the moment you start seeing business growth, things suddenly feel harder instead of easier? 

Like you’ve finally hit a new level, but instead of feeling excited, you’re questioning everything? You want to grow your business—but why does it feel so uncomfortable when it actually happens?

In this episode, I’m breaking down why business growth feels messy, why hitting that next level brings up all kinds of doubts and fears, and most importantly—how to grow your business without letting the discomfort derail you.I’m sharing my own struggles with feeling stuck, battling the fear of success, and learning to reframe challenges as a sign I’m on the right path. If you’re feeling stretched, second-guessing yourself, or tempted to retreat to what’s safe, this episode is for you.

Inside this episode, I’m diving into:

  • Why business growth brings discomfort—and why that’s actually a good thing
  • The sneaky ways fear of success shows up and keeps you stuck in old patterns
  • How to tell the difference between normal growing pains and a sign you need to pivot
  • Why embracing discomfort is essential if you actually want to grow your business
  • The key mindset shift that will help you stop overcoming self doubt and start taking action

Here’s the deal: The moment you stop chasing comfort and start embracing discomfort, everything shifts. And that’s exactly what we’re unpacking in today’s episode.

DM me on Instagram @katyripp and tell me: what’s one way your business growth has felt uncomfortable lately? Let’s talk about it—because I promise, you’re not the only one feeling this way.

And if you’re craving support from a community of women who get it, join us inside Actually, We Can—my private space for midlife women entrepreneurs who are ditching the fear of success and ready to approach business growth in a way that actually feels good. 

RESOURCES MENTIONED IN THIS EPISODE:

Actually, We Can Community

Female Founders Collective

CONNECT WITH KATY RIPP: 

Website: www.katyripp.com

Instagram: @katyripp

Pinterest: @katyripp

Facebook: @katy.ripp

EPISODE TRANSCRIPT:

Katy Ripp 00:00:00  Hey there. Welcome back. My name is Katy Ripp and you are listening to #ActuallyICan. This month we’re talking all about growth. Growth in our businesses, in our personal lives and how we show up for what we truly want out of life. And here’s the thing about growth it really just doesn’t always feel good. I know that sounds counterintuitive. We absolutely want growth, right? We set big goals. We dream about more income, more money, more impact, more freedom, more flexibility. But when that growth actually starts happening, that’s when the discomfort kicks in. And believe me, I have felt this. I’ll be honest, when I’m not instantly good at something, my first instinct is to quit. I like to be great at things. I like to set a goal and hit it. I like to put something out there and see it take off. So when that doesn’t happen, one event doesn’t feel when a launch flops or when I don’t hit my revenue goal, my gut reaction is, well, that’s it, fuck it, I’m done.

Katy Ripp 00:00:53  Clearly, that wasn’t meant to be. And I know I’m not the only one that feels that way. So today we’re diving into why business growth feels uncomfortable. how to reframe that discomfort into something productive, and what you can do when growing pains make you want to run back to what’s familiar. So let’s get into it. Hey there. Welcome to #ActuallyICan, this is a podcast where us female entrepreneurs are going to ditch the hustle culture, build value based aligned businesses, and finally charge what we’re worth. I’m Katy Ripp, a serial entrepreneur, business mentor, rule breaker, and your go to guide for building a profitable business on your own terms. Around here we do things differently. No hustle for hustle sake, no playing small and definitely no more following antiquated business rules that, clearly were not made with midlife women in mind. Each week I’m here to ask the hard questions, share the advice that’s actually worked for me, and bring on a guest or two who decided to say, fuck it.

Katy Ripp 00:01:52  Actually, I can do this my way. Expect bite size, high impact episodes ranging from about 25 to 45 minutes, packed with real strategies, mindset shifts, and rule breaking business insights. If you are tired of business feeling like an endless to do list and you’re ready to make more money without burning out and feeling guilty, you are absolutely in the right place. Let’s go. Why does Business Girl feel so uncomfortable when we talk about growing pains? I’m guessing a lot of us are thinking about kids literally outgrowing their shoes, or their clothes, or even their beds, or their knees, or their joints hurting. And guess what? Business is exactly the same. When your business grows, you outgrow things to your old mindset, your comfort zone, even certain habits or ways of working that used to serve you. And that process is super messy. And here’s why it’s messy. Growth challenges your identity. If you’ve been used to operating in a certain way, and suddenly you have to step into a new version of yourself, by yourself, that’s super uncomfortable.

Katy Ripp 00:03:01  and nobody else really knows unless you’re sharing it every step of the way. So it can also feel super isolating. Growth requires new skills all the time, and maybe you’ve mastered what got you here, but now you need to learn things like delegation, or hiring, or scaling, or upping your visibility, or asking people for help. Again, super uncomfortable. And then growth also means, of course, letting go of control, that elusive control. The more your business grows, the less you can do everything yourself. And that’s super uncomfortable because it probably means asking for help in. The worst part of this is our brains are wired to resist change, to protect us even when it’s good change. She’s like, no, we know we don’t want that. That’s different than what we’re used to. It’s our brains number one job to keep us safe. And when it senses the unknown, it sends up warning signs like, whoa, whoa, whoa, This is too much. Or what if I fail? Or who am I to be doing this? Here’s the thing.

Katy Ripp 00:04:07  Discomfort does not mean stop. It means stretch. And I had to learn that the hard way. There was a time. And if I’m being totally honest here, which I like to be. It still happens when I’d set, like, a big business goal, maybe a certain number of attendees for an event or a financial target, or even something as simple as growing my audience. I’d put in the work I do, all the things I’d get aggressively creative, and then crickets. Maybe the numbers weren’t what I hoped for. And of course, the numbers were only realistic, like I wanted to sell out in the first two minutes. I’m not Taylor Swift, or maybe the response was super underwhelming. Maybe I felt like I was screaming into the void. Nobody was hearing me, the algorithm fucked me, etc. etc. but my immediate thought is always if this is hard, maybe it’s just not meant for me. But isn’t that what we always tell ourselves? That if something is right, it should flow.

Katy Ripp 00:05:03  It should flow easy. It should be. Without obstacles. Except that’s really not how growth works. And of course, I had to have a serious conversation with myself. Am I quitting because this is genuinely not aligned with me, or am I quitting because I don’t like being bad at something? Oof, this one stings for me because truthfully, most of the time it really wasn’t about alignment for me. It was about my ego. It was about my fear of putting in an effort and not seeing results immediately. And here’s what I’ve learned. And I’m still learning every day. Not seeing instant success doesn’t mean you’re failing. It means you’re building something real on a strong foundation. And that brings us to the most important mindset shift we have here. If discomfort is inevitable, the question becomes how do we move through it instead of letting it stop us? And here’s a few ways to do that. Recognize that discomfort actually equals expansion. Instead of thinking this feels hard, which again is just a feeling and it will pass.

Katy Ripp 00:06:06  I must be doing something wrong. Try. This feels hard because I’m stepping into something bigger than before, or I’m stepping into something I don’t know everything about, and I’m still learning. Separate your fear from intuition. We’ve talked about this before. Fear is that gut reaction that shows up when something is new and unknown. Intuition is the deeper knowing of what aligns with you and what doesn’t. So fear says, what if I fail? Intuition says this is actually not right for me. Your job is to learn to tell the difference. Then ask yourself what’s actually at risk here. Most of the time, the worst case scenario is really just not that bad. You make a bold move in business and maybe it doesn’t work out exactly as planned, but that doesn’t mean you’re doomed. No, adjust and you pivot and you keep going. And the Grand Puba, Remember, what got you here is not going to get you there. Every stage of business requires a different version of you. And what worked when you were just starting out will not work when you’re scaling.

Katy Ripp 00:07:12  And let’s talk about that. Why the mindset and strategies that got you here just will not be the same ones that get you to your next level. Let’s say when you first started out your business, grinding was totally normal. You were doing everything. You were marketing, client work, social media, customer service, bookkeeping. You’re the janitor, you are all of it. And maybe you’re still in that grind mode. And that’s totally cool. You’re saying yes to every opportunity, and you’re taking on all kinds of clients and hustling hard just to get your name out there and just to pay the bills. That’s part of the process, and it’s the survival stage. I’ve been there, I get it. If you’re still there, bless you. But here’s where a lot of people get stuck. They try to scale using the same grind mode tactics that they use to start their business or start their venture, and that’s where things break down, because the skills and habits that helped you build the actual foundation are not the same ones that will help you grow sustainably.

Katy Ripp 00:08:09  The mindset shift from hustling to leading is a difficult one, and sometimes we don’t know we’re quite there. But when you start to feel that shift into growing and I really want to grow my business, we have to shift our mindset from doing it all to delegating and actually leading again. In the early days, you wear all the hats, but as your business grows, you have to start letting go of some of those tasks and dare I say it, control. This means hiring. It means outsourcing. It means automating. It means all the things that might feel scary because they require trusting others and also paying dollars. The challenge is you have to stop equating doing everything with being successful. We also have to move from saying yes to everything to saying yes to the right things. When you first start out, we’re all in. We have to take every opportunity mode. You don’t want to turn work down or leave money on the table again. Totally get it. But growth actually requires focus. At some point, you have to shift from taking anything to choosing what actually moves the needle.

Katy Ripp 00:09:16  This was a hard lesson for me. I’ve had to cut the fat on many, many things that I thought if I just put a little bit of effort here and a little bit of effort there, I had to really focus on one thing. Now, this might mean raising your prices. This might mean doubling your prices. So you’re doing half the work for the same amount of money. Or it might mean tightening your niche, going a little bit further down into a focus of people that you actually need to serve, or saying no to projects that really just don’t align with you or your values anymore. And then we need to go from chasing more to finding what actually works. That early stage of business is about testing and experimenting and research and development. You throw all the shit at the wall to see what sticks. But once you’re growing, your job isn’t to add more, it’s to refine. Instead of launching five new offers, five new products, five new services, you optimize the things that are actually already working for you.

Katy Ripp 00:10:13  Instead of chasing more followers, you focus on deeper engagement with the audience you already have. So think about this as casting a deep net versus a wide net here. Listen, I get it. That fear of letting go of hustle mode. We struggle with this. This is a shift because hustling feels really safe. And to be honest, we get reward from this when you’ve spent years grinding and doing it all and saying yes to everything, it becomes part of your identity. I really struggled with this. I have people say to me all the time, I don’t know how you do it all. And I got dopamine hits from that. And I started to believe if I’m not constantly working, will my business fall apart? Or what does that say about me as a person? Does it make me lazy? But your next level requires trust. It requires trusting yourself to make smarter and more focused decisions, trusting that you don’t have to work harder, just better. It’s the difference between being a worker in your business and being the CEO of your business.

Katy Ripp 00:11:18  This is that working on your business versus working in your business, the managing owner, to the silent owner. And that’s a real challenge of growth. It’s not just about external success, it’s about who you have to become in order to handle it. I love this idea of thinking about who you have to become to reach the next level. Think about it like this. If you’re training for a marathon, even A5K, the way you run as a beginner isn’t how you train. Once you’ve decided to run a race in the beginning, you’re just focused on getting moving, right? Maybe you want to get up to a place where you’re walking 30 minutes before you can run a minute. You run when you can. You build endurance, and you just try to keep going without collapsing. But as you get more serious, you have to shift how you train. You start focusing on strategy, not just effort or putting more miles on. You optimize your breathing. You adjust your nutrition and refine your pace.

Katy Ripp 00:12:12  You don’t just run more. You run focused. You run smarter. Business growth is just the same when you’re starting. You’re just trying to stay in motion. You say yes to everything. You take every opportunity and hustle to keep your business alive. But if you want to scale, you have to start running your business like an experienced athlete. Instead of saying yes to everything, you get intentional about what actually moves the needle. Instead of trying to work harder, you focus on efficiency, delegation, systems refinement. Instead of chasing every new idea, you double down on what’s already working and make it better. And most importantly, you stop seeing rest as weakness. If you never stop to recover, you will burn out before you ever reach the finish line. So ask yourself, are you still running your business like a beginner, even though you’re ready for the next level? Because who you were when you started this business is not who you need to be to grow it. And if you’re feeling the discomfort in that shift, it’s not a sign that something is wrong.

Katy Ripp 00:13:13  It’s proof that you’re evolving. And if you’re in that weird, uncomfortable stage of growth where what used to work isn’t working anymore, ask yourself, what am I doing that I needed to do in the beginning? But it actually no longer serves me. Am I making decisions from a place of fear? Staying in the hustle grind mode or from a place of strategy? Focusing on growth and taking breaks? Who do I need to become in order to step into this next level? Grinding is just a stage, but growth is the goal. And the moment you recognize that, you don’t have to keep struggling just because it’s familiar, that’s when things really start to shift. Okay, so you’re in it. The messy middle of growth where things feel really uncertain. You’re questioning everything. You don’t trust yourself and you’re wondering why you ever thought this expansion was a good idea. This is a very dramatic point. So what now? Pause. But don’t retreat. It’s okay to take a moment to recalibrate. Don’t go backwards to what’s safe just because it feels familiar.

Katy Ripp 00:14:16  Just take a beat, but don’t retreat. Okay? Find proof that you can do hard things. We all love Glennon Doyle. I’m a fan. The we can do hard things is not actually running the race. It’s training for the race. Look at your past. How many times have you been scared of something? Done it anyway and come out stronger. These can be little things too. Maybe you like. Didn’t want to go to a yoga class. And then he went to the yoga class and he felt super good after it, but it was still scary. Use that as evidence that you will get through this. The discomfort is just a feeling and feelings pass. Lean into your community. You do not have to navigate this growth alone. This is why I created. Actually we can because surrounding yourself with people who are also growing makes it easier to keep pushing forward. We need people to be in our corner. We need people to be rubbing our shoulders and be like, it’s okay, it’s okay.

Katy Ripp 00:15:10  You’re going to be able to make it. Let’s go, let’s go. Get back in that ring. We need that as we come to the end of March. We’re still going to talk about growth. I promise you, growth is never going to feel easy. But you were not built for easy. You were built for expansion. Owning your own business or starting something new is not for the faint of heart. We are a special breed of people. So here’s my challenge for you. Do one thing this week that stretches you beyond your comfort zone. And if you’re craving a community that gets it and will also help push you, I want you inside. Actually, we can DM me on Instagram and tell me what’s one way your business growth has felt uncomfortable lately? Let’s talk about it because I promise you, you are not alone in this. Thank you again for listening and always being here and I will see you next time. Well, that is a wrap on today’s episode, but the conversation doesn’t have to end here.

Katy Ripp 00:16:05  If this episode resonated with you at all, come hang out with us inside, Actually, We Can. This is my private community for midlife women entrepreneurs who are just done with the hustle and ready to build businesses that actually work for them. Inside, you’ll find support and strategy and a whole lot of real talk from women who get it. You can join us at katyripp.com/community. We can also stay connected on socials. You can follow me on Instagram at Katy Ripp for behind the scenes extra insights and plenty of business wisdom. But most importantly, make sure you follow the podcast so you never miss an episode. If you love today’s topic, please leave me a review and share it with another badass woman who needs to hear this. As always, thank you for being here. Now go do your thing and I’ll see you next time.

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