#ActuallyICan

Dear Katy, I want to start my own business, but I’m scared I’ll fail!

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I'm Katy

Here I spill the tea on balancing hustle and heart with tips and tricks for thriving in business while taking care of yourself, because success is best served with a side of serenity!

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Ever found yourself dreaming about starting something new, but the fear of failure keeps you stuck?

In today’s Dear Katy episode, I am back with my friend Janna to tackle those exact fears that hold us back from launching a business. We dive into a listener’s dream of ditching a job she can’t stand to open a cozy bookstore café and offer some real, practical advice on how to push past the fear that keeps so many of us from taking the leap.

Janna and I get real about our own experiences, sharing personal stories and breaking down the small, actionable steps that help you move forward. 

Tune in to hear us chat about:

  • How fear of failure can hold you back from your dreams and what you can do about it
  • Balancing fear and passion when chasing a big goal
  • Practical steps to conquer doubts and start taking action
  • The reality behind running a business vs. the romanticized version we often hear about
  • Why failure isn’t the end, but a stepping stone to growth
  • Our personal stories of facing fear and making bold moves

It’s time to stop dreaming and start doing. Join us for this episode and let’s take that leap together!

RESOURCES MENTIONED IN THIS EPISODE:

Midlife on Purpose: Workbook

CONNECT WITH KATY RIPP: 

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Facebook: @katy.ripp

EPISODE TRANSCRIPT:

Katy Ripp 00:00:00  Everything in life is on some kind of scale between fear and love. Period. Fear is the ultimate thing that holds us back. Love is the ultimate thing that keeps us going forward. 

Hey there fellow rebels, welcome to #ActuallyICan, the podcast where we say a hearty hell yes to designing life on our own terms. I’m Katy Ripp, a lifestyle coach, business mentor, and serial entrepreneur here to guide you through the wild ride, defining what society expects of us and embracing our authenticity. On this show, we dive deep into taboo topics like death, money, spirituality, entrepreneurship, unapologetic self-care, and personal development, all while swearing and laughing along the way. Expect down and dirty conversations, plenty of humor, and a whole lot of exploration, leaving you feeling empowered to be your truest self. Whether you’re craving a good laugh, seeking unconventional self-care tips, or simply looking for some camaraderie, you’ve come to the right place. We only get this one short life. So buckle up and let’s design yours on our own terms.

Katy Ripp 00:01:08  Ready to dive in? Let’s go. Hey there. Welcome back to dear Katy. Your shoes are cute. Janna and I are here talking about her shoes. These are Stitch Fix my whole world, the Stitch Fix. I know it.

Janna 00:01:24  Works for you, I love it.

Katy Ripp 00:01:26  Yeah, actually, my whole outfit right now is from Amazon, but I love Stitch Fix. Yes, I just like I love everything about it. I’ve had it for years. I tried it for a while and then I was like, this is not working right? Like they were sending me stupid blouses that made me look like 82, I know, right? Like it was just not good and nothing really fit, right? And then I tried again and I kept everything on the first box. I was like, oh, this person sees me and now I just, I love it. Every single thing I get, I just kept it into, oh, my shoes are from Stitch Fix. Every single thing I get almost I keep.

Janna 00:02:01  That’s impressive. They probably are looking at, like, what you’ve previously captured. Yeah, it’s.

Katy Ripp 00:02:06  Just an algorithm, right? Those aren’t real.

Janna 00:02:08  People. Or maybe you’ve toned in your description. I’m always looking for work appropriate things, but I struggle because I still like to have, like, an edge in my workwear. Yeah.

Katy Ripp 00:02:18  Can you wear jeans?

Janna 00:02:19  Well, I did today. Okay.

Katy Ripp 00:02:22  Because you look so cute today.

Janna 00:02:23  Thank you. Oh, because it’s Friday. It’s Friday, and I was literally the only person on my floor because it’s.

Katy Ripp 00:02:29  So nobody was telling you you couldn’t wear jeans.

Janna 00:02:31  I mean, nobody tells me, ever. But it’s just like, kind of not. It’s frowned upon. It seems in my department, nobody wears denim, which is just a sad state of affairs. I just love denim. It’s just like I’ve gotten into denim.

Katy Ripp 00:02:47  In the last like, three years, I would say, because I lived in yoga pants. Yeah, I mean lived.

Katy Ripp 00:02:53  And then I was like, I sort of feeling better about my body. And then I was like, once I started feeling better, I was like, oh, I kind of want to dress it right? Like, yeah, throw a little lipstick on. And then it got to a point where I was like, still just kind of wearing a uniform everyday of like hoodies and yoga pants and whatever, like athleisure.

Janna 00:03:14  Athleisure, athleisure.

Katy Ripp 00:03:16  Yes. I was wearing that every day. And then I was like, I should probably like try to make myself up a little bit. And so now I’ve gotten into a little bit more.

Janna 00:03:24  Yeah, you look adorable every time I see you. You look great.

Katy Ripp 00:03:27  Thanks. I mean, I look up to you for my fashion, so.

Janna 00:03:30  Oh, thank you, I really do, I really.

Katy Ripp 00:03:33  Do. I think you have a great fashion style. You always have, though.

Janna 00:03:35  Always, always. If I could wear denim every day, that would be the happiest.

Janna 00:03:40  I mean, there was maybe a wind suit.

Katy Ripp 00:03:42  In there that maybe in seventh grade.

Janna 00:03:44  That was not great, but, you know, or my hippy years, those are the ones we can.

Katy Ripp 00:03:50  We still made hippie look good like you were committed to hippie at least.

Janna 00:03:53  I mean, I my, some of my very good friends call my stages like Barbie, like I was a Barbie before Barbie became like this generation of like I went through Cheerleader Barbie, then I was hippie Barbie. Barbie? Yeah, I did Hippie Barbie for a long time, and then I was.

Katy Ripp 00:04:16  How long do you think you were in Hippie Barbie?

Janna 00:04:17  I think like five years, like all through high school and maybe the next year after. And then I became Mountain Guide Barbie when I moved out west. Yeah, yeah, yeah. Then I moved home, and then I was Biker Barbie. Uhhuh. For a while.

Katy Ripp 00:04:31  Yeah, for sure.

Janna 00:04:32  Teacher Barbie, Teacher Barbie. And then from then on, I’ve been mom Barbie.

Janna 00:04:38  Oh, I was a librarian. Librarian Barbie. That one. Yeah, but, like.

Katy Ripp 00:04:41  Still sexy, like.

Janna 00:04:43  Sexy leg.

Katy Ripp 00:04:44  Librarian. Yeah.

Janna 00:04:45  So the stages of I.

Katy Ripp 00:04:47  Like this stage fits you the best, I think you. Yeah.

Janna 00:04:50  Like the the denim, the edgy. I went to get new denim the other day because I have an embarrassing amount of denim. And I always want kind of weird talking in a different decade about validation. I opened the curtain because I it was a pair that I it’s not typically my style and it was a younger woman. It was at Madewell which I love their denim. If you haven’t tried their denim and she’s like, you look snatched. And I’m like, yeah, I do.

Katy Ripp 00:05:22  Okay, thank you very much. What what kind of denim?

Janna 00:05:26  They’re kind of like the ones you were in today. They were high waist curvy and then they were wide leg crop. But it was just the weight. Getting the curvy was significant because I have a large rump and my waist is smaller than my body and it like snatched it in and like that.

Janna 00:05:47  Yes, it was amazing. So I left there. I text my cousins the link to get these denim and I said, everybody needs these. I wrote, you all need to be snatched. Snatched up Oh my God, that’s so funny. Because snatch deeds means a very different.

Katy Ripp 00:06:04  Thing in my world.

Janna 00:06:05  Right? 100%. I won’t give you the story, but yes, when we were younger. Yeah, we’re.

Katy Ripp 00:06:10  Really like mans now in snatch means.

Janna 00:06:13  Exactly 20 years ago. That is not what it meant. Even seven days before I went to Madewell, it was not what it meant.

Katy Ripp 00:06:23  But now we’re embracing Snapchat.

Janna 00:06:25  Yeah, so there we go.

Katy Ripp 00:06:27  Oh my God, that’s so funny. Yes, I actually texted Janna right before I left for the Billy Joel and Stevie Nicks concert, because I got a pair of wide leg jeans so good in my Amazon box, and I like them. They fit good. I think that they’re wrong for me, but they’re not.

Janna 00:06:44  They’re perfect.

Janna 00:06:45  They’re so cute.

Katy Ripp 00:06:46  I, I walked out and I told my sister she’s like, oh, those are different jeans for you. Which, you know, whatever. And I was like, yeah, nobody complimented me at work today. So I kind of feel because usually they do, right. Like I walk in every day and they’re like, oh, what’s that from Stitch Fix? It’s so cute, right? Because I’m like a Stitch Fix junkie and I usually get a like compliment or two on something, and I didn’t. The day I walked in, I was like, this is probably not a good idea, but I’m going to do it anyway.

Janna 00:07:17  I’m glad you did. I think that’s.

Katy Ripp 00:07:18  Great.

Janna 00:07:19  Thank you. I’m here for it, dear Katy, here we go. All right. Got it.

Katy Ripp 00:07:23  I have not read this one yet. Right. No, you.

Janna 00:07:25  Have it going in blind here. I have always dreamed of opening a cozy bookstore. Cafe? A place where people can escape into books while enjoying a cup of coffee.

Janna 00:07:35  I have a vision for creating a community space, but I’m terrified of failing. What if no one comes? What if I can’t handle the business side? This fear keeps me stuck in my unfulfilling job. How can I overcome this fear and bring my dream to life? Warmly? Dreamer in doubt. Oh, I love it.

Katy Ripp 00:07:56  Dreamer and doubt. Oh you know this is my jam Yes.

Janna 00:08:02  This is you like. I mean, not you, but like. No, I didn’t write it. But I’m saying this is business c r and but.

Katy Ripp 00:08:10  It also is you because it’s stuck.

Janna 00:08:14  Yeah. You stay at the job. That sucks your soul. I know that life. Is there a way for our listener to do an and instead of an or so like, potentially stay at your unfulfilling job just until you feel confident enough to leave and find a space to open, you can like take steps. You don’t have to open the grandiose. Yeah, you don’t have to leave your.

Katy Ripp 00:08:44  Job in order to start.

Janna 00:08:46  Yeah, or grow it. So maybe somewhere smaller and then grow into something bigger. And is there I mean.

Katy Ripp 00:08:54  The fear of failure. Here is the question, right?

Janna 00:08:57  What if no one comes? Well, first of all, what if I can’t handle the business side? How can I overcome the fear? Yeah. From bringing my dream to life. And I think you’re good at talking about fear, right?

Katy Ripp 00:09:11  Because that is the thing that holds us all back. Period. So everything in life is on some kind of scale between fear and love. Period. Fear is the ultimate thing that holds us back. Love is the ultimate thing that keeps us going forward. And lots of people have fear of love, so that’s a real problem. But what is the fear of? Like you have to figure out what the fear is. So is the fear of failure. Okay, well what’s the worst thing that can happen? That’s what I always go when people say, I’m going to fail, right?

Janna 00:09:47  What’s what’s the going to debt? Yeah.

Katy Ripp 00:09:49  Like what’s the fear. So I’ve done this a couple of times with like speaking engagements. One of the speaking engagements I had was like 75 women. It was amazing. And I said, what’s everybody’s biggest fear? And it was to a bunch of entrepreneurs or people that wanted to start something. And I said, well, what’s everybody like? Somebody yell out their biggest fear? She said, failure. And I said, okay, what are you scared of? Well, what if it doesn’t work? What if it doesn’t work? Like, what will happen if it doesn’t work? And what does that mean? What does it mean when it doesn’t work? So let’s say you put $50,000 into a new business. That sounds like a lot of money. And it is a lot of money to a lot of people. But in the business world, $50,000 isn’t that much money. But let’s say you put $50,000 of your own money and you start it and it fails. Well, first of all, usually it won’t fail in the first six months, right? Like you’re going to put all of your energy and time and money into it.

Katy Ripp 00:10:44  But let’s say it does fail and you lose all your money, and then you don’t go get a job. You just lay in bed because you’re so depressed from the failure that you just lay in bed. You don’t do anything else. And the bank comes and takes your house, and the bank takes your house, and now you’re homeless, right? Because you haven’t gone out and gotten another job, your husband or spouse or whoever you depend on for the other source of your income hasn’t done anything either. Like, you’re both just like laying around sad that you’ve failed at this job. The bank has taken your house and now you have nowhere to live. And let’s say you’ve got a couple of kids in tow. So now nobody’s working. And you’re like, sitting on the side of the road in a box and you are homeless. That’s the fear. Like that’s the fear. People think that they’re going to go straight from opening a business to living in a cardboard box.

Janna 00:11:41  I could yes, I see.

Katy Ripp 00:11:42  Is that fucking reality? No. Are your parents going to let you go into a cardboard box with their grandkids?

Janna 00:11:49  Yeah. No.

Katy Ripp 00:11:50  I wouldn’t let you do that. Do you have friends that would let you and your husband and your son and all your kids go, and your two dogs live on the side of the road, like be at a stoplight asking for money?

Janna 00:12:02  No.

Katy Ripp 00:12:03  Right. So, like, we have to remember that we’ve cultivated enough relationships over our lifetime. And if we’re good people, which most of us are, if we’re good people and we’ve cultivated relationships, they might say, I told you so, but they’re not going to let you die on the side of the road and let your kids starve to death. And what I said to this group of 75 women is look to your left and look to your right. Are you going to let that person in their family die on the side of the road? No. You’re going to figure out a way to take them in.

Katy Ripp 00:12:36  So what we do is we jump from the fear of failing to, I’m going to die because of this, or I’m going to be broke and homeless. That’s not the fear. The fear is likely the judgment that if you don’t make it, somebody’s going to say I told you so, somebody’s going to say I found you out, somebody’s going to say you tried and it did not work. You didn’t have it, you didn’t have the skills. You didn’t try hard enough you didn’t like. They’re gonna push all those buttons that you’re already pushing on yourself. And in reality, nobody’s actually going to say it to your face.

Janna 00:13:14  Right?

Katy Ripp 00:13:15  They might say it behind your back because they don’t have the balls to say it to your face, or they might go behind the keyboard and say it. But as long as you’re living in your truth and you’re doing the thing that you set yourself up to do and you are aligned with your values, there’s no failing and I have failed. I can’t even tell you how many things I’ve tried and failed at and everything I failed at.

Katy Ripp 00:13:37  I’ve learned something from every single time I tried to quit drinking, I learned something. Every single business I’ve tried to open and didn’t work. I learned something about myself, about that thing. So really like diving and pulling back the layers of what you actually scared of. Because the thing we’re actually scared of is not usually the thing that’s going to happen, right?

Janna 00:14:00  That’s a great point. I also think that More urgently, our dreamer in doubt could just start putting pen to paper. Yes. Get it out there. Yeah. How much would it cost to get the real numbers on there before you even doubt yourself? Yeah. Let’s, like, put some things down. How much is it for a coffee machine? How much do you need to live off? Like you’ve said that to me before, when I’ve been in misery at my job. What do you need to survive? Yeah, like start. Actually, start at the bottom and work your way up.

Katy Ripp 00:14:30  Do not. I need to make 100 grand a year.

Katy Ripp 00:14:33  How much do you actually need? Because I think we also have these numbers in our head that we don’t have the bills to back up. We think we owe this much. But then you’re like, oh, actually, I don’t owe that much or I don’t need that, or, you know, whatever it is. The other thing is we’re sitting in your let’s say it’s a corporate job, right? Like sitting in your soul sucking job and you want to leave it so bad you have to, like, look to see if you just want to leave your job or you really want to open the coffee shop. Like, is the coffee shop just an escape?

Janna 00:15:05  A cozy bookstore cafe?

Katy Ripp 00:15:07  Oh, sorry. A cozy bookstore.

Janna 00:15:09  Cafe. I mean, I love that idea. Could use of donuts because there’s just a lack of. There is a lack.

Katy Ripp 00:15:14  Of good donuts.

Janna 00:15:15  Around here, for.

Katy Ripp 00:15:16  Sure.

Janna 00:15:16  So that’s my one. There’s no.

Katy Ripp 00:15:18  Scots pastry.

Janna 00:15:19  Oh.

Katy Ripp 00:15:20  It’s God’s pastry.

Janna 00:15:22  You know, sometimes when you live with a good thing and it’s gone, you’re like, never again.

Janna 00:15:27  Scott’s pastry. My favorites.

Katy Ripp 00:15:29  I mean, I still have like I can still smell that place. Speaking of smell.

Janna 00:15:33  Got it. Sorry. Dreamer. In doubt. We’ve gone to the donut side of things, but I’ve.

Katy Ripp 00:15:38  Dealt with.

Janna 00:15:39  Donuts. But I do think writing things down and just seeing. What would your dream cost? First of all, you know, where would you have your dream? Is there a need for a bookstore or cafe as a view?

Katy Ripp 00:15:51  Yeah, I mean, also like the reality of opening a business is not all it’s cracked up to be. I own a coffee shop. Right? Like it’s not just like sitting around drinking coffee, reading books. Like there’s a whole side of business ownership that looks really romantic when you’re in a shitty job. That’s not super romantic when you get into it. It’s just not the same as what people think it is, right?

Janna 00:16:14  If you’re looking for a bookstore cafe for you to relax in, it’s not the one that’s you’re going to own 100,000%.

Janna 00:16:24  So if you are a lover of a bookstore cafe, maybe just find one.

Katy Ripp 00:16:28  Yeah. I mean, I understand the importance and the attraction of creating community spaces because that’s what I love to do. It’s like create the spaces. Creating the spaces is different than providing the space to a community, right? Like creating it is different than providing it, and I didn’t know that until I got into it. I still love to create them and I still love to have them, but they’re two very different parts of my brain that like light up when we do things around that. And I’m really good at one of them and not so great at the other one. And so I have staff to do that, right? Like, I don’t know, I could go really down a rabbit hole on this one.

Janna 00:17:12  So just a few other things. So I said maybe putting pen to paper. Do you have any other things this person could do to help them get started?

Katy Ripp 00:17:21  Oh yeah. I mean, I like step by step.

Katy Ripp 00:17:24  I hate, you know, like.

Janna 00:17:25  Do you think having a life coach would be a good idea? Yeah, I’d.

Katy Ripp 00:17:29  Be happy to help. Or maybe.

Janna 00:17:31  Start networking.

Katy Ripp 00:17:32  Yes. Like, also take a class. You can be in your soul sucking job and also take a night class.

Janna 00:17:41  Yeah, that’s a great idea.

Katy Ripp 00:17:43  You can do a lot of research on the internet. You can start an LLC, you can start a website, you can get a you can start designing your website. You can do all you can talk to the bank. You can get, you know, whatever it is. There are so many steps. The issue is that we stop ourselves from even trying. Yeah, because we’re so scared we’re going to fail. And there are so many steps from being at your soul sucking job to failing at a coffee shop.

Janna 00:18:15  Yeah, or being successful.

Katy Ripp 00:18:17  But in her, like the fear of that, there are a hundred steps. And to be honest, businesses sometimes fail because people don’t believe they can do it.

Katy Ripp 00:18:29  Like, yes, there are economy issues, there are lots of things around it. But sometimes, like people just don’t believe it. Like they don’t believe that they can do it. And so getting some coaching before then, like getting rid of that fear, figuring out what the fear is because that fear is going to, like, follow you along like a little shadow until you figure it out.

Janna 00:18:51  Yeah. And months ago you had an event here that was for business owners or people looking to start a business, and there was probably the same amount of people that were wanting to start something that were here and owned a business. Yeah. So for the listener, maybe, you know, find an outlet, go on meetup. I was just looking at my phone. I have this app called meetup. I don’t know if you’ve ever even heard this, and you can find groups of people in and around your area that are kind of have the same. It’s a networking app. I didn’t know.

Katy Ripp 00:19:25  That.

Janna 00:19:26  Yes. How do I.

Katy Ripp 00:19:27  Not know this?

Janna 00:19:28  I just learned about it.

Katy Ripp 00:19:29  What were you looking at?

Janna 00:19:30  My friend who is a LinkedIn coach. Oh yeah. Yeah, she was doing an event, so that’s why I initially uploaded it. Oh, cool. Yeah. Or downloaded it, I don’t know, I’m old. Whatever they say with your down or down with your up. I installed it on my phone.

Katy Ripp 00:19:52  But do you know what this is? So Jana and I were laughing.

Janna 00:19:55  This was a while.

Katy Ripp 00:19:55  Ago, actually. This was the first intro podcast that we had that I never recorded. I never well, I hit record, but we didn’t have the microphones plugged in correctly. So we did an entire episode and it didn’t work, but that’s who I am. And we were.

Janna 00:20:08  Talking about.

Katy Ripp 00:20:09  Creating an OnlyFans page.

Janna 00:20:12  Right?

Katy Ripp 00:20:12  Like I don’t know anything about OnlyFans. Like I only hear it in jokes, right? And like memes and stuff. But then we were talking because we have alpacas, right? And I was talking because somebody asked me like, what are you going to do with the wool? Because they’re getting shorn tomorrow, sheared, shorn, whatever.

Katy Ripp 00:20:28  And they’re like, what do you do with the wool? And I said, well, I’m not really sure. Like we still have the garbage bags from last year when we got them done. Of course, they’re just sitting there. We don’t really know what we’re going to do with them, but you can, like, ship them off and they clean them and send you the yarn back and whatever. And I said, wouldn’t it be funny if we just had like an OnlyFans page of Dale in his underwear and a cowboy hat spinning wool? Like I would totally pay to watch.

Janna 00:20:52  Oh my gosh, it’s amazing.

Katy Ripp 00:20:54  Somebody else out there would pay to watch that.

Janna 00:20:56  Yeah, I mean, they might even pay to watch him shear the narcos.

Katy Ripp 00:21:03  And like, assless chaps.

Janna 00:21:05  Yes, please. With country music playing.

Katy Ripp 00:21:08  See, people I know would watch it.

Janna 00:21:10  They would pay for it. Yeah, so it’s fine. That’s amazing.

Katy Ripp 00:21:15  Okay, well, dreamer and doubt you can certainly reach out to me.

Janna 00:21:18  But also maybe, you know, connect with some other people that are looking to start a business.

Katy Ripp 00:21:24  Yeah, right. Wherever you are in the world, there are people out there also thinking about opening coffee shops and other businesses, brick and mortar places. And there’s lots of like female entrepreneur groups.

Janna 00:21:38  And,

Katy Ripp 00:21:40  This sounds like a little bit more like we gotta take a first step.

Janna 00:21:44  Yeah. Overcome the fear. Yeah.

Katy Ripp 00:21:46  Just like take a step. Action is the best way to get out of fear. Take some action.

Janna 00:21:52  Oh that’s good. That was a good one. Thank you.

Katy Ripp 00:21:57  And that’s a wrap on today’s episode. I hope you enjoyed diving deep into the world of living authentically with me. Before you go, don’t forget to connect with me on Instagram. Shoot me a message at Katy Ripp. I’d love to hear your thoughts on today’s episode and connect with you further. And remember, if you want more details on today’s episode, or just want to explore more about designing your life unapologetically, head on over to my website at Katy Ripp dot com.

Katy Ripp 00:22:21  There you’ll find all the juicy details and resources you need to keep the inspiration flowing. Lastly, if you’d like to join me on the show, whether it’s to tell about your experience of designing your own life, to share your expertise, or if you’d like to participate in lifestyle coaching live on air, don’t hesitate to reach out. Your story could inspire countless others on their own path to living authentically. Thanks for tuning in. Until next time, keep living boldly designing your life. And remember #ActuallyICan.

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