Thinking about quitting a job to start a business but paralyzed by fear and “what ifs”? You're not alone.

In this episode, I sit down with my friend and former nurse-turned-entrepreneur Kelly Endres to talk about what it really looks like to go from employee to entrepreneur—especially when you're walking away from a job that felt like a calling.

Kelly’s story of leaving nursing to work side-by-side with her husband in their insurance agency is deeply honest, relatable, and full of the kind of real-talk we need more of in midlife entrepreneurship. If you're craving more freedom in business, more purpose in your work, and less hustle-for-the-sake-of-hustle, this episode is for you.

We’re pulling back the curtain on the messy middle—the doubt, the money fears, the identity shifts—and how Kelly built a business rooted in service, heart, and unapologetic alignment.

In this episode, we dive into:

• What no one tells you about quitting a job to start a business—and why Kelly almost didn’t
• The emotional rollercoaster of going from employee to entrepreneur (especially when the job you’re leaving is one you love)
• Why women often stay in “safe” careers too long—and how leaving nursing finally gave Kelly the freedom in business she was craving
• How to work with your spouse without losing your mind—or your boundaries
• What it really takes to find purpose again after walking away from a helping profession

Let’s chat: Are you thinking about quitting a job to start a business but feeling stuck in fear or guilt? DM me on Instagram @katyripp and tell me: What’s your biggest fear about going from employee to entrepreneur?

I’d love to hear your story.

RESOURCES MENTIONED IN THIS EPISODE:

The Art of Hello

Actually, We Can Community

Female Founders Collective

CONNECT WITH KATY RIPP: 

Website: www.katyripp.com

Instagram: @katyripp

Pinterest: @katyripp

Facebook: @katy.ripp

CONNECT WITH KELLY ENDRES:

Endres Insurance Agency Website

Endres Insurance Agency Facebook

[00:00:18] Katy Ripp: Hey there. Welcome to #ActuallyICan. This is the podcast where us female entrepreneurs are gonna ditch the hustle culture, build value-based aligned businesses, and finally charge what we're worth. I'm Katie Rip, a serial entrepreneur, business mentor, rule breaker, and your go-to guide for building a profitable business on your own terms.

[00:00:57] Katy Ripp: 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.

[00:01:23] Katy Ripp: Hi, Kelly. Hello. I'm so excited to have you. For our listeners, welcome back. Kelly is such a good friend of mine and we have connected really through sort of entrepreneurship. I'm not sure that we would, maybe we would've crossed paths just because our last names are, you know, in, in a small town. Our last names would've crossed paths and we've certainly grown up in the same areas and that kind of thing.

[00:02:09] Katy Ripp: Lots of safety. And then basically went and worked with side by side with her husband running an insurance agency. And she is actually also our insurance agent, which we'll get into a little bit about how you have helped us and how important in like good insurance and good insurance agents are. We will get into that.

[00:02:40] Kelly Endres: did take a while. You helped me.

[00:02:48] Katy Ripp: Bye.

[00:03:16] Kelly Endres: I never had any bad feelings about nursing. Mike purchased the agency in 20. He ensures a lot of like municipalities, fire departments, EMS, and when you do that, you need to be present at the board meetings, which are at night because a lot of these people are volunteers and they have other jobs. So we were starting to have schedule conflicts after having kids.

[00:03:48] Kelly Endres: It's four 30, I'm gonna leave now. You can't do that.

[00:03:52] Kelly Endres: So that's where this process started. It was kids, like kids change you. We've talked about that a little bit.

[00:04:11] Katy Ripp: Or they're prescribed to us or whatever. Women just end up being mostly the caretakers. Even if you have the most amazing husbands. I talk about this all the time, like, I'm not here to bash your husband. I'm not here to like try to make them out to be the villain. It just is how our society is built right now.

[00:04:48] Katy Ripp: And so we're the ones that are leaving jobs to go get kids or to, if you can't get the kid to set up somebody to get the kid. Right. Kid. Like the planning and that, that kind of thing. So yes, a very common story, I would say.

[00:05:08] Katy Ripp: I always say that like they're all lovely. I get it right. Like I have a lovely husband too. He's a very great dad. It just is the role we're in,

[00:05:30] Kelly Endres: I've never met someone that. Loves insurance so much, and I work in insurance, but he just has very passionate about it. He was growing his business very quickly, but he, he kept telling me, I'm not good at communicating with the staff. Like, he's like, I love being the owner. I love having my clients. I love, uh, helping people, but he's like, I'm not good.

[00:06:10] Kelly Endres: Like, what if you came there and it for six months was like a joke? Because I'm not gonna leave nursing and we're not gonna work together. That would be horrible. And then it slowly became not a joke. Like, oh, actually, yeah. I think that these things

[00:06:34] Katy Ripp: Or, I mean, it, it obviously comes into the conversation because it is actually a real thought of somebody's, but it always like, is a softer landing if we're like, ha ha ha. Funny.

[00:06:57] Kelly Endres: What does that look like?

[00:07:13] Katy Ripp: So if the government would've just, rather than a college degree, which I never actually took advantage of, if they would've given me lifelong health insurance, like they could get so many more people into the military, right? Like, it's such a like jacked up system. But it was always like whenever somebody would say that to us.

[00:07:52] Katy Ripp: Right. And so Kelly actually was the one that helped us with our health insurance when we both left our jobs. But was that a factor for you to stay in nursing or maybe not the health insurance, but like the benefits? Yeah. For

[00:08:17] Katy Ripp: I love, I mean, I do love that phrase that's, that's

[00:08:46] Kelly Endres: It wasn't necessarily the benefits and he was not worried about that at all. I was worried about that. Yeah.

[00:09:12] Katy Ripp: Also, I am a money junkie. I haven't always been, but now I'm sort of getting into this like, where is our money mindset as women, and we weren't taught the same as men, period. We were taught that. Some of us were taught that money is scarce and we should have fear around it versus everything's gonna be fine.

[00:09:57] Katy Ripp: I

[00:10:02] Katy Ripp: for sure. Yeah. I really think that that's like a better way to say it, because it just like, it's the difference between safety and security and like risk adverse and pro risk. That's it.

[00:10:17] Kelly Endres: When he was telling me about this purchase he was gonna make, I didn't wanna hear it because I was like, that is. Is an unattainable number to payback. I cannot imagine that. I just wanna keep, uh, I grew up on a dairy farm where you pay with things in cash and you just, you know, that's what you do to be that much debt was like, and, and not saying that farmers don't have debt, but I'm just like,

[00:10:45] Katy Ripp: Yeah. It's

[00:10:46] Katy Ripp: It's like a special, like your money story is you pay for everything with cash and debt is bad.

[00:11:00] Kelly Endres: But he went to business school, so that type of risk, he, he learned about it. He is not as scared about it. I went to nursing school, so.

[00:11:24] Katy Ripp: that you've changed?

[00:11:34] Kelly Endres: And I was like, nah,

[00:12:06] Kelly Endres: And I was social, but social with the people that I already knew. Yeah. So yeah, it definitely changed. Financially changed too, like now that I'm in a business environment. You do develop and grow and learn because there's no other choice. There's no other choice. Yeah. If you wanna make it, you have to keep growing.

[00:12:47] Katy Ripp: I will say that. It's just a, it's a very, because I, I saw you struggle too, like we've had conversations about, you were down to one day a week, right?

[00:13:07] Kelly Endres: But I just, those two days a month were fine. But they weren't. Those are two days a month that I'm away from the office. It's two days a month that I am not focused on what I'm doing. And it just ended up being, you know, what about time for yourself? Yeah. And I still, I don't know if I even told you this, now I am going to volunteer.

[00:13:31] Katy Ripp: I mean, I think that that's awesome, right? Like now you

[00:13:52] Kelly Endres: But yeah, it's, I still almost went back to nursing. I think once you're a nurse, you're, you always gonna have that pull. Yeah. To be in healthcare, but definitely a different, a different way. I'm gonna make it a different way that I can still put my all into my business, all into my family. Mm-hmm. And that's what us female entrepreneurs struggle with, because there's like three of us, there's three different kinds of us, and we always have to keep bringing them back together.

[00:14:20] Katy Ripp: Yeah. And I say this all the time, but I mean, I'm sure people get sick of me saying it, but if there is a line between personal and professional lives for female entrepreneurs, it's so blurred. It's hardly there. When we are not taking care of ourselves personally, it trickles into everything.

[00:14:57] Katy Ripp: They struggle with the purpose. Like I felt very purposeful when I was in nursing or when I was teaching and now like quote, I'm using air quotes, like making money or I don't feel like I'm of service when I'm in the profession. I am in. Even though you are providing a service, right? Like. Even though I provide coffee for people, that doesn't sound like a lot.

[00:15:44] Katy Ripp: Now it helps that you are literally right in our backyard right here, right? Like you are local. This is why you have local people. But there's a different purpose to that than maybe nursing is just EAs, like it just comes more easily. That purpose or teaching comes more easily, or it's more like accepted by society as a real purpose in life, right?

[00:16:18] Kelly Endres: Like I said, I feel sometimes when you're in healthcare it becomes your identity and you're like, you ha you get this perception of other careers, not on purpose, but like, I can't sit around on my butt all day and then you move to an office and I'm like, I'm busier than I ever was, ever.

[00:16:56] Kelly Endres: That's my mission. That's my mission. I mean, mission accomplished. You can be done now. We were talking about what, how much I've changed. I think I am, you know, realizing human connection is what helps. When I was a nurse. I helped people buy, what can I do? What are they nervous about? How can I calm them down?

[00:17:46] Kelly Endres: Um, you can still have those same feelings of accomplishment, helping in insurance in whatever you're doing. Um, in dropping my kid off for hockey, that's what I've learned and I think that's why I am, I've changed. I like to meet people. I learned from people you and I met because we wanted to bring more business to our area.

[00:18:37] Kelly Endres: And you can have a larger impact than I even realized when I first came. Like, when I first came, my mission was to help Mike. Like, I wanna help my family, I wanna help him now, I wanna help staff and help everyone. So it, it's been a cool progression.

[00:19:03] Katy Ripp: And help people like me, like help customers and help grow your team to a place where you are actually running a heart led business. And I think that's part of where insurance or finance or I, I mean there's lots of industries that don't have the perception of being heart led like nursing or teaching does, right?

[00:19:57] Katy Ripp: So I get to teach people from an educational standpoint. But also you get to now bring all of that and manage your people, like your teams in a way that they have the confidence to go out and do that too. It can be different.

[00:20:25] Kelly Endres: This is the way you are not gonna make it. I can't tell you the amount of people that I've told Mike and I, you're not gonna make it with your business model. You need more sales, less service. There's all these equations. And it's like, no, because I don't enjoy calling a big company. Yeah. Actually I can actually, I can.

[00:21:02] Kelly Endres: If you want. We want someone that knows the billing. We want somebody that knows claims. We don't want you to be a ticket in a system. Uh, and it's not failed so far.

[00:21:22] Katy Ripp: You have to have insurance. Well, my dad told me this once when we were young, and I think it came up around health insurance. He was like, listen, you don't have health insurance to pay for your health. You have health insurance to protect your assets. So if something horrible happens, they don't take your assets because you can't pay your health bill like your medical bills.

[00:22:08] Katy Ripp: And so I think one of the things that is so. Refreshing about you guys is like, literally, did I expect you to come over here and take pictures at seven 30? Now, I happen to have you on speed dial because you're a friend of mine, but I don't know that we would be as close if you weren't my insurance agent, right?

[00:22:48] Katy Ripp: And so you approved it to me. And so even if I'm paying more, which I don't think I, I don't even care if I am. I don't even know if I am. So it doesn't matter. I am, I would pay you more forever for that kind of service.

[00:23:09] Kelly Endres: You don't pay anymore. So if you went with the company directly, you're gonna pay the exact same premium. Uh, they pay us a percentage because they don't have to hire staff. They know that we're gonna take better care of our local people. So it's the same exact price. And I tell people all the time, 'cause some people are like, well, I'm just gonna go online and do it myself.

[00:23:51] Kelly Endres: Why would you want that person on your side if it's not costing you anymore? Because your situation, owning a coffee shop, owning the building is very different than somebody that. Rents a building. When you go do things yourself, you're, you're not gonna know what you don't know. That's my favorite part is we don't cost anything, we're just here to help.

[00:24:34] Katy Ripp: Right? Like, yes, if I'm gonna make a reservation, I wanna do it online. Yes. I don't wanna talk to everybody all the time. Uh, right. There's reasons for that. But when I have a claim and I don't know what I'm doing, I need somebody that does know what they're doing. And I talk about this all the time with my female entrepreneur clients, like we need to outsource.

[00:25:27] Katy Ripp: Priceless. I don't know how to like quite explain it. I mean, we had to navigate a little bit of it on our own. I felt like no matter who you hire, you have to navigate some things on your own. If I would've had to navigate any more than we did with this insurance claim, we'd still be waiting. Like, because I just would've gotten so overwhelmed by that kind of, it, it just would've taken up too much brain space that like then I can't spend trying to make more money to pay the premium so somebody else can do it.

[00:26:08] Kelly Endres: Well, and I

[00:26:09] Kelly Endres: one of my bosses told me this one time, you are in this leadership position because you are different from the others. And it has always stuck with me because it's like, yeah, I can't expect the others.

[00:26:38] Kelly Endres: How do I wanna say this? If one client calls in and has a problem, it's gonna get handled. But if it's not getting handled, if the agency who has hundreds of clients with this company calls and is like, I don't like the way this is going way going, which one's gonna get handled more quickly? That's another benefit of using an agency.

[00:27:25] Kelly Endres: Mm-hmm. I had did not like the speed, so we had to get involved and I still would've liked it to go a little faster, but without an independent agency, some clients wouldn't even know what to say. You know? We know the policy, so it's like, where's the business interruption payment? Yeah. A lot of our clients, I mean, we educate them, but like you said.

[00:28:13] Katy Ripp: Like it just gets shoved in a drawer because I trust that you're gonna do the right thing for me. And if you are trying to say, or you think you're trying to save a buck, the amount of time that you are going to end up spending in the end and time is money, right? Like time is finite, money is infinite.

[00:28:52] Katy Ripp: Priceless.

[00:28:58] Katy Ripp: And I think it's just misunderstood. I think people think they're paying more to go. Through somebody that they know or somebody that they like, feels like a boutique or feels like an elective, like, I should be paying for this kind of service. I think it's just an education thing.

[00:29:21] Kelly Endres: Yeah. I think that's part of it. And I think some people, they're with an agent for so long. Mm-hmm. Um, it's a trust thing, but it's like, but has the agent reviewed? Like, because my life right now is way different than five years ago. So have you updated your agent about that?

[00:29:45] Katy Ripp: Yeah.

[00:29:54] Kelly Endres: Yeah. Just, it's like a little bit of everything, but like, like you said before, it does give you that purpose. You said we're just a coffee shop. Well, that coffee shop, when I have been up all night with a sick 5-year-old and I have a lot of meetings, can Sure. Bring me joy to go get my caramel cream before my meeting and it can be just what I need.

[00:30:28] Katy Ripp: it's

[00:30:33] Kelly Endres: Yeah. That's awesome. I just want like that conversation to go well and that person to be like, wow, that wasn't bad. That was, and also

[00:30:41] Kelly Endres: I mean.

[00:30:59] Katy Ripp: Like, this is all cyclical, right? Like, it, it can be really lovely to pay bills to local people because you get to see how it's used and you get to see that, that, I mean, in the end, it comes back and gets a caramel latte for you that comes into my pocket and then it comes right back around. Like I, I then end up spending that money in the same community.

[00:31:50] Katy Ripp: I think I am a bigger believer in, not even a bigger believer. 'cause I don't really have anything to compare it to. But for me, it's not what you know, it's who you know. And I know that when I have connection to people, no matter what I'm doing, it is always going to pay in dividends. So I can learn all the things.

[00:32:31] Katy Ripp: It was so easy when my brother was looking for health insurance to be like, here, this is the person that you need to go to. Right? Like he was going through a divorce and he's like, I don't know where to go for this. And I was like, I got you. Right? Like that was something that I could provide him that I felt really good about on so many levels.

[00:33:07] Katy Ripp: Yeah.

[00:33:12] Kelly Endres: This company has a discount for nurses. Oh, you have that kind of dog. This company's gonna give you better coverage because these six companies wouldn't cover that

[00:33:27] Kelly Endres: dog lover.

[00:33:32] Kelly Endres: Mike and I argue all the time, I would really love a big Fat Rottweiler at my house.

[00:33:51] Katy Ripp: know.

[00:33:55] Katy Ripp: I know, but not fast enough. Right.

[00:34:01] Kelly Endres: Tell us these things. Yeah. Because if you do this online, you're not gonna read the whole policy. You're not gonna read the exclusions. We know where to put you. So yeah, just, just why I would never, could I learn how to change the oil in my car on YouTube? Maybe it would be humorous. Probably, yes. Let's do that next.

[00:34:30] Katy Ripp: Yeah, I mean, I think as we get older, you know, like I've DIYed myself right into where I am right now, right? Like, I've done a lot of things on my own.

[00:34:57] Katy Ripp: Sometimes. I keep trying. The things I'm not good at to think that I'm gonna get better, but I like some things I'm just not really good at. And so it's easy for me to trade my money for time, right? Like I get to trade my money that I make for time back for somebody else to do it. But then the bonus reward of that is hiring locally like this where I get to also watch my money at work.

[00:35:49] Katy Ripp: It just is such a bonus on the other end. It's like an intangible, like an intangible bonus that you don't know you're getting, but like brings you joy on the other end. Absolutely. I don't know, I think it's just such a, uh, such an interesting place to be and that's so different than, we're like so different than what we're told as entrepreneurs, right?

[00:36:30] Kelly Endres: Like, well, and that's such a good, you're so good at that, of, you know, there's nothing wrong with DIY if you like it, but if you, but like, I don't know why we feel, maybe just because we're used to like just doing everything. I don't know why we feel like if you're miserable and you're not doing what you're good at.

[00:36:50] Katy Ripp: Why? Why? Yeah. Why are we not? I mean, I have somebody doing my laundry. I say this all the time, like, Yolanda is my queen. I love Yolanda. I am not a domestic person. I have a messy car. I have a messy house, but I want a clean house. I want a clean environment. Environment is super important to me.

[00:37:36] Katy Ripp: Like she takes all of Madeline and Miles' old clothes. Like she's got kids younger than mine, so like. I get to see that her kids get to use our clothes when we're done with them. So, and she also takes them out of my house. I mean, there's so many benefits to this, but for years I just felt like an asshole because I couldn't keep up with the laundry.

[00:38:19] Katy Ripp: And so I just hired it out.

[00:38:43] Kelly Endres: Exactly what you said.

[00:38:45] Kelly Endres: And we're all coming out ahead.

[00:39:02] Katy Ripp: If I'm worth a hundred dollars an hour, anything less than $50 an hour, I should be hiring out. I mean, in theory and in a perfect world, that's not always the case because obviously I don't get paid a hundred dollars an hour to drive my kids to the mall back and forth 14 times. But if it came to a point where I was making $500 an hour, would I hire a driver?

[00:39:44] Katy Ripp: But all of these things that you're doing, like really being a heart led business owner, these are the rewards we end up getting that are so intangible, but they end up coming back in money, if that makes sense. Like they end up coming back monetarily if you can. What you're giving out in energy, you're getting back in money.

[00:40:10] Kelly Endres: That's a very common question. Um, you know, because it was a fear. It was a fear, yeah. Yeah. And 10 years ago I would've been like. No way in hell. How long have you been married? We got married in 2016.

[00:40:26] Katy Ripp: Okay, so you've been married almost 10 years. Right.

[00:40:48] Kelly Endres: He's on the road a lot. Yeah. So even though we work together, I don't see him that much during the day. Yeah. Sometimes it's really awesome. I mean, we're all super busy parents. It's hockey every night. It's like, Hey, did you talk to your husband yet? I'm like, I haven't even seen my husband in four days.

[00:41:27] Kelly Endres: Yeah. He's the risk taker. I'm conservative. He is. How are we gonna grow, grow, grow, grow, grow, grow. And I'm like, how are we gonna grow while keeping the same service?

[00:41:39] Kelly Endres: We balance each other out. Yeah. I

[00:41:41] Kelly Endres: nice. That can cause conflict sometimes, because we're both very passionate. Like when I have a vision, I'm very passionate.

[00:42:13] Kelly Endres: That's affecting my job. That that gets hard. 'cause that happens already at home. Right. But I think we manage it well. I'm not gonna say there aren't days. Yeah, I am like, what are we doing? Yeah.

[00:42:34] Katy Ripp: Like, would it just be easier to go back to working for somebody else? I think that comes up in my mind more often than I'd like it to. Like would it just be easier to go to work, work for somebody else, get a nice, secure, safe paycheck, and just come home and do whatever I want? Like turn it off. Because my brain never turns off.

[00:43:23] Katy Ripp: Like who tells us that it's not okay to talk about it over the dinner table? Who tells like, where are we learning this and where are we following these unwritten rules? But I'm the same. I think that's human nature. We also are like been, you know, we're bombarded by shit everywhere about like, this is the way you should be doing it and if you're not doing it, you're wrong.

[00:43:49] Kelly Endres: it's hard. Mike and I just talked about this. I mean, like all jokes aside, I do love working with him because we help each other, we understand the stresses. Like when I was a nurse and I would be like, I'm so stressed. This happened today. He had no clue what I'm talking about.

[00:44:27] Kelly Endres: Uh, when we switched computer systems, I think I worked till 1:00 AM 2:00 AM for three weeks straight. That's tiring. And I, I thought about that. I'm like, am are my kids being negatively affected because I'm a business owner? 'cause that's the last thing I want. And then I'm like, no, they are watching hard work.

[00:45:03] Kelly Endres: I just wanna go worry about myself. 'cause we have to worry about, well there's 12 of us at the office. That's gonna be pressure with a ton

[00:45:22] Katy Ripp: But I think mother nature doesn't like let us understand the gravity of that. I think it's the same with employees. Like I don't understand the gravity sometimes of every time I press enter for payroll, that that is going into somebody else's pocket that needs it for food and shelter and to raise their children, right.

[00:46:10] Katy Ripp: And, and some of them, these are their first time, you know, first part-time jobs is 14 years old in the ice cream shop. But then also like, I've got a general manager that this is her career, this is her salary, this is how she's going to raise her family eventually. This is how she's paying for her wedding.

[00:46:43] Kelly Endres: So much of their life at our office, I want them to enjoy it.

[00:47:05] Katy Ripp: Well, everybody knows. Everybody knows somebody that doesn't like their job. And you can tell. Yeah, yeah, exactly. And it's real quick and it's real. Like if somebody doesn't like their job and I can tell, it makes me wonder about either what's going on at the office or why are you stuck? Like why do you feel stuck?

[00:47:46] Katy Ripp: You can tell when somebody that doesn't like their job serves somebody that doesn't get the service that they should. It's just, it's just an ugly cycle that way too. So, yeah. I, I mean, we are very much in agreement. It's just a different way to run business. Mm-hmm. Like, you're doing it differently. You're doing it differently even than Mike did it.

[00:48:22] Katy Ripp: Yeah.

[00:48:36] Kelly Endres: And he appreciates mine. So it isn't, uh, a lot of people like, they, they're not open to that ever being a positive experience. No, for sure. But

[00:48:59] Katy Ripp: Like it's always run this way. Insurance companies have always done it this way, so this is how we're doing it. And you are very much an operator and he is very much an like working in the business while you're working on the business. Not everybody gets both of those in one family.

[00:49:14] Katy Ripp: That part is really cool.

[00:49:29] Katy Ripp: this? Mm-hmm.

[00:49:34] Kelly Endres: So we do compliment each other, which is really fun.

[00:50:00] Katy Ripp: If you were working at a clinic, you had a very like eight to four job, right? I mean eight to four, but you were there until five 30 or six or you know, whatever you had to do when you were there. And you definitely have, you know, quote unquote banker's hours because that's, you know, like you are business hours for an insurance company.

[00:50:39] Kelly Endres: I have done substantially better this year, thanks to people like you, Katie. This is why business coaches are so. Important because I grew up watching my dad. He worked every day 24 7. There's no breaks there. Then you go into nursing and it's very much the same aspect. You work, work, work hard, hard, hard.

[00:51:31] Kelly Endres: So I'm like working till 1:00 AM Is that making my family life better? No. What I truly love is every time hockey practice on Monday and Tuesdays are at four 30 in sock, 20 minutes away from cross planes. If I was a nurse, no way would I be able to do that. Would I have found somebody to get my kids there?

[00:51:56] Katy Ripp: Um,

[00:52:17] Katy Ripp: Mm-hmm.

[00:52:30] Katy Ripp: Yeah. The goal is not perfection, right? The goal is progress, right? Like that.

[00:52:53] Katy Ripp: That's not who I am. It's not who you are. And we were raised and we have stories around that and we have limiting beliefs around that. And I remember, and maybe this is something that you've heard me say before, is I was in a therapy session one time about this particular thing and I said, I just, I feel like I have to work all the time.

[00:53:32] Katy Ripp: Eventually that burned the fuck outta me. But I remember saying to her like, I. I don't think that makes me a bad person. And she said in a leadership role, it sort of does. She said basically you're showing your employees that they can never take a break. That they can never take time off for family. That they have to skip weddings to be there even though you have staff for that.

[00:54:19] Katy Ripp: You're paying them like you're paying them competitively. You're also like giving them bonuses and giving them things that they really enjoy. Like at what point. Are we going to look at this and be like, there's no reason to feel guilty. It took me obviously therapy, but also it took me a, a, a long time to figure out that my schedule could look different.

[00:55:05] Katy Ripp: Except I wasn't actually being productive. I was just like working. And that part really has taken me a long time, but now that I see it, I can see it in other people too. And I'm like, you're not giving the people that need it, the behavior that you want them to have, because they're never gonna be able to take off to take their kids to hockey because you don't do it.

[00:55:49] Kelly Endres: Yeah. Um, hiring the right people, like I will hire a kind, compassionate. Willing to learn person over somebody with 10 years of insurance experience any day. Yeah. Because you're right. My staff wants us to go do these things also because they are carrying people. We're very intentional about who we hire.

[00:56:32] Katy Ripp: And my schedule is very different. Like I am an early riser. I get up and log onto my computer and get so much done at five 30 in the morning until seven. That's just who I am. I also take a nap from 12 to three, or I go to the gym from 12 to three, or I watch Netflix or, or I work, you know, but I just, I, I'm very aware now of my work schedule and when I'm the most productive and efficient versus what the clock says.

[00:57:20] Katy Ripp: Like, just get it done. If it needs to be done, like, I don't care how long it takes you, I had a boss tell me one time, I, Dale always says like. I went in for a demotion. I basically like walked in and was like, I think you're paying me too much. And she, he was like, you know, you're asking for a demotion, right?

[00:57:59] Katy Ripp: I don't care how much time it takes. You we're paying you for what you're doing, not how much time it takes you. And I was like, it was the best thing anybody could have ever said to me going into entrepreneurship because time just doesn't make any sense. To get paid by, unless you're in like a, there's reasons to get paid by the hour, but as a entrepreneur, it's very hard to quantify how much time something takes you

[00:58:29] Kelly Endres: Because we have to be open eight to five. Our clients expect us to be open from eight to five. So it does, it, it still, there are days where I'm like, oh, I'm leaving at three 15 again, but then I need to remember. Yeah. And I let one of our employees take her lunch break from two to three so that she can go pick up her kids.

[00:59:01] Katy Ripp: Well, and that doesn't mean you have to be there from eight to five.

[00:59:07] Katy Ripp: yeah.

[00:59:40] Katy Ripp: So it's just a, it's a work in progress of how can we make this work for us instead of against us all the time. Mm-hmm. And we feel bad. Like,

[01:00:02] Kelly Endres: Honestly, I just like, please write a book called Must Be Nice. That would be my favorite book. I think I am getting a lot better, but the must be nice comment is not something that I needed to hear in healthcare. And healthcare, you know, that that's not a thing. Must be nice.

[01:00:22] Katy Ripp: It's not a thing for healthcare. That is. Yeah. They don't hate that mean sometimes I think you hear that for teachers, right? Like, well, it must be nice to have your summers off.

[01:00:33] Katy Ripp: Like, I, no, no. I, let's, let's, I mean, I worked in the schools, but I have certainly heard like, oh, it must be nice to every, your, every holiday off or whatever.

[01:00:47] Kelly Endres: Right. So like, it took me a long time. Like I am a pretty positive person and I really like everybody. Like, I don't, there's not people I dislike really, but when someone would say, must be nice, there was like two years where I'd be downstairs at 1:00 AM doing my payroll, like just still like listening to that like.

[01:01:33] Kelly Endres: And I try when I hear that, to just smile and take it with grace and not let myself get so upset. But it takes a lot of work.

[01:01:55] Katy Ripp: Like I used to not post vacation pictures. I used to not post like I. If we got something new, I'd be like, well, this is the coffee shop money. And people are spending coffee and they're like, oh my God, it must be nice to be able to go to fucking Hawaii or whatever. But like, it took me a really long time too, and I still am not quite there, but if somebody says, it must be nice to me now, it's pretty easy for me to be like, yeah, it is actually really nice.

[01:02:41] Katy Ripp: I, I mean, I still definitely, um, I have guilt when we're like flying somewhere and I'm like, God, somebody else is working. Or I get a text that like, Hey, we need coverage. And I, I am not available to go in and cover. Like, that's really hard for me. But I had to put some like. Pretty heavy boundaries up around that.

[01:03:14] Katy Ripp: But I. I'm such a stickler now for my schedule, and I love the freedom of it. I don't want some, I mean, I will if I have to, but I had to put some pretty hard boundaries around that part of it. Yeah. It's taken me a really long time to get here.

[01:03:35] Kelly Endres: Or am I just thinking about it still? Yeah. But yeah, yeah,

[01:03:43] Kelly Endres: I mean it like I know people say it. There are people. Oh, but also I think when you change your mindset. People know that, not that anybody was saying that to hurt me, they were No,

[01:03:59] Katy Ripp: Mm-hmm. And so it's very like, your life does look freeing and somebody else is punching a clock and doesn't like it. And so of course the grass is greener on the other side, but they're also not up until 1:00 AM worrying about where they're gonna find payroll money.

[01:04:23] Kelly Endres: Yeah. I chose insurance. I don't wanna work outside when it's negative five outside. I don't want to, I chose insurance. They can, uh, he, I've heard him say it multiple times. Hey, there's always room in insurance. Come on over. And that usually shuts them up pretty fast.

[01:04:44] Katy Ripp: Like, by all means. Yeah. You can come and do it. Like I'm not special. I like, I'm not special. I just like took the risk. Yep. I don't have a college degree, I don't have some like magical thing that somebody else doesn't have. I just decided to take the leap of whatever I'm doing and that's different. And so if it's, if it must be nice, yes, it is.

[01:05:12] Kelly Endres: It's, it's like I love your podcast. I was so honored that I was invited here because the actually I can statement is such a business owner thing. Like it's scary. It is terrifying. But I can actually, I can and I will and I am and that's awesome. And yeah. And so can everyone else, if they're willing.

[01:05:35] Katy Ripp: And I think when I first came up with like, actually I can, it was sort of a fuck you to the world. I mean, honestly, like when Dale, uh, there's a, you know, my little sign behind here is Dale made this for me a few years ago actually around the pandemic part, because what was happening was I got to a point where people were like, no, you can't do that.

[01:06:15] Katy Ripp: I can do it. I just can. And I think that there's so many people out there, so many women, especially, especially in the self-employed industry, that like, we're not special. We just decided. That we could, and we just didn't give ourselves an out. I mean, there's no out for me, I don't have something to fall back on anymore.

[01:06:59] Katy Ripp: I can fail and realize, geez, I'm not really great at this. I'm gonna do it a different way. 'cause I learned and they're just lessons. So that sort of thing, like, Hey, I'm not really good at this, but. I can do it a different way. And actually I can do this differently. I should have probably put differently at the end of can.

[01:07:27] Kelly Endres: Yeah. It's kind of fun though. 'cause I'm the same way as you. Like someone telling me you can't do this, there's nothing that is gonna make me work harder. Find a way to do it if I feel passionately about it.

[01:07:59] Katy Ripp: Yeah,

[01:08:18] Kelly Endres: And about six months later, the company would always send out the sales charts. And seeing my name above his name was like so gratifying. Like, Hmm. Thought I couldn't do it. It's like, but now it's more exciting. And when you surround yourself by PO around positive people, coaches, mentors, it's more like.

[01:08:46] Katy Ripp: Yeah. I think it comes down to the confident, right? Like, actually I can do this and also what else can I do? Because now I've just proven this to possibly somebody else like, fuck you, watch me. I can do this. And I've proven that part. But when you start shifting your mindset, and I think it is just like a natural organic progression into a, like a confident mindset, a confidence mindset, like you said, a really like a place of like, I trust myself, I, what else can I try?

[01:09:39] Katy Ripp: Like now you're volunteering, you probably were like, well, I can't actually spend an hour or two or whatever a month, not making money, volunteering or whatever. Like I can't go to Walt Disney World for times a year actually. Can you, like, could you bring that much joy to yourself and to your kids? I always tell people to like the abundance mindset.

[01:10:26] Katy Ripp: We can make more money and feel good about it because we're doing good things with it. It's just a tool and so like the money part of it too is like it's okay to bring your kids joy or bring yourself joy by going on vacation or buying something that you've really wanted for a long time because that joy then ripples out.

[01:10:59] Kelly Endres: Yep. You know? 'cause we're friends. My Disney obsession. Yes. There's a lot of negativity. Like you either love Disney or you hate Disney. I love that you love Disney.

[01:11:16] Katy Ripp: Disney. I love that. You love it. I do. I love, I mean, I know other people that love Disney. I don't love it, but I love that you love it.

[01:11:32] Kelly Endres: Yeah. I took the kids by myself and people were like, what are, that's the stupidest thing I've ever heard. And it's like, no,

[01:11:41] Kelly Endres: And it was a blast. Like if you let yourself be too scared off by other people's opinions on a life that is not theirs and that is different and has different values, then you're not gonna be able to live here to the fullest.

[01:12:18] Katy Ripp: are,

[01:12:25] Kelly Endres: Like you can care. And finally, I'm not gonna say I don't fully care. I want, well of course I want to be a good person. I want people to think good of me. But if I'm doing my best and you don't like it, I can't. That's not my choice. I can't worry about changing your mind that I took my kids to Disney World.

[01:12:56] Katy Ripp: And we don't want those people as clients.

[01:13:00] Katy Ripp: Like we don't want those people. I don't want somebody to come and be like, well, I wanna work with you, but I don't want to work with you.

[01:13:29] Katy Ripp: And if they don't respect our choices, that is okay. You don't have to like it. I am still being a good person just because somebody is like, I don't understand why you have alpacas. I don't care if you don't understand it. Like they're strictly there for my joy, period. Like, it doesn't matter. I, I mean, my parents were like, what the fuck?

[01:14:10] Kelly Endres: And that's all that matters.

[01:14:11] Katy Ripp: all

[01:14:32] Kelly Endres: Yeah. That's, that's been the best meeting you, meeting other people in the community that have embraced all of these things. Makes it easier. You're not by yourself, and if you are by yourself, find a way to not be Yeah. Go meet people. Make connections. It's, it's the best thing that we've done.

[01:14:55] Katy Ripp: It's just a very, it's a different place to be. It's a different, there's different stressors. There's different, you know, it doesn't mean that there's no stress or more stress or less stress than anybody else. It's just different stress and. Uh, same like I started, or I rather I stopped looking for advice from people that I have no interest living their life anymore.

[01:15:46] Katy Ripp: I think that there's so much value in that, and it's really what gets me up in the morning anymore is just like, who can I connect with today? Mm-hmm. Like, what can they bring me or what can I bring them? I like, it's a lovely, lovely place to be. Does it come with. Lots of baggage. Sure. But we get to do this.

[01:16:10] Kelly Endres: whole day. That is quite a compliment. Since it's Friday. It's Friday and I have a good day today. It's filled with a lot of meetings that I'm really excited for, but I. Really love this podcast and your vision, and I'm so proud of you too.

[01:16:32] Katy Ripp: Yeah. I think that there's so much, and I mean, we started this conversation about connection and that it's a perfect place to close.

[01:16:59] Katy Ripp: 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 katie rip.com/community. We can also stay connected on socials. You can follow me on Instagram at Katie rip for behind the scenes extra insights and plenty of business wisdom.