#ActuallyICan

Quitting a Job to Start a Business: Kelly Endres’s Story of Leaving Nursing

quitting a job to start a business, employee to entrepreneur, freedom in business, leaving nursing

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

EPISODE TRANSCRIPT:

[00:00:00] Kelly Endres: The Actually I can statement is such a business owner thing, like it’s scary, it’s terrifying, but I can, and then I will and I am And so can everyone else if they’re willing to take the risk.

[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.

[00:00:38] Katy Ripp: Around here, we do things differently. No hustle for hustle’s sake, no playing small and definitely no more following antiquated business rules that, um, 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.

[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.

[00:01:18] Katy Ripp: Let’s go.

[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.

[00:01:47] Katy Ripp: But in any case, I think that this really connected us and I have found so much joy in getting to know you, and it’s been such a pleasure. So thank you for being on the podcast. Kelly has a really cool story about basically leaving a nursing job. Which has nice little golden handcuffs, right? Ha ha. Lots of security.

[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.

[00:02:27] Katy Ripp: But first I would love to tell or have you tell a little bit about your background nursing, that kind of history. And then we’ll just get right into how you left. Because it took a while. It

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

[00:02:43] Katy Ripp: Well, I appreciate that. You know, like nothing like, Hey Katie, what should I do? And I’m like, fuck that job.

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

[00:02:53] Kelly Endres: It did. It did take me a long time. So I went to school for nursing. That was my path. That’s what I was always gonna do. I loved it. I still love it. Uh, went to, uh, the clinic right outta college and stayed at that same clinic. Part of the reason it was so hard is because I have friends there. I still have friends there, but yeah, loved nursing.

[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.

[00:03:42] Kelly Endres: So it would be like, well, I have to drive three hours away to this meeting, so you.

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

[00:03:51] Katy Ripp: Yeah.

[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.

[00:03:58] Katy Ripp: Yeah, a hundred percent. And, and we talk about, like, I talk about this a lot with clients, but also on this podcast that no matter what roles we’re in or whether they’re chosen for us or we choose them.

[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.

[00:04:30] Katy Ripp: I think we’ve made progress, but if we’re working outside the home, we are also still the CEO of our families. So it ends up being two jobs, whether you’re working for somebody else, whether you’re a nurse, whether you’re a teacher, whether you’re self-employed or whatever. It’s not necessarily the short end of the stick, it’s just the way it is.

[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.

[00:05:03] Kelly Endres: Yeah, exactly. And even, you know, and Mike is a very involved dad. Yes, yes. They’re all lovely.

[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,

[00:05:17] Kelly Endres: it just kept being the common stressor at the end of the day of like, oh gosh, okay, we’re gonna have a conflict again. Then Mike, so Mike loves his clients. Mike loves the insurance side.

[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.

[00:05:55] Kelly Endres: He’s like, I keep, he just kept coming home with these stories of problems he was having. And in my head I was like, communication. I mean, I kept being like, like, like this is, like, this is what you have to do. This is what you have to do. And we kept having these conversations and eventually we just came to this.

[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

[00:06:28] Katy Ripp: do start out as like sort of folly. Like, oh, what would that even look like?

[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.

[00:06:47] Kelly Endres: Totally. Like, I even remember where in our old house, like where we were sitting when it first mm-hmm. Came up because it was like, wait, like it’s a joke, but wait.

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

[00:06:59] Katy Ripp: I mean, you guys are insurance in insurance and you’re also in health insurance. Like Kelly helped us, one of the biggest questions we’ve always gotten as self-employed people is like, what are you gonna do about fucking health insurance? And I was, I, I mean, at one point or another, I’m a veteran, right?

[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.

[00:07:35] Katy Ripp: ’cause Dale and I have been self-employed for a long time. We’ve been in and out of jobs and that kind of thing. But also self-employed, just entrepreneurs for a long time. And when we were younger it was the first question out of anybody’s mouth is, what are you gonna do about health insurance? And it’s still the question.

[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

[00:08:06] Kelly Endres: me, yes. For my husband, no. More financially mature than I am. I’m financially mature.

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

[00:08:20] Kelly Endres: cute. But he’s very intelligent with finances as a group, as a big picture, and I’m the nervous one, I’m conservative. I like don’t, it wasn’t the benefits, it was if we fail, which we’re not gonna do. Failing is not an option. We’re not gonna fail. But if we fail, having a nursing career is a steady paycheck that comes no matter what.

[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.

[00:08:53] Katy Ripp: Well, it’s security and safety and when we mostly, if we’re talking about females and males and the way we function in a financial world, the women generally like safety and security over risk. And the like opportunity phase.

[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.

[00:09:35] Katy Ripp: Yeah. Yeah, it’s just like the education, it’s like the literacy around it. So I mean, you’re not financially immature, right? No. That was a bad, that was a bad choice of words. Well, it’s not, but it’s like what we’ve been told is like as women we’re like, we don’t know as much, and it’s not sort of fair because we also weren’t taught as much.

[00:09:57] Katy Ripp: I

[00:09:58] Kelly Endres: think probably what I meant to say it is he’s a bigger risk taker than I’m

[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.

[00:10:13] Kelly Endres: You know? Like to have your own business is a huge risk.

[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,

[00:10:44] Katy Ripp: the way I was raised.

[00:10:45] Katy Ripp: Yeah. It’s

[00:10:46] Kelly Endres: way different.

[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.

[00:10:52] Kelly Endres: Yep, absolutely. And he went to business school, like, I’m not saying you don’t have to go to college to do insurance. You just, you have to have common sense. You have to care about people.

[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.

[00:11:14] Kelly Endres: Was smart with my money. We see. Yeah. Financial advisor. But I, the risk taking is something that I definitely need a little push. Um, do you think

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

[00:11:25] Kelly Endres: Yeah, I changed a lot. Oh yeah, I changed a lot. I used to be the type of person when we would come home, Mike would be so annoying ’cause he is like, come out and talk to the neighbors.

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

[00:11:39] Kelly Endres: nah, good, good. I’m gonna be in here reading or like cleaning or hanging out like I don’t need to. And when I moved to insurance, I don’t know what changed, but I. I just love people like, and it’s like, oh no, I actually do like that connection and if I see somebody out, I am gonna go talk to them. That is not how I was five, 10 years ago.

[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.

[00:12:25] Katy Ripp: Yeah. It’s very uncomfortable. But we keep growing. I mean, I have, like, from the sidelines, I’ve been able to watch you like blossom into this like badass founder of a business as a woman. It is. And you’re, you’re quite a bit younger than I’m, and even younger than Mike. So like, it’s a refreshing place to watch.

[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?

[00:12:56] Kelly Endres: Yeah. I slowly, you know, I left nursing, then I went back, I went back. ’cause I’m like, I cannot stop doing nursing. I’m gonna go two days a week or two days a month is what I was down to.

[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.

[00:13:28] Kelly Endres: I’m not,

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

[00:13:33] Kelly Endres: have time to do it. So now that we don’t do health insurance and we’re just property casualty and life, I’m gonna volunteer at a free clinic in our neighborhood once a month. It’s half of a day. It’s gonna be a lot more conducive to our lifestyle.

[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.

[00:14:19] Kelly Endres: Constant.

[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.

[00:14:37] Katy Ripp: Everything. One of the things I’ve heard from a number of nurses, and I’ve had a number of teachers on here as well, that have left the teaching or nursing profession and pursued self-employment, entrepreneurship, partnership, whatever that looks like working for themselves is they struggle with the purpose of it.

[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.

[00:15:24] Katy Ripp: I’m still providing like a community, you know, you’re providing service of like insurance. And for us, like we had a pretty catastrophic flood and a roof, a roof repair that turned into a flood. All of the things like Kelly was here at seven 30 in the morning taking pictures while we were like standing in puddles of water.

[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?

[00:16:09] Katy Ripp: Like this is your, this is your purpose and you happen to get paid for it. How much of that contributed to having, like, having a hard time leaving?

[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.

[00:16:34] Kelly Endres: First I’m, I’m so much busier. The purpose thing, I think you’re exactly right. When a person thinks about a nurse, what they think about compassion, caring, there’s a lot of stigmas with insurance. I mean, people don’t go insurance agent, compassion, caring. Um, that was a hard switch for me. I mean, I do now.

[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?

[00:17:20] Kelly Endres: It’s the same thing in insurance. Insurance isn’t like a conversation most people look forward to. It’s something they need to check off their list. But if we can educate somebody and they actually understand what they’re purchasing, um, I mean, coming to somebody in a middle of a bad claim and just like, I don’t expect my client to know what to do in a claim, that’s what I’m for.

[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.

[00:18:10] Kelly Endres: And I’ve learned so much from that. Um, so I, I’m slowly, I’m not gonna say there aren’t days where I miss being a nurse and that’s who I am, but I am getting the same feeling. And now that my position has changed more to a managerial position, not so much with clients, I’m helping the staff grow. Like I am helping my people help more people.

[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.

[00:18:56] Katy Ripp: Well, and the beautiful thing about that is it’s not an either or, it’s an, and you get to help Mike and your family.

[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?

[00:19:24] Katy Ripp: Like it’s a very feminine place to be, right? Like that’s a very, and not like female, but like feminine, masculine, matriarch, patriarch, that kind of thing. And you get to do that, like it’s such an opportunity. And even when you talk about it, you can feel your energy like, wow, I get to do this differently. I get to change the stigma around insurance by not only connecting with people on a level that’s like caring and purposeful, and I have the knowledge.

[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.

[00:20:16] Kelly Endres: It’s, and, and that’s the hardest thing about being a business owner, right? Is that you’re gonna meet all these people that are gonna tell you, this is the way you have to do this.

[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.

[00:20:43] Kelly Endres: And we are like, and watch me. It’s working. So I don’t, I don’t know when you think it’s gonna crash, but it, it’s never crashed. It’s only helped us. People don’t want to call a one 800 number and press a bunch of buttons. That’s not our, that’s not our model. We want you to call, we want you to talk to the same person every time.

[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.

[00:21:14] Katy Ripp: So I’m waiting. I’m waiting. Well, here’s the thing about insurance is you have to have it right, like there, there’s really no way around it.

[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.

[00:21:46] Katy Ripp: And that has always like. Ran around in my mind for a long time. And so when we pay for insurance, again, it’s not necessarily that we got the roof paid for. I mean, it was nice that we got the roof paid for because our premiums paid for it, but at the same time, like it didn’t take us under because like we, we had the protection.

[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?

[00:22:26] Katy Ripp: Like, I think we were already close, but like it solidified all of my trust and all of my confidence in your business. So now I will refer you to every single person I know because of the service. Now, does that mean that you’re gonna give the same service to every single person? I don’t know that. I’m pretty sure you will, but I got it.

[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.

[00:23:04] Kelly Endres: This is the best part about using an independent agency. My favorite thing, that’s a common perception people have.

[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.

[00:23:31] Kelly Endres: Why? I’m free. We are free. And we do this day in and day out. And they’re like, well, I’ve read all the books. And I’m like, that’s awesome. That’s really awesome. However, when we work, we learn something new every single day. Why wouldn’t you want someone that knows all the intricacies, all the coverages, all the ways you can save money?

[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.

[00:24:10] Katy Ripp: Yeah. And that is a business model that will survive. I, I mean, we are so tired of the button pushing, like, I want to talk to somebody. I know that makes me sound super old, and I’m sure that there’s a whole bunch of people listening like, Jesus Christ. How old are you? I, I’m 46, so I still wanna talk to somebody when it comes to my business stuff.

[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.

[00:24:55] Katy Ripp: I just had this conversation with somebody who is really behind on invoicing. Like, we need to be hiring bookkeepers. We didn’t go to school to be a bookkeeper. We went to school to X, Y, Z. But it wasn’t bookkeeping. It wasn’t insurance, it was, I mean, maybe we didn’t go to school at all and we know a little bit about everything, but hiring people that know what they’re doing and that’s their job and that’s their only job is so.

[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.

[00:25:59] Katy Ripp: I, I mean, it’s a vicious circle when you get into an entrepreneurship, unfortunately has a bad rap of like, I have to do it all.

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

[00:26:08] Katy Ripp: think

[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.

[00:26:19] Kelly Endres: To just naturally do what I do. That’s why they have chosen not to be in this position. But with like a clean situation. All of our companies we work with, we work with over 15 companies. They’re all great, they’re all unique, but there is short staffing going on right now. So I don’t, I don’t know how to say this.

[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.

[00:27:04] Kelly Endres: And we, we usually have a different number that we get to call. So it’s just helpful. And I’m not like talking badly about any, we work with, we work with good, we choose them purposefully. Because we want good companies for our clients, but it just, sometimes you need a little escalation, like in your case.

[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.

[00:27:50] Katy Ripp: They’re busy. Yeah. Like when do, I don’t have time sometimes to like, I mean, I just got a text from my son who’s sick at home. He was like, Hey, I don’t feel good. You know? I mean, like I don’t have time to pay attention to that. I certainly don’t have time to get on the phone for three hours, sit on hold, and then try to read through my policy that comes in a lovely binder from you guys.

[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.

[00:28:31] Katy Ripp: You can always make more money, you cannot make more time. And the lack of worry that I had about it is just priceless. I just, it’s like one of those MasterCard commercials, right? Like roof leaks, you know, floods your ice cream shop, you know, blah, blah, blah. Like insurance agents standing in a puddle with you.

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

[00:28:53] Kelly Endres: I just like those things. Yeah. Next commercial.

[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.

[00:29:17] Katy Ripp: I don’t know that people don’t know that they’re not paying more.

[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?

[00:29:37] Kelly Endres: Um, yeah. Which as a busy person. You get those and you’re like, oh my gosh, I don’t have time for that. But it’s like 15 minute, 15 minute phone call.

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

[00:29:45] Kelly Endres: Is would be all it takes. And, and like you said, some people like electronic. We’ve got that too. Yeah. Like we got online surveys, got a pretty app and all the things.

[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.

[00:30:15] Kelly Endres: And that’s what I love about our office and about being a business owner is that you can choose, like you said, you can choose like, I want my staff to be just what my client needs when they call in. Yeah. It’s,

[00:30:28] Katy Ripp: it’s

[00:30:28] Kelly Endres: not fun to call in and pay your bill, but we can hopefully make you smile when you’re done.

[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

[00:30:40] Katy Ripp: like,

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

[00:30:42] Katy Ripp: This isn’t your responsibility, but like also shifting our mindset to like, okay, well maybe it could be fun to pay your insurance bill because like I am paying Kelly and Mike, and then I get to see them go and give their kids a hockey experience that I love to watch on Facebook.

[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.

[00:31:22] Katy Ripp: So there’s, you know, when people, we have this, like all these buzz words about like buy local, shop local, that kind of thing. But like, I don’t know that people always recognize what that’s doing for the communities and. I mean, that’s a whole nother, we could go into that on another podcast. But also the connection part of it, which I think has been, uh, for me too, it’s because I don’t have the formal education.

[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.

[00:32:12] Katy Ripp: I could learn all the things about, I mean, you can learn anything on YouTube in Google, right? Like I could figure out how to become an insurance agent. I could figure out how to navigate my own insurance policy. But having the connection, and you guys are just an example, but like having a connection to YouTube, like.

[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.

[00:32:49] Kelly Endres: And just let us take that time off your hands like yes you can. Anybody can learn insurance. You don’t need a college degree to be an insurance agent, but if that’s not something you want to do. Why spend three hours researching different companies when I already know that.

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

[00:33:07] Kelly Endres: Our staff already know like, Hey, this company has a discount for first responders.

[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

[00:33:23] Katy Ripp: well, which is gross. But you know, I, yeah, I know. A

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

[00:33:28] Katy Ripp: Yeah. And I mean, I don’t love that, but you know, it is what it is. Whatever.

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

[00:33:37] Kelly Endres: And he’s like, we can’t. And I’m like, yes, yes we can. Yes we can. Like we, we know all of like, there would be no excuse. We can’t do that. I’m like, oh, hate, I hate that. I know, I

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

[00:33:51] Kelly Endres: They’re changing. They’re coming around very slowly.

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

[00:33:58] Kelly Endres: But they’re, uh, that brings up a good point though, like.

[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.

[00:34:19] Kelly Endres: Next. But is it gonna take me all day and I’m gonna mess something up and I’m gonna be frustrated and I’m gonna take it to the local guy in cross planes anyway after I mess it up. Yeah. Yep.

[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.

[00:34:38] Katy Ripp: I’ve also fucked up so many things along the way that I’m just not willing to spend that time anymore. I’m just, I, I think that is wisdom, right? Experience plus knowledge equals wisdom. And I think I’ve just gotten to the point that I’m, I’m just not willing to do it anymore. I know what I’m good at and I know what I’m not good at.

[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.

[00:35:22] Katy Ripp: Like watch it bring joy to you when you go to Disney. Watch it bring joy to you when your kids go and you know, skate for the first time or, and you’re just like a, an example of that, right? Like that’s, there’s lots of local people that I get to watch do that. And that is, it’s such an important piece of like when you have the opportunity to spend money that you’re already spending on people that are local or people that you know.

[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?

[00:36:09] Katy Ripp: Like staffing is horrible. Like payroll is your biggest expense. Like I find that to be one of my greatest joys. Like I get a front seat to these people’s lives. I get to help them do the things that bring them joy in the end. And I also get to figure out what they’re really good at and hire accordingly.

[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.

[00:36:47] Kelly Endres: And you could be passing that off.

[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.

[00:37:11] Katy Ripp: I just don’t want to be the one to do it. Yeah. And so I spend my time making money so then I can take that money, save time in the laundry room and give somebody else a job. She loves to do laundry. I don’t know why, but she loves it. And, and on the like flip side of that, I get to see her kids benefit from our stuff, right?

[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.

[00:37:59] Katy Ripp: In the end, I just realized I hated doing it. So I was like, I, who cares if somebody else does this for me? I like, does my mom hate that I can’t do laundry? Yes, I am a domestic failure in her mind, and that is fine, right? Like I just accepted that I am not that person. I’m good at other things. I don’t need to be good at laundry, so I’m just not.

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

[00:38:21] Kelly Endres: It’s one of those things though, that like it takes a long time to get there, and then once you do, it’s so freeing. Like, it’s like if I can make X amount of money in three hours and this only costs me X amount of money and I’m coming out ahead and I don’t enjoy this. Have somebody else do it that enjoys it.

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

[00:38:44] Katy Ripp: Yeah.

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

[00:38:46] Katy Ripp: Yes. And there, I mean, there’s formulas out here too, and this has always been like a really sort of hard thing to grasp onto is really finding your dollar per hour. Like what are you worth? Like what kind of value are you bringing? So let’s just use round numbers for example.

[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?

[00:39:25] Katy Ripp: Maybe. But then that means that like for anything less than $250 an hour, I should be hiring out. Time is finite, money is infinite. You can always make more money. And that is like an abundance mindset. And that is. We’re, we’re still working really hard to get there. Right. I’m still working hard every single day to get there.

[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.

[00:40:04] Katy Ripp: Yep. Yep. Before we end, I wanna get like, give us enough time to, what’s it like working with your husband?

[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.

[00:40:23] Kelly Endres: We’ve been together since 2012.

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

[00:40:29] Kelly Endres: And so we, yeah. No way. No, and I love my husband, but I was like, I not not do the same thing all day long, all night long. It’s not what I imagined. Good or bad. Yeah. It’s just not just different. It’s just different. I, first of all, he’s very busy guy.

[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.

[00:41:08] Kelly Endres: Yeah, right. Much less. Yeah. You’ve talked to him yesterday. What did he say? Yeah. So in that aspect, sometimes it’s nice, like on a really, when our life is very busy. Maybe I pop into his office for 10 minutes and we’re able to be like, Hey, what about that party? That’s cool. Yeah. We are very different people.

[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?

[00:41:38] Katy Ripp: Uhhuh?

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

[00:41:40] Katy Ripp: think it’s

[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.

[00:41:50] Kelly Endres: When he has a vision, he’s very passionate and they don’t always line up at the right time. Yeah. But I think we manage it well. It, the hardest thing is not bringing it home. I can’t tell you how many times we’ll be at home talking about the office and someone will have to be like, no, stop. Or, you know, it it, what’s, what is hard is like you said you were gonna do this and you didn’t do this.

[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.

[00:42:27] Katy Ripp: Like what the fuck? Like it would just be, I was just having this con, well, I was having this conversation with myself the other day.

[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.

[00:42:59] Katy Ripp: Dale’s never turns off, right? Like we are just work, work, work, work, work. And sometimes I beat myself up about that. And then other times I find myself talking to clients where I’m like, is it bad? Who tells us it’s bad, who tells us that we need work life balance? Like who tells us that we’re wrong because we love our jobs?

[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.

[00:43:45] Katy Ripp: So really trying to navigate your own path. It’s really,

[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.

[00:44:04] Kelly Endres: Now he does. And we both care passionately about the same thing. But I, the other night, and I’ve gotten a lot better about work-life balance. Um, he has two but many nights. I mean, it’s the same thing for every business owner. You’re so lucky you do this, whatever. And it’s like, what you don’t see is that night that I was up till 1:00 AM trying to fix all of the things.

[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.

[00:44:44] Kelly Endres: They are, they are learning determination, hard work, grit. There’s a lot of things that they can learn. And we are there. I am there for hockey. That’s not something I could have done as a nurse. I could been to a 4:00 PM hockey practice. But I do struggle with that too. I think every business owner probably does like.

[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

[00:45:10] Katy Ripp: of responsibility. Yeah, right. Like, and I think it’s sort of like when you have babies, like sometimes you forget like, oh shit, I grew a human. Like I just create, like there wasn’t a human here and now there is another human and I’m responsible for them.

[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.

[00:45:44] Katy Ripp: And to provide a life that is full of joy and full of opportunities and experiences. Like, I think we just, I forget that very often because it’s such a, it’s a very tangible, like paycheck. It’s just like a button on my computer. But. I think it’s hard to realize like, wow, these, I, like, I have 50 employees between everything.

[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.

[00:46:24] Katy Ripp: These are the things that I think it’s almost hard to grasp. And then when it does hit you, it’s like, oh fuck, am I doing the right thing? Am I responsible enough to be doing this? Am I mature enough? Like this is, this seems very adult of me and I’m not really sure that that seems right. Yeah.

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

[00:46:48] Kelly Endres: I tell myself all the time, like, I want all of you to genuinely like it here, or I’d rather you, I don’t wanna lose anybody, but if you don’t like it, you don’t belong here. Yeah. Don’t stay here. I want you to enjoy life, otherwise you’re not gonna be able to give the experience that I want you to give to our clients.

[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?

[00:47:24] Katy Ripp: That I, it always makes me wonder, maybe not everybody wonders that, but I always feel like it’s really important to me to make sure that everybody that works here likes it. Yep. And if you don’t, everybody can feel it. And then it’s just, again, that’s like a, another vicious circle of, you know, on the other end of like, this shit ripples out.

[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.

[00:48:08] Kelly Endres: Yeah. The way Mike would run the business is not wrong. It’s different Yeah. Than what I do. And we just learned I’m a better manager. He’s better at working with the companies.

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

[00:48:22] Kelly Endres: Selling, um, negotiating with the companies. Yeah. We both have our strengths and that’s what’s fun about working with him, is that I can truly appreciate his strengths now because I understand them.

[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

[00:48:46] Katy Ripp: it’s, it can be, it can be. It is what you make it, like you get to, you get to choose how it’s run and if it’s, and you know, to no, like, no offense to Mike, but he probably just ran out like he expected it to be run.

[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] Kelly Endres: Yeah.

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

[00:49:17] Kelly Endres: Mike’s a big picture guy. He like knows where he wants to be in five years. He knows where he wants to be in 10 years. He knows what he wants everyone to do. I’m the one that knows how are we gonna get everybody to do

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

[00:49:30] Kelly Endres: How are we gonna get there? What are the steps? What’s everyone else doing?

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

[00:49:37] Katy Ripp: I need a Kelly Andres. I’m like the vision person. I need somebody like, this is how we’re gonna get there. That’s what I need. I need a Kelly. I say that all the time. I’m like, I need a wife More. More coffee chats. Yeah, more coffee chats. I just wanna like talk a little bit about like what does your schedule look like?

[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.

[00:50:19] Katy Ripp: I talk to a lot of female entrepreneurs that have a really hard time getting out of, I have to be in the office at eight and I have to leave at four 30, and then I turn it off when I get home. Mm-hmm. Have you given yourself a little bit of flexibility in your schedule? Was it hard for you? What? Like what does that look like now versus when you first started in the office, that kind of thing?

[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.

[00:50:59] Kelly Endres: Then you go into insurance and I like to lead by example. So I like to know what my employees are doing, the workflows, and I want to work more hours than them. That’s just I You’re a worker. Yeah, that’s what I do. Yeah. However, I am learning slowly why it took me so long to leave those two days is the reason we made the switch was to make our family life and business life better.

[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?

[00:51:49] Kelly Endres: Yes. I’m not saying my kids wouldn’t be in hockey, but I enjoy being the one mm-hmm. To take them there. Yeah.

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

[00:51:57] Kelly Endres: so it took me a long time to let go of, I have to work harder than everybody at the office. It’s okay if I leave at three 30 because I need to get my kid to hockey. And you know what? I want my employees to take their kids to their sporting too, and, and I need to lead by example.

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

[00:52:18] Kelly Endres: I still need to lead by example. Family is important, but it’s a, it’s a vicious circle. Two months from now, you, you’ll text me and I’m gonna be like, oh yeah, I was working. I’m still working right now. I forgot to do payroll.

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

[00:52:34] Katy Ripp: We’re a little bit better. And it doesn’t make you wrong that your work ethic is like your character is tied up in your work ethic. That’s just who we are as workers, as people. We’re different than other people. Some people can turn it off and on. Really quickly, I’m here for work and I leave and I never talk about it or think about it again.

[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.

[00:53:13] Katy Ripp: I have to be there. You know, at the time we had three businesses open from five 30 in the morning until 1130 at night. And I felt like I had to be in person at those places all the time. I, my face needed to be seen, I needed to be there. I needed to be f like leading by example. I needed to be working the hardest I needed to be putting in the most hours.

[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.

[00:53:55] Katy Ripp: It also tells them that you don’t trust them. And it opened up my eyes so wide because what What was happening is I was feeling so guilty. I was feeling guilty, like I was a lazy piece of shit if I was at my kids’ recital because somebody else was working and they’re like, and she was, my therapist was like, you pay them like they’re not working for free.

[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.

[00:54:45] Katy Ripp: ’cause I’ve always been on the school schedule or, you know, I worked in the schools for a long time, or I worked, you know, 10 to four and those were my hours. So it was really hard for me to, anything after four o’clock if I, or if I wanted to take a break in the middle of the day. It was like, no, no, no, I need to be working.

[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.

[00:55:26] Kelly Endres: Right. Right. And if you are burning the candles on both ends and grumpy and not approachable, you’re not helping anybody. And I’m not gonna say that sometimes we don’t take our kids to hockey and then log back in after we get home. But the flexibility portion is the key. Yeah. Like I can do this and I can also finish my work.

[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.

[00:56:10] Katy Ripp: Well, and you chose to be in the position where the flexibility and the freedom is part of why you sacrificed, why you took the risk, why you took the financial risk, why you took the time, you know, the time risk, why you took all of that. Not everybody does that. So some of the reward of that is total flexibility.

[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.

[00:57:01] Katy Ripp: So if you wanna leave from two to three to have the lunch with somebody and log back on at seven, cool. Like, there eight hours means nothing to an entrepreneur anymore. I really like the, I don’t know where eight hours or the 40 hour week or whatever, where that came in. But if you get your shit done, just get your shit done.

[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?

[00:57:37] Katy Ripp: Yes. I was like, I think you’re paying me too much for what I’m doing. And he was like, listen, this is, he’s like one of my favorite people on earth. He was like, listen, we hired you, you know, 10 years ago or seven years ago, I think it was at the time, for a job that you have now learned over seven years. He said, I’m not gonna punish you for being efficient and being better at your job.

[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

[00:58:27] Kelly Endres: and see, that’s where it can get so hard with guilt, right?

[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.

[00:58:48] Kelly Endres: We make it work as a team, which is so awesome. Like, yes, we have to staff it from eight to five because that’s when clients expect us to be open. But we can all work together to make sure there’s coverage from eight to five.

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

[00:59:04] Kelly Endres: Yeah. And that’s something I’m still, I’m still,

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

[00:59:07] Katy Ripp: I That again, that is progress, not perfection. Right. Like just be, and, and that guilty feeling a, after a while, it, it takes a long time for that, especially if your work ethic is tied into your character. It takes a long time for that sort of feeling. And when time is connected to your value and your worth, I mean, we could go into a lot of this part of it, but there is still a clock that runs and that society still runs by a clock.

[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,

[00:59:50] Kelly Endres: and you know, I think too, it goes hand in hand. You’ve probably experienced this. The must be nice comment. Oh, I mean I’m getting, I wanna write a book that’s called Must be Nice.

[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.

[01:00:19] Katy Ripp: Uh, yeah. It’s not a thing. Yeah.

[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.

[01:00:30] Kelly Endres: Yeah. I don’t, I don’t wanna be a teacher though. Yeah, right.

[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.

[01:00:42] Katy Ripp: Like, yeah. Except I also have to deal like with parents, like you saying shit like that.

[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.

[01:01:09] Kelly Endres: Wish you were here now. I bet you’re peacefully sleeping in your bed, not worrying about 11 other people and getting them paid or making their life like It took me a long time. Now when I hear that, I try to be like, it is nice. And I made it nice. Yeah. We made, my husband and I took risk and we made it nice and we’re making it as nice as possible for 11 other people too.

[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.

[01:01:42] Katy Ripp: I know. I don’t actually hear that as much anymore. I used to a lot or I would make it up in my head that people were thinking that. Right, true. Like not only that people were saying it out loud, but they were thinking it.

[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.

[01:02:21] Katy Ripp: Yeah, because I have worked my fucking ass off for this. Right. And I mean, I don’t think, I don’t think that I hear it so much anymore because I think people have recognized that we’ve put a lot of work into our community. And I think you’ll probably stop hearing it too. And maybe you’re not even hearing it any anymore, but you’re still like hearing it, like residual hearing.

[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.

[01:02:59] Katy Ripp: ’cause otherwise I was in here all the time and I’m, and I hated it. Like, I don’t want to make lattes anymore. I make a good latte. I don’t want to like, sometimes, like I’ll go out, you know, after this I’ll probably go out and get a cup of coffee and they’ll probably be busy and I’ll hop in the computer or whatever.

[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.

[01:03:29] Kelly Endres: I think you’re right too. When somebody would say that and I would get offended, how many times are people saying that to me?

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

[01:03:38] Katy Ripp: yeah. That isn’t to like call you under the bus, like, Kelly, you’re just actually making this up. I don’t mean it like that.

[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,

[01:03:54] Katy Ripp: it was just a, and I think it does come from, sometimes it comes from a place of envy.

[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.

[01:04:17] Kelly Endres: Yeah. I think my husband is the one that helped coach me through this of they chose that job.

[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.

[01:04:39] Katy Ripp: Well, no shit. I mean, there is like something to be said about that particular response.

[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.

[01:05:09] Katy Ripp: This is what I chose and I love it.

[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.

[01:05:34] Kelly Endres: To take the risk.

[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.

[01:05:56] Katy Ripp: And I’m like, fuck you. Actually, I can watch me. And it’s changed over the years. And now I’m sort of in a different mindset, like, actually I can do this for myself. I can do this because I want to. I can do this because I trust myself. I can do this because I’m capable. I can do it because I’m resourceful.

[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.

[01:06:40] Katy Ripp: I mean, we have sort of like you too, like we’ve got our eggs and lots of little baskets, right? Like we don’t have every single thing in one thing. We’ve got lots of little things out there and we’ve learned over the years to diversify and do those things. But for me personally, also, actually I can fail.

[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.

[01:07:20] Katy Ripp: Right. But like I can do this differently. I don’t have to follow, I don’t have to follow, period.

[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.

[01:07:41] Kelly Endres: But it used to, when I think back, it’s like it used to be that hurt and I’m gonna prove you wrong outta spite because I’m not gonna let whatever, now it’s like confidence. Yeah. I actually, I can do it and I want to show you because I’m doing good things.

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

[01:08:00] Kelly Endres: which is a cool progression. And I’m not saying that there’s still, sometimes when someone says I can’t, and I’ll never forget when I first went into health, and we sold the health insurance business now, but, uh, a older, an older gentleman, I like him a lot, but he’s like, by yourself, you’re, no, I, I don’t know what you’re doing.

[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.

[01:08:43] Kelly Endres: It’s just a good feeling for yourself, not somebody else.

[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?

[01:09:17] Katy Ripp: What else can I do? What else is out there that I can try? And if it doesn’t work, it’s okay because what else can I do? I, I do think that there’s something to be said about, and I think if we talk to, it’s actually probably a really good question going forward for me on this podcast of. Geez, what was the next like after you did this one thing, what’s the next thing?

[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.

[01:10:03] Katy Ripp: Like I think that’s where this comes in, that abundance mindset. Like there’s enough for everybody. There’s enough money, there’s enough time, there’s just enough for everybody. We are enough. All of the enoughness in life. But also when we are doing good things in the world like you’re doing, like I like to think I am doing, when we are doing those things.

[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.

[01:10:49] Katy Ripp: It’s our responsibility as whole and capable and resourceful and creative women to make money so we can go out and do good things in the world.

[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.

[01:11:08] Kelly Endres: I don’t love Disney, but I love that. You love it. Mike doesn’t love Disney and does not love that. I love Disney, so I love that. You love that. Love

[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.

[01:11:23] Kelly Endres: I love it so much and I finally last year like, Mike doesn’t, so why does he need to go?

[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,

[01:11:38] Katy Ripp: why? Why? Because actually I can take them by myself.

[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.

[01:11:56] Kelly Endres: We went, could it have gone bad? Could have someone got sick? Yes, but we went, we had so much fun and I was able to come back and work and my cup was full. It’s just letting go of other people’s perceptions of you is hard when you’re. More in the spotlight. I’m not saying I’m in the spotlight, but as an owner, yeah, that’s something you’re like, you

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

[01:12:19] Kelly Endres: people are looking at you, people are judging you, and you get to a point where you just can’t care and that’s freeing.

[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.

[01:12:44] Kelly Endres: If you don’t like that and you don’t wanna be my client. And that’s more an internal fear. Has one person said you, you went to Disney World and took it kids to Disney. I don’t wanna be No. So, no, of course not.

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

[01:12:59] Kelly Endres: Right? Exactly.

[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.

[01:13:08] Katy Ripp: Because Kelly Andres took their, her kids by herself on Walt, like to Walt Disney. I’d be like, I can’t work with you. We’re not friends. Like we can’t work together. And that’s like an abundance mindset of like, there are 8 billion people in the world. Right? How many do we need? We want the right ones. We don’t want the ones that don’t respect our choices.

[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?

[01:13:51] Katy Ripp: You’re bringing in more animals? Like, we’ve got three dogs and we’ve got, you know, 10 cats and three goats and four, all right. Like, do you need more to take care of? And I’m like, Hey, listen, I don’t care. I understand. I appreciate that you’re trying to protect me. I just, I love them. Yeah, that’s it.

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

[01:14:11] Kelly Endres: It’s

[01:14:11] Katy Ripp: all

[01:14:12] Kelly Endres: that matters. It’s not hurting anyone. It’s just bringing you joy. And I think if I had one piece of advice for any business owner, new business owner. New entrepreneur, it would be to surround yourself by people that have gone through it or are going through it and are positive, uplifting people.

[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.

[01:14:50] Katy Ripp: Yeah. It can be very isolating, there’s no doubt, because lots of people just don’t get it.

[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.

[01:15:20] Katy Ripp: I don’t want your opinion because I don’t like your life. I, it’s not that I don’t respect your life, I just don’t wanna live your life, so I don’t need advice from you. Right. I got it. I, I can find advice from people that I really do want to emulate their life and looking up to people, but also helping people that are just a little bit behind you and not behind, but like walking alongside you.

[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.

[01:16:05] Katy Ripp: Yeah. Like we get to do this for an hour and 20 minutes. This is gonna be the best part of my

[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.

[01:16:23] Kelly Endres: Aw, thank you. This journey is very hard and it’s been much easier having you as my friend and Aw. It’s just, it’s just, yeah, you have to surround yourself by good people.

[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.

[01:16:39] Katy Ripp: Mm-hmm. So thank you so much for coming on. I loved every second. Well, that is a wrap on today’s episode, but the conversation doesn’t have to end here. 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.

[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.[01:17:18] Katy Ripp: 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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