When Entrepreneurship Is Hard—and You Keep Going Anyway

Entrepreneurship can be meaningful, joyful, and deeply fulfilling—and it can also be really hard.

In this solo episode, Penny shares a candid look back at 2025 and the behind-the-scenes realities of building a purpose-driven business. This is an honest conversation about what it looks like to keep going when the path feels slower, heavier, or more uncertain than you expected.

If you’ve ever questioned your purpose, wondered if you should quit, or felt the tension between gratitude and exhaustion, this episode will remind you that you’re not alone—and you’re not failing.

In this episode, Penny reflects on:

• Why loving your work doesn’t mean it’s always easy
• The unseen choices entrepreneurs make to support their families and dreams
• A powerful mindset shift around service, humility, and resilience
• What a tough (and slightly unforgettable) moment taught her about not quitting
• How remembering who you’re becoming can help you stay the course

This episode is a gentle reminder that progress doesn’t have to look polished to be real—and that continuing to show up matters more than you think.

Pour yourself something festive and come sit with Penny for a few minutes. She’s cheering you on.

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Or on Facebook: Penny (Kuhlers) Fitzgerald

Transcript

 When Entrepreneurship Is Hard—and You Keep Going Anyway 

[00:00:32] Penny Fitzgerald: ​ [00:00:00] Hello my friend. Happy holidays and if you're listening to this on the day that I release it, it is Christmas. So Merry Christmas to my Christian friends out there. I hope you are celebrating today and this whole holiday season with those you love and have many friends around you and a good cocktail.

So today I wanted to do a little, something a little bit different than I normally do. Um. You have heard me say over and over again how grateful I am, [00:01:00] and I totally mean that. I am so very grateful for all the blessings in my life. I am grateful to have this career, this entrepreneurship, the ability to serve other women, to have fun, to bring joy to people.

I'm grateful for Wine Camp, my Sipper Club, and of course my Serving Superstars program where I get to lead women in finding their joy and creating a better. Life for themselves in their career, but I don't often talk about the behind the scenes stuff. And today I just wanted to acknowledge that because it's not always as.

Blessed or doesn't seem as great as, um, it may come across. So I just wanted to acknowledge that. Um, yeah, my name is Positive Penny. I often hear that, and that is what I tend and what I strive to live for and to be. I choose gratitude and joy. It's not always easy, and I wanna acknowledge that because I know a lot of you out [00:02:00] there are trying to build something meaningful as well.

And it can be a struggle some days and some days it can get the best of you. So I wanted to acknowledge that 'cause it does feel like 2025 has been a year of tests. How badly do you want this? What is your purpose? Are you serving the people that you are supposed to be serving? Are you making an impact in this world?

Are you doing the right thing? Should you go back to work? Should you go back to that corporate career? What, what do you want? How badly do you want this? And who, who is it that you're serving? So I wanna give you a little bit of a background, um, about this. So earlier this year, um, those of you who know me and have been listening to the podcast for a while, you know that I've been podcasting now for a little over two years.

Absolutely love it. The conversations with brilliant women have lit me up, have given me so much joy, and I love to support those women in sharing their stories. [00:03:00] Um. Along with that though, I need to make a way to monetize. And you, you have to feed your family, right? You have to take care of the things that are in your budget and in your life, the things that you want to pay for.

So, um, I, in looking back at what I used to do, I loved bringing joy through my wine tastings. I loved serving my team. I loved leading them, um, giving them some inspiration and training to help them meet their goals. It was great. I loved it and it paid the bills. And now with the podcast, um, it has led me to understand that those things that I did in my.

Previous career can lead me into what I'm doing now, and it's really become clear that I'm following my purpose. I am supporting women in their careers, but just not in the same way as I [00:04:00] was. Now those of you who are entrepreneurs or have built a business, you know, it takes time and sometimes quite a bit of time, or at least longer than you hope it will, or at least longer than I hoped it would take.

For me, it's taken a little bit longer, so it's been two years and I am slowly building and this is becoming a career and becoming. Um, a way that has been, um, that I'm able to feed my family, that I'm able to pay for the things that I need to pay for. However, it wasn't that way at the beginning of this year.

So back then, um, like months ago at the beginning of the career, Jeff and I, or beginning of the year, Jeff and I talked a little bit about, okay, what's this gonna mean? What do we have to do to make this work? And. I ended up, um, deciding to go into a, um, an hourly type job where I am actually [00:05:00] cleaning homes in Florida.

So not many of you knew that. Very few people, I've not told very many people 'cause I, in the beginning I was a little embarrassed about it. And, you know, those things that we do because we have to do them. We shouldn't be ashamed of those things and I don't want to be ashamed of that. I had to. Come to the realization that this is something that I need to do and then flip my mindset around to being, you know what?

I am in service of those people. So the people that I am cleaning their homes, um, I'm doing it to help them. I'm serving them. I'm helping them fill a need. Um, some of them cannot. Any longer, uh, clean their homes, they're getting older and can't do the things that they used to do. So this is a really good way to serve them and then to fill a need in our household as well.

So that's, uh, the attitude I had to take about it. I had to shift my mindset to be, um, you know, thinking of it in a way that was. [00:06:00] Grateful instead of, oh my God, I can't believe I have to go clean a house. You know what I mean? It's just, it, it was a mindset shift that I had to make. Um, and just to give you a little bit of an idea too about how big a shift it was, um, the second time out, and this is kind of a funny story, so, um, this was like back in, I think February or March that I started doing this.

The second time out, my very second house cleaning, I was. Out on the lanai, um, cleaning spiderwebs cobwebs down from the rafters and on the pool cage. And those of you who know me know that spiders are not my thing. I am not afraid of many things. Spiders is one of them. I absolutely hate spiders. They scare me.

And so here I am out on the lanai knocking pool, knocking the, the webs down with a long handled broom. And I took a half a step back. Into the pool. Oh my [00:07:00] god, you guys, I don't swim. Or at least I didn't think I swam. I didn't know that I could swim. It turns out I was just not properly motivated before that incident, so, oh my God.

I mean, it's funny now, but at the time I like, I thought, ah, ah, okay, what do I do? Just stand up. Just stand up in the pool. You'll be fine. Well, I was in the deep end. I couldn't stand up, so. I wasn't sure what was happening, but I was like rolling around a little bit in the pool, fully clothed. My earbuds were in.

I'm like, oh my God, my podcast is still playing. So, oh my gosh, I learned so much that day. But I, um, I thought, okay, I'm not gonna die today. I'm not gonna die cleaning a house. I'm not doing it. That's not gonna happen. So I just kind of pedaled my way. Backwards to the side of the pool and got my bearings about me and started to breathe again and, um, [00:08:00] got outta the pool and, you know, I had a choice to make that day.

And the following couple of days, I'm like, okay, what do I do now? I'm soaking wet. I am, my clothes are wet. I hurt because I twisted my ankle going into the pool. I can go home and say, Nope, this isn't for me. I'm not doing this anymore. Or I could keep going and prove what I'm worth, you know, or, you know, not that that proves what you're worth, but you know, what am I made of?

How badly do I want this? How much am I willing to do? To do the thing that I really know I'm called to do. You know, I mean, these other things are supporting me in getting there, so I stuck with it. I cleaned the rest of the house and another one that day kind of damp, but I got it done and I, I did it. I was proud of myself for keeping going, for not quitting, [00:09:00] for not saying, this is too much, this is, I can't handle this.

Thing that I'm doing and stopping that so. I think to me in the, in the back of my mind, I wasn't gonna quit and I knew that I had to do that to do the thing that I really love to do, which is serve women, is to, you know, help to grow my business more, to be the entrepreneur to. And the person that I wanna be.

So I kept going and um, yeah, that was a really big learning moment for me and, and a little bit tough, right? So, you know, my ankle was torn, not torn up, but it was sore for a good long while. Um, so I wrapped it and kept going, uh, and. You know, looking back at that, it just, I'm proud of myself for not quitting.

You know what I mean? It was just kind of a, a moment that, um, would've been easy to say, you [00:10:00] know what, no, I'm not cut out for this and maybe I should do something else. But, um, no, I kept going and so I just wanted to share that because. You know, for a while it made me a little squeamish or embarrassed to say, and now I'm just, I'm proud of what it proved.

I'm proud of. Proud of what it proved to myself that, yeah, I'm doing the right thing, I'm moving forward, I'm taking care of my business, you know, and at times I need help. So, you know, that was one, that was one thing. Financially needed a little bit of help. And later on in the year, I'm. Moving forward with everything.

Wine camp's going, amazing. People are really loving that and it brings me so much joy too. I just absolutely love that. Sipper club's great. It's growing. My business, was serving women in coaching, in that coaching space is good, but not building as quickly as I want it to. So [00:11:00] I thought, you know, there are some things here that I feel like I'm maybe complicating.

I'm overthinking it. How many of you out there do that? I do that a lot. So I have to learn some of those things myself and my business is only going to grow at the speed that I do, and that's true of anyone. You know, your business will only grow. To the extent that you do as a person. So I hired a coach later on in this year and she's pushing me and I'm learning some new things.

I'm doing some things way outta my comfort zone that I didn't know I was capable of. But you know, I've already proven I can do that, right? All of these things are leading to something bigger and better and helping me grow as a person and helping me grow my business to be able to be in service of more women to create a greater impact.

'cause it's this ripple effect, right? When I can support you and growing your business, you're gonna serve your people and it's just creating this. Beautiful ripple of impact, [00:12:00] positive impact for other people. And I know that when we, when women come together, when we support each other, when we grow, and when we lead.

We're unstoppable and we can create magic and we can create a better world, a better community, a better family, a better life for ourselves and those around us. So that's why I'm doing what I'm doing. And I hope that makes sense, and I hope you understand, you know, I know you're doing it too. I know you're out there trying to create this impact, and I know that it's not always easy.

I, it may look like it from the outside looking in. I've been there. I know it's not easy to every day do the thing, but what helps me keep going is realizing how far I've come and also looking ahead to who I'm becoming. And that older, wiser me is looking back saying, you've got this, you've got this, and you can keep going.

Be strong because. Who you make, who you become, you're gonna be fe [00:13:00] feeling even more proud. You're gonna feel proud of it. You're going to be able to relax and serve your people with joy and dignity and not worry about all these small things that really don't matter. Like being afraid to be seen on social media, like saying the thing.

Like telling y'all that I fell in a pool because I was cleaning a house and knocking down spiderwebs, all the things. So be proud of who you are. Be proud of who you're becoming. Take a deep, deep breath and realize I'm okay. And I'm doing a thing. I'm doing a thing that I said I was gonna do. I'm serving my people.

I'm gonna create a positive, greater impact for the people that I serve. And of course, if you need help, you know that I would love to be there to support you and I'm cheering you on all the way. Happy holidays my friends. Have a wonderful rest of your day, [00:14:00] a rest of your season, and gosh, happy New Year.

Cheers to us.