782: My Biggest Business Regrets I’ve Never Shared

0:01This episode is supported by What Should I Do With My Money? From Morgan Stanley. Okay, can we just talk about how money is legitimately one of the hardest topics to bring up. Like even when you think you have your stuff together, there's always this really weird awkwardness around it. That's why I am obsessed with this podcast. It actually makes money conversations feel approachable. I recently listened to an episode about affording multiple big life things at once, like a wedding, a house, an IVF, if they were all happening at the same time. And honestly, it hit home. So many people are wondering, can we actually have it all without sacrificing our sanity or our savings?

0:42What I love is that they bring in real experts who help break down these massive costs into actual doable steps. It's like having a money mentor in your ear who gets it. Search for What Should I Do With My Money in your podcast player. We'll also include a link in the show notes. Many thanks to What Should I Do With My Money and Morgan Stanley for their support. okay I have been on this ruthless pursuit to purge any clothes that I'm not actually wearing like if I haven't reached for it in months it's gotta go I am trying to be really intentional about what I bring into my closet right now which means I am only buying pieces that I know I will actually wear and use revolve just gets it though I'm literally wearing my brown autri sneakers from there right now and my new suede purse it fits my laptop in it so it's basically a fancy shoulder bag that works for everything.

1:32I love finding pieces like that. Things that look good, but also work hard for my actual life. Their holiday shop is live right now with all the good stuff. Sparkly party dresses, cozy sets, cute gifts, everything you need for whatever is on your calendar. And it's all in one place, which makes shopping feel way less overwhelming. Whether it's a weekend away, a big night out, or a holiday party, your dream wardrobe is just one click away. Head to revolve.com forward slash gold digger shop my edit and take 15 % off your first order with the code gold digger fast two-day shipping easy returns it's literally the only place you need to shop from that's revolve.com forward slash gold digger to shop my favorites and get 15 % off your first order with the code gold digger offer available for a limited time so happy shopping as somebody with ADHD and who is multi-passionate don't ask me that I feel so overwhelmed by that question.

2:26But what is my purpose in life in this stage or this season? Oh, that helps me stay in alignment. It helps me not chase the wrong things or go like shiny object syndrome, which I am prone to do. Hey, my name is Jenna Kutcher and I am obsessed with all things business, marketing numbers, and helping you to navigate both the messy and the magical seasons of this thing called life. I'm a small town mama who took a$300 camera, grew a successful photo biz. And now I work from home and run a seven figure online business. I teach you the tried and true secrets to building a career you adore. Shy away from the real talk?

3:00No way. Money, hardship, growth, loss and marketing are all topics we discuss here. Think of this as your one stop shop for happy hour with a gal pal mixed with business school. Pull up a seat, make sure you're cozy and get ready to be challenged and encouraged while you learn. This is the Gold Digger Podcast. I was just talking to a friend the other day just about how life unfolds for us and how we are always learning. And a lot of times hindsight is 20-20. Areas that we got wrong, areas where we messed up, areas where we were questioning. Those times in our lives really stretched us and helped us grow.

3:37And it's funny because I honestly don't have a lot of regrets, especially in life. But if I'm being honest, there are a few things that I do regret in my business. So today I'm going to look back over my decade plus in entrepreneurship and talk about some of the things I wish I didn't do, the things I wish I would have done sooner. I've got a handful of things that I am confident to admit that I actually do regret from my business journey. And in this episode, you're going to hear them. That is the heart of the Gold Digger podcast. And it always will be. I want to talk about the good, the bad, and the ugly, because here's the thing.

4:13I want you to see the growth that you deserve. And I want for you to skip as many of my regrets as possible if they're aligned with you. So let's dive on into the things that I regret in my business journey that inform my decisions for my future as I continue to move forward. It's all a little overwhelming, isn't it? Help desk software, payment processing, email marketing tools, blogging platforms, SEO tools, deal management tracking. Gold Digger, take a deep breath because you don't need more tools to get more out of your business. You just need HubSpot. Their all-in-one customer platform is a dream come true for you and for every member of your team.

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5:35And then it became six and seven and eight. Today, I'm going to share nine things. Now I'm pretty sure that if I got really quiet with myself and sat around long enough, I could think of an entire laundry list of things that I regret. But I'm going to share nine with you today. And my hope is, is that for you to listen through this episode and use your own filter of like, oh, maybe I need to take action in this, or maybe I'm doing this and I could be going down the wrong path. And again, just my biggest hope for this in sharing my honest regrets is that I can save you from some of the pain or the anguish or the lost energy time or money along the way.

6:12So here we go. Let's dive on it. And I can always tell when I feel slightly vulnerable going into an episode because I tried to put it off for as long as possible. And so this is one of those. I feel a little bit vulnerable, but in a good way. Okay. My first regret is really diving into entrepreneurship, lacking every type of boundary. I essentially set myself up for burnout. Hand me over on a burnout platter. That's where I was headed. And it's really interesting because when I think back to those early days, I was juggling a full-time corporate job. I was working 50 plus hours a week. And so I didn't have the privilege of setting the types of boundaries that I now am able to set in my business.

6:55And so I have so much grace for that version of me. But I also recognize that basically the way that I saw life in that stage of life was like working the corporate job 50 hours a week, commuting one hour each way. And then any extra time basically that I wasn't sleeping, I was working on my business. And so for context, I started my business the year before we got married. And so our newlywed life was really both of us grinding at corporate jobs on the nights and weekends that I wasn't working. I was working on my business. And so it's kind of an interesting thing. And I always say hustle is required to get the dream off the ground.

7:36But if hustle is the only way of sustaining the dream, that might not actually be the dream. And that's something I learned from this regret. So let me paint the picture for you. When I was first starting out, I literally would sleep with my laptop and my phone on my nightstand. I would bring my computer everywhere. I mean, I'm talking literally everywhere. I like had this like fear. It like honestly makes my cortisol rise just thinking of it that like something was going to come in and it was urgent, which is hilarious because now I operate from this place of like nothing is urgent. I didn't have a lot of relationships at that stage of my life.

8:13So Drew, you know, was my partner in crime. We had moved to this tiny village in Wisconsin of 1200 people. I didn't really have a lot of extracurricular time because I was either working or building my business. I also feel like I really just like over committed and overdrafted myself. I was approaching business from such a place of scarcity that I was like, anyone that's willing to pay me, I will take that money. And I was taking pictures of cats. I was doing senior portraits. I was doing boudoir photos, like all these different things that I didn't necessarily want to do. And so I wish that, you know, the boundaries would have been there and like the clarity and the confidence to enforce them.

8:53I actually have an episode. It's a recent episode, episode 758, and it's weird places you need to set boundaries in your business. I linked it in the show notes. If this sounds like you in any sort of way, go listen to that episode. It shares a lot about just what I've learned about boundaries over the years. Okay. The next thing that I regret, man, I hired way too slow. I wrote an entire chapter in my book about learning how to ask for help, like loosening the grip. It's so interesting because for so many years of my business, I was a solopreneur. I was doing it all. As a wedding photographer, I was the photographer, the editor, the invoicer, the contract center, the accountant, like all the things.

9:36And I don't think that many of us start a business imagining that someday we'll be a boss. Like maybe there are people who are like, I'm going to be a boss someday. But like, that was not me. I was like, I would just love to get paid to take pictures. And so, you know, we hustle and we get things off the ground. And a lot of times we are all of the people wearing all of the hats, but I have recognized that I have this tendency because just because I can do something, I do it. And I've learned that like, yes, I can do these things, but this isn't actually where my time and energy and passion is best positioned.

10:12And it is amazing and such a blessing to hire people who love what they do to get to pay them and to get things off of my plate. And so I just tired way too slow. There's the story in my book. And my girl, Caitlin, she literally reached out to me three to four times offering to help me. She was watching my career expand as a wedding photographer. She was a freelance virtual assistant. She worked with other photographers. She knew the industry. She knew the lay of the land. She reached out multiple times and was like, I live 20 minutes from you. I would love to help you. Do you need help? And so many times I was like, nah, I'm good.

10:50I'm good. And in the book, I share this story about how the third time she reached out, we had just gotten the worst news of our lives about there's no heartbeat for my pregnancy. And I like responded with like, I need help. And it was like one of the first times in my life that I could even utter those words. But that set me on this trajectory of learning how to ask for help and get amazing help. I couldn't do what I do without my team. And that was just something that I'm like, man, I probably would have saved myself from burnout if I would have gotten help earlier. I also would have understood that I'm not alone in entrepreneurship a lot earlier.

11:30So hiring too slow. And it's interesting because even to this day, I don't want to have a giant team. We have about nine people on my team, 10, 11, maybe with contractors. There's nothing inside of me that appeals to me when people have teams of 20 and 30. I don't want that. That's just not the type of business I want to run. I want to run a really lean and tight team. And so, you know, I still have that tendency of like, we don't need to hire. We don't need to hire. And I feel like over the years, I've gotten really good at kind of loosening up on that, loosening the grip, letting go of control and getting help.

12:04Okay. This next one might actually surprise you. I haven't spoken about this on the podcast yet, but it is something I've been thinking about so much in my life and having private conversations. And so we're bringing it to the pod. this one might be shocking. My regret is blurring the lines between my personal brand and my personal life. Wait, what? The woman who told us all we need a personal brand has regrets about this? Okay, let's dissect. This is a very nuanced debate, but I'm going to just bring you in to the thoughts I've been having. Even just a few years ago, I would have told you if you looked me in the eye and said, do I need a personal brand?

12:40I would have said yes. And I do believe personal brands are so powerful. Having a personal brand has given me so many opportunities to evolve, to share all of the different multifaceted ways that I love to create and consume and share with the world. And having a personal brand is amazing in so many ways. But I believe that while there's so much power in having a personal brand, there are also limitations and there's an expense to it. I have really been asking myself this question of like, where does the brand end and the human and the life begin? And this might not actually be shocking to you, but it is surprising to me in so many ways because for so long, my life was the brand.

13:26And I love that because I love sharing my life. And when I get to the heart of what I do and why I do it, the heart is, is that I want to help women build businesses they don't hate to live lives that they love. And I am at this place in my life where I love my life. I love my life more than my work. And that might not sound shocking, but like for a lot of entrepreneurs, you get it. I love the things outside of my work so much. And if I don't share my life, people don't necessarily connect to why do you care about marketing so much? Or why do you teach about entrepreneurship? Or why do you love entrepreneurship.

14:04I love entrepreneurship because it's afforded me this life. But I am trying to figure out where the content ends and the life begins, where the personal brand stops and the personal life starts. And I'm trying to figure out how do I want to show up online, quite frankly, because my life is either I'm with my kids and I'm like hands-on mothering, which I don't really show much of anymore, or I'm working behind my laptop, which isn't exciting to watch. And so I'm like, what is the content? Like, you know, what is the point of creating content that isn't exemplary of my actual life, but my actual life might not look very exciting.

14:45And then when I'm actually living my life, I'm not on my phone and I'm not documenting those pieces of it because it feels so sacred. And so this is the conundrum in my head. So what is this regret? Just figuring out. And I think getting very clear on like, these are parts of the brand. These are parts of my life that I feel comfortable sharing and giving out to the world. And these are the things and the sacred pieces of my life that I will put boundaries around and keep just as my own. And getting really clear on that in each stage and season of my life, because it's going to look different as my life changes, as my daughters grow, like all these different things.

15:23In fact, it's really exciting. But in an upcoming coaching episode, I had this huge aha moment for myself while I was talking with Savannah Timofay about how if you don't show the life, people don't understand how you can work in a different way. And for me, I already said this, I love entrepreneurship because I love the kind of life it affords me. And so therefore my life should be a part of my content so people can see that there's a different way to be an entrepreneur. But anyways, that episode is dropping in a few weeks. So just make sure you are subscribed. You do not want to miss that one.

15:53It was so wild. while I was coaching, I was like, wait a minute, I need this as well. Okay, it is officially that time of year. And if you run a business, you know, the holiday rush is no joke. I've done more Black Fridays than I can count at this point. And let me tell you orders at 2am inventory updates, refreshing my site, hoping it can keep up. It never stops being intense. That is exactly why I use Shopify. It keeps everything running smoothly when things get their craziest. Shopify is the commerce platform behind millions of businesses around the world and 10 % of all e-commerce in the U.S., from household names to entrepreneurs who will be participating in their first Black Friday Cyber Monday this year.

16:37They've got ready-to-use templates, AI tools, and support available 24-7 so that selling stays simple even during the peak madness. And ShopPay's quick checkout, well, it's a game changer. It means way fewer abandoned carts and way more happy customers. This Black Friday, join the thousands of new entrepreneurs hearing for the first time with Shopify. Sign up for your free trial today at shopify.com slash gold digger. That's shopify.com slash gold digger. Go to shopify.com slash gold digger and make this Black Friday one to remember. Okay, I have been on this ruthless pursuit to purge any clothes that I'm not actually wearing.

17:18Like if I haven't reached for it in months, it's got to go. I am trying to be really intentional about what I bring into my closet right now, which means I am only buying pieces that I know I will actually wear and use. Revolve just gets it, though. I'm literally wearing my brown Autry sneakers from there right now and my new suede purse. It fits my laptop in it, so it's basically a fancy shoulder bag that works for everything. I love finding pieces like that, things that look good but also work hard for my actual life. Their holiday shop is live right now with all the good stuff. Sparkly party dresses, cozy sets, cute gifts, everything you need for whatever is on your calendar.

17:56And it's all in one place, which makes shopping feel way less overwhelming. Whether it's a weekend away, a big night out, or a holiday party, your dream wardrobe is just one click away. Head to revolve.com forward slash gold digger, shop my edit and take 15 % off your first order with the code gold digger. Fast two-day shipping, easy returns. it's literally the only place you need to shop from. That's revolve.com forward slash gold digger to shop by favorites and get 15 % off your first order with the code gold digger offer available for a limited time. So happy shopping. My next one, I'm going a little bit woo woo.

18:32Stick with me. I don't want to lose you. My next regret is operating out of my masculine energy, like just this level of force. And let me just say very quickly for people that are not familiar with like masculine and feminine energies. It's not about gender. It's not about man and woman. It's about just the different sort of energy and drive that you are using. And it's really interesting because I've been doing therapy over the last year. It's been very transformative for me. And one of the unconscious beliefs that I've carried, especially as an entrepreneur, is just that I can do everything with sheer force.

19:10Like if I just work harder, everything will be okay. I need to get ahead to get ahead to stay ahead to get ahead. Like, those are these beliefs that I've had that have absolutely contributed to my success in so many ways. But I also am starting to recognize that like, I have lost parts of myself, or maybe I've never even explored them of like, I say that I want more peace and ease, which I really do. And so I have to lean into more flow energy and less force, like more trusting that the right things and the right opportunities will come at the right times, not saying yes to everything, not just pushing through and pushing harder, but really like checking in with myself.

19:56And it's really funny because I will never forget a conversation I had with my friend Tiko Nejan. She's an emotional intelligence expert. She's an amazing human. And I told Tico, I said, so I'm very like masculine in business and I'm super like feminine in motherhood and marriage and my relationships. And she like looked me in the eye and she's like, you do know, like, that's not true. And like, you can integrate like both of these things. And I was talking about how, like, I don't want to be emotional in business. I want to be like emotionally available for relationships. And I was like, okay, again, you can't just like shut off your feelings.

20:33And I'm speaking to an emotional intelligence expert here. And so I have just been learning so much more of how to actually slow down, enjoy the slowness, be more mindful, really asking myself, okay, what is the point of this? And getting really clear. We've been slowing down our output. We've been protecting our schedule as a team. We've been leaving a lot more room for margin. These summer months feel light and airy just as I wanted them to. And so I've just really learned that from a young age, I was a very intense gymnast and I was the kind of person who would be doing my homework during lunch hour and recess and on the bus and any spare time because basically after school, I would go to the gym until 8.45.

21:20I'd go home, go to sleep and do it all over again. I did gymnastics four days a week, five hours a day. And that was as a child. And so I learned from a really young age of like how to be super disciplined, how to just put your head down and put the blinders on. But I also didn't necessarily learn how to be carefree and joyful and all of these other things. And so I feel like there's a lot of unlearning and relearning here, but I've just really recognized that so much of my business up until recent years was just like straight out of force. And I think that there's room for both. I think that there's room for force and flow, and I'm learning how to integrate all of that so that I don't feel like I'm totally changing my persona based on if I'm working or mothering, like I am me and the wholeness of me and the whole expression of me.

22:04Again, wooey, if you didn't like it, listen to this one. Okay. Next regret. Oh my gosh. Not prioritizing my health. All right. Let's dive in. I think that when I really reflect, I think that subconsciously, I believed that I couldn't have it all. Meaning I couldn't have, you know, this very healthy body, healthy lifestyle and a booming business. I thought that being an entrepreneur was, you know, getting a lean cuisine and heating it up and eating it at your desk so you could get more work done. Like there was just a lot again of these unconscious beliefs. And I didn't know how good I could feel until I actually felt good.

22:42And I was just talking to someone about this, where I was like, if I could have even had a day of feeling how I currently feel, I think I would have changed healthy habits way sooner. I just didn't even know this existed, this level of energy, this level of vibrancy, this level of desire, like just the way that I feel right now is so different. And I also want to give myself so much grace. You know, those early years of entrepreneurship were just like growth and scale. And then we went into our season of loss. And when I really look at it over the last seven years, I've been pregnant four times.

23:20I've had two miscarriages, two surgeries for those miscarriages. I've had two pregnancies, had to do extra hormones. I have breastfed for four years total collectively between my two daughters. It has been a doozy. So for seven years of my life and my life online, the life that you followed, I was really in the thick of some really hard things when it came to my body and loving it. And what's so interesting to me is that I have loved my body through it all. I've had to learn to love it. And my health journey isn't even necessarily about my body. I do feel better in my body, but I needed energy to do the things I wanted to do, to be the type of mom I wanted to be, to launch my book in the way I wanted to launch it, to record these podcasts, to be able to do and operate at this high level.

24:11And I knew that I needed to make changes. And so, you know, it's really interesting to me because I think, and I see so many entrepreneurs put their health on the back burner. And there's that thing of like, if you ignore your body, it's going to like make you pay attention. Right. And so it's like, you can put your health on the side for a little while, but you can't do it forever. And I can get so much more done. I know this isn't about being productive, but because of the energy I have, I can get so much more done in such a smaller amount of time. I'm like, damn, if I would have this energy like five years ago, what could I have done?

24:45But I think I needed to do everything in my own timing. And so if you're more curious about some of my health-related episodes, we have linked them in the show notes. There's an episode number 638. I do an Ask Me Anything episode all about your top health questions. That's one of my top downloaded episodes of 2023. Episode 735, I do an interview with Tina Anderson of Thrive Health. We love their probiotics. We call them belly gummies for my girls. Episode 760, I share about my recent experience of starting therapy to better my mental health. Like just health is so holistic. And I just really wish that I would have paid attention to it sooner.

25:23I think I would have felt so much better across the board. You can also hop on to Instagram if you want more resources and just DM me the word health on Instagram and I'll send you my favorite health resources too. So I just wanted to drop that. Okay, we're getting back into the business field after floating around in the more personal stuff. Next regret is not operating from clarity or really specific data. So to give context, I have always been a numbers person. I think that a lot of my business success is because I actually love business. And I love looking at numbers. I was on the math team.

25:57I love doing math equations. Numbers give me clarity. But that being said, I hadn't made the investment to really invest in getting super granular, having like data systems set up in my business to provide the level of clarity that I want in the work that we're doing today. And this is definitely more nitty gritty. This is not if you are just starting out as a business owner, though, I would argue that there are numbers you should be looking at in your business to give you that clarity. But when I look at the last decade, we were kind of shooting in the dark a little bit. Like we were, you know, setting goals and be like, well, this sounds good.