914: The 5 Business Mistakes I Learned the Hard Way (So You Don’t Have To)

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2:10Can we talk about business regrets for a second? Because while everyone loves to say they'd never change anything, I'm over here thinking about five things I definitely would have done differently in my first few years. The plot twist? I'm actually grateful for every single misstep. I'm Jenna Kutcher, and I help you trade hustle for purpose and build a business that gives you the life you actually want to live. From a$300 Craigslist camera to a seven-figure business I run from home, I've learned that success isn't just about what you do. It's about how you live. Here, you'll get strategies that work, systems that give you your time back, and steps that turn your effort into results and impact.

2:54If you're ready for clarity, confidence, and a business that feels as good as it looks, you're in the right place. This is the Gold Digger Podcast. There is something so beautiful about looking back at the versions of ourselves who were just in that like figuring it out stage, you know? Like when I think about those first few years as an entrepreneur, I see this woman who was so full of fire and so filled with determination, but honestly had no clue what she was walking into. And I love her for that. She was making decisions from a place of pure intuition mixed with hustle without having the wisdom that only comes from actually living through the mistakes and the burnout and the breakthrough moments.

3:41She was someone who was doing her absolute best with the information she had. And there is something so sacred about that season of not knowing what you don't know. Now, from this vantage point, after years of growth, evolution, and yes, plenty of beautiful and public failures, I can see the patterns so clearly. The places where a little more strategy could have saved me months of spinning my wheels, where better boundaries could have prevented that inevitable crash, where more courage to be seen could have accelerated probably everything. This episode originally aired a while back, but I'm bringing it back because these lessons feel so relevant right now.

4:22As we're in this season of analyzing our goals and chasing down our biggest dreams and maybe feeling that familiar pressure to figure it all out right now, I think that we need this reminder that growth is not linear and that every version of ourselves is exactly who we needed to be. Because here's what I've ultimately learned. We don't get to skip steps. Every single fumble, every pivot, every moment of not having a clue was preparing us for what's next. And if sharing these lessons can help you honor your own journey while maybe sidestepping a few more of the painful detours. That feels like the most beautiful full circle moment for me.

5:00So whether you're in your own figuring it out era or you're revisiting this with fresh eyes, let's dive in with so much love for the versions of ourselves who are brave enough to begin. Okay, I honestly can't shake the thought of this meme that I saw where someone had gotten a no regrets tattoo, but they accidentally spelt regrets wrong and it reads no regerts. And I just keep laughing to myself as I think about that. So if I start chuckling during this episode, that's literally what I'm envisioning. But real quick, before we talk about the wrongs, I do want to make quick mention of the things that I felt went right early on that allowed me to grow quickly and reach the right people and lay a foundation for a solid business.

5:41I'm sorry, but my mom always taught me to seek out the positive in things. So I can't help myself before we talk about what I did wrong. Let's talk about what we did right. Some of those right things include hiring an accountant to handle the tax and finance side of things, becoming legit legally right away by opening an LLC before I was even making money, sharing my work loudly and consistently on social media to attract more of my target audience, being bold and direct enough to send people direct messages or land in their inboxes asking if they might need my services. And I even made small financial investments into my business early on, like taking out a paid ad that ended up paying for itself within a week to promote the start of my new business.

6:26While some of those methods and the advice I offer around them might have shifted in the last decade, I'm honestly quite proud that I took a chance on myself by doing all of that while working a full-time job at the same time. Okay, so enough with the good stuff. Let's talk about the messy mistakes. That's why you're here. it is time I get to the juicy stuff, those mistakes, those missteps, and looking back now, just plain silly things that I did early on in business that I've learned buckets of lessons from and that I hope will help you learn and make better decisions too. So first, I wish I had understood that I should create with a purpose, not just for the sake of creating.

7:04So have you ever heard the advice, if you build it, they will come? Well, I took that a little too literally early on in my business. And I see new entrepreneurs do this all of the time. Just like you wouldn't build a house without a plan or a blueprint, it's important that anything you're creating for your business is tied to an end result. So if you're spending time, energy, or money on something, it's important to tie every action to this deeper purpose. So get this. When I first started out, I blogged five times a week for years, like literally years. I never missed a single day. I honestly don't even know how I came up with enough content to push out that many posts.

7:45And none of them really did anything for me beyond giving me an excuse to share a Facebook post, directing people to my blog before moving on to the next day. The posts didn't grow an email list. They didn't lead to another destination on my website. They didn't include strategic calls to action or set me up as an authority. Those daily blog posts were just content pieces created for the sake of creating. Essentially, they were like my online journal, the space to occasionally share my work without any information about how to work with me, book my services, or stay in touch. If I had either approached writing with this end result in mind and with more strategy, or if I had reallocated that already limited time to create and promote just one piece a week, it would have served me so much better.

8:32Throwing a little strategy behind my creation process could have totally shifted my approach and the response to my work. So nowadays I create less content per week, even though I have a team helping with the creation and the promotion of that content, because we make sure each and every single piece that we push out is tied to this deeper goal and includes clear opportunities for my audience to take action. Whether that's downloading a freebie or using an affiliate link for a product or service joining my email list or signing up for a training. It's less work all around and it's a more thoughtful strategic approach to creating that I totally wish I would have had in those early days.

9:12It is wild to me when I log into my WordPress and see that I have published thousands of blog posts. And when I think about how I literally posted Monday through Friday, it didn't matter if it was Christmas or New Year's or Labor Day, I was literally just creating for the sake of creating. I want for you to hear this. It is not always about creating more. It's about the strategy behind the creation. So remember that don't make the same mistake I did. Don't put yourself on this hamster wheel of creation without tying it to something deeper, a greater end result. Number two, I wish that I had set boundaries that would save me from burnout.

9:49So this is one of those things that I know in hindsight would have saved me a lot of exhaustion and kept me from overworking myself. Like if I could actually go back in time and change my mindset, knowing what I know now, things might have looked wildly different. And I honestly struggle with this one because sometimes burnout leads to the breakthrough, but when it hits, it can be so hard and tricky to navigate. The truth about burnout is that it never should be the goal or the destination, but it happens to a lot of entrepreneurs and usually leads to things like better boundaries and more balance if we pay attention and we use that burnout as a signal that something's got to change.

10:30I honestly don't think there was any other way for me to learn that hard lesson of realizing that I was pushing myself way too hard and that I had to find a better solution to care for my time, my energy, my health, and to really create actual work and life boundaries. From working a set amount of hours and not giving out my phone number, to taking every Sunday off and turning down doubleheader wedding weekends, I had to learn the hard way that boundaries aren't selfish. They actually protect you. They protect your creativity. They protect your passion. They protect your longevity in a career.

11:05There are so many ways to incorporate your own necessary boundaries that can keep you from overworking yourself or hitting burnout. Because the truth is when you start a business, you're usually so passionate and on fire that you find yourself becoming obsessed with the work. and that feeling of progress. It's like once you get momentum, you simply cannot stop. You're also busy balancing the pressure of doing your own thing and proving people wrong, which is kind of what my neighbor found. And you're trying to make it. And so when you take a bet on yourself, you're likely going to work even harder.

11:40You know that that end result is a reflection of you. And so it's really not shocking that we often hit burnout. The first three years, I was on this upward trajectory as a wedding photographer. I was saying yes to just about everything. I did a ton of crazy things. Like one time I shot two weddings in one weekend in different States. I literally finished a wedding in Milwaukee and drove all the way to Minneapolis hours and hours and hours only to get a few hours of rest and recharge my gear before the next day. Like I did not necessarily understand how to say no. And I did not really know how to look at what my time was worth.

12:18I drove all over the place. I was always available. I said yes to everything. I slept with my computer on my freaking nightstand. Like I spent hours responding to inquiries and answering questions. I even missed some of my best friend's weddings because of client work. And I never ever preserved or saved weekends to be spent with family or for time off. Like when I look back at that, it's like honestly soul crushing because I'm like, I was so pumped to be doing what I loved, but I also took on so much responsibility and I struggled to say no. I was the yes girl. My overzealousness led me to be someone who didn't know how to say no.

12:57And I chased more until I was so burnt out that I had totally swashed any passion I had started out with. I hit this point where I just wanted to walk away and my windowless office suddenly became appealing again. I didn't realize at the time that all of those yeses to work meant equal no's to living my life, to being present with the ones that I loved. And for me, it took hitting total burnout and exhaustion to really recognize that more money wasn't making me happy. And that I started all of this in order to get my life back, not to sign it away. Well, I eventually quote, got it and made the decision that I'd rather live on less money to get back my time.

13:37It's a decision that absolutely shifted everything for me. Like that decision of saying, you know what? I am willing to say no to six figures. I'm willing to work for 50K again, just to have a life again, actually change the trajectory of my business. And it would have been nice to have learned this one a little bit quicker, but if you can get out ahead of it, my best advice is this. Try even small ways to protect and value your time and allow for rest to be a part of your workflow by scheduling breaks into your day and allowing at least one full day a week off of work. Like literally, if you're not taking a day off each week, holy Hannah, start there.

14:20But please take this advice to just protect yourself from the rock bottom that burnout can be and do it so that you don't end up burning the candle at both ends and ultimately resenting what you do for a living. Like I look at how I went from this like passionate person who wanted to bring her camera everywhere, who just loved the art of photography to somebody who was so burnt out and exhausted that I was like, man, like checking myself into a hospital for exhaustion sounds like a vacation. That is not okay. That does not have to be what entrepreneurship looks like. And that should not be the vision you are pursuing right now.

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17:41This is hands down the best bedding I've slept on and I'm so genuinely excited for you to try it. Start building your sanctuary of comfort this fall with Bowl & Branch. For a limited time, get 20 % off your first set of sheets plus free shipping at bowlandbranch.com slash golddigger. that's bowl and branch b-o-l-l-a-n-d branch.com slash gold digger to save 20 % and unlock free shipping exclusions apply number three i wish that i had thought beyond my signature service so we're switching gears here but since we're going back in time i want to paint the full picture for you so i was all in as a wedding photographer and i honestly was in this stage of life where like i couldn't believe that i could get paid to photograph people's weddings It was such a surreal experience.

18:29And all I could think of like was, wow, like I'm really doing this. Starting out as a photographer, it was pretty natural to think I only had one thing to offer, which was my photography services. And let's be real. It is wise to master the art of the one thing you want to be known for before expanding into a zillion other offers. I was actually really proud of myself for hitting this point where I was turning down the random family sessions or puppy portrait sessions and telling people. I am a wedding photographer. I specialize in wedding photography. Frankly, that was a really good first step.

19:02But now looking back, I also realized that there were ways that I could have focused on my one thing, which was photography, while also at least thinking through ways that I could potentially create additional opportunities for revenue around that one thing. Now that I know so much about passive income, digital products, upsells and affiliate sales, I wish I had been thinking just slightly bigger at the very beginning to give me a taste of what it'd be like and feel like to make some money without always having to trade my time. I mean, at the beginning, most of us are more than willing to trade our time for money.

19:38In fact, most times it's the necessary place to begin when starting a business and getting it going from the ground up. But there does come a time of recognizing that the time for money game isn't as freeing as what you had envisioned for entrepreneurship. I mean, where are my fellow service-based friends at? You guys understand the struggle of wanting to show up and serve with your skills, but also wanting to take time off of work occasionally without worrying that the income is just going to completely stop. For me, this reality sunk in when I was actually experiencing our second pregnancy loss.

20:12And I actually had to show up to shoot a wedding knowing what was going on inside of my body. Like the reality that I had built something that meant that if I didn't show up, I wouldn't get paid hit me like a ton of bricks. So even if you're not ready to expand your offerings or you're not 100 % sure what additional ways you want to incorporate more passive income, it's important to think about these things even from the early days to help you take action faster than I did. Now, while I eventually figured it out, it took me a few years and I wish I would have at least thought about ways to incorporate and add in extra revenue streams, even if I didn't implement them right away.

20:51Again, it's great to be a master at one thing to get known for that thing, but don't limit your thinking or your dreaming of other ways that you can bring in revenue, specifically ways that aren't trading your time for money. Number four is this. This is my number one business regret. Okay, let's walk through it. I wish I would have started my email list sooner. Now hear me out. When people ask me like, what is your number one regret? It is this. And I know it sounds so silly and it's not really a shiny thing, but seriously, you guys, your email list is the number one indicator of your business's health and longevity.

21:30And it is something I have been talking about literally for years, even before it was cool or people understood why they needed an email list or what they'd send to one if they even had it. I have had so much conviction on this topic that I could talk about it all day. You can literally scroll back and see that I've been talking about email lists for years. So you might've heard the stat that for every$1 spent on email marketing, an average of$42 is made. But did you know the global email marketing market was valued at$7.5 billion in 2020 and is projected to increase to 17.9 billion by 2027. And beyond those stats, there are 4 billion daily email users.

22:15So basically, there is ongoing and exponentially growing power and profitability in pointing your marketing efforts towards email. So much so that 4 out of 5 marketers say they would rather give up social media than email marketing, and I would 100 % fall into that camp. By the way, all of these mind-blowing stats come from the marketing pros over at HubSpot. So my email list is my number one asset in my business. It's my number one focus in my business. It's the number one thing I invest in when it comes to business. And it's the number one way I drive sales in my business. If that doesn't prove how important this point is, well, I'm not sure what will.

22:55What happened is that I didn't start my email list until years into my photography business. And right as I was in the process of starting my side hustle in teaching, it took that pivot for me to realize this and to take action on it because I'd been so distracted by all the other things that I thought I needed to be doing. When I finally knew that I wanted to do something beyond shooting weddings, it felt like I was playing catch up on starting and growing my list. And once I did get started and I can see now I was so focused on trying to win shiny social media points, points that don't actually lead to a ton of results or extended brand loyalty or conversions.

23:33Here's the other point I want to make. I wish I would have started my email list back when I was a wedding photographer because service providers can benefit insanely from the rewards of email marketing. So I wish I wouldn't have looked at it as like something necessary when I entered this digital education space. But I wish that I would have seen it as an asset that was worth pursuing and investing my time and energy and effort into as a service provider. And that would have laid the foundation for my pivot. So when I look back and I was focused on all the shiny things, now I understand the power of a lead or a subscriber and how an email list allows you to thoughtfully serve someone before you ever go to sell to them.

24:13I also love the fact that much of email marketing can be automated, meaning when we're talking about trading our time for money or serving and showing up, it gives you this opportunity to know that you can work smarter and not harder, that people can be served while you're resting, that you can set up automations that do the work for you. So beyond being the biggest needle mover for my business, email marketing is also one of the most powerful ways that most small businesses communicate with their audience, keep them informed and make the most sales. In fact, 64 % of small businesses use email marketing to reach customers.

24:47And that number is growing as entrepreneurs recognize the role that email should hold in their business. It's important when we look at our marketing efforts to recognize that we don't actually own our social media channels and we can't control the experience we offer followers or the frequency our posts are delivered. But with email, we get this opportunity to show up one-on-one into our audience's inbox for this more tailored personal way of communicating and building trust. Okay, number five is this. I wish I hadn't hid behind my work for so long. It's my last regret. This one is a really easy regret because looking back, I can 100 % see and understand why it happened.