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There’s something so beautiful about looking back at the versions of ourselves who were just… figuring it out, you know? When I think about those first few years as an entrepreneur, I see this woman who was so full of fire and determination, but honestly had no idea what she was walking into. And I love her for that.
She was making decisions from a place of pure intuition and hustle, without the wisdom that only comes from actually living through the mistakes, the burnout, the breakthrough moments. She was doing her absolute best with the information she had, and there’s 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 failures — I can see the patterns so clearly. The places where a little more strategy could’ve saved her months of spinning her wheels, where better boundaries could’ve prevented that inevitable crash, where more courage to be seen could’ve accelerated everything.
As we’re in this season of analyzing our goals, chasing down our biggest dreams, and maybe feeling that familiar pressure to figure it all out — I think we need this reminder that growth isn’t linear, and every version of ourselves is exactly who we needed to be.
Because here’s what I’ve learned: we don’t get to skip steps. Every 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 of the more painful detours? That feels like the most beautiful full-circle moment.
So 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 were brave enough to begin.
Mistake #1: I Didn’t Create with a Purpose
Get this: I blogged 5 times a week for years — literally years, never missing a single day!
I honestly don’t even know how I came up with enough content to push out that many posts, and 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.
They 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? They really were just content pieces created for the sake of creating — essentially they were my online journal and a 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 an end result in mind and with more strategy, or reallocated that already limited time to create and promote one piece a week, it would have served me much better. Throwing a little strategy behind my creation process could have totally shifted my approach and the response to my work.
Now a days I create less content per week (even though I have a team helping with the creation and promotion of that content) because we make sure each and every piece we push out is tied to a deeper goal and includes clear opportunities for the audience to take action, whether that’s downloading a freebie, using an affiliate code 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 wish I had had in those early days. It’s not always about creating more, it’s about the strategy behind the creation — remember that!
Mistake #2: I Didn’t Set Boundaries
From working a set hours and not giving out my phone number, to taking every Sunday off and turning down double header wedding weekends, I had to learn the hard way that boundaries aren’t selfish, they help protect you.
There 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 with the feeling of progress. You’re also busy balancing the pressure of doing your own thing and proving people wrong and trying to “make it”, it’s not shocking we often hit burnout.
The first three years, I was on this upward trajectory, saying “yes” to just about everything, I did a lot of crazy things like shooting two weddings in one weekend in different states, and I struggled to really look at what my time was worth.
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 to get back my life, not to sign it away. While I eventually “got it” and made the decision that I’d rather live on less money to get back my time — a decision that shifted everything including the trajectory of my business, it would’ve been nice to have learned this one a lot quicker.
If you can get out ahead of it, my best advice is to 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 or allowing at LEAST one full day a week off of work.
Seriously, please take this advice to protect yourself from the rock bottom that burn out 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.
Mistake #3: I Only Offered One Signature Service
I mean, starting out as a photographer, it was pretty natural to think I only had one thing to offer clients… my photography services! And let’s be real, it is wise to master the art of the thing you want to be known for before expanding to a zillion other offers. I was proud of myself for hitting a point where I was turning down the random family session or puppy portrait session to tell people, “I’m a wedding photographer” and frankly, that was a great first step.
But now, looking back, I also realize there were ways I could have focused on my one “thing” which was photography, while also at least thinking through ways 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 trading it for my time.
I mean, at the beginning most of us are more than willing to trade our time for money, in fact, most times it’s the necessary place to begin when getting a business off the ground. But there comes a time of recognizing that the time for money game isn’t as freeing as what you had envisioned for entrepreneurship.
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. While I eventually figured it out, it took me a few years and I wish I had at least thought about ways to incorporate and add in extra revenue streams, even if I didn’t implement right away.
Mistake #4: I Didn’t Start My Email List Sooner
You might know that for every $1 spent on email marketing, an average of $42 is made. But did you also know that 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??
Basically, there is ongoing and exponentially growing power and profitability in pointing your marketing efforts toward email, so much so that 4 out of 5 marketers said 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.
My email list is my #1 asset in my business, it’s my #1 focus in my business, it’s the #1 thing I invest in in my business and it’s the #1 way I drive sales in my business… if that doesn’t prove this point, I’m not sure what will.
Beyond being the biggest needle mover for my business, it’s also one of the most powerful ways that most small businesses communicate with their audiences, keep them informed, and make the most sales.
In fact, 64% of small businesses use email marketing to reach customers, and that number is growing as entrepreneurs recognize the role email should hold in their business.
It’s important when we look at our marketing efforts to recognize that we don’t 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 to show up one-on-one into our audience’s inbox for a more tailored, personal way of communicating and building trust.
Mistake #5: I Hid Behind My Work
I see this so often with artists and photographers and writers and VAs and social media managers and coaches, I mean, it happens to all of us… and I get it because I did the same early in my photography biz.
I didn’t post any photos of myself or my life until about year 3… truth was, I thought people just wanted to see my work and my photos of clients because, after all, that was what I could offer for them and the service they’d be most interested in booking.
Looking back now, I can see how I was playing small and trying to blend in and I lived with this belief that my work would speak for itself, but what I failed to recognize was that if people connected with ME, they were more likely to appreciate my work.
By hiding who I was, I was actually doing my clients and audience a disservice. Sprout Social shared that 70% of consumers feel more connected to brands with CEOs who are active on social media, which makes sense when we think about our OWN user habits. We like connecting with other people and real faces and personalities, not just logos, faceless graphics, or products…
The quickest way to grow trust is to be true to you, to show off your personality, and share more of the humans behind the offers. There will be a lot of people who do what you do but there won’t be anyone else who can do it the same exact way you do it.
You are the only person with your story and your outlook and your YOU-ness. Sharing pieces of your life, your personality and heart through images of you, stories about you, and your thoughts, beliefs and values allows people to connect not just with your business, but with the mission and heartbeat behind that business. Trust me on this one!
The Big Picture
So now you know all my deepest, darkest regrets. Just kidding, but sort of… In reality, these are things I’m really actually glad to be able to look back and say, “Now I know better and can do better,” and in that sense, they are all pieces of my entrepreneurial story and journey I’m honestly proud of.
They’ve led me to create stronger boundaries, lean into my values, understand who I am better, and get creative with my marketing strategies.
So what do you think? I hope you can take my mistakes and use them for your own benefit, and maybe even cut a few years of your own learning curves off while you’re at it.
It’s always fun taking a walk down memory lane with, so thank YOU for being here! As always, if you enjoyed this episode, I’d love to hear from you, hop over to Instagram @goaldiggerpodcast or leave a review on Apple Podcasts — I literally check them every single week!
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[…] what you do but there won’t be anyone else who can do it the same exact way you do it.” – Jenna Kutcher, Digital Marketing […]