5 times I royally failed in my business (and what it taught me)
There's a lot you can learn from my messy mistakes
This year marked my 5th year in business. 🪩
February 20, 2025 was the official 5 year anniversary of when I divorced my corporate compadres (siting irreconcilable differences—’tis a different story for a different day) and struck off into solopreneurship with nothing but my LEGO Mini Figure collection and some Pilot Razor Point pens I swiped from the supply room on my way out the door.
(Sorry not sorry. They’re legit the BEST pens.)
I didn’t post any celebratory notes this year or even acknowledge it to my email list. To be honest, the date kind of slipped by unnoticed. That tends to happen now that I’m a parent trying to juggle business with bringing up baby. 😏
But it struck me while we were on vacation. And the milestone has been sitting with me ever since.
I distinctly remember those first few months in business, trying to navigate the complexities of this new and very unfamiliar path I found myself.
One that included learning how to build a website, showing up on social media like it was my job (because now it was), and doing Zoom calls with strangers I just met on the internet.
It wasn’t nearly as glamorous as what all the influencers and gurus had made it out to be.
We’re often sold this bill of goods on what being a business owner looks like, that includes, but isn’t limited to:
Manifesting a million dollars in six months from a Pinterest vision board.
Having 6-figure online course launches while on maternity leave.
4-hour work weeks and memberships that bring in oodles of passive income while you sip daiquiris on Sea Island.
Getting thousands of followers from a single Reel and suddenly becoming Insta-famous overnight, with brand deals flooding your inbox.
But 99.999999999999% of the time, the reality is so much messier than that.
When all we’re fed are the successes, we start to believe that our failures make us frauds, imposters, or somehow unworthy or undeserving of the results other people appear to have achieved so “easily.”
But the truth is every single successful self-made entrepreneur that exists only got to where they are because they were willing to fail more times than anyone else and learn their way to the top. It’s why they’re a success. And continue to be a success.
So I thought I’d peel back the curtain in this article and reveal some of the big, hairy mistakes I’ve made over the last 5 years. And more importantly, the lessons they taught me to help me grow my business, instead of pulling me under.
(It’s a meaty one—you’ve been warned. 😏)
1. I threw my heart and soul into a course—and it flopped.
Not long after my daughter was born, I was struggling to keep my business afloat as a new parent. I got it into my head that I would create this massive course on everything I had learned about how to market a new business (it sounded like a good idea at the time…? 🤷♀️) and create “passive income.”
I threw everything I had into that course. Every hour or two I could snag during naptime. Late nights after my daughter had gone to bed. 5 am work sessions before she was awake. All told, it took me a year to put together.
When it came time to launch, I was a stressed out mess. It was hard to schedule live webinars because I was worried my daughter would need me. I was throwing money into ads and making knee jerk decisions. I was desperate for that course to work.
Looking back, it was a powder keg situation.
I fully expected to get at least 20 students. I got 3. I think I broke even on my ad spend. Or maybe came out a little behind. But I was devastated. I worked myself like a racehorse for a year and “all” I got were three students.
I’m not ashamed to admit it took me awhile to bounce back from that.
What it taught me:
People need time to get to know you before they will buy from you. You can’t fire off some ads, do a webinar, and send out a canned email sequence and expect people to buy. It’s a classic example of why email lists that you nurture are so dang important (more on that in a minute).
Desperation is a bad look in business. It makes us do things we wouldn’t normally do, like throw everything but the kitchen sink into an online course and expect people to buy it on a whim.
You need to sell a clear, distinct, and desirable outcome. I thought people wanted to know how to market their businesses. But that’s not what they really want. They want a system for making reliable sales. And they wanted the quickest way to do that, not the 7 hour course curriculum.
Never judge the success or failure of a situation from the 1-week, 1-month, or even 1-year view. Sometimes you need time and distance to see the real impact. Two of those 3 students have been repeat customers in my business for 3 years. One of them is a client who has easily spent 5X her course investment in working with me personally. The universe is funny like that.
Just because it’s what everyone seems to be recommending doesn’t mean it’s recommended for you. I think a big part of why I struggled to sell that course was because it included things like a community and weekly coaching that I was stressed about keeping up with. I added them because I thought I had to, not because I wanted to or thought they were the right choice for me or my business.
2. I had less than 200 email subscribers on my list for 3+ years.
If that seems like a lot to you, keep in mind that I’m a marketer for a living and email is arguably the most important marketing asset a business owner can have. All that’s to say—I should’ve known better.
Even though I’d heard countless people preach that to me since starting my business, I downplayed it’s importance. I told myself I didn’t have time. That I could do it without email. That it was far more important for me to show up on social media.
(Excuse me while 2025 me snorts and shakes her head at 2022 me.)
Then my Instagram account got hacked and I lost all my followers. I had the aforementioned failed course launch. I had a baby.
And I found myself carting around ring lights and staging furniture to get the perfect Insta shot in between breastfeeding and cleaning poop out of my clothes (people should really prepare you better for how much those things poop).
And suddenly I realized I didn’t want to do the (literal) social media song and dance anymore. But it was only then that I realized I hadn’t built a safety net.
All I had were some followers on Instagram. If I cut Instagram, I’d have to start over. But start over I did.
What it taught me:
The only reason you’re even on social media as a business owner is to get people off of social media and onto your website or email list. The minute you forget that and get sucked in to the drama of going viral, beating algorithms, or racking up followers, you lose.
Email is still king. Yes, even in 2025. Having a direct line to your audience’s inbox that no algorithm can f* with is the definition of solopreneur business security. Don’t discount it. If you don’t have one, start one. Today. Like right now. I’ll wait…
In order for email to work for you, you need to show up and nurture it. Having an email list you sit on for years and only email a handful of times is waste. If you want to commit to growing a business, you need to commit to your list.
Social media is like playing the lottery. An email list is like investing in your 401K. Don’t sacrifice long-term profitability on the altar of short-term popularity.
What you focus on is what expands. When you constantly focus on what’s right in front of you (likes, follows, trending audio), you’re too busy worrying about today instead of planning for what’s ahead. When you focus on your long term vision, you build a long term business.
3. I ran a Black Friday campaign that got zero sales.
Last year (yes, just last year) I decided last minute to run a Black Friday campaign for my business.
Literally, it was the Sunday before Thanksgiving, we were busy getting ready to head to Palm Springs to spend the holiday with my family, and this was when I had the notion of offering something to my subscribers. 🙄
The problem was I didn’t really know what to offer.
So I made a couple different offers, a few bundles, some digital products I had. I created a few Thrivecart pages and wrote up two quick emails sharing all of the offers together so people could find the one that worked for them.
I scheduled the emails, flew with my family to California, enjoyed an amazing Thanksgiving dinner, and then waited on Friday for the sales notifications to come through.
I didn’t get a single one.
I was bummed at first. Then annoyed. But then when I thought about it, I realized the lack of sales was my own damn fault. Here’s why.
What it taught me:
Give people a bunch of different offers in one email and you split the focus of the email. Instead of asking them to choose between two options (to buy or not to buy), I was asking them to choose between several. And that makes it harder for them to choose any. It’s something I preach to my own clients all the time, but for whatever reason, on that occasion, I chose to ignore my own advice. 🤦♀️
If you’re not going to fully show up for your people, you can’t be disappointed when they don’t fully show up for you. I know. Stings a little. But it’s true. I thought I’d throw something together haphazardly and get a nice little sales bump at the end of the year. If I’m being fully honest and transparent, my audience wasn’t my priority. I was. They turned out accordingly.
Fail to prepare, prepare to fail. In my rush to get something live, I neglected to realize that two of my four sales pages didn’t even work correctly. Are you judging me a bit? It’s okay, I’m judging me too.
4. I had at least 6 lead magnets that nobody ever downloaded.
Starting out, one of the first things I did was create a lead magnet. I at least knew I needed that much. So I created something. Beautified it in Canva. Pinned a few pins. Posted about it once or twice on Insta.
And when it got zero subscribers, I scrapped it. Because I assumed it sucked and no one wanted it. I set about creating a quiz. Did the same things. I got 1 subscriber. So I scrapped that too. The pattern repeated itself multiple times.
It’s only in hindsight that I realized the lead magnets were likely never the problem.
My lack of visibility was and my poor way of offering them was. If only I’d known it then, I wouldn’t have had to make so many lead magnets. And I could have been actively growing my list much faster.
What it taught me:
No offer will work if you don’t have an audience. If you share an offer to an empty room, no matter how awesome that offer is, people will not buy it. You’ve got to get eyeballs on it constantly if you want it to work. Posting about it twice doesn’t cut. You should be sharing it twice a week, at least.
No offer will work if you don’t promote said offer either. I used to be the queen of putting the link to my lead magnet in my Instagram bio and expecting people to just mosey on up there and grab it. Cute, right? No one is going to download your thing, visit your website, attend your training, buy your awesome stuff unless you (wo)man up and ASK.
Before throwing in the towel, get to the REAL root of the problem. Is it really your lead magnet? Or is it the fact that no one sees it? Or the way you’re promoting it? Or your landing page? (PS, if you honestly have no idea, reach out to me and I’ll help you figure it out.)
Ask yourself why your audience should care. It doesn’t matter why you care about it. It’s not for you. It’s for them. I used to talk a lot about what my offer was and why I created it. I never talked about what it did for them and the quick win or result it helped them achieve. Which is what people are really here for.
5. I have 50+ different offers that never made it anywhere.
At least 50. Canva templates no one downloaded. Bundles no one bought. Memberships I started and then decided I wanted no part of. Loads of things I thought were awesome, but my audience told me otherwise.
I used to take this really personally. Like I’d get myself all twisted up in knots over it. But now I realize it’s just a natural part of the business I’m in. And I wear those failed offers like a badge of honor. Because they’re proof I did something.
Even if they didn’t go the way I thought they should, I’m not sleeping on anything. I have ideas, I create things, some of them take off, others don’t. It’s no different from any other type of professional.
Serena Williams didn’t win every match.
Taylor Swift doesn’t turn everything to gold (lest we forget Cats).
Grant Achatz just shuttered a restaurant he opened in Chicago less than a year ago.
No one is immune. If nothing else, I take solace in that.
What it taught me:
You are not your audience. Just because you think it’s awesome doesn’t mean they will. I’m a marketer who’s also a business owner. Most of my audience are business owners who also now happen to be marketers (against their will in most cases). Sometimes I forget that distinction. But it pays to always try to put yourself in your audience’s shoes.
Sometimes you’ve got to try a lot of things before you figure out what lands. It’s not the most useful advice, but it’s true. We make pancakes in our house every weekend. No matter how often I make pancakes, that first one or two are just never as good as the others. It can take a minute to find your rhythm.
Not every offer is gonna crush it. Let go of the losers, lean into the winners, and trust that the universe is just helping you prune and direct the growth of your business in a way that’s going to be most valuable to you. Come to think of it, that goes for failures in general. 😘
You never really stop making mistakes. Not if you’re committed to growth. Because mistakes and failure and setbacks lay the groundwork. They’re like the dirt that you plant the seeds in.
Avoid the ones you can, learn from the ones you can’t, and don’t let them say anything about who you are as a business owner, except that you care enough to show up and try.
What are some of the messy failures you’ve experienced in your business? What did they teach you? Please share them in the comments! I’d love to know.
Uh! A must read!
Always good to read things like this. It's a helpful reminder not to take our own failures and missteps too personally. Thank you.