The Mistakes I Made When Starting My Business(es)

My first attempt at business was to be a birth doula. I didn't end up attending a single birth.

Apr 08, 2025

(I have a bunch of your questions to answer in my anonymous Q+A form, in honor of practicing Radical Honesty this quarter. One of them asked, “How did you start your business?” I’m shifting that to a messier lens: “What did you f** up when starting your business?” since it lets me dig in a bit more.)

4 Mistakes I Made When Starting My Business(es) 💸

1 | Not considering my ideal structure of a workday/month.

Fun fact: My first-ever attempt at running my own business was to be a birth doula. I got through most of the training and felt ready to start putting births on my schedule! I even got a few inquiries (that led to nowhere)! …And then, pandemic hit, and it was virtually impossible for doulas to attend hospitals. 🍼

At first, I was super frustrated but put my head down. I gave a couple virtual talks online, networked with other local doulas, built a website and maintained a blog, and started using Canva to make social media posts.

But as the months ticked by and doulas still couldn’t doula IRL and my business felt like it was doing nothing (because it was kinda doing nothing), I thought a bit deeper about what I wanted Cascade Mountain Doula to look like.

And it hit me… I absolutely do not want work that requires me to be on call 24/7 for weeks on end. I wouldn’t be able to stand work that tethers me to a location waiting all night for a call that could lead to a 30-hour shift. I value time and location freedom so highly, and this specific work would breach that. (LOL to grammar/birth nerds that I first typed that as “breech” with birth on the mind.)

I didn’t want to be a doula, after all– even after paying a couple thousand for training and soaking up all the resources I could about pregnancy, birth, and postpartum.

Surprise: Those foundations of starting a biz led me to shift to The Hormone Hacker, a virtually-based education business around menstrual cycles. I used a lot of the tools I learned from doula training (both about body empowerment and about building a business) to create courses and content and eventually, a book. 📖

Technically, my first business “failed.” In my eyes, it was a valuable wake-up call to build a business that supports the structure I want in my everyday life.

2 | Believing a bunch of unethical marketing tips.

While starting The Hormone Hacker, like many first-time business owners, I fell for all the marketing “tricks” that the conventional world teaches. Certain practices never felt right to me, but I figured that I had to play by the rules in order to become successful.

For example, when I started teaching courses, I bought into the idea that you need to focus on scarcity and pain points in copywriting, that you should charge penalties for payment plans (yup, even though the people that need payment plans have less money), and that you should end your course prices in $297 instead of $300 as a psychological trick. 🙄

It all felt icky to me, and it even held me back from promoting my own work, but I didn’t know what else to do.

As I got more experience in marketing and having relationships with “customers,” I realized that what would resonate with the people I wanted to most work with wouldn’t be marketing tricks. Instead, I could market my work in a way that felt ethical to me and aligned with my values. Everything changed.

I didn’t have to play someone else’s game — I could create my own. After all, you attract the community and network that share the values you put out. I value transparency, creativity, and fun. So, I try to infuse those in the marketing of the current iteration of my biz. That, in turn, helps me work with people who feel the same. Feels way less cringe.

3 | Focusing on a format of services that didn’t play to my strengths.

Going back to the doula thing. That was basically 1:1 work. A pregnant person would hire me, and I’d work with them 1:1 until after the birth of their kid. That’s the only way I imagined business.

Here’s the thing… I don’t love 1:1 work. In pretty much any realm. I thrive in groups. 🤷‍♀️

Soon after my initial biz pivot, I took the CliftonStrengths assessment. It gave me the language to explain why certain work, situations, and relationships come easily to me, while others give a challenge (and how to apply that insight to future decisions).

According to my unique order of strengths, I find it far more energizing, exciting, and effective to work and perform for larger groups, rather than one-on-one work. That explains why I’m happy and comfortable being on stage inspiring an audience to take action at the drop of a hat, but I don’t feel as at ease chatting with one client on a scheduled Zoom call!

Examining my strengths (and what aren’t them) gave me my own permission to drop one-on-one work from my menstrual health work, and instead focus on group programs and events. ‘Twas quite a relief.

4 | Thinking I’d create one business and get to keep it forever.

Maybe this is why entrepreneurship isn’t for everybody… I believe that being a business owner means always having to shift and change it. There are too many uncontrollables in the world to believe that one business niche, offer, schedule, or structure will always be a good fit for the owner and the customers. (Please, give me an example that proves I’m wrong.)

I truly thought that if I just built the perfect product or service and showed it to the right people, I could just lock it in and coast forever. Y’all, nothing works like that in this world. 🙅‍♀️

When I found myself pivoting and pivoting and “failing” and messing up and trying again, year after year, I finally realized that… this is it. THIS is what business ownership is. Being in a constant cycle of change.

At first, it was a “dammit, that seems like so much work!” feeling. But then I realized, it’s actually the fun part. I get the freedom to experiment whenever the heck I want. I can reinvent my offers, I can “creatively compost” (like how Emily and I just archived all our old podcast episodes to compost them into new, more aligned ones), I can blow everything up to help honor a life change.

By expecting my work to shift regularly, it feels like momentum, not stuckness. 💪

So, no more chasing “forever.” In 2025, I’m designing offers and events and client work that works for right now. And sure as hell, it’s way more fun to be creative and curious about what’s a great fit for my life and work today, not trying to predict what the world will look like 20 years from now.

Tell me:

If you have a business, what’s an oopsie you made in the past?
If you don’t have a business but want one, what’s your dream biz?
What else would you be curious to hear about from my biz journey?