WW 258: My Biggest Business "Fails" in 7 Years - Solo Show

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A Quick Recap from this episode

For this week’s episode, I thought we’d do something fun. I’m going to get a little personal with you and share my 7 biggest business “fails” in my 7 years in business. A few days ago, I was going through my emails and found some emails that were kind of embarrassing, and it made me think of the little business failures I’ve had over the years. My hope is that you’ll hear these, realize where you’re getting in your own way, and be able to learn from these!

A little disclaimer: I’m using the term failure pretty loosely here. I tend to talk about failure in a way that it’s inevitable for us to fail so we can minimize it in a way and make it less scary. In a lot of my certifications we talk about how there’s no such thing as failure, only feedback. So I’m looking at these as the biggest learning moments.

1. I joined a group money mindset program because I thought the universe would repay me.

Now bear with me here. This isn’t necessarily something I’m embarrassed about, but it’s reflective of where my mind was when I joined this program. I was so desperate to make something work that I thought just by paying to join this program the universe would repay me. There’s still a lot of marketing lingo around this today, and while you should be willing to invest in yourself and your business in appropriate areas, today I know that just paying to jump into something isn’t going to actually make it work.

2. I did everything I now tell my clients to avoid doing if possible (I skipped straight to selling a course without doing any 1-on-1 coaching).

This was a fail for me. The launch of the course was rather successful, but I charged such a low price point for it that I would never have someone offer something like that today. I created a course because I thought it was better for me and I wouldn’t be able to scale 1-on-1 coaching. I was scared of getting on the phone with someone. What I learned and what I now teach in the Wealthy Coach Blueprint is to focus on 1-on-1 and creating a solid 1-on-1 offering that gets results and makes our clients take action. Then you can slowly remove yourself from it to create a DIY type course.

3. I too have launched my own group money mindset program, had 2 people join, and (here’s the failure) felt so much shame that there were only 2 people that I made it 1-on-1 coaching instead.

I think a lot of us have this fear. We don’t want to launch because we’re afraid no one will sign up. There’s a possibility that no one signs up or only 1 or 2 people sign up. But we need to remove the word only from our vocabulary. The fact that 2 people signed up is special. We're so often quick to diminish smaller numbers because we look around and see everyone else's huge numbers, but this is your chance to practice and improve.

4. I went a long time in my business feeling too prideful/scared and not asking for testimonials or feedback.

Now I’ve taken this failure and turned it into a teachable moment. I think it’s hard for us to ask for these things because you’re setting yourself up to potentially get constructive criticism. We want to protect ourselves from that, so we end up not asking at all. Not asking is such a big mistake. Feedback helps you improve your program to make it the best program out there for your clients. Testimonials are such a strong way to provide social proof that a potential client can trust as well. You need to ask for these things.

5. After about a year of being in business, I started pivoting too often and too quickly without any outside proof that what I was creating wasn’t working.

I would give so much power to the doubts playing in my head that I would emotionally act off of that and pivot, then pivot again. It hindered my progress in my business and made me take 3-4 years to really gain momentum and get to that full-time status. Remind yourself that those who are most successful in business are quick to make decisions and then slow to change. Be decisive, but then be slow to change your mind. It’s okay to change your mind, but make sure it isn’t because of those thought gremlins that aren’t rooted in anything.

6. YouTube. Oh, YouTube. Even though this was a pretty good success for me, I’m adding it to the list.

I learned a lot from this experience, which is why it’s on here. I started a YouTube channel when I was offering money coaching and I really enjoyed the whole process of it. I don’t, however, have the psychological strength to read comments of people picking apart how I talk, how long I take to get to the point, etc. One of the biggest reasons I quit it was because it was very draining on my psyche. I had to learn to let it go because it just wasn’t healthy for me even though it looked like a success.

7. I spent forever creating and getting up the confidence to launch my first freebie.

I have since learned that freebies are such a waste for a lot of reasons, but back then I spent months doing this. I spent so much time trying to get people’s email addresses without taking the time to understand what I really wanted and what I was going to do with those emails anyway. We spend a lot of time on these “strategies” that feel like what we’re supposed to do without any real knowledge of why we want to do it to begin with.

There you have it: my 7 business failures. I’m curious if you thought those were failures in your eyes or how you’d feel about those. Hit me up @tess_wicks on Instagram and let me know.

A couple bonus ones:
- The first course I invested in, I paid $5,000 for it, quit my job, just to try to build a SaaS product. I realized I had no interest in that and I let it go.
- I’ve definitely called people the wrong names in voice memos, DMs, and emails.
- I have typos everywhere. I’m a stickler for spelling, but still have typos in a lot of places.
- I didn’t understand Instagram etiquette and used someone else’s branded hashtag when I was posting my pictures because I just thought it was a popular hashtag to use.
- Reading the comments on my YouTube videos.
- Going through a period where I called everyone on my email list “babe.” Some people can get away with calling people “babe” or “gorgeous” but it’s just not my style. It was very inauthentic to me.
- So so so many cringey Instagram posts that I made for many years.

So that was fun! Like I said, reach out to me on Instagram and let me know if you enjoyed that or what your biggest business failure has been!

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