Have you ever found yourself regretting a big investment? That’s what this episode is about because I want to share with you two investments I made that were incredibly high-ticket—very costly in terms of money. However, the lessons I got from them are still helping me today. So yes, we’re going to flip the pancake on these mistakes. I wanted to share them with you for two reasons: first, so you don’t make the same mistakes, and second, so you can start to see the bright side of these missteps.
Because really, that’s the only way to move forward in your business—by not dwelling on the things that went wrong and realizing that sometimes, things just have a way of working out in the end.
Hi, my name is Ina Coveney. I’m a marketing strategist and business coach. This is the Superhumans Podcast, where I interview the most successful people I know so I can share their ideas and lessons with you, helping you become a superhuman too. Today, however, is a solo episode. It’s just me sharing something I’ve learned so you can learn it too and avoid stumbling on the same roadblocks I’ve faced.
Today’s episode is like a huge PSA. I’ve made mistakes in investing. One happened about four years ago, and the other was this year. Yes, I am still making investing mistakes. I feel compelled to share these stories in case they can help someone.
Let’s start by considering why we make these investments and why we make mistakes. For me—and I’ve seen this happen with my clients too—it often comes down to seeking that one solution that we believe will completely unlock success in our business. We convince ourselves that this must be it because the testimonials are glowing, and everything about it seems perfect.
But here’s the truth: good marketing is often what convinces us. Nobody is going to showcase their program by talking about how some people didn’t succeed with it. You’re only going to see the success stories—the people for whom it worked. As marketers, that’s what we do. We highlight that success is possible.
Is it possible that some people never even open the program? Yes. Could the success rate be as low as 20%? Also yes. But that’s not information you’re going to see. You’re only looking at the times when it worked. Knowing this probably won’t stop you from investing because things can seem like exactly what you need. I’ve been there, done that.
I’ve made investments that were slam dunks—decisions I’m so grateful I made. But I’ve also had regrets, and two particular investments come to mind. These are ones I totally could have avoided. In one case, I wasn’t strong enough to walk away. In the other case, I didn’t even realize I didn’t need the thing I was investing in.
Let’s start with the first mistake. I’ve always believed that saying no to opportunities means leaving money on the table or not taking my business seriously. For that reason, I’ve often said yes to everything. I worked with a coach for two years who was wonderful. She helped me navigate some really tough moments and unlock new levels of success.
After about a year and a half, I felt it was time to stop working with her and focus on implementing everything I had learned. I had mentally prepared myself to move on. When our deal was coming up for renewal and she planned to raise her prices, I told her I was all set and thanked her for everything. I thought that would be the end of the conversation.
But then she objected. She pointed out that I had a big launch coming up and asked if I didn’t feel like I needed her support for that. She explained how she could help me prepare and make it a success. I wasn’t ready for her objection, and it triggered a thought in my mind: “If I say no to her, it will look like I’m not serious about my business.”
I didn’t want to be one of those people who say no to help and end up failing. I thought, “What if I really do need her and I just don’t realize it?” So I said yes, even though I didn’t feel strongly about it. That decision cost me $18,000 for six months of coaching—a sum I did not make back.
To be clear, this wasn’t her fault or mine. Coaching doesn’t guarantee results. But at the end of the six months, I didn’t have the money to make the final payment. I had to ask my husband for the money, which felt humiliating after three years of running my own business. He was kind and supportive, and I paid the money back a few months later. But that experience opened my eyes to how I was making decisions. I didn’t want to renew, but I did it anyway because I wasn’t strong enough to say no.
From that point on, I decided I would only invest in something if I already knew I needed it before the offer came to me. Too often, we let an ad or a sales pitch convince us we need something, instead of deciding for ourselves first. That’s the lesson I learned from this mistake: the need has to come before the offer, not the other way around.
Now let’s talk about my second mistake, which happened earlier this year. At the start of the year, I restructured my business model, transitioning from a membership to a high-ticket program. I thought I needed help selling it, so I enrolled in a $15,000 six-month sales program. At first, I thought it was exactly what I needed. But after trying their methods for a couple of months, I realized they were completely out of alignment with me. The sales techniques were aggressive and didn’t resonate with how I wanted to run my business.
Although the program didn’t work for me in the way I expected, I wouldn’t say I regret it as much as the first investment. This time, I wasn’t coerced into it; I knew what I was signing up for. While I didn’t get the intended results, I did make amazing connections in the program—people I still stay in touch with today.
What I ultimately learned from these two experiences is that not every investment will work out the way you hope. However, it’s up to you to make the most of them.
For example, I later found a completely different group that offered exactly what I needed—a place to ask questions and connect with successful people. It cost me only $300 as a one-time fee, and it turned out to be the best $300 I’ve ever spent. This inspired me to create something similar: a lifetime coaching mentorship where people can join for a one-time fee and get lifetime access to my guidance and support.
In conclusion, you will make investments that don’t work out. But instead of complaining or saying that coaching doesn’t work, focus on the lessons you’ve learned. When you adopt the mindset that you have control over your outcomes—even when mistakes happen—you set yourself up for long-term growth.
Thank you for listening to this episode. If you found it valuable, please share it on your stories and tag me @InaCoveney on Instagram. I’d love to hear from you. See you on the next one!