Ep #8: Lessons From My Money Mistakes

Have you ever been curious to know the real inside scoop on what kinds of money mistakes high end coaches like me have made? I think the dirty little secret in the coaching industry, the secret no one wants to talk about openly and with honesty, is that money mistakes do happen. So in an age of false positivity, and this relentless posturing on social, I'm here taking a stand for honesty, and pulling back the curtain on money mistakes that can easily happen, even to experienced high end money mentors like myself.

Stay tuned to hear three whoppingly big money mistakes I've made, what I learned from them, and how you can avoid similar mistakes from happening to you. I'm Kendall, and I'm sharing even the most embarrassing money mistakes I've made. It's all here for you in this episode of The Money Coach School Podcast. Let's dive in.

Welcome to The Money Coach School Podcast. To really excel at coaching women, you have to be skilled, confident, and even fearless at money coaching. If you're passionate about women holding genuine money power and love supporting women entrepreneurs, then this is the show for you. Now, here's your host, money feminist Kendall SummerHawk.

Hello, beautiful coaches, and welcome to another fantastic episode of The Money Coach School Podcast. I'm one of those open book people. You can ask me anything, and most likely, I'm going to answer it. I love transparency. But in the coaching space, there's often so much more displaying this perfect image of the perfect lifestyle and the perfectly curated imagery and the perfect relationships. It's like no one ever has a bad, sad, or mad moment, especially when it comes to money.

No one ever seems to have clients who don't pay or who dropped out, or unexpected expenses or a regrettable decision. So in today's episode, I want to pull back the curtain, get very transparent and very personal with you, and share with you behind the scenes three money mistakes I've made in my business. The lessons learned from each of them, how I recovered from them, and how you can use my experiences to avoid these types of mistakes in your coaching business.

In an upcoming episode, I'm going to share the flip side. Money decisions that turned out fantastic and all the learning from those as well. Before we dive in, I would love to connect with you on Instagram. You can screenshot the podcast while you're listening here and tag me with it on Instagram. My handle there is @KendallSummerHawk.

All right, let's get personal and talk money mistakes. Okay? I have to be honest with you. I was a little worried at first that this episode would be negative. Because when you hear the money mistakes I made, they are whoppers. They're really, really big. But I really want you to be able to benefit from them so that you can make amazing, informed choices for yourself and hopefully avoid some of these costly mistakes that I've made.

I also want you to see that yes, even top mentors like myself, money mentors who have made millions and millions of dollars also make mistakes on our journey. It's one thing for me to tell you that you don't have to be perfect with money to be an amazing money coach for women entrepreneurs. It's a whole other next level vibe for me to show you what being imperfect looks like in real life. So here we go.

First, we all make money mistakes in our businesses. We invest in courses or programs that don't deliver or weren't the right fit at that time. Or we have people who are overpaid for what they've done for us, or we make an investment for a reason that isn't really clear why we're doing it, or we do it for reasons like fear of missing out, FOMO.

My point is, it happens. It happens to me as a seven figure business owner. It happens when you're newer in your business, and you feel the pain of every penny spent. It happens to all of us. But here's the thing. When you make clear, intentional decisions about investing in your business and your emotions are clean, which I'll talk a little bit more about in just a moment, then money mistakes are very few and far between. So that's number one.

Second, money mistakes are not a reason to think that you're not good with money or anything negative. Money mistakes are truly a learning experience, and that's the secret. As long as you're clear about what you learned and what you'll do differently the next time then it's really not a mistake, is it? It may be an expensive learning, but a mistake, no. Learning isn't free and sometimes it's not cheap. We pay to learn period.

So let's dive into three of my money mistakes, what I learned from each one, and how each one lead me to something smarter and better. I picked out three that were pretty significant dollar amounts because, like I said, I value transparency.

So money mistake number one, investing in a $25,000 coaching program, not being happy with what it was offering. So then I invested another $45,000 with the same coach for a different program just a few months later. So $70,000. Wow. Or I should say ouch. That is a lot of money. So why did I do it? Why did I take a $25,000 investment that I wasn't happy with and add another $45,000 on top of it?

First, let me be clear, there was absolutely a lot of value in the programs. There was a ton of training. So I'm not faulting the programs in any way. But what happened is I got swept up in the personality of the coach in that she “seemed a lot like me.” She was an introverted extrovert, that's me. She loved to create. She had scaled up to making $5 million dollars a year, which was a goal I had. She loved taking time off, which I also love and do as well.

But what I didn't know until I was in the programs was that she switched directions every few months. She had only been making that kind of money a very short time. So she was making choices in her business that caused chaos for us as clients. Her introvert tendencies meant she would decide to just close the business for a week at a time, and she did that frequently. So, for me who value stability and support, this was not a fit. I also did not fully understand the model she was teaching. Once I was in the program and saw the model, I knew it was absolutely not right for my business. That was a big oops.

Now, I am always going to take 100% responsibility. My responsibility was that I did not do my homework. I thought I was clear about what I wanted, but in truth, I wasn't clear at all. I was vague with myself and mostly told myself well, I would love to have what she's having. So I enrolled. What? I mean that's crazy, right? That's coming from a place of lack within myself and a giving up of my power to someone else. She didn't take my power. I willingly handed it to her from that space of lack.

So how in the world could that be a great decision? I got swept up with a romanticized notion of who she was, what her accomplishments were, and I stopped there. I didn't have a clear checklist of the challenge I was wanting to solve. I didn't ask more questions about the coach to get a full clear picture of her journey. I didn't listen to her podcast. I didn't read articles. I didn't see videos. I just didn't hear enough to understand more fully her perspective and where she was at in her business maturity. So I missed things. That's on me.

That's the lesson I learned. So now, every time I sign up for a coaching program, I am first crystal clear about the strategy I'm wanting support with. I'm clear about the challenge in my business I want to solve. Only then do I look at coaching program options to see which one is aligned with the outcomes I want to create.

Now, this doesn't mean I don't trust my intuition and choose a program that's going to feel right. Of course I do that. But feeling right has to also include checking off the boxes of what business challenge I want to solve for. The learning you can take from this as simple. Be clear within yourself about exactly what it is you want to learn or the direction you want to go in. If you can't clearly articulate it, don't expect any coaching program to make up that gap for you.

Money mistake number two, investing $38,000, yes $38,000, in a VIP day with someone who was at my same level at that time, but with energy that was not aligned with mine at all. Why did I do it? Because I “thought” she knew more. Now this is embarrassing, really, truly embarrassing, but I promised you I would be transparent. So here's what happened.

This was a number of years ago, and a lot of us high end coaches offered VIP days for $20,00, $25,000, $30,000 for each VIP day, myself included. So for years, my business model was offering large workshops then making offers for my coaching and certification programs from the stage. Now I was making anywhere from two to $3 million a year with this model, and had been doing that for a number of years. Our closing rate of the workshop room was quite high. It was higher than most people in the industry. What that meant was that people loved what they were learning, and they wanted more.

So when instead of doubling down on my skills and increasing the number of people we had attend our workshops, I decided that somehow, I wasn't good enough. Because I was selling $1 million from the stage at each workshop, but this other person was selling $3 million.

Now, it sounds really stupid now, but at the time, it felt like a real problem. I somehow must not be good enough was the thought I latched on to and started making decisions from. So I bought a VIP day with her for $38,000. She and her partner flew to my home. We had the day. She told me almost nothing new that I didn't already know or just hadn't fully implemented. The couple of new things, and I do mean just a couple of new things, were so dramatically off brand for me, there was no way I would do them. Plus, I paid for the lunch.

So throughout the day, she kept telling me, she said, “Kendall, you already know this, or this is what you're already doing.” She didn't even try to really look at my model for where it could be improved. The irony here is that people were often comparing the two of us as a study in contrast. They would come to my workshops, and they would say, “Wow, Kendall. What a breath of fresh air your workshops are because we obviously cared about the people attending as people, not just as dollar signs.”

So here I am comparing myself to someone who does not share my values, who is polar opposite of what I a stand for. I decide to feel less than. I pay her $38,000 for a day that literally delivered no value. Crazy, right?

But here's the learning. I'm awesome. My brand is built on values of honesty, integrity, respect, and dignity. I learned from that experience to trust what I know, to improve on what is already working, to make an investment in my business from a place of love and caring and self-respect, not from a place of feeling less than. If I'm feeling less than then the person isn't going to be one I'm happy with or that will work out for me. How could it? Here's the learning I want you to take from this. A decision made from feeling less than will produce less than results every single time.

Money mistake number three, abdicating my power to a team member. Now to be honest, this money mistake is one I've made more than once. But every time, I just keep getting better and better at recognizing the issue and solving for it much, much more rapidly. Abdicating my power to a team member was a huge mistake when I hired a lovely young woman to “do my marketing.” That was the beginning of my abdicating.

Next, her salary was big. It was $72,000 per year, and, of course, payroll taxes and benefits on top of that. So abdication number two was really? Did I really need someone full time? No. Then abdication number three was not having any earthly idea what she was doing each day. She did not have metrics to measure her work efforts, and I let it go because I was busy running my workshops. When we finally did create metrics, they were fluffy and did not tie directly into bottom line sales.

Oh, but wait, it gets better. Abdication number four was there were many, many times each week during work hours when I just couldn't get ahold of her. No email, no answer to a phone call. She could have been, and probably was, at the gym or with friends or shopping. I have no idea. Finally, abdication number five in this situation was that I let it go for like six full months past the point where I knew I needed to let her go.

Why did I let it go so long? Fear of missing out, FOMO. Using hope as a strategy. Let me tell you, hope is not a strategy. Fear of missing out. Well at that time, I was worried about what I might lose out on if I didn't have her on board. Totally crazy, backwards thinking, but it felt real at the time.

When I finally said enough is enough, and I let her go, she was totally fine with it. The whole letting go process took about three minutes, and we were done. So the primary lesson here is you can delegate, but you cannot abdicate. Whether it's a contractor or a part time employee or full time employee. The difference is you have in your finger directly on the pulse of what your team member is doing when they're working, like specific days and hours. You must absolutely know how they're paying for themselves at a minimum of three times what the expense is to you.

For example, in this case at $72,000 even without the payroll taxes and the benefits, she needed to produce a measurable $216,000 a year to make that hire worthwhile. We needed a plan for that with metrics to measure performance.

I have to admit, sharing these behind the scenes with you has not been easy or comfortable for me. I've always joked that I don't make a lot of mistakes in my business, but the ones I do make have been whoppers. I think the dollar amounts of these three money mistakes certainly add up to that being true.

I want to wrap up our episode by talking to you about regret. When you make money mistakes, you have two choices. You can look back on the experience and start shaming, blaming, or pulling yourself down in some way by saying things like well, I should have known better. Why didn't I see this coming? That was really stupid.

But all that does is erode your sense of self-worth and self-trust and confidence. My experience of regret is that it's always based on hindsight and what ifs and there's no learning in it. It just plain feels bad, and there's no upside to it. I think a far more useful and productive way to look at money mistakes is to take responsibility for the choices you made, to give yourself credit for making what seemed like an informed choice at the time, and to get really, really clear, like crystal clear, about how you'll make similar decisions in the future.

When seen this way, a money mistake is an opportunity to learn more about yourself and to refine and uplevel your decision making. Any money mistakes made can just be an experience that helps you grow and gain wisdom so that you make wiser decisions moving forward. It doesn't mean you'll never make another money mistake, but it does mean you're likely not to make that same one again, or it won't happen again for a very long time.

What I really want to leave you with is this. Money mistakes happen. You can't shield yourself from them, but you can minimize the monetary amount of them and keep them to an infrequent occurrence.

What's key is number one, being clear about what challenge you're wanting to solve in your business. Even better, be clear about where you want to grow. What is that new skill you want to learn or master? What direction is your intuition telling you to go in? Investing for growth and skill building and opportunity has always worked out beautifully for me. I'll share more about that in an upcoming episode on money decisions that have paid off brilliantly. So you'll have to stay tuned for that.

What's key number two is never invest from a place of not feeling enough. You are amazing. You are talented. You are resourceful. You are wonderful. Invest in trainings or mentoring from a place of amplifying your skills, amplifying your talents and abilities and knowledge, not from a place of trying to fill a deficit that isn't real and isn't the truth of who you are.

What's key number three is don't abdicate your power. You might not know how to perform certain tasks in your business, but you are still in charge. You can hold the standard that the people supporting you are accountable to contributing to your revenue. If they're not willing or able to do that, they are not the right person for you.

Remember that regret will only hold you back when forward is the only direction you want to go in. So I hope this episode was valuable for you. It's all part of my vision to support you and every woman we can reach to hold genuine money power. You deserve the very best, and the very best is what you get here with me in this podcast. So thank you for listening, and I'm excited to connect again with you next week in our next episode.

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And if you want to learn how to excel at coaching women on money, definitely go to KendallSummerHawk.com and check out the wealth of money coach trainings that we have for you. Thanks so much for being part of this money coaching movement and for tuning into the show every week.