The Biggest Mistakes I’ve Made In My Business:  Investments Edition

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The biggest mistakes I’ve made in my business, investments edition. 

It’s super easy in the online space to just see people’s wins, just see people talk about their 5K months, 10k months, six figure years and signing new clients. In my opinion, as a whole, we aren’t as transparent as we should be about the climbs, failures and struggles that we have along the way. 

A series or a theme that you will find throughout my blog is really talking about the biggest mistakes I’ve made. And today, we’re talking about investments. 

The truth is, I’ve really never been afraid of failure, but it doesn’t mean it doesn’t hurt any less when you make a big error. 

In 2015, I had my first taste of online business.  I started in network marketing, and it didn’t take me long to invest because I always saw the value in the shortcut. In the sense of, if somebody can teach me how to do something and it’s faster, it takes less time, I see a lot of value in that. 

Before I had kids, I had a full-time job, and coming into this online space, everything was brand new. I’m a firm believer that investing in your business has to be a non-negotiable. It’s worth it to shorten the learning curve and have support from people that have been where you are. 

It’s taken me eight years to learn that you really have to make sure you’re investing in the right thing, in the right person at the right time. It makes all the difference in the thought we all have: 

“Will this investment work?” 

If you’re like me, you have probably invested in things and been completely disappointed, or it hasn’t turned out the way that you wanted it to, or it wasn’t enough. These examples are in no particular order. I’m not going to name names, but I’m going to be pretty honest about why these investments were a mistake, share some red flags, and talk about what I potentially would have done differently.

Outsourcing Too Soon

One of the big mistakes I made was working with an OBM (online business manager) and outsourcing a lot of my projects to her before I knew how to do them myself. 

I was taking a lot of her advice and expertise at face value. She came really highly recommended. She seemed to know what she was talking about. 

I will also say this. None of these situations that I’m talking about, none of these people are bad people, none of that. It just comes down to everything not being in alignment. 

Working with this particular OBM is actually what set in stone one of my values as a business owner. It made it very clear to me that it’s actually better to work with someone that is in a similar season of life or has been where you are before. 

I am really a proponent for working with other moms because there’s just this level of understanding that we have for each other. 

This might not be something new to you but I’m a very planned out person. So all of my projects and tasks were planned out, and had due dates that the OBM and I agreed on ahead of time.

I was getting everything to her on time and yet…

Consistently project after project after project, she would deliver late. Or she’d have questions or need something from me at 10pm the day before the project was due. 

If you don’t have kids and you’re working a full-time schedule in your business, if somebody is late on delivering when they said they were going to deliver, a lot of times you can make it work. Not that it’s right. 

But at the time that I was working with her, my kids were home full-time. If I gave her a deadline, it was because I knew that whatever it was had to be done by then because I wouldn’t have time to review it. I wouldn’t have time to make changes. I wouldn’t have time to launch whatever we were launching because it just wasn’t a dedicated work day, right? 

I cannot tell you how many times I was launching on a Tuesday and still didn’t have what I needed from her on Monday, and the stress that it caused and the frustration. At the time, I didn’t have the knowledge to do what she was doing from a back end perspective, especially in such a short amount of time.

There was so much unnecessary stress that working with her caused. I allowed us to be in this bad situation where she would miss the deadline, but she would apologize. She would make up for it. She would send me a Starbucks gift card, and I let it continue on because the other mistake that I made with her is I committed to a massive foundational building package with her versus one project at a time. 

So her and I were linked up for like six to nine months because I was making monthly payments to her. We had a contract. When you’re working with somebody, especially if it’s a VA or OBM, go project-based first until you’ve earned enough trust to build up and you know you can move beyond that. 

The biggest thing that I did was I went to her after I think it was the third or fourth time that she missed a deadline, which caused me to be stressed out. I was so frustrated. I said, I’m done. I can’t keep doing this with you. You tell me whatever we need to do to break this contract because I am unhappy.

I honestly would rather have paid her and have her not do the work so that I was in control of this timeline again. We severed the contract. We came to a financial agreement, and we moved on. 

What I learned from this one, as a business owner, brick and mortar, online, whatever it is, you need to have some level of knowledge of your backend system so that you can do some of the things that need to be done. 

Two, never enter into a long term contract with somebody that you don’t have a significant amount of evidence backing up what they’re capable of doing. 

Three, open your mouth. If you are unhappy, if it’s not working out, if you’re not getting what you promised, we cannot sulk in the shadows. We need to say what is on our minds and hopefully come to some type of conclusion for it. 

FOMO & Group Programs

I signed up for a group program early on in my business and this one actually had a good outcome. 

I signed up for it because I loved the person that was running it. 

I had a lot of FOMO. They had a lot of FOMO type marketing. I really believed I needed what she said this group program was. 

I got into the program and there’s a lot of great women in it. We’re learning. We’re going through. A few weeks in, I’m like, this is not what I signed up for. 

We are spending so much time going over things that I knew how to do three years ago. These are not the level of women that were promised to be in the group. By level, I mean there’s a very big difference between a very new person in the online space and somebody that’s been in the space for two, three, four, five years, and mixing them together, unless it’s a very specific niche, tends to not work. I’ve seen it happen a lot. 

I was incredibly frustrated because I had paid thousands of dollars to be in this group program, and every week we were going over things that I could have been teaching. It was very frustrating. This goes to what I said earlier is we cannot sulk in the shadows and just be victims when things like this happen.

I knew I wasn’t the only one feeling this way because I had made friends with some of the other women in the group and behind closed doors, we were talking about how unhappy we all were. 

In true Giana fashion, I have always been this person since I was a kid. Sometimes it’s good, sometimes it’s bad. I went to the coach that was leading the group and I said to her, this is how I’m feeling. I know I’m not the only one. I really like you. I really believe in what you’re doing, but I’m incredibly unhappy in this program, and we have four more months together. I need you to know where I’m at

When the coach replied back to me, she was so kind. She validated the way that I was feeling, and she came back with a solution for the entire group. The rest of our time together was really beneficial because she course-corrected. So while it wasn’t a full mistake that I invested in her, I definitely should have asked her more questions before I signed on the dotted line.

The biggest takeaway from this that I hope you’ll take away too, is by speaking up and coming from a place of not being a jerk or not waiting until the program is over and leaving a bad review. Come with compassion. I like you. I like this group, but it’s not working for me. 

We were able to come to a solution that made everyone happy, made me feel good about the money that I was spending. It made a very big difference. 

We cannot be victims in the shadow keeping our mouth shut because then it’s our own fault if we’re not happy with the outcome. 

Not Knowing When to Walk Away 

Another investment mistake that I made, this one’s hard for me. I don’t consider myself a people pleaser in general, but if I really, really like you and I really care about you, sometimes it’s hard for me to do what’s best for me. 

A mistake that I made twice, two different situations, two different coaches, is I continued to work with them long after I probably should have stopped. 

But I really liked being in their bubble – I admired and respected them and I just had a hard time walking away. 

I liked the people in the group as well, it was just a vibe being all together.

I kept working with them even when I should have been done. 

When their values or their strategies or what they could teach me didn’t line up with what I needed anymore, I kept working with them. I kept paying them, even though I didn’t really actually need it because I didn’t want to walk away. 

I didn’t want to walk away because I liked them. 

I didn’t want to walk away because I knew what it would have done. 

It put me in a bad spot financially because I was paying for something that I didn’t really need. 

Then you start to build that resentment toward the situation, and you just cannot show up in good energy when you’re doing that. 

What I’ve learned over time is just like going to high school or college or when you’re in a business group, the people that you connect with and you want to keep in your life will stay in your life even after that group is over. 

The online space can be a little bit like a sorority. I just want to remind you, and I often remind myself, you don’t have to pay money to be in rooms with people that you like.  You can create your own rooms. I’ve done that a lot. I have a really great band of biz besties, and I’m not paying for them anymore. 

Searching For The Magical Puzzle Piece

The biggest mistake I made early on as an online business owner is thinking I needed to continue to invest in different strategies to find the one magic puzzle piece that would bring it all together. 

The truth is, I wish I would have invested in mindset coaching very early on and really leaned into it and dug into it because strategy tends to be something that can be fixed easily. 

For me personally, strategy comes easy. The mindset piece, you could have the best strategy, you could be posting the best content, you could be firing on all cylinders, doing all things right. But if your mindset is jacked up, if you have a bad money mindset, those blocks can drastically stand in the way of your strategy actually working for you.

You need both. I feel like in the online space, it’s very divided. It’s like you need mindset or you need strategy. You need both. 

At the end of the day, with all of this investment stuff, it’s figuring out what do I personally need the most right now? 

Who can I trust to actually deliver that to me? 

Is now the right time? 

Depending on the season of life you’re in, it doesn’t make sense to invest in things if it’s not a time when you’re going to actively use them. 

I’m not the type of person that lets programs die in my inbox, but I know that is something that happens very regularly. 

That happens because one of two things: 

  1. you’re investing based on FOMO 
  2. you’re investing at a bad time.  You’re investing in something you need, but it’s not the right time. 

Knowing when it’s the right time for you to invest in a certain thing is very important to not waste money or time. 

If I had to tell baby Giana back in 2015 about investing, I would tell her that you know more than you give yourself credit for. 

You are capable of doing some of this behind the scenes stuff, even if it takes you time. Figure it out first and then find somebody you trust to do it. 

The foundational pieces matter. Ignore the shiny stuff. Ignore the next best thing vibe. 

Mindset over strategy for now. But sometimes it’s strategy over mindset. 

It’s looking at exactly what you need right now to get to where you want to go. 

I just invested in an SEO camp because I know nothing about SEO. The whole AI thing is blowing up. I invested in it without even a blink because I want my content to live longer and be more discoverable so I can spend less time on social media. SEO checks that box. I wanted to do it from somebody that’s an expert at SEO and comes from a place of integrity and using AI in a not-gross way.  She checks that box. 

There’s this little checklist to go over in your head, and it was the right time because I was slowing down on other things in my business. It’s the summer, so I was taking less clients. It all made sense for me now. If it would have been the fall and she was launching this, I probably wouldn’t have signed up because it wouldn’t have been the right time. 

Take all these things into consideration. Hopefully, you can learn from my mistakes and avoid some of them. Or if you’ve made these mistakes too, hopefully reading this blog makes you feel better about your mistakes.

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