Just ask my husband: I get irrationally upset with myself when I waste money.

(Yet somehow, I STILL forget to return items to Amazon before the refund period runs out?)

But making an investment you regret is, dare I say, inevitable, when it comes to self-employment. (Especially if you’re 22 when you start your business and know nothing about business.)

It *stings* when you realize your efforts didn’t pay off as hoped.

I’ve made some *pretty* expensive mistakes over the years. Some of them were gambles that didn’t pay off, some were honest efforts that were ill-timed…

… and then others? They were just plain dumb moves on my part. 

You probably know by now that I’m a lover of transparency, and lest I leave you with the impression that I’ve never made a misstep, here we go:

The 5 worst investments I’ve made in the last 13 years:

1. That time I bought a $7,000 “coaching” program that was actually just an online course in disguise. This one goes down as a decision made 100% out of fear & panic. It was Spring 2020 and I was freaking out over cancellations and postponements, and wouldn’tcha know it, I got hit with an ad or a promotional email from an educator promising to help with my EXACT PROBLEM.

So we scheduled a call with the educator’s team, were told they could solve all our problems. And hey- if we enrolled in their program before the call was over, they’d love to offer us a “scholarship” because, you know, times are hard. We asked for a couple extra hours, consulted with a few people we trust, and took the plunge. 

And after just a month or two in the program, we were kicking ourselves. It turns out this coaching program we were sold on the phone didn’t really exist- it was more of a glorified course, and we’d just paid $7,000 for our mistake. And it was mostly my fault.

Lesson learned: do your research before dropping that kind of cash, and do not let the pressure of a “limited time discount” [scarcity] make you sign up for something you might not have signed up for otherwise.

2. Over-the-top-styled shoots- this was more something I did in my early days as a wedding photographer, and kicked myself for afterwards. Why? Because they were so out of place in my portfolio. They stuck out like a sore thumb, so I never ended up doing anything with 99% of the styled shoot photos I took. Bummer.

I know vendors who’ve used styled shoots as a powerful way to build their businesses- specifically, photographers like David Abel come to mind- he’s used editorial shoots to build up a MAGNIFICENT portfolio.

But I’ve also seen SO many photographers pour money and time into participating in or hosting their own styled shoots, only to find that the images have no place in their portfolio because they’re SO FAR from a photographers’ portfolio of paid work.

Styled shoots are a great way to practice a new skill, build vendor relations, and yes- add to your portfolio! You just need to approach with care- if you’re going to craft or pay to participate in a styled shoot that’s completely different from your existing body of work, know that there may be limited options for you to showcase that work because of out out of alignment it is with your existing brand presence.

If you’re someone who’s intentionally trying to make a pivot into a new market, a new aesthetic, and styled shoots are how you’re planning to showcase what you CAN do, go for- just make sure those photographs are presented alongside intentional messaging that also reflect that change of direction.

3. Sponsored table at a bridal expo– I’m not saying this a surefire bust across the board, but it wasn’t the right fit for my business, because it wasn’t where my clients were hanging out. I didn’t book a single client off of that gig, which just goes to show you how important it is that you choose a marketing channel where your clients actually spend time.

A few years ago I participated in a wedding show at one of my favorite local venues, and I didn’t book a single wedding off of the experience. Which, and the end of the day, didn’t shock me at all- it was the first and only bridal show I’d ever done, and I put in minimal effort because I had a gut feeling the setting wasn’t a good fit for my ideal client. My target audience wasn’t finding their vendors at an expo, they were choosing from a curated list their wedding planner sent over. 

4. Paying for coaching without knowing why- this was a separate program from #1, with a really good coach. The issue here was me- I didn’t really know what I was hoping to get out of the relationship. I wasn’t clear on what a “next step” looked like in my business and hoped a coach would tell me what to do next… but that’s not *really* how entrepreneurship works.

I wasn’t even sure how I needed them to coach me, or where it was I was hoping coaching would take me. So our sessions ended up consisting mostly of fixing little issues that came up in the day-to-day minutiae of business, instead of deeper or larger scale growth that I couldn’t have achieved on my own. The coach was great at helping me navigate the small stuff, but these days, that’s not what I want to hire a coach for- I want to come in with intention, some sort of bigger picture shift that I need help either refining the vision for, or assistance with executing. 

5. Hosting a gallery show- betcha didn’t know I did that, did you? That’s because I never talked about it- I was too embarrassed! A few years ago I got into a conversation with a shop owner about our mutual love of France, and when I mentioned I have a whole series of fine art photographs from Paris, they suggested we collaborate on a gallery show to display in their commercial space.

I IMMEDIATELY said yes… but it was a decision made purely out of my ego. I spent something like $2000 on framing + printing of my fine art Paris photographs and sold two. pieces. I think I made $150 total? I didn’t even blog about it, I was that embarrassed. Pride goeth before the fall… and ego goeth before a $2k loss. Oops.

The lesson learned here was to make sure there’s legitimate demand for a product before you invest in creating it.

I let my ego make the decision about the gallery show- it sounded cool, like what a REAL artist would do, so I went for it. But there wasn’t enough demand to warrant the expense, it was ONE person who told me “you should do that!” and so because of my ego, I ended up with $2000 less in my bank account, and 23 framed and matted prints sitting in my attic. We’ve used them to decorate our home throughout the last few years and I’ve given some as gifts, but it’s still a little twinge every time I go into our attic and see that box of white frames. Ya live and ya learn!

We will ALL make moves in our business that we later kick ourselves for. It’s not a matter of “if,” but “when.”

And WHEN that happens to you, you can 1) berate and belittle yourself, 2) blame the other party, or 3) glean what you can so that you’ll hopefully avoid the situation in the future.

I choose the third option- that sounds way more constructive.

Want more content like this? Check out these posts! 

Prefer to listen? Check out my podcast, The Artisan CEO

Top 5: Worst business investments I’ve made

July 18, 2023

  1. Karen Field says:

    I love the honest way you share your experiences in your blog!

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