My Biggest Business Failure

I’ve been running this business for 11 years now, which means I’ve experienced tons of learning experiences. I’d like to share a story with you of a really hard moment that happened a few years ago (that I’ve never spoken negatively of). From Wanderlove Calligraphy + Design.

I’ve been running this business for 11 years now, which means I’ve experienced tons of learning experiences. I’d like to share a story with you of a really hard moment that happened a few years ago (that I’ve never spoken negatively of).

In November 2016, as a member of the (defunct) Etsy Wholesale program, I was asked to partake in a trunk show at Macy’s Herald Square. What the what? Little ol’ me? At the largest department store in the world? Yep! As (what I considered) a super small business, this opportunity had me over the moon excited, extremely nervous and running through a really crazy range of emotions.

I had to ask myself a lot of serious questions: Was I really ready for something that could totally change the face of my business? Would I be able to make enough inventory? Was I totally going to embarrass myself?

Ultimately, I decided I had to try. Even if it ended up being a failure, the exposure alone and opportunity to say that I was selling my items at freakin’ Macy’s would make it a huge success. Right?

A few logistical details

My trunk show opportunity was the first Friday and Saturday in November. Macy’s would be providing me with an area to set up—right next to Starbucks (so a high traffic area)—and I would be the one and only vendor.

My coordinator told me to aim for a sales goal of $8000.

I remember reading that email and laughing hard. My most expensive items at the time were wood signs that retailed for $40. My most popular items were greeting cards, which retailed for $4.50. I’ll let you do the math, but $8000 of inventory to create in about 2-3 weeks, when most of my pieces were hand lettered and individually made, was near impossible. I discussed with them, talked about my fears, and ultimately settled on bringing inventory to cover about half that.

Now after Etsy and Macy’s cuts—which were pretty high—my actual take would be far, far less. But this was about the exposure and the opportunity. And either way, it was going to be the most money I ever made in a two-day span (up until that point).

I was all in.

So off we went.

Brad and I took the day off of work on Friday, packed up the car, and headed in to New York City to be there by 7AM. Our goal was to be set up with plenty of time to spare before the store’s 9AM opening.

This is where my big opportunity takes a downturn. Unfortunately, no one at Macy’s that day knew we were scheduled to be there! This meant that no one knew where we were supposed to go, there was no table available for us to set up on, and all of the UPC labels that I needed for my products weren’t printed. So, if someone wanted to buy something, they couldn’t, since there was nothing to be scanned at checkout!

It was chaos, and really discouraging from the start to feel like we didn’t belong and weren’t wanted. It’s a feeling that I can still vividly remember three years later.

A simple table set up for a wholesale show at Macy's Herald Square. From Wanderlove Calligraphy + Design.

But it got better, right?

So remember I said we were doing this for brand exposure and for the opportunity? Well, it turns out, a lot of people don’t understand that Etsy is a collection of independent artisans and that we don’t actually work for Etsy. In fact, most people who stopped by assumed that I worked for Macy’s and was just manning the Etsy area.

I barely spoke of calligraphy or painting or running my own small business. Instead, half of the people who walked by were bleary-eyed and heading to Starbucks for their caffeine fix and the other half (who did stop by) were there to inquire about how to find the bathroom.

As an entrepreneur, it was discouraging and disheartening. As a person, it was embarrassing.

By the end of the day, we were exhausted and sad. Brad and I made the most of it and enjoyed our time together, joking and laughing and making light of the situation (and we had just found out we were pregnant with Lincoln… so there’s that). However, it wasn’t fun, it wasn’t a good representation of my business; it wasn’t the opportunity I had worked my ass off for.

We decided not to go back the next day.

I’m not a quitter, so making the decision to bail on going back for Saturday was really hard. I didn’t want to let anyone down and I felt bad until I realized that ultimately everyone else let me down and no one else felt bad. I needed to take care of ME.

After travel time, the day off of work, tolls into the city, parking, liability insurance (which I needed to provide to Macy’s), food/drinks, and my cost of supplies, we spent hundreds to be there.

Here’s where I’m going to be more honest than you might expect. At the end of the day, when the funds from my Macy’s x Etsy sales came through (after their wholesale fees and charges), my cut was $46.50. I sold a few Christmas ornaments, a few cards, and one sign. I didn’t even come close to covering our costs to be there. I’m pretty sure breakfast and lunch was more than that!

So what’s my point of rehashing all of this?

Well for one thing, I can look back on the whole experience and laugh. It was one of the most bizarre experiences I’ve had since starting this business. But I also want to use this to illustrate two things:

How things appear on social media and how they are in real life are vastly different. In 2.5 years, I have never once spoken negatively about the experience. I’ve referred to it and posted about the “amazing” opportunity and how honored and thankful I was (all true). I didn’t admit this failure and did my best to hide it, which means anyone looking at my journey and comparing my “progress” to theirs may have felt less than. It’s hard not compare where you are to where you dream of being—and seeing others easily find this success can be disheartening.

And the second thing is that, though I called this “my biggest business failure,” I don’t actually think that I failed. There are certainly things I could have done differently, but I also think a lot of people failed me. I couldn’t solely shoulder the weight of the failure, and I certainly, going forward, can’t shoulder the weight of all my business missteps and setbacks. This was a huge lesson in self-care fo me. And, if nothing else, I was able to learn so much about the retail process and the consumer perception of Etsy (something I’m still thinking about years later), and about working through the imbalance between real life and expectations.

Here’s hoping my story makes you realize that you are not less than and you are doing amazing things, even if in comparison it doesn’t always feel like it.