Jenna Rainey


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I’m Jenna Rainey. 

I'm an artist, self-taught designer, and multi-faceted creative entrepreneur who is hell-bent on teaching everyone how to find their inner creative voice.



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A highly creative nerd with a unique breed of humor and the proud earner of a self-bestowed award for being the world’s most curious and driven human.

Hey I'm Jenna!

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It’s like Netflix-binging Bob Ross videos, but with a dose of dry + quirky humor and fewer happy little tree references. 

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3 of My Workshop Nightmare Stories

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Ahhhh, workshop nightmare stories…I have quite a few! And I hope these stories help you in planning and teaching your own workshops or online courses! Before we dive in, I want to tell you about a FREE Workshop Cheat Sheet I have that will help you avoid these nightmares. From the prepping phase, to promoting and teaching, we’ve got the entire checklist here so you know when to start ordering supplies, what to pack for your workshop and more.


I have my fair share of nightmare workshop stories. From not packing enough paper for a watercolor workshop and having to run down the street to an art supply store halfway through teaching, to having to cancel a workshop the night before due to food poisoning. 

Over the last 7 years of teaching, I’ve experienced it all! While none of these scenarios were fun in the moment, they were all HUGE learning moments. Now that I have my system and set up DIALED in for teaching workshops, we thankfully never run into these frightening experiences anymore (I mean, never say never I guess)… 

I want this episode to help you avoid the same nightmare mistakes. Whether you teach workshops, you do live art at events, or anything related to showing up for a group of people…this episode will give you a good laugh at my expense (you’re welcome) and some great advice on how to prepare for the worst. 

Related: Are You Ready to Teach Workshops?


#1: The Website Nightmare from Hell

About 4 years ago, I had a workshop booked for a beautiful weekend in San Diego with a venue that I’d taught with multiple times before. This venue had just switched website platforms in the middle of promoting my workshop.

It sold out and they sent me a list of names so that I could start packing kits. I arrived at the workshop and the students started trickling in. I usually cap it at 20 but more and more people kept showing up!

I always always pack extra kits—usually 5—in case somebody got missed or the venue forgot somebody’s name…whatever. Five kits is plenty extra. 

It turns out the website oversold the workshop by 15 people!

After using the extra kits, that still left 10 slightly angry, frustrated workshop students for me to stare at for 30 minutes while the venue tried to scramble and figure out what the heck was happening. 

To know that it was completely out of my control and I couldn't do anything about it was absolutely infuriating, embarrassing, and just the absolute worst. 

Moral of the story: Double check every angle from every angle. If the venue is selling the workshop and hosting registration on their website, make sure there is a cap on the workshop. So whatever your max is, is your max. 


#2: The California Traffic Nightmare

This was another story from the same San Diego venue! (They’re totally NOT cursed, btw. They’re one of the most beautiful workshop venues and this was completely not their fault.)

I was planning on arriving 1.5 hours early before any students would arrive to set up, grab some coffee, maybe a little breakfast, etc. And being based in Southern California, I always leave early but this morning had an exceptional amount of Saturday morning traffic due to an accident.

Well…I arrived over 45 minutes AFTER the start time of the class. I sat in my car for over 3.5 hours and could do absolutely nothing about it. I was mortified. 

Thankfully I had the number of the venue on speed dial just so that they could call all of the students and tell them the workshop was going to be starting later and so that they didn't get there super early. And thankfully, the students were all super gracious because some of them were also stuck in traffic with me!

Moral of the story: I know that things like traffic or an accident on the freeway you can't completely avoid. So you just have to be flexible. You gotta prepare for things like that and know what to tell the students when a scenario like that comes up. Maybe including some sort of disclaimer on your sales page letting them know what will happen in the event that any sort of last minute things come up. 


#3: The Dingy House Nightmare

This final workshop story is the worst. It is the epitome of nightmare and I now have an agreement for all of my workshops because of what happened that day. 

About 5 or 6 years ago, I was teaching at one or two venues most weekends. I wanted to start to branch out and teach more frequently but also offer more varied locations. So I wanted to find a venue in South Orange County. 

There was a venue that I discovered on Google and they had beautiful photos—really bright white studio space with amazing tables and a great setup. And it looked like a perfect workshop venue with all of the pretty Instagrammable things. 

I emailed them and they came back to me with the rundown of the split fee, location, available dates, booking process, etc. I booked the workshop and listed it on my website because they didn't have a website, only a Yelp page. This should have been my first red flag. There were no reviews, which should have been another red flag. But I was new and I didn't think I needed an agreement because the two other venues I'd been teaching at at up to this point were friends or friends of friends and I just trusted them. 

At first, everything was smooth sailing. We sold out the workshop with 20 people. I packed all the kits up, arrived on time and I pull up to the “venue.” It was a private home in a residential area! 

I would never, ever, ever have workshop students come to somebody's house. There's a liability issue there if anybody trips and hurts themselves. You're entering into somebody's personal life. It just puts a weird taste in people's mouths. If you're doing a workshop for friends at a friend's house or your house or whatever, fine. Shouldn't be an issue. But because my workshops were starting to get more popular, people were coming that I didn't know and I wanted to provide this experience that was professional and beautiful that people would want to share on Instagram. 

I arrive at this house and immediately start crying. The lawn was dead grass overgrown…and not trying to be offensive or anything here, but it literally looked like a house in the bad part of town.

I call John, my husband, and I'm freaking out because I'm angry. I feel misled and I'm like, people are arriving at this workshop in an hour and it's hideous. There's nothing I could do. I can't have the workshop in my car. 

I put on my brave face, I walk up to the house thinking maybe it's this immaculate space inside.  They open the door—mom, dad, and 3 kids—with McDonalds all over the place.

The mom tells me the workshop is set up in her “workshop area,” which was her living room where she also ran a daycare. Toys everywhere. Nasty shag carpet. Leather recliners and couches alongside the folding chairs and tables. No natural light!

I was livid. People were arriving in less than an hour. I had to set up, I had to provide them with the best damn calligraphy workshop I possibly could,  teach them the best information and content I possibly could. 

After the workshop ended, I emailed all of my students immediately and apologized. I was absolutely mortified. I was led into this scenario with these beautiful photos on Yelp that was not at all what I walked into. Thankfully, everyone was really gracious. 

The family did reach out after the workshop wondering if I wanted to host another one. And I said, absolutely not. I told them they were lucky we didn't have an agreement because I'd be pursuing legal action for how they misled me.

Moral of the story: Go visit the place if you can! Have a workshop agreement. Because if it's too small, if it's too loud, if there's no bathroom, if there's no AC…all of these things make a huge difference in the outcome of your workshop and whether those attendees tell their friends about you or share their experience on Instagram. 


Comment below and tell me your biggest takeaway from my nightmare stories! Or have you experienced some tough lessons of your own?

by Jenna Rainey 

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