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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5 of My Biggest Mistakes as an Entrepreneur

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Every entrepreneur's journey is riddled with mistakes. Over the past eight years of creative entrepreneurship, I've had my fair share! From angry clients and eating thousands of dollars in mistakes, there were many times throughout my career where I thought about throwing in the towel. But, I am incredibly thankful for the mistakes I made. These mistakes have helped me really measure my performance and know where things are moving the needle in my business.

Along with that, when you make a mistake, you are likely to not make it again! It stings so bad, you never forget it! In this post, I'm listing out my FIVE biggest mistakes as an entrepreneur to hopefully help you avoid them yourself, or maybe provide you with reassurance that you're not the only one making mistakes!


#1: Didn't get client's approval

This first mistake happened early on in my career as a creative entrepreneur when I was a custom wedding stationery designer. The first few clients I had were pretty much all learning mistakes for me. Because I wasn't trained, I didn't know any Adobe programs, how printing worked, how to quote for jobs, etc.

But for my VERY FIRST stationery design job, I was hired by a couple to design their save the dates and address their envelopes. The bride asked for a gold ink on a sage green envelope for the addresses, and without thinking about it, I addressed them all without sending a photo proof! Which, at the time didn't seem like a big deal, but after sending out all of her save the dates to the guests, they were all returned to her from the post office. The ink color was too light and hard to read! They ended up firing me after that and that was my very first job.


#2: Didn't trust my gut

We all have intuition. But over time, a lot of us have stifled that inner voice because we either need the money, or we think it's going to be good for exposure, or we just have a really hard time saying no.

About two years into my creative career, I said yes to a job that I just knew from the beginning was going to be a nightmare. I knew I wouldn't be able to satisfy all of the needs she had, mainly because I had so many other clients that I had to pay attention to. She was asking for things that I didn't have experience with yet. We ended up getting into a disagreement over paper colors and I decided to end our contract together. It was mainly over a small miscommunication, but the stress it was causing and the time this relationship ended up taking was something I could no longer afford. I had other clients to tend to, and nothing I could do would please this particular client. You can't please everyone. Ending this contract resulted in me having to eat some of the cost (a couple thousand dollars)! I was early on in my business, so I couldn't really afford to lose a job, let alone lose money from a job, so that mistake REALLY stung!


#3: Email list-building

My third biggest mistake or regret I have is not showing up to serve my email list sooner. I've always had an email list. Basically since day one of starting my business, back in 2013, I would send emails to my list about new products in my shop, or new workshops, etc. but, I didn't show up to serve my email list. I would only come around when it was time to promote something, then for the rest of the year…crickets!

If you have consistent communication with your email list subscribers, you can actually form genuine relationships with these people by providing them value. Your email list is something that you own and not controlled by an algorithm (Instagram). You do not own your followers on social media. My email list is growing all the time and is at a really good size, but had I started earlier, who knows where it'd be now?


#4: Distracted by a bad idea

My fourth biggest mistake is the most weird and the biggest sting to my ego. I spent thousands of dollars on custom furniture for a co-working space and nobody signed up for this co-working space. In 2015, John and I lived in a 3,000 sq. foot warehouse. It was huge and super rad. I would teach workshops on one side of the warehouse, there was a photo cove infinity wall that we'd rent out to photographers. And another side of the space had a huge area for desks, a kitchen, a lounge area, etc. In theory, it was perfect for a co-working space! On a whim, we decided to pursue it. We spent $10,000 on furniture, put together a photo shoot, and tried for a little while to get people to sign up. NOBODY DID.

That's the year I signed my first book deal, so I became incredibly busy writing that book. I never had time to promote it and my audience knew me as an artist, not as an available space for rent! We basically saw something shiny, that looked and sounded like a good idea because we had the space, but it ended up distracting me from what was really working in my business already.


#5: Not paying attention to income and expenses

This last mistake (I've made countless more than just 5), is super common among creatives. But for a few years, I avoided looking at my profit and loss report sheets and my books, because I was too afraid of what I might find out. Your profit and loss reports helps you measure how your business is doing! What's working, what isn't…what expenses you can cut out, etc. I had an accountant and bookkeeper from year one of starting my business, but it's so important for every entrepreneur to be in there themselves, at least once a week! This will help you keep a pulse on if your business is growing each quarter, and where to focus your time and attention!


So, there you have it! I've made LOTS of mistakes over these last eight years. I'm definitely making less as time goes on…I'm learning from each failed attempt or face palm, but we're all human! We're going to make mistakes. But instead of running away from starting something new because you're afraid of making mistakes, let those mistakes become your biggest teaching moments!

My mistakes have had a direct impact on the growth of my business and they can do the same for you!

by Jenna Rainey 

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  1. Jenna, I was looking for the online platforms you mentioned like Creative Live and Brit (something) in the show notes for teaching online. Where do I find the links if there are any? Thank you so much!

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