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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Pros and Cons of Being a Custom Stationery Designer

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Wondering about the pros and cons of being a custom stationer designer? I've got some insights for you. For the first 5 years of running my business, I was a wedding stationery designer. It was my in for self-employment and my way out of the desk job I hated.

While I no longer take on wedding stationery clients (read this post to see why), I have a lot to owe to the industry itself. Over the last 7 years, I was able to grow my kitchen table hobby from scribbling calligraphy on envelopes, to a highly reputable and successful six-figure business designing top tier wedding stationery.

From celebrity clients to being published in Harper's Bazaar, Vogue, Brides and more, I've learned a lot from my experiences in the industry.

But about three years ago I said good-bye to the wedding industry. My career started to pivot into products and licensing my art, and I no longer needed to take on custom client work.

Licensing is a much more passive way of earning money as an artist, and it suits the lifestyle and business I desire to run, where working with custom stationery clients means a lot of gaps in income. No work = no money when you don't have passive income streams set up, and the wedding industry was no longer fitting my interests as an entrepreneur. While there's a lot of stress and responsibility that comes with working in the wedding industry, there are also some great perks to this career choice…

including the fact that people are always getting married! 


Pros of Being a Custom Stationery Designer

1. Little to no up-front investment needed to start up

Thankfully, when starting my stationery business, there wasn't much start-up cost. John and I were broke at the time, and with the little extra money we did have, I was able to slowly afford to purchase things like a desktop computer and Adobe software. At first, I was going to my parent's house to do all my design work using Photoshop on their computer, but eventually, I saved enough and bought a desktop and Creative Cloud membership. No business loans needed to be taken out, and thankfully with Instagram, it did the majority of my advertising (and it's free)! Besides that, a scanner and some art supplies, you really don't need much to get started. I was able to pay for a domain and website about 6 months into running a business, and just used Squarespace at the time…no major costs for hiring a custom site designer!

It's not like you need to put this huuuge deposit down on a retail space or even hire a team to get it up and running!


2. Great way to break into self-employment

Because you can get away with operating as a solo-preneur, with little cost at startup, it's an amazing way to break into self-employment! Since then, I've pivoted in so many different directions with my business, but for 5 years, wedding stationery is all I did! It helped build my reputation, business savvy-ness, learn about pricing, and so much more! AKA, it taught me A TON about owning and operating a creative business!


3. Amazing exposure

Think about it! With so many vendors working on ONE wedding, tagging about that ONE day, you're likely to be tagged by at least 2 vendors from one job! And if you do it right and attract jobs that bring in some BOMB vendors, then you're getting reposted by photographers, planners, etc. that have bigger followings than you! This is why it's so important to make sure your clients know to tell their vendors to TAG you in reposts!


4. The wedding industry is always growing

People are always getting married! The industry is massive and there are sooo many different types of clients to work with!


5. There's very little training required

While working at an agency requires a degree or some form of experience, I started my custom stationery business on NO knowledge in design, art, or business. Yes, you read that correctly. I had never touched an Adobe program, I had only worked in food service (and a brief stint at an office job), and my art sucked at the time! You can build a custom stationery business with little to no training…just gotta be willing to WORK!


Cons of Being a Custom Stationery Designer

1. Long hours and irregular income

Wedding clients means you are working with people that are planning the biggest event of their lives, during non-office hours. Most clients are sending emails, picking up the phone, etc. in the evening. They're off work and able to focus on wedding things, makes sense right? Along with that, wedding clients are usually receiving a lot of opinions and feedback from family members, other vendors, etc. There's a lot of revisions that happen within one job because of these opinions! Along with that, it's hard to have a predictable income. It's definitely doable, but especially in the beginning, it's difficult to know how to spread your invoicing out and pay yourself after you pay for printing, shipping, and all the other material costs that come with this type of service.


2. The competition is intense

The wedding industry is saaaturated. When I was first starting almost 10 years ago, the competition wasn't as fierce as it is now. Today with the internet, anyone and everyone is a wedding calligrapher, stationery designer, etc. The same thing happened with wedding photography a few years ago! This doesn't mean you can't make it in the industry, you just have to start thinking differently. What's going to set you and your brand apart? What's unique about what you offer? Who is your ideal customer?


3. High pressure & responsibility to deliver perfection

This goes without saying, but working in the wedding industry is incredibly high pressure. These people are usually expecting perfection, why wouldn't they be, and sometimes mistakes happen. We're humans! But, the thing is, even down to the way you write your welcome emails and schedule the timeline is being watched. If you deliver a stellar client experience, things will go smoothly (psst…I teach about this in my Pen to Press online course!), wedding clients are more sensitive than if you were working with a manufacturer or a company on branding.


4. Emotions are high

I'm not saying this in a bad way at all…I mean, these people are getting freaking MARRIED. That's a huge life decision. And expensive! Every little decision they make from the paper color to printing method and stamps they use, it's all filtered through that lens. As it should be! But as a custom stationery designer, this requires a lot of guiding the customer, being on your toes and anticipating every next move!


5. Family members 🙂

Do I need to say much here? Lol. I get it, mom and dad are usually paying. Because of this, they are ABSOLUTELY allowed to have opinions. However, I've literally had a mom go behind her daughter's back and request that everything be changed. Literally. Her daughter (my client) had just approved the design of her invitations and they were being printed and the mom offered to pay me to stop production on what the daughter wanted, and start over. Behind her daughter's back! Could you imagine what would've happened if I did that? Her daughter would've expected her dream invitations to go out to all her friends and family, then when she opened everything…completely different. What?!


With all of that said, I'm hugely grateful for my time in the wedding industry. It taught me a ton about client experience, running my own thing, and working hard. It also helped me narrow down and pivot into what I'm actually passionate about, which is teaching online courses and licensing. I know that working in weddings isn't for everyone, but for those who are in it, it can be amazing! The stories you get to tell for your clients, the keepsakes you are trusted to make and the relationships! It truly is a wonderful industry and a great way to make money as an entrepreneur!

What's great about being a custom stationery designer too is, you can work remote! Like, most days I'd be caught still in my pjs at 2pm, creating bougie paper goods, so that's fun!

Are you a stationery designer or want to become one? Check out my course Pen to Press for the blueprint to running a custom stationery design business!

by Jenna Rainey 

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