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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My Business Deal Breakers for the New Year

Business Resources


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Anyone else in complete shock that we’re in a new year already?! This past December, I signed up for an online course (I’m the student this time!). It's about courses, funnels, and more. In one of the early lessons, the instructor asked us to write down our 5 business deal breakers and I thought it would be fun to share my answers with you all.

Now, this isn’t the first time I’ve written down or made a list of deal breakers in my business. But this time, what I wrote down was a bit shocking. Let me explain. When I started my business back in 2013, my income for YEARS was dependent on the amount of time I spent working. If I worked harder and longer hours, my income would increase. If I needed to take time off? My income would stop. Taking long breaks felt like my world would crumble and everything I’d built thus far would just fall apart.

Does this feel familiar? Well, for the last two years, my business has drastically changed. I no longer work with clients and feel the need to bend my days to another person’s requests. I mostly create and launch courses now and also create artwork and patterns for licensing collaborations. However, I still work my little booty off and my main focus for 2022 is making some big shifts in my business. They're summarized with my business deal breakers.


My 5 Business Deal Breakers for the New Year 

As you read through these deal breakers below, keep in mind that I’m nearly 10 years into owning this business! We didn’t get here overnight.


Deal Breaker #1: My business must have at least a 40% profit margin or more

This is so important to me. Nothing sinks a business faster than having a negative margin (and not realizing it)! I’ve never been one to naturally love looking into the finances and money side of being a business owner. But it’s so crucial! Knowing exactly how much money is coming in and out every month on average will give you a good idea of what your profit margins are. Having a good profit margin means that when business is slow, you have more leeway and flexibility. Smaller margins can strain businesses quickly. Seems pretty straightforward, but are you tracking this in your business?


Deal Breaker #2: Earning 75% of the Income Passively

This is a big and bold statement for me and the business, but still realistic. Here’s a breakdown of how I earn money in my business:

  • Online Courses

Right now, the bulk of the income coming from my online courses comes directly from launch weeks. While launching a course is fun, it also requires a TON of work! Leading up to a launch, we’re creating sales pages, writing email campaigns, setting up links and triggers within emails, creating downloads, writing and recording course content and updates, editing videos, promoting the course, answering questions, and more. But one of the reasons I’m taking this course is because I want to set up a more “evergreen” system with my courses. That way, I don’t have to be launching all of the time and I can focus more on painting and my licensing work.

  • Shop

I have a few tools and mini courses for purchase in my online shop. Having these items creates passive income for me, but I would like to increase traffic and sales to this shop through my email funnels in the new year.

  • Licensing

This section of my business is where I’d like to shift my focus to. While I love teaching and creating courses, my true reason for this business and passion is painting! I’d love to work on more collabs this year. Licensing can still be very passive depending on the collaboration and the requests the brand is making.

  • Books

All passive for my first two books, and I’m writing my THIRD book with Ten Speed Press right now (coming out in Summer 2023!), so it’s not fully passive just yet. 

  • YouTube and Patreon

Filming tutorials for our YouTube channel is very much NOT passive, but it’s something that I really love. While the filming and editing isn’t passive however, we do earn money through ads and affiliate income through the supplies I recommend in the description of each video. YouTube is a great way to boost passive income if you love teaching and have something great to offer! My Patreon channel is also not passive, but it’s a great way to build ongoing monthly income through their subscription model.

  • Affiliate Income

Through links to supplies, resources and items I recommend in blog posts, Instagram stories, free downloads and more! We’re wokring on ways to increase my affiliate income in the new year!


Deal Breaker #3: I Can Work From Anywhere

Having the ability to work from anywhere in the world is a big deal to me. A few years into my business, I hired in-person employees, had a studio space and was packaging and shipping prints and shop orders to customers all over the world. This felt so restrictive to me. Anytime I wanted to go on vacation or needed to be out for sick days, it seemed as if my business would crumble without me in the office. Once I shifted away from having an office space and focusing only creating digital products and licensing my artwork to manufacturers, this all changed. This is a big one for me!


Deal Breaker #4: I Can Take Time Off and Not Worry

This one ties into my previous deal breaker. Having 75% of my income generating on auto-pilot, without having to launch, without actively working is a huge goal for us this year. Evergreen sales funnels and setting up automated systems that lead potential customers to our courses and products will help a TON in this department. We already have some funnels set up, but we really want to clean this up and make it more efficient this year!


Deal Breaker #5: Increase Monthly Giving + Saving

Having a business that gives back is really important to me, while also saving for retirement, my kid’s future and all the things…it’s a lot! Since I was 23 years old, I’ve been working with my uncle who is a financial advisor on these two things. It’s something we will be increasing and dedicating more to this new year.


If you’re a business owner, I highly recommend writing out your business deal breakers. Mine are here as inspiration and to get your wheels turning. Just make sure yours are in line with what YOU need and want with your business. Having the ability to dream and make goals is great as a business owner. But, it cant be easy to get stuck in a business we hate, doing things we’re not excited about. Make it a priority to write a list of deal breakers and check on them often!

by Jenna Rainey 

add a comment

  1. kristen says:

    Do you mind sharing the name of this course you’re taking as well as any other courses you’ve taken that have been valuable?


  2. tamaka says:

    good write up. perfectly listed tq 🙌🔥

  3. Dan says:

    Hi Jenna, that was a great post! Thanks for the useful stuff you share. You’re a real inspiration to me and millions out there. Keep painting and making videos and all the good stuff you do. God bless you!

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