Jenna Rainey


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hey friend!

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!

(with me)


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 business mistakes

The Biggest Business Mistake You’re Currently Making

Business Resources


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Don't you just wish you could predict the future?

Like, what if you could know how it's all going to turn out…your risks, creative endeavors, etc.

Unfortunately, creative entrepreneurship doesn't come with a blueprint or roadmap, and there's a 100% guarantee that you will make mistakes. Rough, right? But, one thing that I'm particularly passionate about is passing along the lessons I've learned over the years and that's what I hope to do with this post.

…as Maya Angelou says, “When you learnteach, when you get, give.”

My goal is to grab your attention and give you insight into the biggest business mistake you're currently making. And if you're saying “how do you know I'm making this mistake, Jenna?” well, just trust me. I was in YOUR shoes not that long ago.

Before I get into this, I want to provide a little disclaimer.

Mistakes aren't bad. In fact, I'm a firm believer that they are SO GOOD.

My mistakes have hit me hard, knocked me down, but they've also proved to me that I CAN get back up. Mistakes are also those things that you never forget or do again, right? So be grateful for them!

With that said, there are some mistakes that are actually mindsets, that are incredibly hindering. Especially within the female entrepreneurship category. Not to say men don't struggle with what I'm about to share at all, or to put us into a group…just from my experience with my own business and coaching other female entrepreneurs, I've found that we are incredibly obsessed with doing it on our own. The scrappy, problem-solver types. All great qualities, if you ask me, but at times can be a huge hindrance in business.

Here's what I mean:

You're not willing to invest in your dream

Chasing your dreams is, well, exhausting…right?!

For the first 4-ish years of operating my business, I was hustling from client to client feeling overworked and completely spent. The gaps between invoices being paid and the next job were a constant tug of anxiety and grinding hard to fill in the highs and lows of income.

Because of this, every dollar I made was held super close to my chest. I wasn't willing to spend any extra money I made on paying for courses or hiring a coach, etc… are you crazy?! Yes, I was able to scale my custom stationery business to a six-figure income alllll on my own, BUT it took years of mistakes, pitfalls and constantly feeling like I needed to “catch up.”

As of two years ago, I was near a breaking point.

I couldn't keep working the way I was.

I wanted to expand.

I wanted to grow and I desired a business that could float on its own a bit more…you know that “get paid while you play” stuff, right?

After putting in years of 60-80 hour work weeks, feeling tied to my desk, I took a risk and invested in a course. Normally I'd discredit paying for education as something I could just figure out on my own. But let me ask you something, would you say no to something that could get you farther along, faster? Would you say “oh I don't have the funds for that course right now, even though I know the skills I'll learn will help me make back my investment and THEN some.”

The course was on growing a profitable email list. It was over $600 and for me at the time, that was a big stretch. I remember feeling sick to my stomach about the decision. I thought to buy courses or invest back into my business for education was a waste of money.

Well, not only did I get my money back from that course within a month, that year I was able to generate an extra $100K solely because of a couple of skills and tricks I learned in this one course!!

And yes, these were lessons I could've pieced together over years and years through google searches and mistakes…but instead, I took a couple of weeks to work through a course and that time and $600 earned me $100K way quicker than I would've been able to on my own.

Crazy, right?

What if I hadn't taken that chance? Or a different angle…what if I was able to shift my mindset earlier in my career. Where would my business be now?

Now, am I saying that just by taking one course you'll be on your way to make $100K? Absolutely not. There are so many courses out there and some are just crap…I've taken some! In fact, I spent over $1,000 on a course recently that contained so many promises and way under delivered. Because of this, I'm so passionate about educating and providing YOU with the best information, whether it's in my courses, YouTube channel or whatever it might be!

Along with that, you can't expect the course to do the work for you. You have to put in the time to work through it and apply what you're learning. Take action!

Trust me. I get it. Business is hard. It's confusing. It's exhausting. But you don't have to figure it out on your own, and YOUR dreams are valuable and worth investing in. YOU GOT THIS!

by Jenna Rainey 

add a comment

  1. Jaì says:

    That was really well written Jenna and really informative with that “Get up and get at them” attitude to inspire and help progress those wanting to build a personal business. It is very refreshing to read and learn there are some people out there really willing to help others achieve through their own learning of the highs and lows.

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