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. 

Wanna Learn Watercolor?

i wrote some books



Beating the Feast and Famine Cycle in Your Business

Tips for Overcoming Imposter Syndrome

Art Topics


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If you're like so many of us out there feeling like a total fraud or like someone is lurking behind you, just waiting for you to mess up so that they can point out to the world that you're an imposter, you don't actually know what you're doing and you shouldn't be here or you don't belong. Well, join the club. I'm going to give you a few tips on how to overcome Imposter Syndrome and mindset shifts that will really help you show up more confidently!

Imposter syndrome is an epidemic. Really. We all feel it. We all go through times where, especially after many mistakes we've made, where we feel like, you know what? I really messed up this time. I do not belong here. Somebody else take over who's been doing this forever and knows all the ins and outs of how to do this because I am truly a fraud and um, yeah, I shouldn't be here. If you're nodding your head and you're saying amen (I'm pretty sure you are), I've been there too. I know so many entrepreneurs feel the same way. And the thing is, the more you take steps forward and you keep learning, the more that voice in your head, that imposter syndrome voice in your head that's telling you you're a failure or you don't belong here or you're a fraud, the more it softens and just becomes background noise.

With practice, it's just like anything, you're not going to show up to the gym for the first time and know exactly how to use certain weird equipment machines. And you don't show up to a jazz dance class for the first time knowing all the steps. You can't have such high expectations of yourself when it comes to what you're pursuing or what your career is because we don't have it all figured out. All right. So with that out of the way, let's actually talk about some tips for overcoming imposter syndrome.


Tip #1: Keep Showing Up

Keep showing up. If you've read this post, then you know I've made lots of mistakes.

I had my very first client fire me because of a huge mistake that I made. I could have given up and said, I don't belong here and gone back to my day job. Instead of that, I kept showing up because I was excited about the potential that my future could be. I was excited about what I was working on, on the side. I was excited about the people that were hiring me and were excited to work with me. And even if you don't have people hiring you yet and you're just in the very early stages, you have to keep showing up and keep showing up consistently.

And if it's just not working, then it's not working. You have to be honest and vulnerable with yourself about that. Not everybody should be a boss. But my biggest learning curves have been from my mistakes and they've helped provide really big results in my business. If you keep showing up, even after you make a mistake, this can happen for you, too!


Tip #2: Invest in Your Business

Whether that's time or money, invest in your dream and business! When I started investing in my business financially, my business began to scale very rapidly. In the beginning, I HATED spending money on my business in things like mentors, courses, etc…and I'm not saying to spend money on just any course, coach or mentor! They have to be the right fit for your business. But about five years into my business, I invested in some courses and mentors that completely changed my life.

So, whether it's your own time or money, invest in your business. It will help you grow and learning from someone who's gone before you is the best way to achieve results!


Tip #3: Mindset Shifts

A lot of us have this mindset around what we do and offer as not being valuable.

Why would anybody purchase this? It's just a watercolor print… it's just a design course… it's just a ______.

However, the truth is, value is a spectrum. It's a really wide spectrum. You could be providing your audience or your potential customers with a complete transformation where you're helping them overcome addiction or achieve health goals. There's obvious value there. However, someone who's an artist or a designer, a marketer, etc. provides value that can be anything from joy, happiness, laughter, etc.

And that mindset value has a direct result on how you talk about your products/services, and ultimately how you SELL to your audience. Because if we truly believe that what we have to offer is valuable, our potential customers can sense that. When it comes time to talk about our offerings, it comes from a place of authenticity because we actually believe in what we're talking about!


Tip #4: Just Frickin' Do It

Just freaking do it. It gets easier. That imposter syndrome voice becomes more and more distant the more you continue to show up.

If you fail, join the club.

by Jenna Rainey 

add a comment

  1. Kaylyn says:

    Needed to hear this today! Thank you!!

  2. Kimberley says:

    Hey Jenna,
    I feel like this every time I sit in my art room and paint, every time I give my art as a gift, and every time I sell my house portraits. Thanks for giving me some tips to overcome impostor syndrome.

  3. Linda says:

    You know Jenna, you are a really cool person. I love that you are sharing your wisdom and mistakes along the way to help the rest of us. That’s generous. You are making a positive difference for many people, myself included. Keep it up! And, THANK YOU.

  4. Jennifer Koistinen says:

    I really appreciate your open, honest attitude! Keep sharing, I really enjoy hearing what you have to say!

  5. Tamy Ellis says:

    Listening to this was just what the Dr. ordered. I refuse to let the past (losing my daughter) define me, instead refine me and embrace to the utter most our journey together for 29 beautiful years and eventually it will so through my painting and it will be noticed 💜

  6. Daniela says:

    Thank you Jenna – as usual! Your stories and wisdom are always spot on.

  7. Anne Procopio Scott says:

    Thanks Jenna. My painting practice has improved already. I love your classes- even the basic color theory classes have helped me tremendously! All I want to do is paint. Having the right supplies has truly made a difference.

  8. Patricia says:

    My mom was a artist..she could draw and oil paint the most beautiful beach scenes. I am now 58 years old, retired and going back to my first love art. I am doing it has a hobby because I love it..not because I’m good or trying to make it rich..simply because I love it.
    Thank you for your blog and podcast

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