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!

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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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goal setting

How to Make 2020 Your Best Year YET!

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I can't believe it. 2020 is HERE and it's a new decade!! I love the energy around a new year. It's so invigorating and exciting when thinking about all the possibilities! So, to help set you up for success in this brand new decade, let's talk about a few ways to make 2020 your best year YET!!

To kick it off…


Goal Setting

Goal setting is something I used to never do in my business. I didn't understand the importance, and just felt TOO busy to stop and set goals. But after spending the past couple years really looking at what is working and what isn't, I've seen some INCREDIBLE results from goal setting before heading into the New Year.

So, with 2020 literally days away (OMG I can't even believe it), I thought I'd let you in on some tips for goal setting and for making 2020 your best year yet!

1. Set aside 1-2 days

With the launch of my podcast happening January 1, 2020, I KNEW I had to get down and dirty to plan out the upcoming year. Otherwise, episodes wouldn't get recorded and published! If content is already hard and time-consuming for you, trust me…spend an ENTIRE day or two where your only focus is on planning out your content for the year. Yes, the entire year!

Don't worry! You can always make adjustments and tweak launches etc. Put on some good tunes, and get scribblin'!

2. Plan out your most major launches first

If you're wondering where to even start, we started with mapping out our FOUR major course launches for the year. Because these are online courses, we wanted to make sure to spread them out enough so it wouldn't feel like I was constantly promoting and selling to my audience. We also wanted to make sure to avoid launching during any holidays or times of year where potential customers wouldn't be eager to buy.

3. Cushion those launches with content that acts as a runway

The next step is the fun part for me. It's building out your runway to a launch. If you're in my course Instagram for Creatives, then you know ALL about how incredible building a solid runway before you launch a new product, course or service, etc. is CRUCIAL to its success!

So, for example, in March I'm launching a brand new course all on how to teach creative workshops. In my podcast leading up to the launch, I'll be sharing stories on workshops, how it lead to book deals and steady monthly income, etc., so my audience is PREPPED about hearing me talk about workshops! This also allows them to think about teaching workshops as an incredible opportunity in their own business!

4. Never underestimate the power of writing it down

I bought this huge 2020 dry erase calendar. It's amazing to look up and see when upcoming launches are, what I have coming up this week and more. This helps my entire team stay focused and what needs to be tended to next!

Most of my team (besides John) is remote, so we input all of the launches, podcast episodes, YouTube content and more in THIS calendar so we can all access it!


Become a Future Thinker

*Sound the alarm!* Failure to keep an eye on the future in business will lead to some mega pitfalls! We live in an ever-evolving society, people. Social media trends ebb and flow, consumer trends come and go, and what works today is most likely not going to work tomorrow.

I see SO many creatives making the mistake of just going with the flow and not keeping an eye on the future. According to Fundera, 20% of small businesses fail in their first year, 30% of small business fail in their second year, and 50% of small businesses fail after five years in business. Finally, 70% of small business owners fail in their 10th year in business.

Small businesses are closing their doors all the time, and that’s a terrifying statistic! The rise and fall of trends has a direct effect on businesses today and now more than ever, there’s more to stay on top of! The world of online marketing alone can make a small business owner squirm and hide, but it’s also what can keep the doors open if met with future thinking!

Think about it…


Before the age of email and Facebook, business owners relied solely on paper mailers, cold calls and door-to-door sales! Newspaper ads and leaflet drops may sound pointless to you now, but think about businesses 10, 15, 20 years ago! That’s how they were able to thrive!

It’s so crucial nowadays to have a solid, future-thinking strategy behind marketing. Apps will come and go, and your tiny space on the internet is only becoming more and more crowded. Google Adwords, email marketing, and constantly researching trends within social media is a great way to start future-proofing your strategy! (Psssst. I have a super helpful post on Instagram HERE)


Think about your specific industry. How is it shifting? Who’s the new competition on the scene? What sort of strategies do they seem to implement? Research is SO crucial, so put your nose down and make sure you’re implementing this!

Beyond Trends

Don’t just stop at what’s a trend and what isn’t, or what you think might be down the road…think about outside technology and how that will affect your business. Remember when Steve Jobs was like, “oh hey, you can now have a computer AND a phone in your POCKET! And it’s ONE device!!” That was detrimental to landline phone companies and any business model that only focused on separating computer software from the technology in cellphones.

How can your business shift when huge changes come to play within technology?

What if social media were just to dissolve one day? How will that affect the way your customer discovers your business? Will this affect how people take in information and make purchases on the internet? Where can you TODAY ensure you will be seen TOMORROW? Your little “.com,” or corner on the internet is something you own…you don’t own your profile or followers on Instagram. 

While this may sound a bit *dooms day-ish,* I hope it gets your wheels turning. The reality is, things come and go…businesses, trends, etc. and it’d be totally ignorant and detrimental to not understand the importance of future thinking in business!


Create Before You Consume

Exhale and take it one step at a time.

Seek out inspiration via other mediums

Ok. Now, this tip may seem contradictory to the first one, but hear me out! Everyone needs some sort of spark or idea for inspiration. While I’m not encouraging you to just consume images to replicate, this strategy helps to dig through color palettes and textures and other elements that can contribute to an idea! A lot of what I paint for jobs comes from my Pinterest boards that are literally centered around specific color palettes! The one below is from my board: Yellow Palette Inspiration.

When I’m painting or designing something for a client project, I usually have guidelines and specs to follow. Typically this requires a specific color palette, subjects to paint, etc. and it can be really challenging to just come up with original ideas just out of the blue, so, pulling up one of these boards that relates to the specs is SO helpful! Let’s say I needed to paint an abstract pattern with yellows…well you see in the image above, far right picture of those leaves? Those golds, ambers and yellows mixed with the shapes of the leaves…wouldn’t that make for a fun watercolor pattern? Boom. There’s how it happens!

Go for a walk with someone close to you (or favorite podcast) to talk ideas and get pumped

May seem silly or simple, but it works! There’s been so many occasions where I’ve felt completely overwhelmed and it makes me feel like I’m frozen and can’t get anything done. I’m at a standstill. Going for a walk outside not only physically gets you moving, but mentally, creatively, allows the ideas and inspiration to start flowing and moving. Don’t ignore this one! Even if it’s just for 10 minutes, it helps!


Technology Detoxes

Since mid to late 2019, I have been doing Social Media Free Sundays. The first couple of weeks, I noticed myself clicking on Instagram as a habit, so I decided to up the ante a little bit and change it to SCREEN Free Sundays!

Yes, the entire day I go without screens. No Netflix, no email, no phone calls, text messages…and it's AMAZING.

I get SO much house work done. I read, I go for walks, I journal, do yoga…and it sets me off on the right foot before the new week begins. Allowing yourself a break from screen time helps you sleep better and allows you the mind space to actually focus on a task and get something done. This is probably the thing I'm most excited for during my weeks now because it helps bring clarity around my week and allows me to enjoy a big dose of family and outdoors time. So refreshing!


Batch Working

This last one is something I've done for the past few years now. Being a mom and a business owner, I don't have to tell you that time is precious. We all need productivity hacks and ways to “get back more time”…well, guess what? We all have the same 24 hours to work with here, but batch working allows me to be more efficient! For example, every Monday and Friday, my entire focus for those days is, Podcast outlines and writing blog posts. That's it. I don't hop on email throughout the day until I get what needs to be done out of the way first. That way when I sit down in the morning to start working, I don't waste time thinking about what I should do first, or getting sucked into my inbox!

Obviously if something is urgent, that becomes priority, but setting up boundaries around your day to sit down and crank out 4 blog posts in 4 hours, or all your emails to your newsletter for a month in one sitting…it does huge wonders for helping you stay ahead of schedule so you can anticipate any sort of hiccups along the way!!


If you're as pumped about the new year as I am, head on over to Instagram and share this post! Make sure you tag me! I would love to chat with you there and share with my audience!!


by Jenna Rainey 

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  1. Congratulations on on your goals! Loved reading your blog today! I start every year not knowing what my goals are. Thanks for giving me the knudge to get going!

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