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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herringbone painting as an example of daily creative challenges

Daily Creative Challenges You Need to Add to Your Routine

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Creativity is the heartbeat of our artistic endeavors. It fuels our passion, drives innovation, and brings our wildest imaginations to life. As artists, designers, creatives, humans – we thrive on this boundless energy, don’t we? But how do we keep the creative juices flowing day after day? Today, I want to share the power of embracing daily creative challenges (with a few tips and exercises to add to your routine).

In my experience, daily creative challenges are your secret weapon to staying inspired, honing your skills, and finding joy in your craft. So, grab your sketchbook, camera, or journal, and let's get started!

What Are Daily Creative Challenges?

First, let me back up a second and explain what I mean. Daily creative challenges are small, manageable tasks designed to ignite your creativity. These challenges push you to create consistently, which helps creativity become a habit for you. They also strip away the pressure of perfection and encourage you to explore new ideas, mediums, and techniques. Think of them as bite-sized creativity boosters that keep your artistic spirit vibrant (and can help you get out of a creative rut too!).

daily creative challenges painting

Benefits of Daily Creative Challenges

Beyond just bringing you joy (which is reason enough!), here are a few more reasons to bring daily creative challenges into your life.

  1. Improved Problem-Solving Skills: Engaging in creative activities regularly enhances your ability to think outside the box. It nurtures a mindset that embraces curiosity, experimentation, and unconventional solutions. It might surprise you, but even at work, the World Economic Forum has predicted that creativity will rank among the most important soft skills to have in the workplace.
  2. Reduced Stress: Creativity is a powerful stress-reliever. It offers an escape from the demands of everyday life, and can even decrease your cortisol levels. Whether you're painting, writing, or crafting, the act of creating brings a sense of calm and fulfillment.
  3. Enhanced Innovation: This goes hand-in-hand with improved problem-solving skills, but by making creativity a daily habit, you open the door to endless possibilities. This continuous exploration fosters innovation and keeps your work (and LIFE) fresh and exciting.

Tips for Successfully Integrating Creative Challenges into Your Routine

Before I share some daily creative challenges to try, here are some tips to help you embrace this new (favorite) part of your routine.

Start Small

In my experience, starting with simple tasks is key to avoiding overwhelm. I would rather encourage you to start with a 5-minute sketch, a haiku, or a quick doodle than commit to something you won’t be able to sustain. These small steps build momentum and make it easier to commit to daily creative challenges so remember, the goal is progress, not perfection.

Set Clear Goals

I like to think I’m one of the most ambitious type-b people you’ll ever meet. If it helps you, set goals for yourself. Having a clear purpose provides direction and motivation. Whether it's completing a short story, learning a new song, or mastering a watercolor technique, setting goals helps you track your progress and more importantly celebrate your achievements.

Create a Dedicated Space

Having a specific area for your creative endeavors can enhance focus and creativity. Set up a small art studio, a writing nook, or even just a cozy corner for journaling. This dedicated space can become your creative sanctuary, free from distractions and filled with inspiration. It also makes it easier to “jump right in” to what you’re doing instead of feeling like you need to set up/clean up every time.

Embrace Failure

I know this sounds cheesy but it’s true. Whatever you choose to attempt creatively, understand that not every attempt will be perfect, and that's okay. Embrace failure as a natural part of the creative process. Learn from your mistakes, revisit failed projects with a fresh perspective, and use them as stepping stones to improvement. 

Limit Digital Distractions

This one sounds obvious too, but if you’re like me, there’s a chance that you’ll find your creativity decreases when you’re spending too much time on social media. Consider creating social media boundaries or screen-time limits for yourself, and watch your daily creative challenges improve too. 

Sleep Well

Last but not least, make sure you’re sleeping well. This one needs no explanation (because I think most of us know we need to be better at this), but it’s worth repeating here, too. It’s hard to be creative when you’re tired. 

Daily Creative Challenges to Try

If you know you want to incorporate more daily creative challenges into your life, here are a few places to get started.

Morning Pages

Start your day with Morning Pages—writing three pages of stream-of-consciousness first thing in the morning. This exercise (from Julia Cameron’s book, The Artist's Way*  clears your mind, sparks ideas, and sets a positive tone for the day. It's a powerful way to dump your thoughts on paper and make space for creativity to flow. It’s also a huge part of my process that I share in Flow School in my course The Art Within. 

*This is my affiliate link which means if you purchase after clicking, I earn a small commission at no extra cost to you. It's just a little something to help support the free content I share!

30-Day Challenge

I love a good start date and end date when I’m challenging myself to do something. This can be anything you want it to be, but one idea is to commit to a 30-day drawing challenge where you draw something every day for a month based on a prompt list. This challenge improves your drawing skills, encourages daily practice, and pushes you to explore new themes and styles. Plus, it's a fun way to see your progress over time.

Creative Journaling

Combine writing, doodling, and collaging in a creative journal. This exercise encourages self-expression, tracks your artistic growth, and serves as a visual diary of your creative journey. I’m personally a big fan of journaling anyway, as I think it helps you practice self-awareness, too (read more about that here!).

Move Your Body

I’m a big advocate for moving your body every day, regardless of if you prefer to go for a walk, practice stretching, dance, or do something else that brings you joy. If you want to learn more about this connection, check out this article from Psychology Today here.


Just a few minutes of daily meditation can clear away mental clutter, making room for fresh ideas and innovative thoughts. It helps you tap into a deeper sense of peace and clarity, which can spark new creative insights and inspirations. You can find some of my favorite meditations for getting into flow here.

painting as a daily creative challenge

Incorporating Daily Creative Challenges Into Your Routine 

Daily creative challenges are a powerful tool for artists, designers, and creatives of all kinds. They keep our minds sharp and our spirits joyful. Remember, creativity is a journey, not a destination. I can’t wait to hear about the transformative impact that these practices can have on your art and life (so make sure to follow me on Instagram and keep me posted!).

by Jenna Rainey 

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