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!

(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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jenna in front of brick

What No One Tells You About Being Your Own Boss

Podcast - Featured


written by




Are you your own boss? Or want to be?

Seems like the hottest job on the market right now is creative entrepreneurship.

Just have a look through social media for long enough and it seems like everyone’s talking about their endeavor, their online shop, their new (fill in the blank). Every major city is riddled with co-working spaces stuffed to the gills and somehow every creative entrepreneur, freelancer or 1099er has a perfectly curated life and workspace with all the plants and natural light…or so that’s what Instagram tells me.

There are artists, photographers, woodworkers, stylists and now social media influencers that don’t really have a traditional creative talent or trade per se but have a knack for communicating, an eye for product and the best angles for Instagram. These people are movers, these people are shakers, and most of them have no idea what they are doing.

It’s the truth!

Jenna and calligraphy



When I quit my corporate cubicle job in 2013 to start doing creative entrepreneurship full time, I started as a pointed pen calligrapher for weddings. I didn’t paint yet, I had never touched an Adobe program in my life, and what’s a contract?! Was I good at calligraphy at this time in my “career”? Nope. But people were hiring me, so I didn’t pay much attention to that. Becoming a business owner allowed me a glimpse into a free world where I didn’t have to dread waking up every day working for someone else, where I could “make my own rules,” and essentially wear whatever I wanted, do whatever I wanted and live comfortably financially while doing all this.

*This is where you hear me break that last sentence with an outburst of laughter because of how naive I was when I started.*

The first few days and weeks were thrilling. I had a new, white Ikea desk set up in the front window of our upstairs apartment so I didn’t have to work from the kitchen table anymore. 90% of my days were spent just doing art things that I wanted to do while 10% was filled with client projects. My life looked pretty great on social media…Instagram was definitely not the beast it is today and my photos were not the quality that would last these days on any platform, but my desk was pretty, people were commenting and liking my art, life was good!

Have I set the scene well enough yet? What I’m basically trying to say is I had no idea what was about to come for me. Now, I don’t want to seem like I’m complaining whatsoever or being a Debbie Downer. There are obvious upsides to being your own boss, which I’ll list below in a minute, but I do believe with Instagram and social platforms it’s easy to lose sight of reality. People can make their lives look so dreamy on the ‘gram. I’m guilty of it! But we have to remember that these are SNAPSHOTS of PIECES of our day. One shot on my Instagram doesn’t cover the stressful morning I had where I spilled my coffee and burnt my breakfast, where I cried because I couldn’t handle the stress or my husband and I got into a silly argument. I mean think about it, how weird would it be if I held up my phone to story while John and I were fighting?! But we do fight! My marriage isn’t perfect, my life isn’t perfect, my business isn’t perfect.



  • You get to work when you want to
  • From where you want to
  • You call all the shots
  • You hire the help
  • Dream up projects and set goals for your future
  • People hire you for things you create or purchase that pretty thing you made. How encouraging is that?
  • You receive amazing feedback on social media, constantly. Like more encouragement in a comment section that should be bestowed upon any one person
  • You look really, really cool on social media
  • All your friends with *regular jobs* will comment on how cool you look
  • Social media essentially makes it seem like you hop from one big, amazing meeting to another, landing this big client and that incredible partnership.

But I told you I wanted to keep it real… so let’s look at the flip side.



  • You work all day long…no, you never stop working actually.
  • Sometimes you work from bed to make it appear to your body like you’re sleeping, but you’re still working propped up by 45 pillows. Your body is very achy.
  • Sometimes you don’t know if you’re making the right decision and you feel like no one’s there to help you through the toughest calls.
  • You hire help because you can’t work 20 hours a day anymore, but you end up paying your assistant more than you pay yourself.
  • You thought of listing those cool prints in your shop to make a few bucks because people said they’d buy them but you end up selling NONE. YES, I’ve sold *none* before. And now you have that printing invoice to pay and all that inventory to store.
  • Entrepreneurship can be lonely. While you’re receiving tons of likes and encouragement on social media, your personal life and relationships can suffer at times because you constantly have to cancel or back out of things to finish deadlines. Friends won’t understand and most of them will move on.
  • Remember what I said about marital arguments and spilling coffee? Super cool.
  • It can get frustrating hearing how *cool* your life looks when you sometimes feel like it’s completely falling apart.
  • While you are landing exciting projects and working with big companies, you can’t show too much of the icky, hard stuff – that’d appear ungrateful and negative and complain-y.



…that you knew nothing about before:

  • Accountant: Making sure you know who and when to pay how much money based on your income and expenses
  • Bookkeeper: Organizing and labeling all your income and expenses and realizing that you’ve spent way too much money and are barely making it
  • Customer Service Rep: This is the you who wakes up to open their email at 2:34am to a message from a client about their order that was wrong… which you then decide to redo with money from out of your own pocket, making you take a loss just to make sure they are shipped their new job overnight because you feel so awful.
  • Web Developer/Copywriter/ Social Media Director and Marketing: While dealing with unhappy clients, reconciling your books and figuring out how you’re going to pay taxes this quarter, you still have to keep up with your website, write copy for new shop items, promote those new shop items on social media, and make it convincing to purchase.
  • Errand Runner/Shipping & Inventory/Misc.: Yes, you do this too. It just doesn’t look cool on social media.

Let’s see, and after all of that, you still have to make sure your legal ducks are all in a row AND you have to get artsy and still want to do the creative part.



I know for some of you this may come off as ungrateful and even seem like I’m complaining, but believe me, I’m not. I wouldn’t trade all of the bummers for anything…you know why?

You figure it out.

Yep! While you’re sitting there stewing with anxiety over a job you failed on today, there’s always tomorrow.

Google is always there to help you understand the legal jargon and help you with those big decisions.

You start to really understand how business works and how to wear all the different hats.

You start to pay yourself AND live comfortably like you always dreamed!

You don’t stress the upset client emails or bad reviews that much anymore, you are ONE human and one human can’t please every person out there. That’s just fact.

While you had that one upset client, you also had 9 emails from customers raving about your work and talking about how happy they are. That feels good.

Your quality of life gets better, new friendships come along and you’re able to go out again.

Now, I’m not saying that everyone is cut out for entrepreneurship and can arrive here…and by “here” I mean a viable business, by no means do I feel I’ve *arrived*. Some people who strive for being their own boss end up throwing in the towel. And that’s ok! There is NOTHING wrong with being an employee.

But to those of you reading who are The Boss, it’s all worth it. While no one will be there with a list of warnings and hardships that are to come when you start your business, there’s no better way. What if it was all laid out for us? The mistakes, the late nights and the tears make YOU a better problem solver, a better business owner. So, here’s to YOU solopreneur! I see you, wearing the same yoga pants for the past three days, your house in shambles and bags under your eyes…you’re doing it! And you’re doing awesome.


by Jenna Rainey 

add a comment

  1. Danielle says:

    Love this so much! I’ve worked from home for several years and it’s so funny that everyone’s reaction is “you’re so lucky” and although I am super grateful it definitely comes with it’s own set of junk 🙂 Love the new site too!

  2. OMG this was the post I needed to read this morning as I’m here on my day off (let’s be real ..there are no days off) to catch up on all the stuff that is just piling up. Thank you for your honesty, it helps fuel those of us who struggle with comparison (which is the thief of joy by the way!) And never feeling “___enough”.
    You are an inspiration and I appreciate you!

  3. Leigh Karsch says:

    Thank you for writing so honestly about this Jenna. I’m in my 11th year of creative entrepreneurship, and girl, it IS hard. But also way more rewarding in so many ways than my previous ‘corporate life’. It’s exhausting, and lonely, and requires such strength, especially in those times of tough, big-girl decision making. And it’s about WAY more than pretty pictures. I’ve always said that 9 out of 10 people who ‘own their own businesses’ actually don’t know a damn thing about jobs 1, 2, 3 and that doing job 4, doesn’t make you a business owner. What makes you an entrepreneur is agility, kindness, strategy, and learning to say, ‘no’ to the good, in order to say, ‘yes’ to the best. Oh, and getting a good night’s sleep every now and then, so you can think clearly, REALLY HELPS. Believe it or not, not every decision needs to be made ‘right now’. Just my two cents anyway! Big fan of yours. Thanks for doing what you do.

  4. Janice Myers says:

    …3 days in the same yoga pants…that’s me! You’re amazing Jenna and I’m so blown away at all you’ve accomplished! You go bossypants!!!

  5. Preach it, girl, PREACH! I couldn’t imagine doing anything differently than being an entrepreneur and business owner, but there are days…seasons! But in the end, I absolutely love it. Cheers!

  6. Melinda says:

    Thank you for writing this post and for touching on the “dark” side of starting a creative business. It. Is. So. Hard. It’s encouraging to hear your story. Thanks for being real and for the encouragement!

  7. All those job titles….and I am terrible at changing hats. I feel like I spend most of my time doing all the things I have to do, and so little time on the creative things that I want to do.
    Thank you for your well-timed post. It’s a little less lonely behind this desk today.

  8. cheryl steffen says:

    All so true – great blog!

  9. Luz says:

    Jenna! this is such a great summary of being a boss. 100% with you in all of this.
    Thanks for sharing it. 🙂

  10. Elizabeth I says:

    Wow. Thank you for being so transparent and honest!! I started my little creative business a year and a half ago as a 16 year old and SHEESH I still feel so overwhelmed! I’m terrible at all things money, record keeping—basically all of the business side of it ? Business is picking up though, so I guess I need to get things sorted out soon.
    This helped me a TON. Thank you again ?

  11. Amen!! I couldn’t agree more!
    I’ve always wanted to own my own business and now I’ve been doing it for 5 years. The workload is no joke. Sometimes I’m ok with not having any active jobs, because I’m tired and mom guilt is a real thing. But it’s also SO rewarding. Thank you for your honesty, it’s so true we only see the pretty parts on social media. ❤

  12. Zaryn Sharon David says:

    So much truth in this. I’m just starting. Not sure what I’m starting out with though. ? Oh well, one for on front of the other. Very. Slowly.

    I am confident that I will make it. ?

    Thank you for this informative read Jenna.

  13. Thank you so much. It has been a very, very bad few weeks for me and I’ve secretly considered throwing it all in. But maybe if I can get some painting done today while my husband looks after the kids it will be okay.

  14. Esmée says:

    Nice blog!
    And nr 8 and 9 from the first list haha!
    I am just atarting out my own business/studio illustrating and it is so scary! But it’s the only thing I can see myself doing (:

  15. Anupama says:

    I hear you and am totally in the same boat. Thank you for putting it into words. Just what I needed.

  16. Sandra says:

    Thank you for your post.
    I just left a decade of waitressing in the fine dining world to dive into the art world where I’ve only dipped my toes before. I’m finding my voice as an artist, and listening to every motivational podcast I can. I know I have a long and difficult journey ahead, but with a little ambition, and a strong will to go through all the things, I know I can make it.
    I’m so glad I found your page on Instagram.
    (AT littlesandie )

  17. Claudia says:

    Exactly what I needed! You’re amazing!

  18. CBGEMS says:

    Love this, it’s all so very true! I like your writing style Thankyou for bringing light to this subject!

  19. MarieB says:

    Thank you for sharing your experiences Jenna, really informative.
    I have a creative ‘side-hustle’ along side a full time job. One day I’d like to make something more of it and I really appreciate your experiences so as to know some of the real life challenges.

  20. Lynn says:

    Finally!! Someone who speaks truth and is brave enough to let us know we aren’t alone. Even if all I do are small galleries and small shows and small classes, I’m happy. Cause it’s all I can handle along with the other hats I’m wearing and all the other job titles I fill.
    Blessings to you!!

  21. Oh how I so needed to hear this today!!! Feeling all the pressures and not the perks of the job today. Thank you for the encouragement. Believing that one day soon I’ll see the fruit of the labors!

  22. Carrie says:

    And this is why I love you! It’s like watching a ballerina – looks so easy from the audiences perspective but they are working their TAIL OFF! I’ve always been involved in the arts and every time it starts to be a job I lose the creative inspo- so I choose to keep it a hobby. Congrats on all the success and years of hard work! You’re very inspiring to watch

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