What It's Really Like Working for Yourself

jenna rainey

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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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What It’s Really Like Working for Yourself



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Seems like the hottest job on the market right now is creative entrepreneurship—the freedom to pursue something you love doing, answer to no one (except yourself) and the ever-dreamy life you create for your Instagram is truly enticing.

There are artists, photographers, woodworkers, stylists and now social media influencers that don’t really have a traditional creative talent or trade per say 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 many of them are winging it a lot of the time.

It’s the truth!

When I quit my corporate cubicle job in 2013 to start doing creative entrepreneurship full-time, I began 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.*

Related: What No One Tells You About Being Your Own Boss

Here’s what one side of working for yourself REALLY looks like (you know, the side you don’t hear about all that often):

You’re now an accountant.

Someone’s gotta make sure you know who and when to pay how much money based on your income and expenses and how to file taxes properly…who’s gonna do that for you? The CPA that charges more than your monthly rent for their filing fees? Ok, I guess I’ll do it myself until I can afford one :).


And a bookkeeper.

The person who organizes and labels all your income and expenses (line items) and realizes that you’ve spent way too much money. *Insert crying emoji here*


And a 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 being wrong… which you then decide to redo with money from your own pocket, making you take a loss just to make sure they are shipped their new job overnight because you feel so awful. 


And a web developer/copywriter/ social media and marketing director

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.


And an errand runner/shipping & inventory/misc

Yes, you do this, too. It just doesn’t look cool on social media.


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, 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.

While working for myself and owning my own business has been one of the best decisions of my life, I wanted to be real about what it looks like behind the scenes. I remember starting my business in 2013 and feeling SO overwhelmed. I was feeling like a total imposter and I know you feel like this at times, too! It’s a part of the gig. But what’s truly amazing about it all is that it DOES get easier!

Related: How to Make the Right Hire

I was able to hire my first accountant and bookkeeper about 1 year into being a business owner. I now have an Operations Manager who manages my customer service and helps me stay on task with everything. And whether you end up being able to hire people or not, you do become more efficient and skilled in departments you were never trained in, and that’s truly incredible!

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  1. This feels so true
    In the course of owning your own business you are not working 9-5 but rather almost the whole day. you become the owner, photographer, designer, packer and a lot of roles but this is what makes the business grow.
    Really loved the blog post.

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