6 Reasons to Freelance & be a Creative Entrepreneur

If I can be totally transparent with you for a second, I am writing this off of a hella inspirational Periscope #BizTherapy session that just happened. Listening to other entrepreneurs express their goals, their backgrounds, their lives, their struggles, their successes, and how it all led up to where they are right now blew my mind.

When I look back at myself over the years, especially in that awkward middle school age, I think it’s pretty obvious being an internet-based creative entrepreneur was always in the cards. This is a fun fact that only my family and boyfriend really knows, but I was a SUPER active member of an online forum (yes, about Harry Potter) in middle school, developed life long friendships and pen pals over the internet, and honestly, felt more connected to people there than I did in person. As I got older, I thought, “what a weirdo.” But now that history is repeating itself, and I’m a super active member in this creative entrepreneur, business blogging online community, I see how it all makes sense.

This also is why I feel so strongly that I am just not meant for a life at a 9-5. I remember having fits of depression and crying to mom, telling her I felt bored by everything related to school and routine, throughout high school. I mean, I did it “right” – I was a cheerleader, student body president, etc. But I wasn’t ever fulfilled.

Transition into college, I immediately chose a fine arts major, where I actually felt challenged intellectually and loved learning – but still terrified of what would happen next. I worked at a large ad agency the summer after graduating, and though the people were awesome, the work was… boring. Uninspiring. Then I worked for photographers, being their in-house designer, marketing strategist, and wearer-of-many-hats. That, I actually loved, but I think mentally I always knew it wasn’t a “forever” thing. I recently moved and started a job at a small agency and though the people are mostly nice, I began to feel bored, monotonous, uninspired, and depressed. That’s when The Crown Fox really kicked into gear and became less of a hobby and more of a lifeline.

I tell you this whole story, to lead into today’s blog topic, which is 6 Reasons to Freelance & Be A Creative Entrepreneur:


I can definitely attest the reason that most of my jobs and paths have left me feeling utterly useless and depressed, is because I gave absolutely no cares about what I was doing. I didn’t care if it succeeded, or failed. I just showed up, fulfilled expectations (barely), and went home. For some people, that might be okay. I think for generations before ours, that was okay. But now, it’s just not. There are so many success stories of people taking their personal dreams and making them realities, that it’s impossible not to feel like “Why can’t I do that!?”

I know people, I have friends, that don’t think this way. Or if they do, they somehow manage to shut it down. They are content working on someone else’s dream for the rest of their lives. If that seems crazy to you too, you might have an entrepreneurial calling.

The thing about starting your own business, is that it’s YOURS. YOUR product, or YOUR service, and YOU make it, and YOU know it’s awesome. I worked in retail, selling cell phones, for two years. You know what sucks? Lying to people and trying to convince them something is fantastic and worth their money, when you truly don’t feel that way. When you are creating your own content, or whatever it is, and making an income off of that – suddenly you aren’t even selling. You aren’t trying to convince anyone, of anything. It’s yours, you created it, and you know it’s worth their while.  You can confidently stand behind whatever you are offering to the world, and when it succeeds and does amazing, you can reap the benefits.


This ties into my last point. Working for someone else sucks. It sucks for a lot of reasons, but for me, it sucks because I tend to think my way of working is more efficient. I’m sure that anyone who has spent time being an employee has thought, “this is ridiculous” about some system that his or her boss puts into place.

You know what’s amazing? When you are an entrepreneur, doing your own thing, YOU create the systems. YOU create the workflows. YOU create the processes. If you decide it’s not working anymore, YOU can change it. If you think that part of your process must be that you work in your pajamas, you can enforce that policy. YOU ARE THE BOSS!

Another point that ties into this, is that when you are the boss, you decide who to work with. As a graphic designer, at my 9-5, I have absolutely no say in who are clients are. Yet, I spend day in and day out working for them. Creating their success. They could be selling products I despise, but oh well. They could be the worst people in the world, hiring child workers in third world countries, but I have to make their advertisements. That really bugs me! I mean, I’m being really extreme in my examples, I don’t think any of my 9-5’s clients are that terrible, but I am trying to prove a point. As someone else’s employee, you have no control over anything. As your own boss, you can determine which clients you work with.

Me? I have a really specific target client. I work with creative female business owners almost exclusively. If a company approached me, and they made cigarette candy that marketed to kids, I could easily, simply, and happily say, “no thank you, I don’t think we are a good fit.” Because I’m working for my business. My way. My rules.


If I analyze myself, and the reasons for starting this business, a huge factor is financial independence. I used to be the girl that thought, I’d find a guy and live happily ever after. Well no shade to those people, but I came to realization that I can’t do that. I’m dating a lawyer. I could weasel my way in there and figure out a way to be “set.” But… then what? What happens when he pisses me off, or when I think how he invests money is stupid? I would have literally no say-so in anything, because I’d be dependent on him, and he would know that.

And it’s not just relationships that make financial independence matter. Don’t you want to be in control of your finances? Know what’s coming in and going out, and have the power to say where you think it’s wise to invest? I do! I want to make sure I am making my money grow and last. I don’t want to be dependent on an employer that could up and decide one day he doesn’t like me. I don’t want to be worried about being fired, or divorced, or any of the issues that potentially could come up.

This goes back to point 1, but when you work for someone else, you’ll always be giving him or her some of your money. My boss makes money off of my work. When you really think about that, it sounds terrible. Someone is making money, skimming away the top layer, of something I earned. Uh, yuck. I want my money, please and thank you.


I used to say, like 100 percent honestly, that I never would want to own my own business. I’d say, “That’s way too much work.” But now? Oh, bring on the work. I want to do it all. For myself. And learn and develop and grow so big and successful that maybe I can manage to block out those silly thoughts from my past.

If I stayed at my 9-5 now, the most I’d ever, ever, ever be is a graphic designer. Maybe I’d get the title of “Senior” at some point. I’d never become anything more than that though. I’d always report to someone else, pay someone else some of money, and be miserable.

With starting your own business, and being an entrepreneur, there are literally no limits. None. There might be obstacles, sure. There might be setbacks, and hard times, and challenges. But once you get past those, you can grow infinitely. You can have whatever title you want (again, you’re creating the rules). You can make unlimited amounts of money, you can work with unlimited amounts of clients, and you can write unlimited amounts of books or courses. You can collaborate with other people unlimited times. You can do whatever you want, because there won’t be a ceiling. There won’t be a boss standing over you saying, “well you are really fantastic, but you’re always going to be second in command. PS give me some of your money.”  Nope. None of that. Just open skies and unlimited paths and lots of fulfillment.


This definitely gets placed on the back-burner in people’s lives. Since I’ve moved, my diet has taken a plunge for the absolute worst. I actually had wine and popcorn for dinner, tonight. Mentally? I’m a hot mess. I wake up angry, because I’m dreading driving for forty minutes in bad traffic to get to work and deal with sexist comments and annoying clients. I spend all day stressed that I’m not working on The Crown Fox related things. Then I get home, and I’m stressed because it’s already 6:00pm and I want to go to the gym, but I also know I need to see my boyfriend a little bit or he’ll feel neglected, but I also need to write a blog post or do client work.

So I’m not saying that to make you pity me, I’m saying it because when we aren’t doing what we love, when we are trying to “do it all” it negatively affects our bodies and our brains.

I know, know, know, when I make that jump to full time freelancing one of the first things I’ll do is make time for the gym again. Want to know why I know that? Because I’ll be determining my schedule. I won’t be regulated by some “9-5” mentality, where I really spend TEN HOURS of a day (including commute) doing something I hate.

I know there are full time freelancers/entrepreneurs who still sacrifice their health for their work. I know that’s not a struggle that is limited to 9-5-ers. I think everyone, myself included, should pay way more attention to his or her health. For me, that transition into being a full time freelancer will allow me to make those adjustments and treat my body and brain better.


These points might seem kind of silly, but I think about these everyday I’m at work. You know what you get to control when you are a freelancer? The thermostat. The music. Lunch time. Break times. Doctor appointment times. Seeing your family on the holidays time.

I live in Florida currently, where the days average about 85 degrees still (this is Fall, here) but when I get to work do you know how cold it is? Cold enough that I wear long sleeves AND a jacket. And God forbid if I forget the jacket. Do you know what my coworker does? She plays scream-o, circa 2006, without headphones. Loud. Do you know what happens if I have a doctors appointment? I have to make up the time and stay late.

I KNOW. I KNOW I SOUND LIKE A BRAT. I know my parents had to work late for doctor’s appointments their whole lives. I KNOW. But I also know that it DOESN’T HAVE TO BE LIKE THAT. It doesn’t. Plain and simple. I can be successful and work from my home, or my own office space. I can be in control of the thermostat. And I can give myself an hour break in the middle of the day to go to the doctor. I don’t have to live the “expected” way, filled with misery, 5 o’clock road rage, and crappy scream-o music.  There’s a light at the end of that tunnel, and it’s called freelancing.


I hope this motivated you to make moves in your life. Writing it out motivated me even more than I already was. If you ever want to talk about these sorts of things, I’m open ears! #BizTherapy

Happy Monday (I just realized this post was #MotivationMonday!) and Happy November, y’all! 


I’m Kaitlyn, your design assistant! I work with successful creative entrepreneurs to create cohesive, clean, and compelling visuals for their businesses. You can keep being the #girlboss you are (but with more time to focus on growing your empire)! Let's set up a time to chat!