Of course, I love sharing all of my very best tips and tricks with you when it comes to design, branding, social media and basically all things that could be summarized as “the day in the life of a creative entrepreneur.”

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But, I know that one of the most challenging parts of being your own boss and serving people with your gifts is simply getting started. That’s why I jumped at the chance to be interviewed my newest internet friend, AnnMarie Rose. AnnMarie is a content creator and the host of a new podcast (like, so new that this post is going out before the show is even available on iTunes) called Inspired to Impact. Her show is all about pulling back the curtain on exactly how thought-leaders, influencers and entrepreneurs got their start.

This is a topic that not too many people talk about — maybe because it’s just not that glamorous? When you’re starting a business, the beginning can be a little, well, messy. Decision-making can be confusing and moving past roadblocks isn’t always a piece of cake. That’s why AnnMarie gave me the thumbs up to share a sneak peak of our conversation in this post. She and I both believe it’s important to share our answers and experiences, so that more big-hearted creatives can get clear on what steps to take to become their own boss.

Check out our conversation to see how I decided to start serving the world in a bigger way with Jess Creatives. (My responses are below the bold questions. And be sure to check out the specific takeaways I’ve highlighted for you in italics under my responses.)

How to start your own business:

When did you know you wanted to be a designer?

When I was in high school, I knew I wanted to be a designer. I was one of the very first kids to take design classes at my high school, and up until that point I’d pretty much signed up for every art elective I could. Art was kind of my thing. But I always liked doing the practical design projects. In fact, Jess Creatives was sort of “born” out of a college project. As part of our senior portfolio, one of our assignments was to brand ourselves. So, for the most part, everyone else branded themselves —  but that’s when I created Jess Creatives.

If want to start your own thing, but you’re struggling to decide how you actually want to serve people, think back to your childhood — what was your “thing”? What were your favorite classes in school? What sort of things did you love doing for fun? The answers to these questions should give you inspiration to start exploring some options.

What made you actually “launch” Jess Creatives?

During my first year out of college, I was doing some design at my day job. After a while, though, I really wasn’t designing much at all — plus, I really wanted to be designing the stuff I wanted to design. At the time, I didn’t know a single person who did freelance work. To be honest, I didn’t really know it was a thing. But having Jess Creatives in the back of my mind made me want to put myself out there and start taking on some side projects. I remember one of the first things I did was sit down and create my Jess Creatives Twitter account. Oh and the first tweet…which went out to my, at the time, two followers…was announcing a big sale around the holidays. I had no clue what I was doing. And no one was interested in my big sale in case you were wondering.

Putting yourself out there can be a little nerve-racking. And chances are, it’s going to be a little clunky at first. But there aren’t too many risks when you just go for it. Hardly anyone will see you stumble, and you’ll forget your fears so much faster than if you just sat around thinking about starting and planning to take action.

How did you decide when to go full-time?

Eventually, I started to understand a little more about how this could actually be a business. Once I started to gain some momentum, I would get up early to work on my client projects before going to my day job. I was making good money but I was very hesitant to go full time. I just wasn’t sure that it would be a financially stable decision. There were even a solid three months when I was pretty miserable at my day job, and all I wanted to do was Jess Creatives full time. But I didn’t think I could. So I went on that way until finally, I got all of my financial information together and looked at the numbers — I was making as much, and sometimes more, with Jess Creatives versus my day job. I’d been making that much for a consecutive nine months. At that point I thought, “What am I doing? I can do this. I can go full time with Jess Creatives.”

It can be a lot less stressful to build your business a little bit at a time while you’ve still got a steady paycheck coming in. But if you’re doing well with your side hustle, you’ll probably hit a point when you’ve got to make some tough decisions about which work to prioritize. Look at the numbers. If  you love both your day job and your side hustle, maybe tweak some of your own business processes to save yourself time during the day. If you want to go full time with your business, allow those numbers to give you confidence in making that leap.

For you entrepreneurs, what’s the #1 challenge you faced when you first started? If you’re thinking of starting something of your own, what’s the #1 thing that’s stopping you?

Share in the comments below!

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