Real Talk: How to Decide When You’re Ready for Freelance Life

There are a lot of misconceptions about working for yourself. From the outside looking in, working in your pjs and taking calls from the couch may seem like a walk in the park—the truth is freelance is anything but easy. We wanted to share some of the basics about freelancing in a creative field. Rather than just list out a bunch of bullet points, we decided to share a more conversational format based on our personal experiences. Turns out there’s a lot to say so we split this up into two posts. Keep an eye out for the second half next week. And please feel free to share any follow-up questions in the comments.

When did you know you wanted to work for yourself?

Jess: I never really wanted to work for myself; my goal coming out of college was to have health insurance and a nine to five. Having that and getting the promotions and pay raises still didn’t make me happy. I kept thinking about where I wanted to be later in life. I knew I didn’t want to be doing the same thing, so I sat down and thought about what I needed to do to change that.

Caylin: For me, I got to a point in my magazine career where I was looking at what the goal was and realizing it wasn’t what I wanted anymore. I didn’t want to be the editor in chief of a magazine. My life didn’t feel right. I was doing everything I thought I should be doing and it wasn’t making me happy. I wanted to push myself a little bit more.

J: I think that is a big part of it too. You kind of have to scare the shit out of yourself.

C: When I first went freelance I kept rereading this quote: Leap and the net will appear and it’s so true. I didn’t have any success until I dove in headfirst. Which is scary but at least you’re moving in the right direction.

J: Obviously I started my blog not really thinking that it was going to be my next career move. Once I started, I realized that maybe it was something I could do but it wasn’t until I quit my job and started doing it full time that I felt like….

C: Things started happening?

J: Exactly.

Jess Ann Kirby grabs a coffee at Bolt Coffee Co in Providence Rhode Island

Is there a financial goal you should hit before going freelance?

J: I think I kind of jumped the gun, but it was because it was such a bad time in my work environment. They were doing layoffs and everyone was miserable and tense. I felt like I couldn’t take another day of it. That said, I didn’t have a good plan in place. I had some money saved, and we had moved to a cheaper place, but I didn’t sit down and make a plan. Then the reality hit of the paycheck being gone and the health insurance was gone. It’s like woah. What did I just do?

C: The funny thing for me was that I loved my job. But it was one of the only good things in my life at the time and I wasn’t OK with that. I kind of changed my job so I could change my life. I was commuting into the city, two hours each way. Losing all this time. Working really hard and loving it but had no quality of life. So I think for me it was a personal decision to go somewhere else and leverage my skills in this new place (RI) because I could no longer handle working in New York.

J: That’s so much of it too. Quality of life is everything. There were things I loved about my job and people I worked with. I felt like I couldn’t have the quality of life I wanted there.

Are there career skills you should develop before going out on your own?

C: Consider your skill set. I wouldn’t advise starting a freelance career right out of the gate. In the beginning of your career you establish relationships and develop your skills. And then you have a body of work to point to when you’re approaching clients.

J: I think that is a good point. I’ve been getting a lot of emails from people looking for internships, which I think is great and I applaud people for being proactive. I think you need to put yourself out there though, if you want to be in a creative field you need to stand out from the crowd. Show me your Instagram or Tumblr. Show your body of work beyond your resume. Think about how to showcase your work and do it better or differently than other people.

C: Something that I started doing once I went freelance was growing my skill set in less of a linear way. I took skills I was using as an editor and started developing each of them more. The more you can do the more valuable you are. Obviously you don’t want oversell or market yourself as something your not, but play to your strengths. Think about your business in a multidimensional way.

J: Yes to that. Know your strengths and stick to that. I see people sometimes trying to do too much and be everything. No one is good at everything. Don’t be afraid to find people who are really good at what they do and can help support you. And that goes for everything: from your accountant to collaborators. I knew I couldn’t do what you do so I was psyched when I found you. I recognize what I’m good at and what I’m not.

Does freelancing get lonely?

C: It’s important to have a community of people. There is a lot of fear and competition out there and there doesn’t need to be. We don’t all want to do the same things. We’re not all good at the same things. I love being able to promote other talented people in my own projects or interviews. It’s this symbiotic relationship where you’re working with really talented people who make you better.

J: And that goes for people who are doing the same thing too. It’s so important to have people you can talk to who understand what you’re going through. You need people to bounce ideas off and ask questions. It’s so important to find people who complement your strengths. And vise versa.

Check back next week for part two and please let us know any additional questions in the comments.

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  1. Emily wrote:

    I love this, its a nice laid-back yet honest way to discuss something that seems so interesting to me. Can’t wait for part 2.

    4.18.17 | Reply
    • Jessica wrote:

      Thanks Emily, so glad you liked it. xx

      4.18.17 | Reply
  2. MacKenzie Stevenson wrote:

    This post couldn’t have come at a better time! I’ve been thinking more and more about my future and what it looks like and I don’t think it’s in the corporate world.

    I’m already taking notes from both of your experiences! Excited for part 2!


    4.18.17 | Reply
    • Jessica wrote:

      That’s so great to hear, so glad you liked it MacKenzie. xx

      4.18.17 | Reply
  3. Beverly wrote:

    This blog post came at such a good time! I have decided to go freelance in September and I am so scared and then I saw this! What great timing!! I honestly can’t wait for the second post!! A question I have is how do you get clients or brands to work with?


    4.20.17 | Reply
  4. Beverly wrote:

    P.s, can you guys please address confidence when becoming a freelancer. Thanks!

    4.20.17 | Reply
    • Jessica wrote:

      Hi Beverly,

      Thanks for your comment. Can you expand on that? xx Jess

      4.22.17 | Reply
      • Beverly wrote:

        Thank for the response! What I meant was, how do you approach brands with confidence and know how to negotiate with them. Also, how get brands to work with you? I hope that made sense!

        4.24.17 | Reply
  5. Somia wrote:

    Really Nice post! I am not yet in freelancing or something but its really helped me because gonna start things like this. anyways waiting for the part 2!

    4.26.17 | Reply

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