Real Talk Part 2: Realities of Freelance

Thank you so much for your all of your great follow up questions from the our previous post on freelancing. Hopefully part two answers any lingering questions you might have. As always the conversation continues because there is no one, best answer. At the end of the day trust your gut and do what feels best for you. And keep your questions coming, if you like this content we are happy to keep it going.

Does blogging get lonely? (continued)

J: I was in a little bit of a silo when I first moved home, because I was in Rhode Island which isn’t full of a ton of bloggers. There wasn’t any sort of existing community and I was way too shy to reach out to anyone. Now I have a group of girls I consider true friends that also happen to be bloggers. It has made it more fun for me.

C: I think it ends up being more collaborative and creative.

J: It’s so important to have people to talk to who are doing what you’re doing and understand what you’re going through. People to bounce ideas off of, or ask questions.

C: You can’t exist in a vacuum. You need the perspective and I think it’s helpful to talk to other women about money and rates, obviously in a tactful way. The more you talk about it the more empowered you are to push for what you’re worth. Not talking about it keeps your earning potential a lot lower.

J: It’s hard because we’re raised with the idea that you shouldn’t talk about money, and you still have to be smart about it. There is so much gray area in this business, talking to people about what to charge for things is just good business.

How do you do the work and keep growing your business simultaneously?

C: It’s really hard to do the work that needs to be done and keep growing, but it’s a juggling act. When you get into the right rhythm it’s great. Some days you’re just trying to do what needs to be done. It’s hard to think into the future on those days, but you need to constantly be reaching out.

J: That is a constant struggle. It’s always going to be top of mind. Even when you’re busier than you’ve ever been, there’s always this little voice.

C: I think they call that self-doubt?

J: Do I have enough planned? Is there enough in the pipeline? Some of it is self-doubt and you need to find ways to deal with it.

C: I think you just have to do it. When I first started freelancing I was so afraid to reach out to people because I thought why would they want to hear from me? And you just have to get over it. I’m not saying mass email people but take the time to reach out to people you genuinely want to work with. Don’t be afraid. The worst thing they could say is no which is not that bad. It’s like a muscle, it develops the more you use it and it gets easier.


J: If you’re starting your own business, you don’t want to do more than what you can do well. I’m not saying undercharge, but know your worth. If you’re first starting out you’re going to have to pay your dues. I did so much stuff for free when I got started because I was trying to build a portfolio and show people what I could do.

C: Value isn’t just monetary. Here are the questions  I like to ask myself about any project I take on. Do I feel passionate about this brand or magazine or website? Is it going to add value to my portfolio? Is this something I’ve been wanting to do? Is this something that would challenge me? You have to do that because there is no one else who is going to challenge you. You have to push yourself.

JAK: The flip side is, as you grow, knowing when to say no. There are going to be people who come to you with something that seems really appealing and you have to think about whether or not it’s right for your brand. Does this fit me and who I am? People pay attention to that.

CH: You have to be genuine in the partnerships you form. It’s tempting to jump at a paycheck, you’ll end up regretting it.

JAK: You never want to think halfway through the project that you wish you never agreed to it. We’ve all been there, you live and you learn.

How do you approach brands and get them to work with you?

C: I would say first of all you need to have a nice body of work to point to. Basically be in a place in your career where you can show them the work you’ve done. Some of my all-time favorite branded content clients have hired me off of a cold email. I had reached out because I love the company, wanted to work with them, and had an idea of how I could help out. Be creative and specific in your pitch and know about the company. Don’t mass email, it’s always obvious.

J: Exactly. It’s also about building relationships, but to your point, be specific. Tell the brand why you want to work with them, share some ideas you have, and be genuine in your approach. See more of my advice on working with brands here (I think this applies to many freelance jobs not just blogging).

If I am not in a creative field, how should I market myself to creatives?

C: Any person who is in a creative field always needs great people to help keep everything running smoothly, whether it’s IT or accounting. I’m always drawn to people who have personality, while still being on top of everything. I really appreciate people who don’t make me feel like an idiot for not knowing what they know. I want someone who takes the time to explain things in a language I can understand and who doesn’t seem stuffy and unapproachable.

J: That’s exactly why I like my accountant and financial advisor so much. Not only because they both answer all of my questions but they explains things to me in a way I can understand. There is never a dumb question, even though I am sure I’ve asked a few.

C: In our defense, no one teaches this stuff.

J: And I feel like trust is huge too. Especially when it comes to your finances.

C: You definitely need to know you have someone working with you who will do right by you.

Have a good grasp on your finances.

J: I can’t stress enough, the importance of knowing and being aware of your finances. There will be times when it takes forever to get paid. Sometimes it’s fast, other times it’s months.

C: If you are considering going freelance have some savings, it helps when you’re not worried about living paycheck to paycheck waiting for payment to come through.

J: Give yourself at least a couple months cushion so you’re covered.

A few points on the importance of being resourceful:

C: It’s always great to talk to people you know and trust about dilemmas you might be facing, and have mentors. I think it’s also important to do your own due diligence. So much info is out there. You can do so much on your own. Don’t make yourself look like a total newbie by reaching out to someone you admire and asking a question you could have easily Googled yourself. It’s not a good look. It makes you look unmotivated.

J: The over arching point of that is, you’ve got to get your hands dirty. Some of it won’t be handed to you on a silver platter. Do your research first, then you can approach someone with questions.

C: There are so many things I learned by simply doing them and figuring it out. And sometimes that’s the best way.

How do you handle scheduling? How do you structure your day?

J: I’m the worst. That’s something where you need to know your strengths and weaknesses. I’m super ADD and I’m really bad at sticking to a schedule. I’m a work in progress.

C: You are the Google calendar queen though; I bow down to your calendar scheduling skills.

J: I calendar everything. It’s all in there. I have to do that because otherwise I’ll forget. I’m very visual. I have to see everything laid out. I want to see how everything fits together. Plus if you have to travel for work you have to be so careful with your time. Plus I try to schedule so I’m not working 24/7. That is consistently one of my biggest challenges. Especially when you work for yourself and work from home.

C: Let’s talk about this because I think there is a big misconception about working from home. Yes it’s great sometimes, it’s convenient with no commute time. I think people think that you’re working less because you’re home but I work longer hours now than I ever did when I was in an office.

J: It’s a give and take. I work more now too now that I am working for myself. But it’s way more rewarding too.  I like what I’m doing and it doesn’t feel like work.

C: Oh yea I turned my hobbies into my job.

J: But you have to make time for other things like your health and your relationships/friendships. It’s so easy to get on the computer at 7AM and still be on at 10PM. But it ultimately hinders your creativity. It’s not good for your relationships. So that’s why, to bring it back to where we started, it’s important to have a schedule.

C: I think you need to be patient with yourself too though. I had a lot harder of a time being disciplined when I first got started. But it quickly becomes apparent that if you’re not working you’re not making money. You’ve got to put the hours in. It gets easier and easier to sit down and do what you need to do. Once you get some wins, it helps too. There are weeks where I look forward to Monday because I’m waiting to hear back from someone I’ve pitched, it’s exciting.

J: Give yourself time off too.

C: I’m so bad at that.

J: We may be the two worst people to ask about this.

C: Do as we say not as we do.

How do you handle social media overload/or feeling inadequate?

C: I take a step back and remind myself that you never know what is going on behind an image. A photoshoot is like open heart surgery with one little pretty piece in there. If you could see what it looks like outside the camera frame it’s anything but glamorous. I’ve been living by this motto: stay in your lane. I’m going to do what I do and do the best I can, and not be looking around at everyone else. Tune out the noise.

J: I have this convo all the time with blogger friends of mine. Especially in blogging because it seems like everyone’s life is on display. You never know how someone got that collaboration or that trip. You never know what that person is going through at home. It’s a complete waste of time to sit around worrying about what someone else is doing or what they have and compare it to your situation.

C: I think it’s human nature, but to focus on it too much is detrimental and unnecessary. When you embrace talent and surround yourself with talented people you become better. I have a cheering squad (full of people who do what I do) who see the greatness in me in even when I don’t.

J: Be that for someone else too. When you have people like that, and you can be that for someone else, it makes you feel good.

C:  People don’t tell people enough that we like something they did. And I like to try to take the time to do that.

J: You never realize how much that means to a person.

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  1. Julie wrote:

    Great stuff girls, thank you! Nice to learn from successful girls who are far more ahead than you are. I am struggling to find fellow bloggers of my age or who aren’t too stuck up that they don’t mind welcoming in their group a tiny blogger. I don’t know if it’s a big city thing (I live in London – UK) or maybe that’s because I am so tied up with my 3 little ones I am struggling to be available enough. I would love to hear how you reach out to other bloggers to create that nice little community you are both talking about? Julie

    4.27.17 | Reply
    • Caylin Harris wrote:

      Thanks so much Julie! Honestly I think it takes time. Try to let it happen organically and connect with people through work events that you’re able to make it to or projects you’re working on. It never hurts to reach out and ask to take someone to coffee either! Stay open and keep trying, you’ll find your people.

      4.27.17 | Reply
  2. Maggi wrote:

    I love these posts so much. I was wondering if you had any ideas for connecting with other bloggers since I am from a small town in the middle of nowhere. I do not have the ability to go to partys or such in big cities. Thanks!

    4.27.17 | Reply
    • Caylin Harris wrote:

      Thanks for reading Maggi! Use technology to your advantage. Just think, if you feel disconnected there are other bloggers out there too who aren’t in big cities. Form a secret group on Facebook to connect with people or try setting up phone calls. You’d be surprised who would be interested.

      4.27.17 | Reply
      • Maggi wrote:

        Thank you for the great ideas!

        4.27.17 | Reply
  3. Michelle Johnson wrote:

    I love when you do these type of posts! So informative!

    4.27.17 | Reply
    • Caylin Harris wrote:

      Thanks for reading Michelle!

      4.27.17 | Reply
  4. Beverly wrote:

    Loved this so much!! Thanks for answering all those questions!!

    4.28.17 | Reply
    • Caylin Harris wrote:

      You’re so welcome Beverly! Thanks for reading. xx

      4.28.17 | Reply
  5. Caitlin wrote:

    Ahhhh okay I really enjoyed reading this! You two are both super talented and I love following you. I’ve been blogging for a while now and for so long I was afraid to put myself out there. Once you do, and your patient, it’s amazing how the opportunities come.

    Keep inspiring! Also, your photography / videography is absolutely stunning. I got into photography last summer and I constantly look at your photos for inspiration.


    4.28.17 | Reply
    • Caylin Harris wrote:

      Cait so glad you enjoyed this. Exciting to hear that opportunities abound for you! Thank you ever so much for your kind words. They mean a lot! xx

      4.28.17 | Reply
    • Jessica wrote:

      You’re totally right Cait, a lot of it is patience and persistence. And thank you so much really appreciate the compliment. xx

      5.2.17 | Reply
  6. Abby Walker wrote:

    This is my first visit to your site (I followed the link from Lemon Stripes’ “Life Lately” post), and I’m so glad I did. Your “Real Talk” posts are just that, real, and motivating. I’ve been struggling to give myself the kick in the butt I need to follow my passion of baking, and somehow mix it with my other passion of writing (gotta use those two English degrees somehow!), and these honest posts have helped move me forward. It’s a little scary at 35-years-old, married, and with a toddler, but scary doesn’t make it impossible. Love your brand, and I’m definitely a regular reader now.

    4.28.17 | Reply
    • Jessica wrote:

      Hi Abby! I’m so glad you found us. So great to hear this post gave you a little motivation. It’s so hard to challenge ourselves and get out of our comfort zones but so important to pursue the things that make us happy! Happy to have you. xx

      5.2.17 | Reply

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