Kelsey Cronkhite

Kelsey Cronkhite is the Creative Director of Pinegate Road, a design firm that she established in 2011 to build brand foundations for creative businesses. At Pinegate Road, Kelsey works with clients to find their core values and turn them into inspired designs and lettering. When Kelsey is not designing and managing her team you can find her on The Pinegate Road podcast chatting about the creative journey. And as luck would have it, just last week she interviewed Jess Levitz, Freelance Wisdom's founder!

Thank you Kelsey, for sharing your insight, positive vibes, and valuable resources with us today!

Kelsey Cronkhite | Freelance Wisdom

Tell me about your path to becoming a freelance designer.

I became an accidental freelance designer in grad school at SCAD in Savannah, GA. I was thrown into this world of design theory, and wasn’t doing much actual design practice. While I was spending most of my time reading and writing, as a designer, I was missing that tangible creative work. Because of this, I started my now business, Pinegate Road. It started as a personal blog where everything was a huge mess. It was just my fun place for creativity and exploration. This was back in 2011 where blogs were just becoming a bigger part of design culture, and there wasn’t much pressure to create wonderful content. Having a post with a picture of a fun dress and saying “I like this dress” was really enough to get by as good content back then. Hah! Anyways, as I started this blog, I was putting myself and my name out there more and more. Eventually, I got a few inquiries about blog design. I started doing blog design for other bloggers for about $300 a site. These were my first clients, and while I was drastically undercharging, I had so much fun building out blogs that matched these client’s personalities. Over the next two years, I honed in on my offerings, raised my prices, and by the time I graduated in 2013, I essentially had a full-blown design studio that I was running in my spare time. After graduating, I took a job in Cleveland, OH at American Greetings where I worked as a stationery designer for three years. It was an amazing job, and one that I didn’t think I would leave for quite a while. All along, I was running Pinegate Road, and I had a steady flow of clients coming in. Sometimes I would tell myself that it was too much, and that I needed to give up something, but then another fun client would come in and I would keep on going! It was pretty much insanity, but an insanity I am so thankful I kept up with. This past year, I was diagnosed with endometriosis. When this happened, it put me into a pretty devastating place, and I knew that my body couldn’t keep up with the pace I was working at. I decided to leave my job, and focus on Pinegate Road full-time. Because I had been saving and making money on the side all-along, I knew I would be OK taking the leap. It was coming face-to-face with this disease that forced me to take the step back and make the choice for my future health and the life I wanted to live. If you’re struggling with health issues, or wanting to know step by step how I made this decision, I go over this in-depth in the third episode of my podcast, The Pinegate Road Podcast.
Kelsey Cronkhite | Freelance Wisdom

In the beginning, how did you attract your first good clients?

Not having my freelance business be my sole financial backbone certainly made this easier! Freelance money was my side money, so I was able to only take on clients that I felt aligned with my values. While not everyone was the most perfect fit, I think this is really something that you figure out the more you try. Now, I’m thankful to have built my portfolio with clients that were dream clients while working on the side. This is helping me continue to get those dreamy clients while Pinegate Road is my sole income. I also think that going to conferences and collaborating with people in your industry (or slightly outside your industry) is key! When you meet people in person, they are much more likely to want to connect with and hire you before they go to someone they don’t know. While I’ve always genuinely gone to conferences to learn and meet new people and to be inspired, this weird side thing happens where you get to know people who have all these amazing skills. It’s only natural to collaborate and hire from these new found friends. I’ve been both on the receiving end of being hired from people I’ve met at live events, and also have hired people I’ve met. You get to that next level of trust when you can talk and meet someone in real life. Can you tell I’m a huge proponent of going to conferences? :)

 "Going to conferences and collaborating with people in your industry (or slightly outside your industry) is key! When you meet people in person, they are much more likely to want to connect with and hire you before they go to someone they don’t know."

Kelsey Cronkhite | Freelance Wisdom

Do you have any tips for being your most productive?

At first, when you’re working all alone and trying to make this big dreamy business come to life, your schedule is going to be your best friend. Here is the crazy schedule that I put myself through for a couple of years while I was running Pinegate Road and working full-time. I think finding the time that you do have in your schedule to be productive and work on your business, and really getting to work when you have that time, was key when I was trying to build my business. Now, one of my favorite productivity hacks is working in pomodoros. I’m still in the early stages of working for myself (three months in), so I’m in that stage where working from my couch in my pajamas is my everyday reality. Some days it makes me feel super productive, and other days I feel the laziest. As long as I’m not getting behind on deadlines, and I’m keeping my future goals rolling, I don’t feel bad about not being the most productive every day at this point. I’m giving myself some grace as I transition. I know that I have the tendency to over-work, and that only leads to burnout. I don’t want to go through that or deal with the kind of health issues I experienced before.

What has been your greatest struggle as a freelancer so far?

Getting dressed. Hah! But seriously. That’s been a hard one for me ;) Guys, I’m honestly still in the honeymoon stage with this all. Every day I’m grateful that I am able to make my own schedule, and that I am able to live life on my own terms for the first time. It’s seriously incredible. I have a feeling that I will eventually have struggles with budgeting, and if everything goes as planned in my personal life, juggling a kiddo in the next year or so. Oh, and I hate forms and technical things. That is probably terrible to say as a person making their living on the internet, but it’s the truth. Thank goodness for amazing team members who help me out!
Kelsey Cronkhite | Freelance Wisdom
Kelsey Cronkhite | Freelance Wisdom

Pinegate Road is a team and you are the Creative Director, can you tell us about your decision to bring on employees/collaborators?

YES! At first I started bringing on contract designers while I was working my full-time job. I wasn’t able to keep up with the demand of work that Pinegate Road had, and I wasn’t wanting to turn work down. I knew the only way to keep growing while running my business was to hire out the design work, and act as the creative director for projects. This was so hard, but a huge leap for my business. I was able to contract out work to two designers, and they helped with projects throughout the last couple years. At the same time, I started changing directions from pure logo design to more holistic branding solutions — going into the brand strategy, business planning, identity design, and web design for creative businesses ready to take that next big leap in their businesses. With this, I was now bringing in experts in web development, copywriting, and photography to make sure that Pinegate Road clients were getting the best experience and brands built for them. Since my leap to full-time freelance, I have been handling all the design work for the past couple months, and I have hired a virtual assistant who now runs my podcast. We started off with 20 hours per month, and are now expanding to 50 hours per month with new duties. She’s amazing! I’m launching a new site for Pinegate, as well as a new business plan and strategy that she is helping me implement. There are a lot of changes happening now that I’m able to devote myself to my business 100%, and having her has been helping me not get so stuck in the details and the busy work. She also has amazing insights into growing a business, and knows more technical aspects than I do. She helps me through so much, and is a huge asset to our team. Hi Sarah!! :)

Do you have any advice for handling communication as a Creative Director?

If you have a regular assistant like I do, scheduling a weekly meeting to go over all tasks is very helpful. We meet every Thursday morning via skype, and go over all of our to-do’s for the week and brainstorm new ways to better our systems. If you’re working with contractors like I do often for other projects, making sure that you have a clear procedure set up before you start is key. Having this is essential to know what each of you should expect from the other. I also use asana to keep all tasks for both my VA and my contractors up to date with deadlines, expectations, files, and general conversation. I work a little differently with each of my contractors. Some I’m on texting relationships with, and that works best, and others email back and forth. I’m sure as things grow further, these communication efforts will need to be systematized, but for now it’s working a little differently for each person. Google drive is great for documents and folders of any work that needs to be transferred from person to person. We can even link those folders up in asana, which keeps everything in one place for people to access as needed.
Kelsey Cronkhite | Freelance Wisdom

What is your favorite thing about working as a team?

I love being able to have a second opinion, and to know that someone has my back if I’m doing something crazy. Especially with my VA, and the next new steps for Pinegate, we’ve been brainstorming different ways to make certain things happen. She’ll often have great ideas that I would never have thought of on how to go about a certain process, or knows a cool way to make something look even better or work better than I could ever dream up. Knowing that you don’t have to do it all yourself is a huge relief. I also love hiring contractors that have exceptional skills — they bring the best to the table, and I love that they can focus on their expertise without having to deal with the project management side of things. I secretly love being a little bossy too, so when I work as a project manager, I feel like I’m working in my element as well ;) I’ll always be doing some design, because that’s my true passion, but knowing that my business can keep growing and moving along even when I’m sick or want to take a vacation is priceless.

How do you continue to attract your ideal clients?

I think this goes back to making connections with people you LOVE being around. This means going to conferences, sharing your passions, sharing your voice, so people can hear you and say ‘ME TOO’ to what you’re putting out there. I’ve met future clients on Instagram, through Pinterest, in person, and through referrals. It’s all about consistently putting your best work out there, and giving more than you’re taking. I’ve always been a cheerleader of people following their passions, and now I get to do that through my business. The more I cheer, help, and empower, the more clients I seem to get that are aligned with that vision as well. I get so awkwardly attached to my clients and their vision. I think putting that heart and soul into the work and process shows, and that propels more of the same to keep coming at you.
Kelsey Cronkhite | Freelance Wisdom

"The more I cheer, help, and empower, the more clients I seem to get that are aligned with that vision as well."

Do you have any tips for dealing with the nitty-gritty business details? 

Freshbooks! That seriously changed my money game! I send that to my accountant each year, and they are able to do my taxes from that. Also, seeing my money come and go, and being able to invoice so easily keeps me on track. At first, I was hand-designing all my invoices (I know guys!!!). That was frustrating, took way too much time, and I probably forgot to invoice half of my clients because I wasn’t keeping track of all that was going on. Freshbooks made it 100% easier to keep on top of everything, and it makes you look really professional as a business owner. I also have hired an accountant for the past couple years. I don’t get taxes and all things that have to do with forms (gah, I’m the worst!). So giving this all to someone who knows what they are doing saves me so much head space come March and April. As for contracts, I’m still doing these all by hand in illustrator. I love making them look pretty, and due to the custom nature of our work, this is best done that way for now. Other systems I love using are Evernote for personal note taking and for those moments when I have all those business ideas or thoughts about something and I want to get it all out of my head. I use Google Drive for collaborating with clients and with contractors. Asana is my go-to project management tool for collaborating with my VA, and for writing out tasks for myself. Also, I have recently begun bullet journaling, and I’ve been loving that for keeping track of my daily to-do’s

Since you are your own boss, do you have any advice for maintaining a work-life balance?

Finding my personal and business values was a HUGE first step in making that balance somewhat a reality. I don’t believe in a true balance, but I believe in a more balanced ebb and flow. When I realized that one of my core values was friends and family, that let me know that I absolutely needed to keep room in my schedule for making that a priority. Even when I was working full-time and running Pinegate Road, I still kept the majority of my weekends free to spend time with friends and family. Things were crazy, but I was able to make it happen even during the most stressful times. Now that I’m working for myself, I still keep my core values at the top of my mind, and make sure that I’m filling each of those buckets up in little ways throughout the week. There will certainly be days or weeks where things aren’t ideal — that’s life — but if you find your core values and make them a priority, you’ll find more and more of that balance as you go through running your own business. This is totally a shout out — hah! — but if anyone is interested in finding their own core values, I’m going to have a free course on Pinegate Road that goes over what they are, how you can find them for your life and business, and how you can start using them in your life and business to get to reach your dream future. Going through these exercises has been the biggest thing in me reaching my happy life right now, and so many people ask me about finding them and keeping them a priority in their life and business. I wanted to put this out there so I could stop talking about it all the time like a weirdo, and actually help people work through the process! If you sign up for my newsletter now, I’ll send you more info when that launches. If you’re reading this after December 2016, just head to Pinegate Road, and sign up on the homepage! If you’re not into taking a course, I would suggest doing a lot of free-writing and figuring out what themes come up that make you feel joy. When you do that and notice it, you’re heading in the right direction :)

"If you find your core values and make them a priority, you’ll find more and more of that balance as you go through running your own business."


The 3 greatest attributes you need to be a freelance creative are:

curiosity, persistence, optimism

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