Side Hustle Story: Kelsey Cronkhite of Pinegate Road

I'm so excited to share another Side Hustle Story with you!

This time, we're talking with Kelsey Cronkhite, the Owner and Creative Director at Pinegate Road! 

If you aren't following Kelsey on Instagram already, do it now and get ready for some seriously inspiration. Her brand is consistent, her design is killer, and she's even nicer than I imagined! 

Keep reading to learn about how Kelsey manages a successful business while working a full-time job, her favorite tools and resources, and her biggest piece of advice for other Side Hustlers! 

Tell us about your business, what you do, and how you got started.

Pinegate Road is a brand visioning studio for creative makers and shakers. We help businesses define their core values and live these out through all of their business touch-points. This usually includes identity design, web design, and any other design that the brand showcases visually. I love starting from the foundation, and building from there to create a solid brand experience for my clients so that they are putting their best foot forward.

I started with Pinegate Road when I was in grad school studying at the Savannah College of Art and Design. I needed an outlet from my studies, so I started a blog to catalogue...well, anything! It was a mess :) Over the years, I started honing in on what Pinegate Road was, and slowly started to find my own brand vision. I gathered clients along the way and helped them with one-off projects throughout the years. I eventually landed on focusing on hand-lettering and branding, and now this is leaning more to the holistic brand experience with why we're calling — brand visioning. 


Tell us about your full-time job. Is it related to your side hustle?

Yes, and no! I work full-time at American Greetings as a stationery and sticker designer in the surface design studio. I love being able to work with clients like Target to carry out their strategies through our work. Things are in constant flux around work, and I'm happy that I'm able to have my hands in lots of different projects, even beyond stationery. Occasionally I'll freelance hand-lettering for other departments, and it's so fun to find the lettering I'm doing pop up on cards around the country! My job is definitely related to Pinegate Road in the fact that it is 'graphic design,' but my day-to-day duties are very different. I try to add in as much branding and strategy as I can into my day-job, and I'm lucky that my position is open enough for me to do that occasionally.


What does your typical day look like for you? 

Please see here! ;) It's a little crazy, but I've been able to keep this schedule up for several months now and it seems to be going well! Before I made this, I felt like I was constantly going to drop the ball. Now, I have some structure and am much better at planning out how and when I can have deliverables to clients. 


How do you find time (and energy!) to work on your business?

I honestly love it! I love hearing from clients telling me how working with me has helped them grow their businesses, and I love being a part of their stories. That kind of stuff keeps me going. If you read through my schedule, I take the time to recharge on the weekends. This makes all the difference. I tried the working-all-the-time thing, and I burn out. That's not good for me, or my clients. If I don't schedule time off, it won't happen.  With my full-time work, I know that financially I can take the time off when needed. I'm lucky to only take on projects that I'm passionate about, and that passion keeps me so energized!


How long did it take your side hustle to be profitable? 

I never meant for my side hustle to be honestly! I was blogging as an outlet for at least a year before anyone contacted me to do any work. Being in the graphic design field, there is not much overhead. I've gained more in the recent months with accounting software, subscription products, and new designers. I'd say it was about a year before I started to make some extra money — I started in 2011 — and only in the past two years that the extra income became significant enough to really make a difference in my life.


What have been some of your greatest challenges and how did you overcome them?

Saying no has been my biggest challenge. I get so excited over everyone's dreams, and I have a hard time not wanting to help people reach them! For about two years I had been complaining to my family about my lack of time to do ANYTHING. I wasn't working out, I wasn't eating healthy, and I was never taking time for myself. My dad suggested hiring a designer to help out with my work. I finally took the advice a couple months ago, and it has been life-changing! Before, I felt like it took me for forever to get my clients what they needed, and now it's getting done in half the time. Having my full-time job allows me not to worry about this expense, and lets me still work with the clients I hope to help even when I do need some time off. Doing this has taught me that I love doing more big-picture thinking and strategy, which has lead to Pinegate Road's new focus in brand visioning. Amazing what a little delegation can do. 


What is your favorite part of your business? Least favorite?

My favorite part of my business is completing each project and seeing how our clients build their brands from there. I've been so lucky to work with clients who really get design and have awesome visions for their businesses. They keep their brands going beautifully after we work together, which makes me all sorts of happy to see. My least favorite part would be the logistics. Emailing, budgeting, organizing...I don't love it. For now, it's a necessity!


Have you hired any one to help you in your business (i.e., Business Coach, Virtual Assistant, etc.)?

Absolutely! I have two designers that work with Pinegate Road to pick up client work as needed. I also invest in several online courses and conferences to keep up to date with what is going on in my field, to stay inspired, and to meet others that are going through similar journeys. I'd say 50% of my clients have come from networking through classes and conferences as well. That is not why I am doing these at all, but it's always so cool when that happens! This past year I have taken Be Free Lance, Instagram with Intention, Life with Intention Online, and the Braid Method E-Course. I definitely count these as 'hiring help' :) Don't even get me started on the personal development books...


How do you stay organized? Any tools or resources you couldn't live without?

Ahhh, I need to get better with everything organizational! I live by my day designer. I'll be going on my fourth one this year! I don't think I'll ever get used to keeping a calendar digitally....except...I keep an ical with my boyfriend to plan out dates we need to know about throughout the year. We keep pretty busy on the weekends, and it's nice to keep that digitally so we can both update and have that available when either of us is scheduling anything while the other is away. I've been working with google docs and sheets with a client lately, and that has been such a huge help keeping all of our thoughts and needs in one place. I use freshbooks for accounting, and that has been a lifesaver! I love being able to send clients invoices easily and it gives them a way to pay online. Before, I was designing individual PDF's for EVERY invoice. It became too much. Now, I kind of enjoy accounting, which is super weird for me to say!


Any advice for other Side Hustlers trying to build a profitable business?

I'd say to not worry too much about the profits at first! Take some time to figure out what really makes you happy, and grow from there. I have never had the most solid plan with my business, but being open to experimentation and evaluating what is working and not working for me has lead Pinegate Road to a pretty awesome spot. When you are trying anything new out, strategize a process first though. Having a step-by-step procedure for how clients work with you will be so helpful for you and them! I never started with this, and that is one of those live and learn things that I can tell now makes all the difference.


Where can we find you online (i.e., website, social media profiles, etc.)?

Studio + Blog:


Megan Minns

Business Strategist for Side Hustlers