Jennifer Briggs

Jennifer Briggs is a member of our Creative Lady Directory and the owner and creative director of Nicole Designs a brand and web design studio focused on building stunning brand identities and websites to help female entrepreneurs launch their daydreams. We loved getting a chance to hear how her freelance journey has unfolded and how ultimately, her passions have inspired her business offerings.

Jennifer Briggs | Nicole Designs | Freelance Wisdom

Tell us about your path to becoming the creative director of your own brand and web design studio.

I started out working on designs for my friends. Once I realized I really enjoyed designing, I decided it may be time to start my business. At the beginning of my journey I offered wedding invitation design but realized I had more of a passion for branding and web design.

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

I used social media to attract my clients. I also joined a few different wedding groups and organizations to learn more about the wedding business. When my business began to focus more on branding and websites, I used social media faithfully to increase my reach and attract small businesses, mid-size businesses, and other creatives.

Jennifer Briggs | Dope Girl | Freelance Wisdom

How has your offering grown and changed since you started Nicole Designs?

My offerings have definitely grown. I began to realize how much of a passion I had for creating cohesion across social media. I started to offer social media curation and content creation services to help others create a well thought out and planned Instagram feed.

It looks like you launched Milk Marketing relatively recently. Can you tell us a bit about your inspiration and motivation to create this offering?

Milk Marketing is actually owned by another entrepreneur who really loved my design style. She was looking for a graphic designer who was local to Dallas. We worked so well together with one of her clients, she asked if I would like to be the Creative Director for her brand.

Jennifer Briggs | Milk Marketing | Freelance Wisdom
Jennifer Briggs | Milk Marketing | Freelance Wisdom

You have such a strong vision for both Nicole Designs and Milk Marketing. Do you have any tips to help our readers step more strongly and confidently into their own visions?

I definitely agree that it is so important to have a business strategy and then a social media strategy. Social media is where you can reach most of your audience. They want to see what you’re doing, what you’re working on, and how you can help them. It’s the best way to showcase your work and your passion and let people know who you are and understand your vision.

You offer many different services, do you have any tips for balancing your offerings and being your most productive?

I think it’s always important to strategize about your bandwidth for service offerings per month. For example, can you complete two websites in a month or just one? Can you complete one website project and one branding project? Can you do one of each per month? Whichever works best for you is the best way to stay balanced and be the most productive.

Jennifer Briggs | Live Your Purpose | Freelance Wisdom

What has been your greatest struggle as a creative business owner so far?

My biggest struggle has been trying to help everyone. Some clients are just not for my brand and that’s ok. There is someone out there for everyone.

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

I would say definitely have a CRM that can help you with bookkeeping and invoicing. Definitely hire an accountant for taxes and business filings, and a lawyer for contracts. Also, once your business grows, you may even have to hire an assistant. Don’t turn down help because you’ll never know when you’ll need an extra hand because being an entrepreneur is hard work.

Jennifer Briggs | Freelance Wisdom

What is one thing you wish you knew when you were starting out?

When I first started out I wish I knew how important it is to make sure you have balance. It’s really easy to get excited once your clients discover you and you want to help everyone. However, your work can suffer when you have too many clients with different needs and expectations.

How do you stay creatively inspired?

I stay creatively inspired through other designers. I love seeing really good design and it inspires me to create more. I also scroll through Pinterest and Dribble often.

Jennifer Briggs | Social Media Curation | Freelance Wisdom
Jennifer Briggs | Social Media Curation | Freelance Wisdom

Any music, podcast, or book recommendations that you'd like to share?

I definitely love Fiona Humberstone, her dedication to making brand design easy has helped me to make sure I outline my processes for clients and help them to understand the importance of having a good brand.

Anything else that you'd like to share?

Just be you. People will find you!

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

Patience, empathy, and strategy.

Jennifer Briggs | Just be you | Freelance Wisdom
Jennifer Briggs | Building Brands | Freelance Wisdom

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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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Liz Grant

This week we have the sincere pleasure of chatting with California-based graphic designer Liz Grant. Liz is passionate about creating thoughtful design that has a touch of simplicity and the unexpected. This passion comes through in her work and in the words she so kindly and openly shared with us. We recommend taking a break so you can sit down and soak in all this goodness. 


Tell me about your path to becoming a freelance graphic designer.

After graduating with my B.S. in Graphic Design, I first worked for a college in Washington as one of their in-house designers. At the time, I was long-distance dating my husband who was attending law school in California. Since long distance wasn’t ideal, I started looking for design jobs in California, and was hired by a software company as their designer. During the recession the software company did not have enough full-time work, so I was unexpectedly transitioned to part-time employment. That was when freelance sort of became an option more out of necessity than a deep desire. Now, I had of course done small projects here and there for people on the side, but nothing on a consistent basis. I began networking on social media, started collaborating more with other designers, and created an online portfolio. I found some amazing designers through twitter that had the same passion for design and started forming friendships and working relationships with them. By doing these simple things I started getting freelance work. I certainly didn’t go into the field of design with the intention of becoming a freelance designer, but I am so lucky life veered me in that direction because I truly love the work I do.  

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

Word of mouth. Referrals have been huge for me since the start. Doing good work for each and every client you have, no matter how big or small, is so important when running a small business. You never know who may be referred your way by past clients, so treating them well is crazy important. I also have had clients find me through Instagram, Twitter and even Pinterest. Social media is such a great tool for bringing in clients who connect with your work, value your aesthetic style, and want you as an individual because of what you personally bring to the table.
Liz Grant - Freelance Wisdom

"Doing good work for each and every client you have, no matter how big or small, is so important when running a small business. You never know who may be referred your way by past clients, so treating them well is crazy important."

Graphic Designer Liz Grant - Freelance Wisdom

Do you have any tips for being your most productive?

I really think it is vital to find when, how, and where your productivity and creativity is best fostered. Whether that be the time of the day or your environment, through trial and error, try to nail down what works best for you. Some feel creative in the wee hours of night, while others enjoy knocking out their work before the sun comes up and the day really begins. Some work best in shared office spaces with the energy that comes from being around others, while others prefer the quiet solitude of a personal home office. Find the best formula that breeds creativity and productivity.
For me personally, I have found that I work best in the mornings. Focus has to be one of the biggest keys to productivity. My mind is the most focused at the start of the day so that is when I work on items that need my creative attention the most. I like knowing I have gotten something done early on, just in case the rest of the day gets away from me. I usually try to tackle the most important items on my TeuxDeux list and do my best to try to avoid the productivity killer of social media. But as you all know, that is always a challenge. During those hours in the day where you know you aren’t the most creative, maybe prioritize admin items, and email responses. Don’t try to force creativity, let it come to you in an organic way. I try to make sure I allow for time to create an array of bad content, so that I am not stressed out and have time for that good content to come to fruition.
Graphic Design - Liz Grant - Freelance Wisdom
Liz Grant | Freelance Wisdom
After having a babe, I have had to be much more flexible with my ideal work time. I have just finally started to get back into a creative groove again after the transition of having a baby this past year, and I have rediscovered my productivity vibes in the early evening after he goes to bed as well. I am definitely not taking on the amount of projects, or working the amount of hours I use to. I do get some babysitting assistance from my in-laws, who we recently moved closer too. That time is limited, however, so I have to really try to prioritize and work as efficiently as possible within those hours. I know eventually I may want to hire someone to help with babysitting allowing me to get more done on a daily basis, but I am also trying to be present while he is this age. I know these days where I get to be home with him are numbered and before I know it he will be in school and I will have more hours to focus on work, but for now I am trying embrace these days.
I will say I have definitely become much more selective in the work that I take on in this season of life. I only have so many hours to create, and I want to work with folks who value my work as a designer. If I am going to be sitting at my computer, I want it to be for the purpose of creating work I am proud of. I truly want to be evolving as a designer, and taking on the type of projects that propel me forward and into areas that challenge me creatively. Taking breaks, walking away from the computer when you are forcing creativity, getting out into nature, these are just a few ways I have found that helps me to work more efficiently and create in a more productive manner.
Brand Design - Liz Grant - Freelance Wisdom

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

Learning to say no. I use to say yes to everything. Now, at the start I don’t think this is a negative. When you are first starting out into the world of freelance design I think taking on work where it is offered is a way to hone your skills and build your portfolio. But, once you are more established in your field, I think saying yes to everything can start to really kill your creativity. After a good amount of trial and error, I have figured out that it pays to take the time to get to know a potential client before taking on a project. I am not a good fit for every client, and in the same way every client is not a good fit for me. Ask the right questions right at the start. Figure out what projects are truly in your wheelhouse and which ones you should pass along to someone who is a better fit. Early on in the conversation I analyze whether the project is something I want to take on, if I am the best fit for the specific needs of the project, and if the design direction lines up with my own aesthetic. Having those different elements align helps me to feel inspired and create the best outcome and final product for my clients.

What is your favorite thing about freelance?

The flexibility and versatility that comes with working for yourself in an area you feel passionate about. Choosing projects and clients that I connect with drives me. Those first stages of concepting the design direction and creating a mess on your artboard are always crazy. At different times you think, nothing is working how you want it to work. But, then when you finally land on something and find a visual solution you know truly represents their brand, that is the best feeling.
Graphic Design - Liz Grant - Freelance Wisdom

"Those first stages of concepting the design direction and creating a mess on your artboard are always crazy. At different times you think, nothing is working how you want it to work. But, then when you finally land on something and find a visual solution you know truly represents their brand, that is the best feeling."

How do you continue to attract your ideal clients?

I think presenting a cohesive vibe through your social media presence is pretty crucial. Try to use a similar voice throughout your online presence. I hate to use the word ‘authentic’ because it can sound so cliche, but presenting your truest self will bring in the type of clients who will want to work with you. Also, lately I have been doing my best to try to post more recent work in my portfolio. It is so easy to work for clients and never take the time to work for myself. I find it so much more challenging making time for my own brand. But, I think it is really important as designers to put the work we create out into the world, showing the kind of work you want is necessary to bringing in more clients that speak the same language visually as you do. What you put out you get back. If you don’t want to do anymore wedding suites, stop posting those. If you want to design book covers, start a personal project and challenge yourself to put it out for your audience to view. Whatever you put out there, that is what is going to resonate with people. So show only the best and the type of work you want to be doing more of.

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

Hire people who know what they are doing and who have strengths in areas that you may not be as solid in. This allows more time for you to focus on the aspects of your business that are your strengths. For example, I hired someone right at the start to help me set up and teach me the basics of Quickbooks. I had no idea what I was doing, and spending that time learning how to account for items correctly and how to invoice clients was such a lifesaver. I also have decided to pay someone to do my taxes each year. Just doing these two things has saved me a ton of headaches and made things much more organized once tax season comes around every year.
Illustration - Liz Grant - Freelance Wisdom

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

This is the constant struggle. I honestly don’t think there is an exact perfect formula to finding a work-life balance. I think at different times in your life the balance shifts between both, if that makes sense. Before I had a baby, I used to work super late at night, through the weekends, but it wasn’t exactly necessary and I wasn’t working all that efficiently. About two years ago I started to slow down, and started trying to work better and smarter. Of course anyone who has little ones knows how your time changes once those babes come into your life. Priorities shift and your days are not just your own. This can totally be an amazing time and a positive thing if you try to flow with this change and learn a new way of how to work, and be flexible with it all. You really have to prioritize differently by working better, creating more efficiently, and doing it all on a bit less sleep. I really want my little boy to grow up seeing his mama happily pursuing something she is passionate about, hopefully it will inspire him in some small way to find something he loves and feels a purpose in and then work for it.

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

Organization, Good Communication, Drive.
Brand Identity - Liz Grant - Freelance Wisdom

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