Jess Levitz

This week, we are so excited to get the full scoop on Jess Levitz's freelance journey. If you don't yet know her, Jess is the graphic designer behind June Letters Studio, co-founder of Shoppe Theory, and the founder and brains behind Freelance Wisdom, the Creative Lady Directory, and the Creative Lady Collective!

Her career began in the tech world as an in-house designer. After years in the start-up world she was ready to strike out on her own, and she hasn't looked back since. As June Letters Studio, Jess focuses on creating thoughtful and beautiful brand identities for her passionate clients.

When not designing, Jess enjoys spending time with her scientist husband and their son Izzie, collecting random vintage memorabilia, and supporting female creatives on this platform right here. 


P.S. Be sure to let us know in the comments what you'd like to see come out of this creative lady community in the future :)

Photo By Loren Crosier

Photo By Loren Crosier

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

My journey began in college at American University in Washington DC when I took an “Intro to Graphic Design” course as one of my general education art requirements. I had always been creative but wasn’t sure what direction I wanted to go with my career (I was 18 after all!). But the graphic design class really solidified for me that I was meant to be a designer; I adored every project and discovered that it was something I excelled at. I then went on to major in Graphic Design and Communication Studies. At the end of college I applied for a few jobs and ended up landing a Junior Designer role at Yelp back in the California Bay Area (where I am from and my boyfriend now-husband was living). I worked at Yelp for several years as their in-house designer for their community team. I mostly spent my days creating posters and collateral for Yelp sponsored parties, which was pretty dreamy for a first job! I also worked with the marketing team on direct mail, web advertising, and in-house presentations.
After some time as a Junior Designer I was promoted to “Designer” and then I was asked to join the UX team to work on designing the Yelp website. While excited for this promotion and new endeavor I quickly realized that the Yelp engineering team was not the right place for me. Fortuitously at that time a friend of a friend reached out to me about a start-up she was working for that needed to hire their first lead designer. After a grueling interview I was asked to join the team of an e-commerce start-up. I was so excited to have the opportunity to build a brand from the ground-up, touching every aspect of the business from the website design, to marketing materials, to packaging. While I liked many of the people I worked with I realized that I was not the right fit for the macho around-the-clock working style of the company, and I was not given the opportunity to make many improvements to the brand like I had been promised.
So I decided to apply for a company I really admired called True&Co., a lingerie brand that had a vision to improve the bra buying experience. While it was an intense start-up as well, I was a much better fit for the brand and the work culture. I was the lead designer and once again touched every part of the business and truly learned so much about e-commerce, fulfillment, and marketing. At True&Co. I also hired my first junior designer, Do-Hee Kim, who would become my good friend and business partner (I will talk about that more later!).  While working at True I still realized that something was not quite right, I loved the brand and the work I was doing, but I really disliked going into the office (I love working from home!)  and only working with one brand style. At one point we hired a freelance designer to come in on a project and I realized that what she was doing, was what I wanted to do. I wanted to be a freelancer.
Jess Levitz | Freelance Wisdom
Once I made that realization, I started to make a plan. I chose a business name (June Letters Studio), improved my website, started blogging daily, and began taking on any freelance project that came my way. My blog quickly began to get traction and the inquiries were coming in at a steady stream. I was having trouble balancing my full-time job and my freelance career so I decided to make the leap and quit my job. But instead of fully leaving the company I became a retainer client for them and worked for a set amount of hours a week for several months while my own business picked up. It was a great transition to freelance because I still felt financially stable and by the time I left completely, my own business was humming along.
This month is my 3rd anniversary of officially going freelance full-time! While freelancing certainly has it’s ups and downs, I have never regretted my decision to start my own business.

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

As I mentioned above the first thing I did was start to blog daily. I created a self-imposed project called The Moody Project where I created a moodboard everyday for 60 days. Doing this project proved to myself that I could create content everyday. So after the project was over I created a loose editorial calendar and started blogging daily. I hand-lettered quotes, created illustrated outfit posts, wrote about my life, created tutorials, and shared my work both for clients and self-initiated. I also made it known on my social channels that I was taking on freelance projects and pretty soon inquiries started to come in! One project for a photographer was a big jumping off point for me. Our taste was very much aligned and the logo and brand I created for her helped to attract a lot more clients. I charged very little compared to what I do now, but it helped springboard my freelance career and was well worth it. In the beginning it is totally okay to charge less because each project when you are first starting out is such a learning process. As you continue to hone your craft, gain more experience, and have more confidence in your client process you can then continually raise your prices as your value increases.
Jess Levitz | Freelance Wisdom
Jess Levitz | Freelance Wisdom

Do you have any tips for being your most productive?

The times that I am the most productive is when I have a very clear schedule for the week. When I can easily plan out what needs to be done each day, I feel so much more ready and creatively open to accomplish the tasks at hand. I use Asana to plan out my deadlines and exclusively use the calendar page. I love seeing my color-coded schedule and checking off my completed assignments! When I am feeling in a rut, I like to step away from the computer, go for a walk or take some time to sketch. If my deadline is the next day or later, I like to completely step away and try again the next day. Some days I am just not feeling creative, but the next day after taking some time away I always feel better.

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

I have quite a few so it is difficult to narrow it down, but I think many of my struggles exist under the umbrella of “wanting to do it all”. I often overbook myself with clients and personal projects because I get really excited about new creative endeavors. I honestly can get pretty manic about it, I will have an idea and am suddenly announcing to the world that I will be doing that thing - then realizing a few days later that I really don’t have time for that thing. When I first had a baby two years ago this impulse went into overdrive as I was re-discovering who I was as a person and a creative (hah Freelance Wisdom came out of that time!). I recognize that part of why I am a good freelancer is this drive to be creative at all times, but sometimes it can be really tiring. As much as I would love in theory to focus on just one thing - I know that I will likely never be that way, so instead I need to learn to be more fastidious about what I pursue.
Jess Levitz | Freelance Wisdom

What is your favorite thing about freelance?

My favorite thing about freelance is pretty simple - I get to work where I want to, and on what I want to. Being freelance and positioning my business in a way that is true to my style has made it so that I attract clients that want to work with me specifically because they like what I do. Of course there can be dud clients and situations that end up being difficult - but overall I feel so lucky to work with clients that really appreciate my work. And on top of it all, I get to work at home in my pajamas, or at a cafe, or anywhere in the world I happen to be - that freedom means so much to me.

You recently launched Shoppe Theory a petite design studio with Do-Hee Kim. What inspired you to join forces and design together?

As mentioned earlier we met when I hired her as a junior designer at True&Co. -  but while it began that I was her superior, her role quickly grew and by the end of our time working together Do-Hee, having found a love for UI design, was taking on all the web work and I was taking on the brand work. We also discovered that we worked together really well - we have similar easy-going personalities and complimentary design styles. We both are very open emotionally, have a strong work ethic, and a passion for design - basically we are pretty much design soul sisters. When I left the company to pursue freelance full-time, I missed working with Do-Hee and would often recruit her for projects.
I don’t remember exactly when it was, but at some point in 2015 (about a year after going freelance full-time) I sent an email to Do-Hee with an idea. That email turned into many phone calls and frantically excited text messages. The idea was this - why don’t we join forces to create brands and websites for e-commerce companies? Our talents and experience were so perfectly aligned for this idea. I discovered that I really did not enjoy web design, and Do-Hee had come to really love designing web experiences, especially for e-commerce. Shortly after this idea was sparked, a perfect project came into my inbox and we decided to give the partnership a shot. We loved working together on the project and thus Shoppe Theory was born. Since then we have worked on numerous projects together and we are slowly shifting all of our work to be through our studio.
We discovered that working together allowed us to focus on the aspects of a project that we really love, and we were better and happier together than apart. We could bounce ideas off one another and we could also vent to someone that really understood what we were going through. After working solo for quite awhile it felt right to join forces and create a studio that was more valuable than what we could create on our own.  Our biggest struggle has been getting our website up since we keep pushing it off to work on more client projects (hoping to launch this summer!!). We have big plans for Shoppe Theory and are excited about where this new venture will take us.
Jess Levitz | Freelance Wisdom
Jess Levitz | Freelance Wisdom

Do you have any advice for handling communication as a partnership that works together from different states? Are there any tools that you use to make this easier?

Constantly communicating has been so important to feeling like a real studio. We like to chat online and text, and then once a week we do an hour long facetime check-in. It helps to see each other via video, almost feels like we are together! We also see each other in person every few months which is great - luckily we live in places that we each visit often so it has worked out well. We do hope to someday be in the same city though!

What advice would you give someone who is considering joining forces with a spouse, friend, or colleague to design as a team?

Work together first. And always be open with each other. Nothing is worse (in any kind of partnership) then holding in all your feelings until they explode. I also think it is important to not be afraid to hold each other accountable - we are often checking in with each other to make sure we are hitting our deadlines and being our best with clients.
Jess Levitz | Freelance Wisdom
Jess Levitz | Freelance Wisdom
Jess Levitz | Freelance Wisdom

How do you continue to attract your ideal clients?

Since I have slowed down on blogging and marketing, most of my clients now come from referrals from friends/acquaintances of past clients. I do though continue to get inquiries from people that found me on Pinterest, Instagram, and Dribbble. Once we have our website up with all of our new work we are hoping to get more direct inquiries to Shoppe Theory.

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

Even after three years I am still not the best with these nitty-gritty items and am honestly awaiting the day when we can afford a project manager to do all of our invoicing, contracts, and bookkeeping! But until that day comes, I use Freshbooks for invoicing, Asana for project management, and have an accountant that helps me out around tax time!
Jess Levitz | Freelance Wisdom

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

It is funny because I wrote this original question and have read so many answers, but I am still struggling to answer it! I don’t think there is such a thing as a perfect work-life balance when freelancing - but something I am trying to do is not work on weekends at all. It sounds like such a simple thing but is a pretty big deal for me!

Your little one is approaching 2 (is that right? how can that be!) How has becoming a mom changed how you work and/or the types of projects you take on?

It honestly changed everything for me. Before my son came along I would work day and night, taking on 10 clients at once. It was crazy and tiring but I had the energy and passion to do it. But after my son was born I just couldn’t work like that anymore. I had much less time to work especially during the first year when I only worked 3 days a week. My first six months back to work I started taking on way too many clients and personal projects and hit a complete breaking point. After that point I contacted a retainer client I had worked with before and fortuitously another client contacted me looking for a regular designer. This allowed me to cut down and only work with 2-4 clients at a time. Now that my son is nearly 2 and in daycare full-time my schedule has opened up a bit, but I am still much more choosey about the types of clients I take on. I notice red flags much sooner and I have raised my prices significantly which has helped me to be able to take on less at once and feel better compensated and appreciated. It is still a constant struggle to balance motherhood and work, but it has gotten so much easier as my son has become older and more independent. So new moms out there - it does get better! Look to simplify your work life and it will help you tremendously.
Jess Levitz | Freelance Wisdom
Jess Levitz | Freelance Wisdom

What do you do to stay creatively inspired?

I love to sketch, visit museums, go to flea markets, visit used bookstores - and most of all walk around. NYC is a goldmine for keeping me creatively inspired!

I know you are constantly taking on side-projects in addition to your client work, what are some of your favorite personal projects that you are are working on right now?

The two projects (besides Freelance Wisdom!) that I am most excited about are the course I have been working on for over a year, and a shop of kids art prints and apparel.
The Hand-Lettered Brand is an online course built specifically for lettering-focused designers that helps you hone in on your unique personal style, learn about my client and creative process designing hand-lettered logos, create a self-initiated project with feedback from me and the class, and create a plan for marketing yourself in a way that feels genuine to you. I am hoping to launch at the end of the summer! If you are interested, get on the list here and get a free download ;)
On the side I have also been designing kids products for fun for my son. Designing these shirts, blankets, and art prints has brought me so much joy that recently I decided to make it into a real business. I am not ready to share it just yet, but stay tuned for Yah Kids!
Jess Levitz | Freelance Wisdom
Jess Levitz | Freelance Wisdom

Since we are lucky enough to have this platform...can you tell us about the motivation to start Freelance Wisdom and what you are dreaming up for it in the future?

I started Freelance Wisdom because I had a lot of questions and I was feeling pretty alone in my desire to freelance. The interview series started on my blog and I was struck by the kindness and openness of the women creatives that I reached out to (many of whom I deeply admired and never would've dreamed would respond to my email!). The series prompted a lot of love from my readers and I saw so much potential in creating a community around female freelance creatives. So during my crazy post-baby time I decided to turn the series into a full website that offered interviews, resources and was a hub for inspiration and wisdom. I was amazed by the response and how quickly the Instagram grew.
I loved having the weekly interviews and Instagram but felt like we needed something more for the community. So a few months ago I launched the Creative Lady Directory and more recently the Creative Lady Collective facebook group. I have been so excited to see the growth of both communities! The CLC facebook group has been especially amazing to watch grow (over 1,000 members!) and I love seeing all of the incredibly kind and helpful conversations that take place on a daily basis. In the future I would love to merge all of these endeavors under the umbrella of the Creative Lady Collective. I would love to help foster meet-ups around the globe, improve the directory so it is easier to search, create fun swag, and eventually plan a retreat. But of course I am curious - what would you like to see come out of this community?
Jess Levitz | Freelance Wisdom

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

Talent, kindness, drive.

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