Creative Director

Lindsay Kelly

Lindsay Kelly is the Founder and Creative Director of JaneMade, a full service branding studio that focuses on working with female-founded and female-led brands with an ethos of community over competition. She is also a member of the Creative Lady Directory!

We’ve loved watching her company grow and really enjoyed hearing how she’s handled that rapid growth. Be sure to read all the way through to Lindsay’s just starting out advice. We have a hunch that you’ll want to add it to your mantra list.

Lindsay Kelly | JaneMade | Freelance Wisdom

Tell us about your path to becoming JaneMade.

After working in-house for over ten years, I wanted to partner on projects with clients that shared my mission and values of women helping women and community over competition. I built up enough freelance work to be able to be able to take the plunge to working for myself and never looked back. After 6 months or so of freelancing full time, I officially established the company and have poured my heart into it since then.

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

After working for so long, I had built up quite a network over the years. Those former co-workers gave me work, and referred me to other folks. In this sense, maintaining strong relationships was really important. I let former colleagues and friends know that I was out on my own, and got a lot of referrals that way. I also learned, very early on, the benefits Instagram has and receive a lot of inquiries through it after posting work. I’d say about 90% of our inquiries still come from Instagram, which is wild, but we definitely use it to our advantage and post what seems to work.

Lindsay Kelly | JaneMade | By Rosie Jane | Freelance Wisdom

When did you make the decision to grow your team and how has that growth been?

I’m not one to say no if there’s a project I want to do, and knew it was important for the growth of JaneMade to say yes to everything that aligned with us. This meant finding the support of designers I’d worked with over the years and bringing on a writer in the early days. Since then, I’ve brought on a partner who leads strategy and marketing and several gals who help out with design and copy. My client relationships are very important to me, so it’s been a tug and pull to find team members that completely mesh with us, but we’ve found several along the way and have a solid team in place.

As your team has grown has your role within JaneMade evolved?

Truthfully, not really! I’m a bit of a control freak, so I’m still touching every project, every logo, working directly with all of our clients. Our reputation is really important to me, and I want to make sure that every client feels as important as the next, regardless of project size. I’m trying to be better and let go of some responsibilities, and have brought on a studio manager to help with those efforts. As we grow, there’s more phone calls, more emails to answer, and less time to design, so I’m really trying to take some steps to get back to doing what I do best.

Lindsay Kelly | JaneMade | Citrine | Freelance Wisdom

Do you have any tips for creatives who are looking to expand their team?

I think it’s paramount to make sure that you work with people who “fit”. Everyone has different skill sets, strengths + weaknesses, but what’s most important is that any team member you bring on is working for the greater good of your business. Make sure that your supporting team members are clear on what’s expected of them, what your process and timelines are like, and if you have any “rules” they need to follow. But if you’re getting busy, find the help sooner rather than later. This will definitely remove some of the stress of being overwhelmed and needing to find help in that moment.

How do you continue to attract your ideal clients?

My partner, Kerri, has started doing some really great outreach to like-minded women in categories we want to work in or build up our client base in. I also try to go above and beyond to make sure all of our clients feel their needs are met, because a recommendation from a former client is a huge mark of success for me. We get a lot of referrals from past clients, so we really try our best to make all of our relationships smooth and successful. And, of course, still Instagram! We make sure to push relevant content, both visual and strategy wise, to really reflect who we are as a brand: aesthetically and value-wise.

Lindsay Kelly | JaneMade | Coveted Market | Freelance Wisdom
Lindsay Kelly | JaneMade | hiring team members | Freelance Wisdom

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

I’m a right-brained thinker, through and through. Owning a business means managing clients, taxes, payroll… all the things that aren’t intuitive to me. I’ve hit some bumps along the way (all of which I’ve learned from!) but definitely still struggle with some of the more “business” related side of things. I got myself a new accountant, brought on a studio manager, and started to put more processes in place to help with the management aspect of it. Rapid success is definitely met with growing pains! But we’re constantly evolving our ways of doing things for what’s best for us.

Do you have any tips for being your most productive individually and as a team?

Making lists definitely helps me. Sometimes thinking about everything I need to do gets really overwhelming, so I’ll list out what I need to accomplish each day. It keeps me focused, organized, and feels great when I start to check things off. I also try to not schedule too many calls in one day, so that I have enough time to do “actual work.” As a team, I try to make sure everyone has the information they need to work efficiently and to the best of their ability, which means getting things organized before they get started. There’s nothing worse than wasted time when there’s so much to do, so keeping everything documented is great. We use both Trello and to help us from a project management perspective.

Lindsay Kelly | JaneMade | Hauswitch | Freelance Wisdom
Lindsay Kelly | JaneMade | HausWitch storefront | Freelance Wisdom

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

So many! My biggest advice is definitely to get an accountant. Like immediately. I’m 3 years into being self employed and am still messing up (less now!) and wish I had known what I know now back then. Also, make sure you’re protected, which means using a contract for every job. makes a great free one. I track everything through Quickbooks, which is an easy way for me to forecast financially.

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

Truthfully, I wish I’d known it would all work out. I had a lot of anxiety around taking the plunge -- we’ve got kids and a mortgage so i needed to be able to contribute my share. Projects would end and I’d get nervous from time to time that there wasn’t enough work in the pipeline. But everytime, something amazing would come along and my worry was for nothing. It’s been a lot of work and I’ve certainly been spread a little too thin on occasion, but it’s so worth it.

Lindsay Kelly | JaneMade | Still we Rise | Freelance Wisdom

How do you stay creatively inspired? What do you like to daydream about?

My team does a great job at keeping me inspired. Our newest designer, Ashley, is a breath of fresh air -- she’s so thoughtful in how she thinks about design, and it’s refreshing to see things through a different set of eyes. I love to look at photography for color palette and layout inspiration, and all of our branding projects stem from a huge gathering of images. I do my best not to go down a bunny hole of design references -- sometimes it’s hard to get them out of your head and stay original (especially in the Instagram world), so I really like to stick to studying photography and typefaces to get my juices flowing.

I love to daydream about the future! I’m always asking “what’s next?” for JaneMade and brainstorming with Kerri about how we can constantly grow and evolve. Our hope is to leave a successful, thriving business to our daughters so it’s important to us to always strive for greater.

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

I get way too distracted to listen to podcasts, though I try sometimes! Reading is also a luxury I unfortunately don’t have, with two small kids and a business. But! I’m really into Spotify’s daily mixes and discover weekly. I listen to music all day long while designing. Faves include Alt-J, Langhorne Slim, Keaton Henson, and old folk music.

LindsayKelly | JaneMade | Follain | Freelance Wisdom
Lindsay Kelly | JaneMade | Creative Inspiration | Freelance Wisdom

Anything else that you'd like to share?

If you’ve thought about / are thinking about becoming a freelancer, do it. There is so much work and opportunity out there, and I wish I had taken the jump sooner. Full time jobs will always be there to apply to, but you were born with talent for a reason!

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

humility, tenacity, kindness

Lindsay Kelly | JaneMade | HausMagick | Freelance Wisdom

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Anna Charity

Anna Charity is a Designer, Illustrator and Creative Director of all things Headspace where she has been creating and nurturing the design aesthetic and brand since 2012. Her passion is to create experiences that make a positive impact on the world through design, illustration, character and storytelling.

We are lucky to have come across her work through our Creative Lady Directory and are so glad to be sharing her wisdom and whimsy with you today, enjoy!

Anna Charity | Freelance Wisdom | Designer at Headspace

Tell us about your path to becoming a freelance designer and illustrator and eventually head designer at Headspace.

I’ve always been fascinated by the way that illustration and characters can inspire and delight an audience. You can use simple lines and colors, create a face, and suddenly we can relate to it! And I was drawn to humor in animation through people like Terry Gilliam - I loved the animated sections in Monty Python from a very early age. I just loved the silliness of them. So I've always been creating stories and made-up characters, playing around with the quirks and foibles of life. From a stylistic point of view I like to experiment, but it’s the tone-of-voice and humor that's most important for me because it's those details that add the charm and relate-ability. Little things are important, even down to the voices, the subtleties of how they sound. I was also inspired by the American illustrator/designer Seymour Chwast. His work showed me that illustration didn’t have to just be confined to children's books, that it could stretch across design, advertising, editorial and, most importantly - that it could be used to communicate ideas, wrapped up in that similar surreal sense of humor of Terry Gilliam.
So after graduating with a degree in Illustration I moved to London and worked for various agencies and production companies such as B-Reel and The Mill. Then I met Rich Pierson in 2011 (the co-founder of Headspace). A mutual friend had shown him my portfolio and he liked my illustrative aesthetic. I had never previously meditated or thought about mediating, I think I was put off by all the mysticism and cliched imagery associated with it! So it was obviously a very exciting challenge to have the opportunity to essentially rebrand meditation and design an experience that feels far more accessible. Since 2011 I have created and lead the development of the design aesthetic and seen the company grow from 5 to 200 people!
Anna Charity | Freelance Wisdom | Headspace Photograph
Anna Charity | Freelance Wisdom | Headspace Logo

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

By networking and speaking to as many relevant people as possible! And also by keeping my portfolio regularly updated and making sure it contained the kind of work I wanted to do, so I would get the kind of projects I was passionate about.

Do you have any tips for being your most productive? Do these tips differ for freelance versus full-time design work?

I think sitting at a screen all day requires a regular change of scenery. Whether that’s going for a walk, taking a break to read or sitting down to write or sketch. Though this takes some practice. When you’re working from home these activities can sometimes turn into procrastination! I’ve recently been doing morning pages (one of the exercise’s from ‘The Artist’s Way’) which involves writing 3 pages first thing in the morning, as a process to unblock the creative pipes. I’ve found the activity of writing (even though I am anything but a writer!) hugely beneficial for my productivity. I have noticed I’m questioning less and doing more.
Anna Charity | Freelance Wisdom | Headspace Screens

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

The transition from individual contributor to managing a team and other people’s expectations has been a challenging one. I think for a lot of creatives the idea and act of managing doesn’t necessarily come naturally. It takes a very different mindset to genuinely feel passionate about nurturing someone else’s creativity outside of your own.

With the task of designing consistently for the same brand, how do you keep inspired?

I think it’s so important to keep a regular practice outside of our day jobs. Our real creative juices extend from our true passions in life. So I make sure to keep nurturing these which pretty much always feeds into my day job. I also get a ton of inspiration from traveling, reading, drawing and music in it’s many forms!

If you could give one piece of advice to your "just starting out self," what would it be?

Stop procrastinating, start doing and believe in yourself.
Anna Charity | Freelance Wisdom | High Five Gif
Anna Charity | Freelance Wisdom | Believe in Yourself

Do you have any music, podcast, or book recommendations that you'd like to share?

Where do I start?! I’ve recently been listening to a guy called Part Time, he’s got the low-fi 80’s vibe down. I’ve always been a big fan of Adam Buxton - a British Comedian. His podcasts are the perfect combination of informative, silly and hilarious. As mentioned I would also highly recommend ‘The Artist's Way’ for developing and growing your creativity.

Anything else that we missed that you'd like to share?

Don’t overlook the ordinary, question the hell out of everything and just remember we are all going to die anyway so make the most of it!
Anna Charity | Freelance Wisdom
Anna Charity | Freelance Wisdom | Question Everything

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

Curiosity, courage, and a sense of humour :)
Anna Charity | Freelance Wisdom | UK Science Poster

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Melissa Cripe

This week we have the pleasure of speaking with Creative Lady Directory member Melissa Cripe. Melissa is a Creative Director, Prop Stylist and Set Designer who seeks to create tangible worlds of colorful chaos that mimic both the light and dark which fill our everyday lives. Her clients include Tumblr, NBC, Disney, Comedy Central, Pocky, and many more. We are loving the vibrant energy in her work and can't wait to see her upcoming projects come to life. Oh and her advice is top notch. Dive on in!

Melissa Cripe | Freelance Wisdom

Tell me about your path to becoming a freelance Creative Director, Prop Stylist & Set Designer.

I began creatively directing my own shoots when I started a blog in 2015. I’d concept ideas, gather all the props, find the location, hire a friend to photograph, and would usually edit all the images. After a year, I decided to step out of the frame myself and focus more on the directing aspect of the process (which I’ve always been more drawn to anyways). Simultaneously, I was working full time on a team at Tumblr for 2.5 years helping to produce content with artists from around the world. I was sort of living a double life - the 9-5 schedule during the week, and personal creation on the nights & weekends. After I’d built up a small, but steady flow of projects, I began partnering with brands to bring my flare to their products and also started to challenge myself on a larger creative scale. I wrote and directed a short film called ‘The Claw of Life’, set designed for some brands, created a live physical installation for BeautyCon, and am continuing to try on all the hats I can in this new freelance space.
Melissa Cripe | Freelance Wisdom

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

In the beginning, I treated myself as the client when no one was actually paying me. I’d make schedules, budgets, moodboards, call sheets, and conducted the photoshoots with friends as professionally as I could. I was spending my own money and using all of the resources already around me - i.e. my living room, an old tripod I found in my childhood garage, friends as models, DIY lighting setups, borrowed clothes, you name it. In doing this, I became less scared of “real” clients because I knew I’d treat that process no differently than my personal one.

However, my first few paid clients reached out to me based on the style of work on my Instagram and website that I’d been forming on my own. That was thrilling because it validated all the personal efforts I’d been working on quietly for years without compensation. And then, other clients came from connections I’d garnered over years that knew what I was capable of and gave me a shot to prove it.

Can you tell us about your prop styling/ set design process?

I always try to let the message bring alive the visuals. I start with a concrete, simple thought I can’t get out of my head. Then I sit down and write every word, color, shape, place- anything really that reminds me of the theme in this freestyle form. From there, I categorize all these thoughts and just start mad-libbing what they’d look like together- different color combos with emotions, places with props, people with different costumes, etc. From there, I create a super specific moodboard and off to the thrift stores and spray paint aisle I go! I definitely still have a lot to learn about the process and especially the designing tools, but I’m finding that I’m absorbing so much from forcing myself to be in new positions, which is really exciting (and often a little bit scary!)

Melissa Cripe | Freelance Wisdom
Melissa Cripe | Freelance Wisdom

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

To be honest, where I’m at with the freelance life, I’m not working everyday. So I feel like on paper I’ve had a lot more “free time”. However, too much empty time on my hands stresses me out. I’m learning to find purpose in all the hours - not just the profitable ones or scheduled hangouts - but the silent midday brainstorming strolls and the late night creative research scrolls.

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

Without a doubt the greatest struggle has been trusting in the process. Working with the ebbs and flows of insane stress and absolute silence. I constantly am reminding myself that what I gave up in the financial security of a 9-5 job, I gained in the freedom of choosing projects that matter to me on a deeper level.

Melissa Cripe | Freelance Wisdom
Melissa Cripe | Freelance Wisdom

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

I wish someone had stressed to me how hearing “no” is NO BIG DEAL. Ask upfront for a little more budget than you think you need to prepare for things going wrong (which inevitably in any production, something usually will). If that number isn’t what the client is able to pay, and you hear a “No” THAT’S OK. Always pitch the idea, even if you assume it’ll be followed with a “no”. At least you asked! Get comfortable with it and learn to replace the initial feeling of rejection with the joy of knowing you put yourself out there in a hard way.

Also, even if it feels weird- find people you can ask candidly about how much to charge for your work. Unfortunately, there’s no solid source on industry standards, so it becomes really daunting and confusing when you’re new to the game to know what’s normal with rates. The only way in my experience to be certain you’re getting fairly compensated, is simply to ask other people you trust directly about it and get a data range of those working in your field.

How do you continue to attract your ideal clients?

I think I continue to attract ideal clients because I aim to be super clear in my vision, yet flexible in the process. I know oftentimes there are so many cooks in the kitchen approving each step in the timeline, so I just try to do my part the best I can. That means - being upfront with budget, offering solutions, and responding timely. Also, from time spent at my old job on the producing end, I realized how important it is to simply focus on being a kind person to work with. I think sometimes artists forget to prioritize the humanistic level of working with clients because they’re so certain their talent is the most valuable. While this is absolutely true (and I’m still learning the balance myself) the fact of the matter is that people want to pay people they like. Period. The client isn’t only factoring in your skill, but also how easy you are to work with because selfishly it’ll make their lives more enjoyable too. Sincere advice here is to just remember to keep it pleasant y’all.

Melissa Cripe | Freelance Wisdom

Your portfolio is wonderfully cohesive. You are able to adapt your style to many different assignments. Do you have advice about how to choose which projects to take on?

First of all- thank you! That means so much to hear. Especially because nowadays there are so many perfectly curated feeds using the exact same filter for every photo to create cohesive individual branding. For me, I know my visual style has a lot of variability. Sometimes I love using bold primary colors, sometimes I enjoy the dreamy pastel palette and other times, I get excited by dark, low lighting. However, the aspect I like to keep cohesive is my point of view - the ability to bring lightness and fun to anxious fears or silliness to seriousness. I really believe in the necessity and balance of light and dark, and I’m glad to know that others can go along for the ride - even if it’s not as visually consistent as a lot of the other content i’m seeing on the internet daily.

What do you do to stay creatively inspired?

I’m always finding new artists and studying older ones that excite me creatively. I’ll scroll Vimeo staff picks or Nowness or even Criterion Collection for references and ideas. However, I’ve realized to truly stay inspired that I need to force myself to take the time to sit silently with my own thoughts and believe in their power - no matter how big or small. If not, I always feel like I’m copying and incapable of creating anything that will have any sort of lasting impression.

Melissa Cripe | Freelance Wisdom
Melissa Cripe | Freelance Wisdom

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

This might sound silly, but I honestly used to think that if I expressed how much I enjoy the organizational part of producing my own work, that it would make me somehow seem less creative. People would be quick to say “oh then maybe you’d enjoy being a producer more!” - as if the two don’t go hand in hand, either you’re the one organizing everything or you’re fully creating. BUT now more than ever being full time freelance, I realize just how valuable it is to spend an equal amount of time on the process of producing as it is the creation. I enjoy projects SO much more in the moment when I feel prepared and take the time to be meticulous, than when I just let the creative energy guide the whole thing. So yes, spreadsheets are my savior. I recommend making yourself a system that is personal to you and sticking to it. Have one place where you keep a breakdown of every cost, date, and timeline. It’s tricky and messy at first, but once you get into a groove you can follow that becomes second nature on the business side, you free up more room to focus on the creative. I also just recently learned the importance of putting specific terms on your invoice to make sure you get paid exactly when you expect to (that’s a big one!)

Are there any projects on which you're ruminating that you'd like to make time for someday?

Plenty! & Even more in the works that I’m still finishing! Right now, I’m mainly focused on finishing a photo series I started last year called ‘The Grownup Club’. I’m planning to turn that into a Zine and exhibit it in a gallery setting which I’m really excited about! I’m also going to release a small photo series called ‘Hot & Bothered’ on the physically violating feeling of the male gaze and another series where I’m hoping to explore the medium of collage. So stay tuned for some funky new works :)

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

Flexibility, organization, & self motivation.

Melissa Cripe | Freelance Wisdom

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