Monica Obaga

Monica Obaga is a Kenyan graphic designer and illustrator, currently based in Los Angeles. Up until 2015, she was the founding Head of Digital Marketing at, Africa’s first online VOD channels, and the first to be acquired by a media giant in 2016. She has a special interest in projects that promote the diversity of artistic self-expression in the African community and is currently writing and illustrating her first book.

Monica Obaga | Freelance Wisdom

Tell us about your path to becoming the designer and illustrator you are today. 

I thought I was going to be a fashion designer until I turned 12. I made my first gown about 2 inches high, for my teeny tiny doll when I was 6. For almost the entirety of primary school (or Grades 1 through 8) I was doodling in every workbook. Halfway through an extremely competitive high school, Art didn’t make the cut as part of my final seven subjects. I didn’t draw much after that until 4 years ago. I started my Instagram page as a quiet place to begin doodling again just for fun and after a year or so I began collaborating and then getting client requests. I still have a long way to go as an illustrator but I’m enjoying the journey.
Monica Obaga | Nairobi Air BnB | Freelance Wisdom

In the past few months you have shifted towards freelance design. What inspired this shift?

I’ve been teetering at the edge for so long since three years ago. I finally got curious about what would happen if I took it seriously.  

What are you loving about this transition? What is challenging you? 

Knowing that I earned every cent that comes in being 100% myself is such a boost. I am working with amazing people changing the world in their own special way. They inspire me to keep growing.
Some of the challenges are that I am running it on my own, so there’s only so much I can do at once, but I keep plugging at it anyway because it’s so worth it. The other challenge is just the irregular nature of creative work. Sometimes it comes right away and other times it takes longer when I can’t crack a problem but I have to be patient and show up every time.
Monica Obaga | Letters to Self | Freelance Wisdom

Do you have any tips for being your most productive? 

Know yourself: Try things and be mindful how they make you feel. I tried productivity planners physical and online and found that post its kept me more consistent in my daily to dos so I switched.
Automation: A trick I learned from a Tim Ferris podcast, whenever I fell off the exercise wagon, I trick myself by wearing my gear even if I’m resisting exercise. Literally the second day in I can’t resist any longer. 
Health: You know what’s good for you. Do more of that. Start small and build up at your own pace. It makes the rest of life so much easier.
Monica Obaga | Jonah Letter | Freelance Wisdom

What are your favorite ways to stay creatively inspired?

Walking in the woods (or forest bathing if you’re fancy) is such a powerful recharge as is being by any large body of water. Visually stunning or original films, stores and installations makes me feel like I’m bathing in art. I follow design publications, photographers, designers and illustrators for inspiration as well.

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

Of course! So many ideas I’m not quite certain where to start. I’d love to finish a few stories I’m writing. They are a little different from my illustration style so I’m not sure who will want to experience them, but they are the very type of story I love, so I hope to do them justice.

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

Persistence, professionalism, purpose (Don’t forget why you started!).
Monica Obaga | Monmon | 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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Kiffanie Stahle

We are so excited to introduce Kiffanie Stahle, a lawyer, photographer, fellow small business owner, and an active participant in our Creative Lady Collective Facebook group. Kiffanie has been helping artists and creative entrepreneurs in her law practice since 2011. Practicing law has solidified her passion for teaching the creative community about the law. Through the artist's J.D. she provides resources that empower you to tackle and understand the legal aspects of your creative business.

There is so much goodness for everyone in this interview. Seriously, put down what you're doing and dive in; you won't regret it. 

Kiffanie Stahle | Freelance Wisdom

Tell us about your path to becoming a lawyer for creatives.

Before law school, I was a wildlife biologist. And after nearly a decade of counting birds and rodents, I was ready for a change. But I wasn’t sure what that change was.
At the time, I was showing my nature photography in galleries and I debated trying to go full time.
But law school had always been something that called to me. And after much thinking and discussion, I decided to take the leap.
During law school, I continued to show my work. And once the secret got out that I was in law school, everyone started asking me questions.
Sometimes I could help. But often, since I wasn’t an attorney yet, I couldn’t.
So, I started searching the San Francisco Bay Area for a law firm where my friends would feel comfortable and treated respectfully and fairly. And while I found good options, I couldn’t find exactly what I wanted.
Because of that, I decided to open my own firm and create the place that I couldn’t find for my friends.
And that’s what I did. I graduated law school in May 2011, took the bar exam in July, and impatiently waited until November for my passing score. On Friday, December 2, I was admitted to the California bar. And within an hour, three friends agreed to be my first law firm clients.
I’ve been helping creatives as their attorney ever since!
Kiffanie Stahle | Freelance Wisdom

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

From Day 1, my good clients have reached out because a friend told a friend, “Call Kiff and she will help you. And if she can’t help, she’ll tell you who can.”
Because a mutual friend is involved, we already know we have things in common and shared values. We already have a little bit of trust with each other. And these are all ingredients necessary to make a good attorney-client relationship.

Your pricing structure differs from many other lawyers'. What inspired this unique structure?

There’s a reason that attorney-client confidentiality exists. It’s there because an attorney’s job requires knowing the whole story, even when parts of it make you look bad.
And when we both sign the dotted line to make me your attorney, I need the inside scoop. I need the good, the bad, and the ugly. I need to have your trust. I need to be part of the team.
And charging on an hourly basis makes that harder. Because when you bill hourly, there isn’t an alignment of motivations.
My client is afraid to call or email me because she's afraid to start the hourly billing clock. So, she doesn’t tell me everything. This is fine by me because I know that eventually, I'll get the whole story. And the longer things drag out, the more and more money I make.
But when you switch over to billing on a flat-rate basis, our motivations line up.
My client is paying the same amount regardless of how many times she calls or emails. And she doesn’t mind when I ask a ton of questions (and even more follow-up questions). She shares her story with me. She shares her fears with me. She shares her hopes with me. And by listening to her, I get what I need to efficiently wrap things up.
Of course, there’s a risk for both sides with flat-rate billing.
Some projects will go as planned and the flat rate lines up with my desired hourly rate. And some projects will be super easy and I make out like a bandit. But other projects drag out and my hourly rate is a tenth of what I want it to be.
But for me that risk is outweighed by my client knowing I’m on her team.
Kiffanie Stahle | Freelance Wisdom

Can you tell us a bit about your motivation to start the artist's J.D.?

After a couple of years as a lawyer, I started being able to predict who would create a successful, thriving business. And it all boiled down to one factor, was a creative business owner willing to:
  • learn about the legal side of her business
  • take action on what she learned to build her business on a strong foundation
But the hard part was convincing my friends of this. And when I did, the resources I found for them were confusing, full of legal jargon, and didn’t have examples relevant to creative businesses.
So, I started creating what I was trying to find. I created resources for my friends that added ease to the legalese of running their businesses.
And that’s still what I’m doing today at the artist’s J.D.
Bit by bit I’m helping you find the answers to your questions, discover questions you didn’t know you should be asking, helping you take action, but most importantly injecting a little ease into the legalese.

Since you run your own law practice and facilitate at the artist's J.D., do you have any tips for being your most productive?

Over the last seven years, I’ve used lots of different methods to keep myself organized.

I’ve time blocked, played workstation popcorn, used a bullet journal, picked three most important tasks, used the 1-3-5 rule, and lots of others.

Currently, Asana keeps the big scary task list and helps me project manage. But I switch up how I execute what appears on that list based on my workload, mood, and what feels best because I’ve learned that the most important productivity tool is listening and trusting myself.

I’ve learned I have to accept and give myself grace when things aren’t working. And when that happens, I give myself permission to mix things up and experiment with something new.

Kiffanie Stahle | Freelance Wisdom
Kiffanie Stahle | Freelance Wisdom

How do you recommend freelancers set up their business when just starting out?

There are five must-do legal tasks that every freelancer needs to tackle:
  1. getting an EIN and business banking account so you can get your financial house in order
  2. getting business liability insurance so you can cover your ass(ets)
  3. picking the right legal business type so you can sleep at night and protect your family
  4. getting any permits or licenses so you can cross off the legal red-tape
  5. creating a client contract so you can be the kindest freelancer around
But once you do these, the terrible lawyer answer of, “it depends,” is the best answer. Because the next best use of your time and resources depends on your goals and how you define success.

What are some of the biggest legal mistakes that creatives often make?

The biggest mistake (that also can have the longest impact) is signing a contract that you don’t 100% understand.
Contracts are always written to favor the person who created it. And while some companies try to be fair, they aren’t going to point out where the contract favors them.
So it’s important that you 100% understand how this contract impacts you immediately, and in the future. (I’m especially talking to those of you who sign licensing deals!)
Yes, having a lawyer review a contract isn’t cheap. But if you find the right attorney, it's a game changer. Because it will not only empower you about this contract but be an investment in every future contract you get.
You should get your attorney to explain:
  • why this contract is/isn’t a good deal
  • what changes they are making and why
  • what specific clauses mean
  • what you should look for in future contracts
  • what clauses are deal breakers given your goals/plans
  • how this contract might impact you today and 5/10 years from now
And take copious notes.
If you do this, you’ll have a better understanding of what your next contract says (and if it’s a bad deal).
You’ll be able to review contracts and start identifying red flags and deal breakers without involving an attorney. And if for a specific contract you do bring an attorney on board, you’ll do so already knowing areas that give you concern.
Kiffanie Stahle | Freelance Wisdom

Are there any contract must-haves that you would advise freelance creatives to include? Curious if there are essential items that you notice creatives often leave out?

Contracts get a bad rap, but they make you the kindest biz owner around, because they exist to make sure everyone is on the same page, and that you don't disappoint your client because you had different understandings of the goals, process, and outcome.
Once you realize this is the goal, then what you need in your contract becomes obvious. Your contract should cover the places ripe for misunderstanding:
  • who does what
  • what they’ll get
  • when it’ll happen by
  • what changes or input your clients get to make on the deliverables
  • what each of you can do with the deliverables
  • how much it’ll cost and when and how payments will be made
  • how either one of you can exit gracefully if it’s a bad fit
Of course, there are other things you might want to include depending on the project. You can see all 17 possibilities here.

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

Curiosity, courage, and endurance.
Kiffanie Stahle | Freelance Wisdom