Lessons on Freedom and Money from Six Creative Pros

Last week I mentioned a project that’s been in the works for more than six months: a comprehensive toolkit to help artists and designers of all kinds make more money and achieve creative freedom.

We started by looking at the story of Jen & Omar, the authors of the new resource. They’ve built a fantastic business (and as I said, the best part about it is that it’s replicable), but we also wanted to study the successes of other folks as well.

This post features six people who earn a good living through their art. They’ve all unlocked the secrets of convergence—working on something they love that other people value enough to pay for.

How did they do it? The full version of each story, along with lots of details and a step-by-step plan, will be available in the upcoming product that launches next week. But here’s a quick preview…

Dave Radparvar (and others): HOLSTEE.COM

Dave Radparvar, his brother Mike, and good friend Fabian built, a creative illustration business with a mission to encourage mindful living.

You’ve seen the Holstee manifesto. Even if you think you haven’t, you have. It’s been shared more than 60 million times and has been translated into at least twelve languages. Have you ever wondered where they got the idea for this amazing successful illustration that hangs on walls all over the world?

Funny thing is, this company started out in 2008 with the dream to make t-shirts with fancy holster pockets (hols-tee… get it?). When the original business idea failed, they regrouped by writing down what they believed to be true despite their business failings. The result? A viral manifesto.

Holstee quickly learned an important lesson in creative entrepreneurship: start with what you know, build on it, and then adapt until it works. Sometimes you’ll need to step in the opposite direction, eliminate products that are no longer working, and create more by focusing on less.

A creative freedom lesson from Holstee: Adapt to succeed. Start with the idea you have now, but don’t be surprised if it leads you to something even greater.


Rosa Park created U.K.-based Cereal Magazine, a global publication targeted at savvy travelers who love and enjoy great food. She built her business on a passion as a starting point—but knew it would take more to actually turn what she’d “loved” into her full-time work.

In July 2012 Rosa started work on her high-end artisan magazine to combine her lifelong obsession with food and travel with her skills in style and design. Early on she recognized that setting a schedule to ship and sticking with it would be key to her start up success. She gave her dream a deadline: she’d launch the first issue by the end of 2012 and focus her creative energy to make this goal a reality. The result: after one year in business, Cereal has readers in forty countries and sells over 20,000 copies of each issue.

A creative freedom lesson from Rosa: Passion + progress yields success. Set a deadline to turn what you love into something marketable and scalable.

Lauren and Joel Gryniewski: OLD TOM FOOLERY

Lauren and Joel left their jobs as veterans in the advertising industry and dove head first into the big world of stationary to create a unique line of humorous and offbeat unisex greeting cards.

They loved quirky greeting cards, and it dawned on them that writing and designing cards was a lot like their full time work of designing ads (but a lot more fun). Dreaming of more, the creative duo decided to repurpose their skills. They picked up a $500 letterpress on Craigslist, printed their first run of fifty-two cards in their kitchen, and hit the New York stationery show. “You never feel like you’re ready but you just have to dive in,” Lauren explained. “There will inevitably be some things that go wrong along the way, so you have to be willing to roll with the punches, think on your feet, and make the best of it.”

A creative freedom lesson from Lauren and Joel: Light a fire under your ass (“quitting our full-time jobs was our version of this”). No one else is going to push you to get started (“and you won’t ever succeed unless you start”).

Jeff Sheldon: UGMONK.COM

A less-than-inspiring work experience in a poor economy drove Jeff Sheldon to build an outlet for his creativity in the design-driven lifestyle and apparel brand of Ugmonk. Today Jeff creates minimalist, silkscreened typographical shirts and other simply designed (yet premium priced) awesome, artisan products.

Jeff’s side project of designing t-shirts (while working full-time) started with four simple styles and 200 shirts. Today Ugmonk’s products are sold online and in 60 countries, but this growth hasn’t happened by accident. From the first day and first design, Ugmonk has been intentional about its focus on creating awesome products and giving their customers great experiences. Jeff sweats over the details because he knows they add up to a unique quality product “I won’t design a product that I won’t personally wear or use,” Jeff says. “Even if there are hot trends that might be easy to jump on, I try to stay true to my personal tastes as a designer and create things that are more timeless.”

A creative freedom lesson from Jeff: Like jobs, many products lack inspiration. Pay attention to the details and ignore the trends.


Anne Holman had been crafting vintage inspired sterling silver jewelry for more than a decade before she took the leap into building her business online.

Anne, a single mom, dreamed of working for herself to be more available to her son, yet she wasn’t sure she had the business savvy of a successful entrepreneur. While crafting artisan jewelry on on the side, Anne worked a day job in the custom art department of a fashion textile company. What she didn’t realize was that the essential business skills that she was learning every day at work were the exact skills and experiences she would need to create her own thriving brand. When Anne made the leap, she learned she already had the net—she knew what do. It wasn’t a matter of learning the skills; it was taking the step to use them.

A creative freedom lesson from Anne: Pay attention to what you’ve learned through traditional employment and other work. You may already have the business skills you need. (See also: skill transformation.)


Wendy Downs built a hand-crafted artisan bag business and found success by recognizing when it was time to grow beyond herself.

She couldn’t find a well-designed bag that fit her needs, so she did what artists do—she made one herself. When people saw what the bag she made and offered to buy it, she again did what many artists do to make money on the side—she sold them on Etsy—handcrafting every one by herself and working day and night to keep up with an ever-increasing stream of orders. When she started selling more bags than she could possibly make, she recognized she needed help—but staying true to her hand crafted design was critical. Since 2007, Moop has grown to include a team of four production assistants that cut, sew, and finish each bag by hand in her local Pennsylvania workshop.

A final creative freedom lesson from Wendy: Know when to grow. You can scale without selling out as an artist.

And That’s Not All!

Once the new guide is live, you’ll also hear stories and lessons from all of these additional artists and experts who partner with creative professionals:


I’m incredibly grateful to all these amazing people for sharing their lessons, and we’re excited to move closer to launch of a resource that will encourage other people to pursue creative freedom. Our goal is to create more success stories like these!

On Thursday we’ll have more info on the product itself, along with a big giveaway. Good things are in the works…

Feel free to share your comments.


Subscribe now and you’ll get the best posts of all time.


  • a terrible husband... says:

    So cool. I can’t wait for the toolkit!

  • teresa says:

    I have 2000 rapid rewards points from southwest what can I do with them??

  • Chris says:


    Not much. 🙂

  • Anita Chase says:

    Thanks for sharing all of these inspiring stories! This is more fuel for the fire of passion for my own creative ideas and more inspiration that eventually being able to make a living as a full time artist is achievable! Yay everyone, great work!

  • Susan says:

    Those are great stories-dreams made true
    Here is another one for you. This woman is amazing, what she did to get to where she is ,is outstanding. Talk about a change if direction-numerous times (without a clue she was making the turn).
    She helped my business to become my dream made real
    If you have time, check out her story
    Have a beautiful day

  • Caroline Frenette says:

    Thank you for sharing these incredibly inspiring artists & their websites!

    ->LOVE the concept behind Holstee
    ->NEED Ugmonk t-shirts for my fiancé
    ->ADORE the design of Cereal Magazine (I could feel myself breathing deeper as I was browsing their website, which says a lot quite frankly…)

    I will be sharing your new program with my peeps!

  • Uncle Beefy says:

    This is SO exciting, Chris!!! Can’t wait to see the whole shebang! Pre-congratulations!

  • Grant says:

    I produce family friendly web content. Both audio and video podcasts. Will this guide help me? Most of the examples seems to be people who create things to sell: jewelry, cards, etc.. Is this a good guide for musicians, painters, content creators, like me? Thanks. I’m a big fan.

  • Naz Laila says:

    I am eagerly waiting for the tool kit as I have taken the crazy steps of moving out of my professional career to pursue my creative passions and I trust whatever product or project you are doing Chris will be of great value to your tribe.

  • Anna says:

    So inspiring! Thank you, Chris, for sharing these stories. Your toolkit must be outstanding!

  • Ree Klein says:

    Oh….my….GOD…. I’M SO EXCITED!!!!

    I read the $100 Start Up and got fired up…
    I’m registered for the 2014 WDS and can’t wait!!!

    …you have the marketing thing down because I’m on pins and needles waiting to hear what’s next!!!!

  • Claus F. Berthold says:

    Thank you Chris, it is always an Inspiration listen to your writing.
    Do you think about a german transalation of the toolkit?

  • Le Minxxx says:

    These are great – Thanks for sharing!

  • Maria says:

    This is so funny! the past weeks I’ve been spending my time on preparing my own business. I had the idea about 4 months ago, but then got disappointed by my family’s discouraging reaction..According to their beliefs nothing could ever stand higher than the maritime sector, which is my educational and working field. Adding to that, it seemed outrageous to them to start a business in the middle of a crisis, from something so small and with a non- existent capital.
    Then I remembered a scene from one of my favorite movies ‘The Pursuit of Happiness ‘, where Will Smith tells his son..”You have a dream? you’ve got to protect it!”, here I am, working like crazy on my idea and everyday that passes by I kinda jump on successful stories like these that make me smile and work even harder!
    Thank you so much for your inspirational guidance Chris!! I’m planning to buy your $100 start up guide next week and enjoy your emails every single time!! I wish you could plan to come to Europe during 2014, as one of your trips.

    p.s. Hopefully, in a year’s time, I’ll send you my successful story as well!!

  • taura says:

    I am so thrilled! Thank you for compiling and sharing this wisdom!

  • Oliver says:

    I think the Holstee manifesto and its inspiration and passion still can be considered a creative pioneer. There are a lot of others to be found lately and some brilliant ones as well, but whenever I hear the word “manifesto” my mind almost inevitably connects the dots… 🙂

  • Britt Reints says:

    I’m noticing a trend:

    None of these people do a ton of looking around. They don’t copy or compare or tell themselves “well, someone else has already done that” because they don’t view the world from the outside in.

    Thanks for sharing, Chris!

  • Chris says:

    I’m curious if we can conclude on several skills that each of these thriving entrepreneurs have in common!

  • Mac McGowan says:


  • Nicole Delger says:

    Wow! Nicole Delger here from What inspiring creative leaders! Chris, Jen, and Omar, best of luck on the launch!

  • Karina says:

    I have shared the Holstee Manifesto with all of my friends and I’ve often looked back at it for inspiration. These stories are all so interesting! I can’t wait to hear more about them in the near future.

  • Ursala @ Diamond-Cut Life says:

    I love how this is about how practicing your passion and learning from the process uncovers treasures in life. Now to figure out the angle to light my own fire under my ass! Diamond-Cut Life talks about cultivating more of what you love in life by focusing on how to be rich in what matters. <3 Thank you for sharing best practices from some successful people Chris. 🙂

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  • Denise Duffield-Thomas (the Lucky Bitch) says:

    Wow – the world is full of amazing entrepreneurs. It makes me laugh to think that when I was in my day job, I barely knew ANY people who made a successful living – you just need to look!

    Thanks for sharing these stories!

    x Denise DT

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