Do-What-You-Love Stories: Anna Measures

The people who are lucky enough to do what they love everyday come from all walks of life and take lots of different roads to get to their dream careers. Some people know from day one that they want to be their own boss. Others find that what they love to do is part of a regular ol' 9-to-5 job that they look forward to going to everyday. And then you have those who tend to dabble in lots of different work environments until they find one that just "clicks".

Today we get to hear the Do-What-You-Love Story of surface pattern designer, Anna Measures and find out what it is like to go from in-house designer to a self-employed freelancer, how to make the transition less scary, and some great resources for switching your creative brain into "business mode"… 

Tell us who you are, where you are from, and what it is that you do.

Hello! I'm Anna Measures, an illustrator and surface pattern designer. I help sell products with design. I'm a creative business-owning vegetarian based in Southern California who works remotely anywhere there's wifi. You can see some of my work at Toys R Us, Babies R Us and the Kennedy Space Center Gift Shop.


What made you decide to pursue this career path?

I knew when I was 9 that I was an artist. Later in college, I had a hot male model in my first figure drawing class. That didn’t hurt. ;)


After majoring as an Art Major, I got a job as a Giftware Designer. I designed “My Name,” personalized products for the juvenile market. Some product programs were mugs, drink bottles, sippy cups, melamine bowls and flashlights. It was great being an in-house designer for the experience. Now I’m a freelance designer.


What is the best part about running your own business? What is the most difficult part?

For me, the best and worst about running my own business is the same...the freedom.

It's very easy to get into a procrastination binge. I don't mind when things are slow because then I have more time to take a class or create personal work that might lead to a work opportunity later. That’s what I signed up for.

What’s hard is shutting down the internet, to keep promises to myself. Being a solopreneur is a marathon!


What is your most popular product/service?

Why do you think people like it?

Freelancing is my most popular service right now, my customers like it because I never miss a deadline. I like it because it expands my style and I always love a challenge designing for different markets. If I don't think a potential customer and myself are the right fit or the timing is off, I'll recommend another designer.


What advice would you give to someone who wants to pursue their creative dreams as a career?

Let's see…I'm going to give advice as if I had a magical time machine & was speaking to my younger self. 


Get on your lab coat & approach your dream like a test! 

Start small, like freelancing on the side while still working your day job. It takes a LOT of pressure off. Plus you can see firsthand what being in service of your customers is all about. See if you like it! Creating as a hobby is different than for your career. 

(I freelanced on the side for a year before I put in my 2 weeks notice. At the time, I was the only one in my job's Art Department NOT laid off, so it was really good timing. I started as an in-house designer for children's novelty items & giftware.)

Pssst...It was a bit like winning Survivor and walking away ;)

You can see more about how I went from side business to FULL time by signing up for my email updates.


What are you currently working on?

I'm working on developing a brand that's consistent & recognizable. 

I can design in different styles so I've been trying out new things…

Also I'm freelancing and have been working on product designs. I LOVE collaborating with my Customers. I eat feedback for breakfast. 



Where would you like to see your business in 10 years?

I'd consistently deliver the best experience & service to my Customers.

I hope to reach more people so I can show n' tell how gorgeous the world is! 

I traveled a lot as a kid. I'd like to share that rush whenever I found a beautiful new place or object. 

I plan to hire out all the parts I’m not good at (or don’t want to do) so I can focus on what I do best. I love to make time for continuing classes like figure drawing. 

I always want to S-T-R-E-T-C-H myself. 


What are 5 resources that you use most or that has positively impacted your business the most?

There are some wonderful how-to classes out there. I’d like to focus on resources that helped change my mindset from employee to business-owner. Here are some great resources that has helped the most:

  1. Seth Godin's Blog
  2. Steven Pressfield's Book, The War of Art
  3. Simon Sineak’s TEDx talk, Start with Why: How Great Leaders Inspire Action
  4. Brene Brown’s TEDx talk, the Power of Vulernability (cause putting yourself out there can be intimidating at first) 
  5. has free live online classes - (I like the classes that focus on business/marketing) Check out their calendar.

What is your favorite movie? 

I like a lot of movies, but Rocky 4 will always have a special place in my heart. It has the most montages I've EVER seen in a movie. 100% CHEESE. 

What's one thing on your "bucket list"?

I’d love to go to India. Places with some major history. I live in Southern California so 200 years to me is old. 

I hear Thailand has gotten a lot of influences from India so I want to see if I recognize similar things. (I used to go to boarding school in Thailand. The uniforms were like Harry Potter students' — except without the wizard robes.)

Anything else you'd like to share with us?

I only share certain stories to my email subscribers. 

(Including what REALLY happened when I went into a Tiger Cage.) 



My subscribers also get the latest news & free gifts like:

Free Guide: 5 Mistakes when hiring a designer that you don’t know you’re making

Wanna free copy? Download it over on my website.

All images above were provided by Anna. You can find Anna using the following links: