GOAL DIGGER

The Secret to Happy Clients

Jenna Kutcher 

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March 25, 2019

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The customer is always right. Sure, you know that, but as an artist how do you balance your own creativity AND give your clients exactly what they want? Today’s guest found the perfect balance of her own creativity and a client-centered strategy to really give the people what they want AND grow her business.

Olivia Herrick is MY graphic designer, working on all things Jenna Kutcher, and she’s the artist behind the new Goal Digger branding that we launched at the beginning of 2019. Olivia calls herself a chronic creator, and today she’s sharing how she creates value for clients, the one thing she does EVERY morning, and how educating your clients can make you BOTH happier.

Meet Olivia

Olivia wanted to be a designer as long as she can remember. As a kid, she remembers creating logos in Powerpoint and pinning them on a bulletin board (the first iteration of Pinterest, maybe?) With two creative parents she always had the support to pursue a career in design. She earned her degree from Drake University and tackled a range of jobs in her first years out of school, eventually landing in a Creative Director position. It’s easy to paint 9 to 5 life as the enemy, especially as we talk so much about entrepreneurship on Goal Digger, but Olivia actually loved her job. She felt she learned so much in her time as an employee and the stability of consistency and health insurance was a great benefit. However, Olivia realized that she missed actual DESIGN, something she got to do less and less in her overarching role that include marketing, too.

How to Quit and Go Freelance

We get this question a lot: How do you prepare to quit your job and stay afloat as a freelancer or entrepreneur? This looks different for everyone, but for Olivia the catalyst for quitting her 9 to 5 was landed two retainer contracts while she was still employed, and one of them was her employer! She pitched her employer the idea of having her on as a graphic designer for 40 hours a month, and they’d still have the flexibility to hire someone to focus fully on marketing and make it a priority. It worked out as a best case scenario for both Olivia and the employer/client, because Olivia already understood the business and could continue doing the part of her role that she loved the most.

Olivia and I have similar stories when it comes to quitting to go full time freelance/entrepreneur. We both set ourselves up with a year runway, a full year of planning and preparation for what it would look like to no longer have the security of a full time. Olivia’s two 12-month retainer contracts were enough to replace her salary, giving her the same sense of financial security that her job gave her.

What She Knows Now

Oh, I know the feeling of looking back at the start of my entrepreneurial journey and thinking, “If only that version of Jenna knows all the things she knows today!” I loved talking to Olivia about what she’s learned about freelancing and running her own graphic design studio. She said the first thing she wishes she knew when she was just starting out is that in a service-based industry, especially a creative one, it’s never personal. “Accepting feedback and criticism from clients is just part of what we do, it’s just part of the business. The sooner you can realize that the easier your life is going to be.”

Second, Olivia said, “When you run your own business, every problem is YOUR problem.” This can be both bad and good. You pitch a job and you don’t get it? It sits with you. A client is unhappy? It’s on you. But on the flip side, if there’s a problem in your business, you’re the one who gets to solve it and be the solution maker. Lastly, Olivia learned later in her business that the earning potential in the creative field is actually pretty high. “I thought the only way I would sniff six-figures would be as a creative director for a big, well-respected agency in downtown Minneapolis… And that’s just not the case.”

Creating Just to Create

Every morning when Olivia wakes up, before she starts working on her client projects, she creates something entirely for herself. “In the current entrepreneurial climate, there’s this belief that everything has to be monetized,” but Olivia gives herself space to create because she just LOVES to create. A lot of the time these creative projects get stored away on her computer and never see the light of day, but others get shared on her social media, and some serve as practice exercises for client work she’ll be working on later in the day. For example, if Olivia has a client logo to create and it needs a dark, moody vibe, her for-fun design in the morning will start to reflect that so it’s an easy transition when she switches into creating for that client. It’s like a warm up for work!

Balancing Client Needs and Creativity

Olivia is creative, she’s an expert designer, and her eye for color and form are stellar. So what happens when the client comes to the table with ideas of their own that don’t quite match with what she would do if it was her own passion project? These are Olivia’s three tips for anyone working in a service-based and client-facing creative business.

  1. Be open-minded. Often times, clients have incredible ideas (and sometimes they don’t!) but what they do know better than Olivia is their own business. Olivia helps her clients translate their knowledge of their business into the visual realm.
  2. Feel an obligation to voice your opinion. When someone hires Olivia, she knows it’s because she’s an expert and proven problem-solver. But how she offers her opinion, in a thoughtful way with clear explanation and tact, is the difference between turning down a client’s ideas and building a trust to ultimately create exactly what the client wants.
  3. Success has to be defined as what the client wants and what makes the client happy. If you produce a project and you’re excited to have it in your portfolio, but the client doesn’t love it, you have failed at your job. With this definition of success, Olivia says, “It becomes less of a battle for you, which is what you want in client work.”

More from This Episode

Olivia was actually recruited away from her own studio by one of her clients, going back to a full time role after working for herself… So what did that look like? Was it worth it? Olivia often says, “What’s easiest for me is not what’s best for my clients.” What does that mean and what is her “client-centered strategy” approach? Also, we dig into the Goal Digger Podcast rebrand process! Talking with Olivia for the first time outside of my own design needs was incredible, and I’m excited for you to tune into the full episode and hear her super helpful, tangible advice for building your business in a creative service industry. Check out Olivia Herrick Design as you tune in on the player above!


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A small town Minnesota photographer, podcaster, educator and puppy rescuer, my happiest days are spent behind my computer screen sharing my secrets with the world. I'm glad you're here.

I’m an expert at online marketing, a nerd when it comes to the numbers, and my obsession is teaching others how to make a living doing what they love (without it taking over their life). 

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