Anna Grymes - How to Break into the Corporate World as a Freelancer

“Creatives and solopreneurs can turn on a dime. We are able to bulldoze big companies because we can innovate so quickly.”


The business world is changing. Where once the formula for success started with college and ended with a 40-year corporate career, we’re now seeing a shift towards creativity, fast innovation, and the risk-willing work ethic of the entrepreneur.

Anna Grymes is the master of both dynamics, having successfully navigated the corporate world while still maintaining a creative spirit. Anna’s passion is connecting creative freelancers who are corporate clueless but would benefit from the big contracts provided through corporations. She also works with corporations who wish to implement innovation and stay ahead of the curve.

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Years ago, the economy was dominated by big businesses with plans, budgets, and 10-year strategies. Now, smaller, scrappier companies, like Uber and Airbnb, have come up from behind and introduced affordable, accessible services based on social media mastery and the modern willingness of most people to step into a stranger’s car or sleep in their home.

Entrepreneurs frequently feel lost in this new landscape. Most freelancers and business owners working for themselves are blessed with creative minds but no experience climbing the corporate ladder. Unfortunately, most of these solo-preneurs also need high-paying clients.

“What corporations are painfully realizing is that they can’t take 2 years to implement a marketing strategy. The really scrappy companies that are coming up behind these hundred-year-old corporations have no problem saying, ‘We’re super-versatile and we’ll throw our strategy in the trash and start again in a day’s time’.” - Anna Grymes


If you are a freelance writer, looking for a way to access big contracts, Anna Grymes can help. She is master at bridging the gap between freelancer and corporation, offering instruction in resume-writing and general presentation, as well as navigating the environment. This allows creative minds the security and exposure of working with a large company, without feeling boxed-in or stifled. It also grants the companies in question access to faster innovation and a fresh, outside perspective.

Listen in to the episode to hear more about disrupting the industry, conquering fear of the unknown, and working with the quirks of a creative brain. As a creative, it could seem overwhelming to break into the corporate industry. However, take a moment to imagine the impact your success could have on the world around you.



Some Topics we talk about in this episode:


  • Introduction - 1:01

  • Anna’s story - 2:00

  • Corporate creativity (old vs. new) - 8:00

  • Risk aversion - 11:20

  • Anna’s mission - 14:30

  • The process - 21:15

  • Leveraging the corporate budget - 23:45

  • Wrap-up and Takeaways - 27:00



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Janelle Lara