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October 24, 2023 23 mins

Many times on the freelance journey we can feel like we’re hitting a wall… Growth feels stagnant and opportunities seem scarce. But it’s in moments like these that the community we surround ourselves with is so important. Often, just leaning on others in the same boat can give us enough inspiration to break through.


Welcome to season three, episode two of the Freelance Founders podcast. We’re talking to Libby Connolly, a Chicago-based creative director and founder of Studio Libby Connolly. 

Today, Libby is telling us about being a small business owner without a business background, crystallizing her goals, and why client communication is so important.


Some Questions asked:

  • When you went freelance, what was your strategy to build a network? (01:23)
  • What has been your biggest challenge going freelance? (04:02)
  • How does understanding the psychology of a brand influence your work? (11:05)
  • How would you measure success for yourself? (13:06)
  • What are some of your goals for your own design studio? (15:11)


In This Episode, You’ll Learn:

  • How Libby got into design as a career (00:33)
  • Libby’s process when it comes to getting started with a new client (06:52)
  • Why Libby once canceled a client contract (11:49)
  • The advice Libby would give her 20-year-old self (19:10)


Connect with Libby:


Let’s Connect:


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