Episode 029 – Caitlin Pyle – From Fired to Freedom: Overcoming Challenges to Create a Life You Love

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Caitlin Pyle is a 29-year-old former desk jockey turned business transformation consultant. And her journey to success was anything but easy. In this chat with Tony G., Caitlin shares with her trademark authenticity how she went from fired to freedom – creating a million-dollar business and living a life she loves. She discusses her experience as a personal trainer and how that helped her find her true path teaching others design their own life, creating the freedom they deserve.

How to write your own story and create a life of #freedom, on this episode of The #Entrepreneur Unplugged Click To Tweet

Writing her own story – coming back after being fired.

For Caitlin, a major turning point came when she was “relieved of her duties” at the age of 24. She shares with candor the experience of being let go by a group of women who not only fired her, but also personally attacked her. Caitlin discusses why this was such a formative experience for her and how it led her to the life of freedom she’s created. She shares insight into how she became a personal trainer, as well as why it wasn’t the right fit for her. It’s clear Caitlin has written her own story and she openly shares it with others to help them do the same.

Creating a life of freedom.

Once Caitlin decided it was up to her to design her own life, she found her way to proofreading transcripts. She started several blogs, and saw her proofreading income steadily grow over the next several years. Caitlin started sharing her knowledge with others in the form of eBooks and online courses, which would eventually grow into the flourishing businesses she runs today. Caitlin, along with the support of her husband Ben, now has courses and websites including The Work Anywhere Life, Proofread Anywhere, and the Monetize Your Genius course. Through this work, Caitlin is able to help others learn to recognize their genius and build a life of freedom around it.

Breaking free of the 9-5 and designing a life of freedom, on this episode of The #Entrepreneur Unplugged Click To Tweet

Moving beyond comparison and embracing your own brilliance.

Caitlin shares an obstacle she’s faced recently: comparison. She discusses the danger of comparison and how she managed to get herself out of playing the “comparison game”. Caitlin discusses with great openness how easy it is to fall into the trap of seeing what others have accomplished and how she managed to break away from that trap by sharing her struggles with others. According to Caitlin, if you don’t focus on how far you’ve come, you’ll end up worrying about where you haven’t been yet.

Filling your mind with hopeful things.

Caitlin goes on to discuss the role her husband Ben has played in growing the business and the importance of being able to live a life of freedom with him. She shares how they’ve managed to build this empire together and what it’s like to travel the world, while still making money. In closing, Caitlin offers some tips for struggling entrepreneurs who are trying to make it work. Her advice? Devote some time to filling your mind with hopeful things; surround yourself with positive people; go out and learn so you can gain the skills to get you there.

The value of surrounding yourself with #hope and #positivity when starting a business Click To Tweet


  • [1:13] Tony G.’s introduction of his guest, Caitlin Pyle.
  • [2:01] Caitlin’s backstory and how she found online marketing.
  • [5:05] Caitlin discusses what it was like to be let go and what life was like.
  • [9:18] Caitlin shares what it’s like to build a million dollar business and be able to travel the world.
  • [11:42] Caitlin talks about her product.
  • [13:54] How did you realize you didn’t want to be a personal trainer?
  • [15:26] The biggest highlight of your life this week.
  • [16:05] The biggest obstacle you’ve faced in your life this week.
  • [17:18] How did you stop playing the “comparison game”?
  • [19:47] How does your husband support you in your business?
  • [24:28] Caitlin’s “special sauce”.
  • [26:28] Caitlin’s advice for the struggling entrepreneur.
  • [28:03] How to connect with Caitlin.
  • [28:43] Some free tools you’ve found that can help people with writing, proofreading, etc.


Proofread Anywhere

The Work Anywhere Life

Monetize Your Genius Course



“#Comparison is the thief of joy” ~ Theodore Roosevelt, more on this episode of The #Entrepreneur Unplugged Click To Tweet

Learning to recognize your #genius and build a #business around it Click To Tweet

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