Classroom to Copy #17: Celebrating Copywriting Wins with Ex-Teachers Charlotte & Ben

podcast Oct 24, 2023

When my friends Ben Henken and Charlotte Ellis posted about their latest copywriting wins on the Copy Chief forum, I knew I had to get them back on Classroom to Copy to celebrate and share HOW they did it. 

It took a long time to schedule this across 3 different timezones — so this episode is an accomplishment in itself.

Here’s what we discussed when we finally recorded the episode in Nashville, with Charlotte calling in from New Zealand:

01:26: Learn about Charlotte’s past life as a preschool teacher in New Zealand, her freelancing journey, and the amazing copywriting role she just landed in Auckland…

02:07: Discover how Ben went from 12 years as a high school math teacher and assistant principal to becoming a freelance copywriter and email marketer — PLUS the life of freedom he’s pursuing with his family…

05:32: Follow Charlotte’s journey from freelancing to landing her agency job (which she applied to on a whim!), including how she aced the application process, crushed group interviews, and overcame imposter syndrome along the way…

16:48: Discover how Ben landed his biggest retainer client yet and impressed them with THIS fantastic strategy for turning an Upwork assignment into a long-term project…

25:37: Do you get lonely as a freelancer? Or do you prefer having control over your schedule and who you work with? Hear our varied perspectives on the pros and cons of freelancing vs. full-time copywriting work…

29:23: Learn about Ben’s month-long adventure traveling across Northeast U.S. in an RV with his wife, two kids, AND two dogs — while ALSO freelancing and scheduling meetings around spotty WiFi!

37:25: Get Charlotte and Ben’s BIGGEST tips for getting steady work as a copywriter — whether you’re freelancing or looking for full-time work — and the #1 most overlooked way to find the best opportunities (hint: it’s all about mindset).

You can connect with Ben and Charlotte here:

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