Episode 038
Trading Security for a Dream Right in the Middle of a Health Crisis with Toby Myles
Her husband was diagnosed with cancer. She quit her job.
Not the plot of a rom-com – Toby Myles’s real life.
And it led her exactly where she was meant to go.
Toby Myles had a plan – a dream, really. Leave her corporate job of 15 years, grow her handmade jewelry biz, ride into the sunset with her newly retired husband and a few restored motorcycles. But life had other ideas: incurable blood cancer kind of ideas.
Most people would cling to the job, the benefits, the security blanket. Toby handed in her notice on New Year’s Eve and took the leap anyway – with zero guarantees and one giant motivator: time is a non-renewable resource.
In this moving and funny and wildly practical episode, Toby shares what happened next. Spoiler: it involves a copywriting side hustle that bloomed into a full-blown career, Friday chemo dates, a hand injury that rerouted her whole business, and the realization that storytelling (not just jewelry) was her real magic.
We talk about grief, risk, the real reason people avoid storytelling in business, and why sometimes the "bad timing" is actually the best timing there is.
“You can’t copy someone else’s story and expect it to land. Yours is the one that connects.”
Connect witH TOBY:
- LinkedIn: linkedin.com/in/toby-myles
- Instagram: instagram.com/tobymyles_copywriting
- Website: tobymyles.com
Timestamps:
00:00 – Meet Toby Myles – Jewelry, Copywriting, and One Big Curveball
02:30 – Her Husband’s Diagnosis: When Everything Changed
04:48 – The MRI, the Misdiagnosis, and a New Reality
07:05 – Quitting Her Job Anyway — and Why Her Husband Pushed Her to Do It
08:45 – From Jewelry to Copywriting – A Business Pivot Fueled by Life
11:40 – The $200 Copywriting Course That Changed Her Path
13:30 – Caregiving, Cancer, and How They Made It Work
15:14 – Taking Care of Her Own Health and Sanity
16:40 – Positivity, Partnership, and Choosing Joy in the Middle of Chaos
20:49 – Doing Work That Feels Good — Not Just What “Should” Be Done
23:30 – Boundaries in Business – How She Learned the Hard Way
26:30 – Storytelling as a Confidence Tool (Especially for Women)
29:50 – You Don’t Need a Rags-to-Riches Story
31:00 – Everyday Stories That Build Connection
33:45 – The Power of Origin Stories (and How to Find Yours)
38:54 – Her Podcast: Her Origin Story and Why She Finally Launched It
39:36 – Where to Find Toby, Her Free Course, and How to Work With Her