On Starting Over with Courage

This is an anonymous advice column. I remove any major typos or information that may reveal the writer's identity. However, to preserve authenticity, I do not edit the tone, language, or personal details shared in the message. In this letter, I edit some curse words.

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“Dear Isis,

I'm a 36 year old man who's been inspired by your creative journey for a while now. I came across your Instagram 2 years ago and within months you had announced your exit from business coaching. I'm a business coach as well which is why I initially followed you but something in me was awakened by your "quitting." It's incredibly encouraging to watch you lean into your writing. In a way, I want to do the same. But, as no man likes to admit, I'm scared sh*tless. I hope this doesn't give away my identity, I don't mind if it does, but I messaged you last year about my desire to pivot. In response, you sent a prayer and told me about The Artist's Way's concept of a shadow artists. That brought me much clarity, I've been a shadow of myself for so long. I'd like to be a Filmmaker. But, it's so different from what I do now and what pays my bills. How would I explain my career change to my audience, clients, and peers? I'd love to go to film school, I applied on a whim and got accepted, but should I go? I'll be 40 when I graduate. I never thought I'd be unsettled at 40. I also keep thinking about all the money I put into my marketing degree. I don't know what to do and will appreciate any words of wisdom you have.

- Scared Sh*tless”

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Today’s advice column is for those who…

🔘 Think it's too late to pursue their dreams.

🔘 Worry they’ll disappoint others in the process of changing.

🔘 Feel trapped between choosing financial security or creative fulfillment.

🔘 Are “Nosey Nancies” like myself & love being in the know… I see you.

P.S. This post is paywalled, but free subscribers can read a little further before the paywall hits.

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Dear Scared Sh*tless,

Last year, I was booked for a speaking engagement in Los Angeles and purchased a $740 dress to celebrate. It was the most money I've spent on clothes, and I'll probably never spend that much again. But this dress? It was so LA-worthy. It was handstitched in Ghana with ivory beads along the collar. It looked like a 70's mini dress, a complete show stopper —which was exactly what I was going for.

And then, months later, during a "how to heal naturally from endometriosis" deep dive, I learned that my beloved dress was made of polyester and acrylic. I had to decide between keeping a beautiful, toxic dress that was literally making me ill or letting it go. I chose to let it go.

Just because I spent way too much money on it, doesn't mean it was worth my health. And from the looks of it, your dress—business coaching— is making you sick, too. How do I know? Because you've been anxious about it for over a year. 12 months after your initial DM to me, you're still typing a letter, probably with your stomach feeling queasy and your heart feeling heavy, asking for permission, yet again, to leave. So here's your permission slip. GO.