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”
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.
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.
I do remember you, actually, and the near thousands of other (self) tortured souls who've messaged me for advice. Even if I don't remember your names or faces, I always remember the stories you've shared. You, in particular, reminded me of a good friend that I met while teaching Kindergarten. At 38, they'd always tell me about their dreams to leave teaching, too. They wanted to one day marry, become a parent, and go back to school for their MBA. They'd say, "Oh, I wish I was as young as you! I could take all the risks!". I was 24 at the time, and that never quite made sense to me… how are we expected to only change our lives before turning 30 if we're still learning who we are in our 20s?
I'm going to tell you what I told them: We only have one shot at this magnificently tiny life. Don't spend it in fear and regret. Please.
There's a movie I love called Ticket to Paradise starring Julia Roberts (who I don't particularly love). But I do love her character's mantra, "Why save the good stuff for later?" If all you had was say… 10 years left to live (God forbid) would that make the decision to chase your dreams a little easier?
Consider this, too: What kind of person do you want your children to see when they look at you? And if you don't, can't, or don't want to have children, what kind of leader do you want to be? The kind that teaches people that their dreams don't matter as much as other people's comfortability? The kind that silences their calling and inadvertently inspires others to do the same?
And yes, you're a leader my friend. Because anyone who has the ability to influence someone else is a leader, and we all have that ability.
You also mentioned that you'll be 40 when you graduate. So? Won't you be 40 if you don't? If life goes well, you should have about 50 more years of living after graduating. Do you want to live the whole second half of your life as a miserable business coach who can no longer stand their clients or waking up in the morning to go to work or as a celebrated filmmaker who hosts grand parties to celebrate winning the Oscars1 and invites people like Julia Roberts over (and promises not to tell her that I'm not a fan of hers).
I hope you choose the latter.
There's a scripture that I think you might need right now, it's Isaiah 43:2 and it basically says, "when you go through deep waters I (God) will be with you, when you walk through fires, I will be with you."2 I appreciate knowing that I will never drown because God will be right there to pull me out of the waters, but what I love most about this scripture is the word WHEN.
When you go through the waters, not if. I have no data to back up this next point, nor do I feel like reading through research journals right now, but I'd bet to say that most of us humans try our darndest to avoid pain, hardship, heartache, and strife… but it's inevitable. You will go through hard times. You're going through them now, and look, you're okay. And you'll keep being okay when you decide to go to film school, graduate, grow in the industry, and clink glasses with Julia Roberts.
In essence, what you're asking is if you should say "yes" to followers, clients, and comfortability, or your dreams? And to that, I'll leave you with one of my all-time favorite quotes:
"Every time you're given a choice between disappointing someone else and disappointing yourself, your duty is to disappoint that someone else. Your job throughout your entire life, is to disappoint as many people as it takes to avoid disappointing yourself." - Glennon Doyle.
I have no idea if filmmakers win Oscars, but you get the gist! Haha
“When you pass through the waters, I will be with you;and when you pass through the rivers, they will not sweep over you.When you walk through the fire, you will not be burned; the flames will not set you ablaze.”
