✨Weekly Insight
There’s always going to be an edge. Stress that was never fully resolved. A conversation you’re avoiding. The low hum of something unfinished. Alcohol doesn’t answer any of it. It just turns the volume down long enough for you to stop asking.
When you get sober, the edge doesn’t disappear. But you stop having somewhere to put it. Which means you have to actually look at it.
That’s the harder work. It’s also the more honest one.
What’s the thing underneath the thing? The drink was never really about the drink. It was about whatever you needed to not feel for a few hours. Name that, and you’ve got something to work with.
When you feel the pull, don’t reach for a drink or a reason not to drink. Reach for the thing underneath.
Ask it: What do you need?
Then actually wait for an answer.
Most people never get that far. That’s the practice.
🎙️Clear Conversations: Creative Minds in Sobriety
Kerry Hoffman didn’t have a rock bottom.
No dramatic low. No intervention. She just got honest with herself somewhere over the Atlantic, flying home from Aruba, reading Sober Curious cover to cover on a 17-week library waitlist she’d finally reached. By December 2019, she was done drinking. She never looked back.
Her story is quieter than most you’ll hear in this space. College drinking that felt normal, law school in New York that felt normal, a tech job in her thirties where everyone went out after work and showed up the next day less than stellar — and that felt normal too. The difference for Kerry was that she recognized nothing external was going to force the change. No kids on the horizon. A husband and a cat who weren’t going anywhere. “If I wanted to make a change,” she said, “I was going to have to proactively decide to make a change. The change wasn’t going to happen to me.”
So she made it.
What came out of that decision was a writing life. Kerry runs The Proactive Life on Substack — a newsletter about travel, creativity, work, relationships, and what she calls the subtle art of managing a messy, beautiful life. She writes about the tension between planning and spontaneity, between chaos and craft. She’s a project manager by trade, four years independent, and approaches both her work and her creative life with the same orientation: figure out the system, then make it more fun than it has to be.
That instinct shows up everywhere. She showed up to a hot sauce expo once unprepared and left vaguely destroyed. The second time she packed chicken nuggets for everyone in fanny packs and mapped the whole event in three laps — mildest to hottest — so nobody burned out early. It’s a small story, but it’s also exactly who she is.
She’s working on a book proposal. The writing community she’s been building around herself — a five-person writers’ group meeting in New York, events, connections made on Substack — is part of how she keeps going when the work is invisible.
That part landed with me. So much of what we make, we make alone. Kerry’s figured out that community isn’t optional to the creative process. It’s what keeps the fire going when no one can see what you’re building yet.
You can listen on Spotify and Apple Podcasts as well.
My Next Guest on🎙️Clear Conversations
Episode 047 with Orel on April 2 at 9:30a EDT
This week, I'm sitting down with Orel Zilberman — a software developer who spent years disappearing into 12-hour gaming sessions before a single book cracked something open in him. What followed was a complete rebuild: he quit his job, launched a business, failed for 600 straight days, and kept going anyway.
Now he runs WriteStack, a six-figure SaaS for Substack creators, and writes about every step of it at The Indiepreneur.
His story isn't about a dramatic rock bottom — it's about what happens when you finally put down the thing that's been keeping you small, and what you find out you're capable of on the other side.
🌿 The Reset Begins in Two Days
Kerry didn’t have a rock bottom. She had a flight home from Aruba and a book she’d waited 17 weeks to read.
That was enough.
What she found on the other side wasn’t dramatic either. Just access. To her writing. To her creative life. To the version of herself that had been there the whole time, waiting underneath the edge she kept turning down.
That’s what 30 days can do.
Not a program. Not a negotiation. A guide who’s been on both sides of it, helping you reach the thing you haven’t been able to get to yet.
You don’t have to figure out what’s underneath alone.
Kerry’s story is so important. We often wait for a disaster to spark change, but the proactive 'no-bottom' path is actually much more courageous. I’m fascinated by Josh’s idea of 'the edge'—in sobriety, we don’t lose that edge, but we finally stop running and start asking it what it truly needs. That is real freedom.