Kerry Hoffman is a project manager. She builds systems. She connects dots. She is, by her own admission, very type A.
So when she found herself going out and planning on two drinks, knowing she’d have three, and ending up with four or five — she noticed the problem. The drinking wasn’t following her rules. She was following the drinking’s.
There was no dramatic bottom. No external pressure forcing her hand. She and her husband had decided not to have kids, which meant there was no built-in forcing function on the horizon. No one was going to make this change for her. As she put it plainly: “The change wasn’t going to happen to me.”
So in June 2019, somewhere over the Atlantic on a flight home from Aruba, she read Sober Curious cover to cover. By December of that year, she stopped entirely. And what opened up in that space surprised her — mornings she could actually use, a brain that wouldn’t stop generating ideas, a writing life she hadn’t known she was waiting for, and a book about how to stop letting your to-do list run your life.
Kerry is the voice behind The Proactive Life on Substack, where she writes about systems, grief, travel, creativity, and what it looks like to build a world rather than just a career. She came to Clear Conversations with no performance of recovery — just the clear-eyed account of someone who saw a gap between who she was and how she was living, and closed it.
[00:56] The Drinking Years: College, Law School, and the Tech World
Kerry started drinking in college and continued through law school in New York City, where going out was simply “what everyone did”
In her 30s, after pivoting away from law into tech, the pattern persisted — late nights with coworkers, mornings that were less than stellar
She reflects that she was “in this boat together” with everyone around her, which made it easy to normalize
Key Insight: “When I look back on that, I think, oh, that feels like bad behavior, but we were kind of all in this boat together.” — Kerry Hoffman
[03:03] The Moment of Recognition: Control and Identity
Around 2018-2019, Kerry began noticing the disconnect between who she was and how she behaved when drinking
As a type-A project manager, she set rules she never followed: planning on two drinks and ending up with four or five
She recognized that without an external forcing function — kids, health crisis, relationship pressure — the change would have to come from her
Key Insight: “I knew that if I wanted to make a change, I was going to have to proactively decide to make a change. The change wasn’t going to happen to me.” — Kerry Hoffman
[09:12] The Strategy: One Drink a Week
Rather than going cold turkey, Kerry chose a single, clear rule: one drink per week
She felt an all-or-nothing approach would set her up to declare failure at the first slip
A trip to Japan four months in tested the rule — she broke it, felt terrible, and came home more committed than before
Key Insight: “I knew that a complex set of rules was going to be too much to manage and too easy to break.” — Kerry Hoffman
[15:30] What Sobriety Gave Her: Time, Writing, and the Morning
Kerry began waking at 5 a.m. to write, journal, or read — time that had previously been lost to winding down and rough mornings
She describes a consistent observation: even without a hangover, drinking disrupts sleep and slows the brain’s startup the next day
She flew herself to Savannah, Georgia for a self-designed three-day writer’s retreat, then did it again in Raleigh
Key Insight: “Ever since I stopped drinking, my brain is always exploding with ideas and fun things to write about, things to do, things to try.” — Kerry Hoffman
[18:52] Creativity Beyond the Canvas: Curiosity as a Practice
Kerry challenges the idea that creativity belongs only to people who paint, play music, or write
She describes themed dinner parties, a daily photo practice from a writing class with Ann Napolitano, and actively looking for unexpected details on daily walks
She connects creativity to curiosity, calling it the most appealing quality in another person
Key Insight: “I think creativity is very closely linked to curiosity. And that’s, I would say, the most appealing quality to me in another person — someone who is curious.” — Kerry Hoffman
[27:46] The Proactive Life: Systems, Grief, and the Book in Progress
Kerry is writing a book about using systems-level thinking at the personal level — becoming the project manager of your own life
Her argument: goals rarely make it onto the to-do list because people don’t operationalize them alongside the daily demands
She also writes about grief, travel, and books on her Substack, and recently started a writer’s group of five people in New York City
Key Insight: “Too often, what we want to do, our goals, the things that we aspire to do, they actually don’t make it onto the to-do list, right? Because there are things that we think about, but we don’t operationalize it.” — Kerry Hoffman
Key Quotes
“I knew that if I wanted to make a change, I was going to have to proactively decide to make a change. The change wasn’t going to happen to me.” — Kerry Hoffman
“The drinking is in charge, not me.” — Kerry Hoffman
“I knew that a complex set of rules was going to be too much to manage and too easy to break.” — Kerry Hoffman
“Ever since I stopped drinking, my brain is always exploding with ideas and fun things to write about, things to do, things to try.” — Kerry Hoffman
“I think creativity is very closely linked to curiosity. And that’s, I would say, the most appealing quality to me in another person — someone who is curious.” — Kerry Hoffman
Resources Mentioned
Sober Curious — the book Kerry read on the flight home from Aruba that sparked her decision to change her relationship with alcohol
Bird by Bird by Anne Lamott — referenced at a book talk Kerry attended
The Happiness Project by Gretchen Rubin — Rubin’s practice of choosing a visual theme for daily walks
Ann Napolitano’s writing class — where Kerry learned the one-photo-a-day practice
Athletic Brewing — mentioned as an example of how the NA market has expanded since Kerry stopped drinking
Where to Find Kerry
LinkedIn: Kerry Ann Hoffman
Instagram: @soverycary
Website: soverycary.co
Thank You
A heartfelt thank you to Heidi's Guitar Stuff, Florence Acosta, Inge van de Graaf, Noelle Richards, and everyone who joined us live for this conversation, and to Kerry Hoffman for her extraordinary honesty and insight. Your presence and engagement make these conversations possible.
With The Reset, You Get To Choose
Kerry didn’t wait for a reason. She looked at the gap between who she was and how she was living — and she chose to close it. No external pressure. No dramatic low. Just a clear-eyed decision that the drinking was in charge, and she wanted that back.
That’s exactly the kind of person the Reset is built for.
If you’re getting things done, showing up, functioning — but mornings take longer to come online, focus breaks more easily, and your output doesn’t match your effort — that’s worth paying attention to. Alcohol doesn’t have to feel like a problem to be quietly costing you.
The Sober Creative Reset starts this week. It’s 30 days. One container. Daily reflections, weekly check-ins, and a private space for accountability and support.
No labels. No lifetime decisions. No pressure to decide forever.
This is the Release phase of the work — removing what’s obscuring your footing so you can see what’s actually there.
And this cohort is pay your own price. You decide what it’s worth to you.
Kerry said it herself: the change won’t come to you. You have to decide to make it.
