Gary Allen had his first drink at 19, a pint of Harp he didn’t even like. He kept drinking it anyway, because for the first time, he felt like everybody else. Gary grew up in rural Ireland, the oldest of three, and has used a wheelchair full-time since he was 13. Alcohol became the thing that closed the distance between him and the room. He didn’t fully realize that’s what it was doing until decades later.
For 26 years, drinking looked completely normal. Nights out with his brothers turned into nearly 20 years of sharing wine on the couch with his wife. Nothing about his life looked broken. He had a steady IT career, a mortgage, and a stable home. At 45, he just noticed something simple: it was getting in his way now.
That one observation, made on a flight home from Barcelona in January 2018, led him to commit to 100 alcohol-free days. He hasn’t had a drink since. Within weeks, he stumbled onto a coaching course and knew almost instantly it was where he belonged. Nearly nine years later, at 54, Gary runs his own practice, the Life Design Collective, helping people in midlife ask the same question he once asked himself: is this it, or is there something else?
[03:06] Growing Up Different in Rural Ireland
Gary was born and raised in rural Ireland and has used a wheelchair full-time since age 13.
He didn’t have his first drink until 19, well past the age most of his peers started.
Drinking made him feel like part of the group in a way he hadn’t before, since he grew up looking different from everyone around him.
Key Insight: “It just made me feel like everybody else.”
[07:04] The Wake-Up Call at 45
His drinking shifted over time: nights out with his brothers in his 20s, then almost 20 years of sharing wine with his wife on the couch.
Nothing about his life looked dramatic. He had a steady job, paid his bills, and everything seemed fine on the surface.
At 45, he simply noticed alcohol was in his way and decided to see what life looked like without it.
Key Insight: “It’s getting in my way now.”
[07:46] From IT Career to Full-Time Coach
On a flight home from Barcelona in January 2018, Gary committed to 100 alcohol-free days. He never had another drink after that.
Within about two months, he found a coaching course and knew right away it was what he wanted to do.
He ran two full workloads at once (coaching and his IT job) for years before finally leaving tech in 2023 to coach full-time.
Key Insight: “I didn’t actually go, okay, I’m quitting my job and I’m going to sell a house and move to Bali.”
[10:57] The Pattern Behind Change That Sticks
Most people start by naming what they don’t want: hangovers, health problems, tension at work or at home.
Once that clears, the real work begins, which is figuring out what you’re actually moving toward.
Change rarely works on the first try. Every attempt adds information, and the streaks get longer as people learn instead of judging themselves for slipping.
Key Insight: “It doesn’t ever really work the first time.”
[13:04] Curiosity Over Judgment
Gary calls curiosity, instead of self-judgment, the biggest shift he sees in people who make change last.
Instead of asking why they failed, the useful question becomes what they could try differently next time.
This mindset reaches far beyond drinking. It’s the difference between staying stuck in a cycle and actually moving forward.
Key Insight: “If you can treat it with curiosity and not judgment, that’s the real game changer.”
[17:00] Creativity, Clarity, and Finding Substack
Gary spent almost 30 years in software, which he describes as genuinely creative work, even though it was never quite the right fit for him.
About six weeks into sobriety, he experienced a level of energy and clarity he’d never felt before.
That clarity opened the door to writing. He’s been on Substack for close to two years and is nearing one full year of his weekly newsletter, Second Act Sunday.
Key Insight: “Creativity almost by default jumps in.”
[21:02] What Happens When the Numbing Stops
Removing alcohol doesn’t remove hard feelings. It just means you feel all of them, not only the ones you’d pick.
Gary resisted gratitude journaling at first. “Thank you very much, I’ll pass,” he says of being told to write down three things he was grateful for.
The practice ended up helping him see what he already had and who he already was, built by parents who raised him to believe he could do anything.
Key Insight: “It did allow me to kind of see what I have and see who I am.”
[29:19] Building a Second Act After 40
Gary pushes back on the idea that life needs to be fully figured out by 40, and that any change after that is too hard or too late.
His program, the Second Act Blueprint, is a seven-week experience helping people mostly between 40 and 60 design what comes next. The sixth cohort starts next Tuesday, with two spots still open.
He didn’t blow up his life to make his own change. He changed slowly, over eight years, while keeping his job, his house, and his marriage intact. He’s now compiling a year of his newsletter with an eye toward turning it into a book.
Key Insight: “It took me, really, eight years of slow change.”
Key Quotes
“It just made me feel like everybody else.” — Gary Allen
“It’s getting in my way now.” — Gary Allen
“If you can treat it with curiosity and not judgment, that’s the real game changer.” — Gary Allen
“I didn’t actually go, okay, I’m quitting my job and I’m going to sell a house and move to Bali.” — Gary Allen
“It took me, really, eight years of slow change.” — Gary Allen
Resources Mentioned
One Year No Beer — the program Gary joined to change his relationship with alcohol, where he later became a coach and led a team of nearly 20 coaches
Life Design Collective — Gary’s own coaching practice, built around midlife redesign
The Second Act Blueprint — Gary’s seven-week program helping people in their 40s, 50s, and 60s design what comes next (Next Cohort Starting on Tuesday July 21)
Second Act Sunday — Gary’s weekly Substack newsletter, closing in on its first full year
Richard Rohr and Arthur C. Brooks — authors Gary reads on the idea of a second act in midlife
Where to Find Gary
Email: hello@garyallen.ie
Website: https://garyallen.ie/
Thank You
A heartfelt thank you to everyone who joined us live for this conversation, and to Gary Allen for his openness and wisdom. Your presence and engagement make these conversations possible.
Building Your Own Second Act
Gary’s story keeps coming back to one idea: change that lasts doesn’t come from a dramatic overhaul. It comes from removing the thing that’s been quietly draining your energy and clarity, then giving yourself time to rebuild from there.
That’s the same work at the center of The Sober Creative Method™, my 90-day, 1:1 coaching experience for people who want to remove alcohol as the barrier to their full creative capacity. No labels, no rock bottom required, just a structured path back to the energy and clarity that’s already yours.
If this episode resonated, send me a message and tell me where you’re at. I read every one.
