He Quit Drinking and Discovered He'd Been Masking His Whole Life

Sometimes the blanket that keeps you warm is the same one keeping you from seeing clearly. Brian Kirkland's story is about what you find when you finally pull it off—not clarity, exactly, but the beginning of knowing what questions to ask.

Brian Kirkland was a senior director at a major association, able to hold his liquor and show up at 6 a.m. for logistics meetings—and that behavior was rewarded. When he stopped drinking, the security blanket came off, and what was underneath wasn't what he expected.

In this conversation, Brian talks about the long, uneven road after getting sober: chasing dopamine in new forms, walking into a job he knew was wrong within weeks, losing four people close to him in a matter of months, and eventually being told by a coworker in crisis to just leave it at home and get the work done. He also shares how diagnoses of PTSD, ADHD, and autism—arriving years apart—didn't simplify his story but gave him a way to stop calling himself broken.

This isn't a recovery arc with a neat ending. Brian is still in it, still figuring out how to lead with empathy in spaces that don't always make room for it—and now building 501(booze)(free), a resource for the association community around sobriety and harm reduction.

HIGHLIGHTS

00:03 — KiKi introduces Brian and the terrain of this conversation

01:30 — Brian names this chapter: "Pills and Thrills and Belly Aches"

03:43 — What rushes in when the security blanket goes away

05:05 — Chasing dopamine, shame, and the surprise of being supported

09:16 — Why Brian decided to go public about his sobriety

11:08 — What nobody tells you about what comes after you stop numbing

14:04 — The career spiral: burnout, a bad job decision, and a workplace that went Lord of the Flies

16:42 — Four losses in four months and a coworker's devastating response

19:10 — PTSD, ADHD, and autism: diagnoses that arrived years apart

22:06 — From "fundamentally broken" to understanding the wiring

25:25 — 501(booze)(free) and bringing sobriety talk into association spaces

27:42 — What feels risky—and what doesn't—about doing this publicly

33:11 — Brian's biggest takeaway: lead with empathy, not assumptions

34:23 — KiKi's closing: you don't have to be the bravest person tomorrow

Resources

Brian Kirkland, CAE — LinkedIn: https://www.linkedin.com/in/brian-kirkland-cae-5296774/

Ungovernable Context — Brian's LinkedIn Newsletter: https://www.linkedin.com/newsletters/7432243137835753472/

501(booze)(free) — Substack: https://501boozefree.substack.com/

About the Things Go Sideways Podcast

When life or leadership goes sideways, the story's just getting interesting.

Things Go Sideways with KiKi L'Italien features honest conversations with leaders, creators, and changemakers navigating disruption, uncertainty, and identity shifts. Each episode explores trust, resilience, and what it means to stay human when certainty breaks down.

New episodes share real stories about rebuilding agency and meaning without rushing to quick-fixes, spiritual bypassing, or pretending clarity comes easy.