Dana Kay’s first memory of alcohol is from a dinner party when she was five or six years old. She spent the night sneaking sips while the adults were turned away in conversation, and by the end of the night she’d passed out on a beanbag in the middle of the room. Nobody worried. Everybody laughed. It became a family story people told for years, and it planted something in her that took over four decades to undo.
By the time she reached her late 30s and early 40s, that early fascination had turned into two DUIs, years of drinking vodka out of water bottles during real estate inspections, and a daily system so precise she could stay “sober” for the school bus pickup every single day. She went to treatment twice in 2016. The first stay didn’t hold. The second one did, and it changed the entire direction of her life.
In this conversation, Dana walks through what actually separated her two attempts. It wasn’t willpower, and it wasn’t a stronger program. It was the difference between trying to stop a behavior and committing to becoming a completely different person.
As she approaches her ten-year sobriety anniversary on September 1st, she shares what that shift required, what she had to grieve along the way, and why she stopped trying to fit her writing into one tidy niche.
Show Notes
[00:00] Welcome and Introduction
Josh introduces Dana Kay as a writer, connector, and nurturer who’s been alcohol-free for over nine years, and the two immediately find common ground.
* Dana has been alcohol-free for nearly a decade, with her ten-year mark landing on September 1st
* Josh and Dana discover they’ve both had a DUI, and neither of them remembers much of the night it happened
* The tone is set early: honest, unpolished, and willing to go straight into hard material
Key Insights: “I got the police report in the mail... and I was reading the police report going, that happened? I didn’t remember.” - Dana Kay
[02:11] Growing Up “Cute Little Dana”
Dana traces her drinking back to childhood, growing up the youngest of eight (two big brothers, five step-siblings) between two very different father figures after her parents’ divorce.
* She had a well-provided-for upbringing but didn’t recognize it until she started paying her own bills
* She followed “the expected track”: graduated high school at 17, college at 21, became an elementary teacher, then moved into real estate in 2006
* She names her own talent and ability to always get hired as a “double-edged sword” that fed her drinking later on
Key Insights: “You can over-rely on your achievements and your talents... and that definitely played into my alcohol use for sure.” - Dana Kay
[04:43] The Beanbag Story
Dana describes her first conscious memory of alcohol in detail: sneaking sips at her parents’ dinner parties around age five or six, and passing out on a beanbag while the adults laughed above her.
* Her parents didn’t send her to bed during parties; instead they gave her small jobs, like bringing guests drinks, which kept her in the room
* She picked up early that drinking was “the absolute cool thing,” because she saw adults enjoying it and wanted to feel what they felt
* Looking back as a mother herself, she’s had to reckon with recreating some of the same environments for her own kids without realizing it at the time
Key Insights: “Instead of worrying or being sad, they were laughing. And they thought it was really cute.” - Dana Kay
[09:22] College and the Double Life
At UC Davis, Dana joined a Christian youth group (originally because the boys were cute) and found faith on a retreat at 18. But she kept a second, separate version of herself for home.
* Her day-to-day life revolved around a sober Christian friend group, while trips back to her hometown meant drinking, flirting, and partying
* She describes the pull of that split identity as its own addiction: “The complete rush was, what can I get away with?”
* After friends celebrated that she’d “never party again,” she made a conscious decision in the car to keep that part of her life hidden from them going forward
Key Insights: “It was a complete rush, more than alcohol itself. The complete rush was, what can I get away with?” - Dana Kay
[15:00] The Rock Bottom Years
By her late 30s, working in real estate, Dana’s drinking became a fully hidden system built around her family’s schedule.
* She lied to her husband about needing to “drop off flyers” or run open houses so she could go drink, and he had no way to track her irregular real estate hours
* She drank vodka out of water bottles during home inspections for over a decade, including with an inspector she’d known for 15 years who never suspected a thing
* She built a daily rhythm: sober and present for morning drop-off, drinking through the day, then timing a nap so she’d appear sober again by the time her sons got off the bus
* One morning in late August, her organs seized and she couldn’t move out of bed; she still told her husband she “just had a tummy ache” before he left for work
Key Insights: “That energy of wanting to get away with it, and fooling everyone, lived more in me than the substance did.” - Dana Kay
[17:49] First Treatment vs. Second Treatment
Dana explains the moment that sent her to treatment the first time, the relapse that followed, and the deeper shift that made the second stay permanent.
* Her therapist stopped a session mid-conversation and said, “we can’t get any further until you’re honest about alcohol,” which Dana had been carefully avoiding
* That night she Googled “how do you know if you’re an alcoholic” and discovered she’d searched the exact same thing on Christmas Eve, in a blackout she had no memory of
* After four sober months following her first treatment, she relapsed on a trip to Europe with her son, telling herself a little drinking wouldn’t turn permanent
* The second time she got sober, a therapist helped her see the real difference: the first attempt focused on stopping a behavior, while the second required building an entirely new identity
Key Insights: “If you’re going to be successful at this, you have to have an entirely new identity.” - Dana Kay
[34:29] Building the New Identity
Dana describes the practical, unglamorous work of rebuilding her life around the new identity, not just the absence of alcohol.
* She had to consciously change her driving routes because her car would automatically head toward familiar bars
* She built accountability into her schedule by not leaving gaps between appointments, and leaned on close friends and her husband to hold her to it
* She started a morning journaling practice, writing down small changes so she could reread her own words later, on the days she felt weak
* She noticed real physical changes, like hitting new personal records at the gym, and had to stop denying that sobriety was the reason
Key Insights: “No, Dana, you know that this is going to lead to that. This feels so much better. You wrote it right here.” - Dana Kay
[38:07] Noticing, Grief, and the Sunrise
Dana connects her recovery to a growing capacity to actually notice her life, and the grief that came with realizing how much she’d missed.
* She began noticing details on ordinary drives, like trees, mountains, an eagle, or a deer, that she says she never used to see
* She describes a memory of watching a sunrise in Mexico while drinking, and realizing only in hindsight that it was really “a place to go hide and drink”
* She’s come to believe that grieving what was missed isn’t just okay, it’s a necessary part of the process
* She also became more honest in her business relationships, without the manipulation she now recognizes she’d been running for years
Key Insights: “Not only is it okay to grieve that, it’s important to grieve that.” - Dana Kay
[41:11] Family Roots, What She Writes Now, and Where to Find Her
Dana closes by connecting her story to her family’s long history with alcoholism, and explains what she writes about today.
* Her grandparents were pillars of the local AA and Al-Anon community, and she grew up helping serve pie and coffee at their meetings, even while her own aunt struggled with alcoholism without full openness from the family
* After years of trying to force her writing into one niche, she’s landed on a simple framework: Connection, Acceptance, and Noticing (C-A-N)
* She writes about sobriety, motherhood of older kids, being single in your 50s, and starting over later in life, all under what she calls the umbrella of love
* She’s active on Substack and Instagram as Dana Kay, offers one-on-one calls, and leads gratitude and connection sessions at retreats she’s invited to
Key Insights: “There is no saying no to whatever your dreams are, whatever you want to do with your life. There’s just no no.” - Dana Kay
Key Quotes
“The complete rush was, what can I get away with?” - Dana Kay
“If you’re going to be successful at this, you have to have an entirely new identity.” - Dana Kay
“My identity took me into relapse because I still wanted to be the pretty, fun, cool girl, mom, friend, daughter.” - Dana Kay
“Not only is it okay to grieve that, it’s important to grieve that.” - Dana Kay
“There is no saying no to whatever your dreams are, whatever you want to do with your life. There’s just no no.” - Dana Kay
Resources Mentioned
* Gabor Maté’s approach to addiction — Dana references his idea that instead of asking “where’s the addiction,” you ask “where’s the pain”
* AA (Alcoholics Anonymous) and Al-Anon — the community Dana’s grandparents helped lead, which shaped her early exposure to recovery
* Dana’s C-A-N framework — Connection, Acceptance, and Noticing, the three principles she now writes and coaches around
Where to Find Dana Kay
* Instagram: Dana Kay
* 1:1 Calls: Dana offers personal calls for anyone working through what she writes about, from sobriety questions to relationship decisions
* Retreats and Workshops: She’s invited to lead gratitude circles, forest walks, and connection sessions at corporate and soulful retreat spaces
Thank You
A heartfelt thank you to everyone who joined us live for this conversation, and to Dana Kay for her extraordinary honesty and wisdom. Your presence and engagement make these conversations possible.
Your Next Step
Dana’s second treatment worked because she stopped trying to just stop drinking and rebuilt an entirely new identity instead. The first time ran on willpower, and it wore out by June. The second time gave her whole system room to actually recover, and that’s what held.
The Sober Creative Reset is built around that same shift. It’s a guided 30-day alcohol-free reset, with one-on-one coaching from your first session, not a program you follow alone. The fog and depletion so many high performers carry aren’t a discipline problem. They come from recovery that never fully completes. No labels, no moralizing, no lifetime sobriety vow, just real support while your energy, clarity, and follow-through come back online.
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