Holly Whitaker on regrets and growth in sobriety
And the hungover morning I Googled “how to stop blacking out”
I first encountered
online in early 2014. It had been a little over a year since I graduated college and moved to New York City and my blackouts were getting scarier. One bleary hungover morning I typed “how to stop blacking out” into Google and found an early version of Holly’s then-blog, Hip Sobriety. I pored over her posts, desperate for the answer to my plea. I wasn’t ready to stop drinking altogether, but I was intrigued by the idea of another woman who had struggled with alcohol and was writing to me from the other side.Over the next decade, Holly helped pioneer a movement. Sobriety had long been shrouded in shame and her work aimed to destigmatize it for a wider audience. She founded Tempest (formerly Hip Sobriety), a digital recovery program that was acquired by Monument in 2022, and wrote the bestselling book, Quit Like A Woman, which offers a road map to cutting out alcohol. Today, Holly writes
, a weekly newsletter, and is working on a second book.Holly and I took different paths to recovery — she has been notoriously outspoken about her qualms with twelve step programs, while I got sober with the help of one. Regardless of where you stand on the subject of how to get sober, there is no denying the impact Holly has had in starting important conversations about recovery modalities, women and drinking, and how we view addiction. Her work played a huge role in the rise of sober storytelling and helped pave the way for a new generation to explore sobriety.
I was so excited to talk to Holly about the impact going public with her sobriety had on her private recovery, the controversies she has weathered along the way, what she regrets, and how she continues to evolve in recovery. An abridged version of our conversation is below.
Note: Holly has previously spoken and recently published a two-part essay about her decision to use psychedelics in her recovery from alcohol. While there are many different versions of recovery, I do want to acknowledge that this may be triggering to some who practice an abstinence-only approach to sobriety. As I’ve shared in the past about my personal recovery, I choose to abstain from any substance that affects me from the neck up. There is no single “right” way to get or stay sober, nor is there a universally accepted definition of what sobriety means. As always, I encourage anyone thinking about their own recovery to share their experience and perspective in the comments section.
Hi Holly! Thank you for talking with me today. Let’s start at the beginning. You started writing about your recovery very early on. How long had you been sober before you went public with it?
I started writing in May of 2013, which was one month after I got sober. I had a blog called Little Miss Surrendered, which I think is still up somewhere. It was anonymous. Around early February 2014 I published one of those Facebook posts about being sober. I was less than a year sober and all my coworkers, ex-boyfriends, everybody from my life, was active on Facebook at that point. Pretty much overnight, something like 3,000 people read it. And it was crazy because it was so unconventional at the time. There were a couple of anonymous bloggers, but there were so few things that I found online. For me it wasn’t like “I want everyone to talk about recovery” so much as I was really enraged about how we talked about addicts and alcoholics and the “other-ing” that happened around it.
When Philip Seymour Hoffman died, I was furious at the feedback of trying to rehash what had led to his demise and this sense that it was something he did to himself versus it being this obvious cultural issue we had that was totally enabled through anonymity. I was so mad that addicts and alcoholics got publicized when it was the worst case scenario and it was pathologized to be this individual problem. I had such a different perspective and, at the time, I did not see my view of addiction reflected back to me. My view was that it was a really beautiful experience; a life giving experience. It wasn't sad. The ideas we have about junkies and addicts are just really perpetuated by how few people actually are visibly recovering.
So that was the beginning. From there, the only way I could get people to care about what I was talking about was if I turned it into a lifestyle blog. It really came from the 2013 ethos of turning yourself into a brand and using the tools of the Internet and influencer culture to get your point across. My intention was to bring awareness and I didn’t know how to do it other than cloak it in the way everyone else was getting attention.
And it worked! I remember finding your blog when I was struggling with binge drinking in my early 20s and searching for sober women I could relate to. I didn’t get sober until 2017, but I always remembered your writing. Even now, with more voices in the space, the stigma that addicts and alcoholics face – especially women – is so intense, and your early work was so instrumental in chipping away at the shame.
I’m curious what it's been like having your personal recovery be so intertwined with your work for all these years. I didn’t start writing publicly about my recovery until I had a little over a year sober under my belt, and in retrospect that was still so early. Now that you’re a decade into your recovery, do you ever feel burnt out or like you don't have all the answers? How do you continue doing the work alongside those emotions?
Well, the first thing is that what I set out to do has been accomplished. I didn't do it by myself; I was one of a lot of people experiencing a changing consciousness around anonymity and sobriety and addicts versus non-addicts. It was all emerging already. Jean Kilbourne was someone who spoke about it really early on, and there was Sarah Hepola and organizations like Women For Sobriety. So there was this trajectory, and then there was a tipping point where I felt like “I don’t need to do this anymore.” There are so many people furthering that work of holding Big Alcohol accountable or raising awareness around drinking or helping shepherd people through the process of recovery. So I don't feel any sense of obligation to it like I used to, to be honest.
I think that the biggest issue is that recovery is a really long process and I'm ten years into it. What has felt detrimental about it is that I've changed so much and there is this feeling, sometimes, of being chained to my earliest ideas because they still exist. They're still alive out there, so people think they're still alive within me. I do feel this outsized responsibility to my own recovery and sobriety that people who don't have a public persona or a public career around it probably don't feel. And so that's been a blessing and a curse.
On one hand, there's an accountability factor there that I think has been really important to me. But it’s also a curse in that I feel responsible for decisions that I make and people tracking too closely to my example. I’ve been exploring that in my writing over the last couple of years, and there are people who follow my work now and let me know they are really mad and disappointed with me. Because my voice has changed and my values have changed from what I wrote in my book in 2019.
What do you think people are disappointed by?
I have to be really clear: it's not everybody. You can get hundreds of pieces of positive feedback, but if you have a fear about yourself and you get one message that reflects it back to you, you can feel like it’s a whole thing.
But there is this sense that I'm not allowed to change and grow and expand, which I don't actually believe. There is feedback at times that I need help and that I've lost my fire. We're all in a liminal space post-pandemic and, on top of it, I'm ten years into my recovery. Also, there are really specific stages of recovery. There is the raw stage. The pink cloud stage. There is the “I will be this way forever” stage and then there is the “why am I doing any of this?” stage and the “what's the meaning of this?” stage.
I've been going through a really rough transition in my own life that has me not talking or writing about alcohol that much. I'm not writing a listicle of “12 Ways to Tell People You're Not Drinking” or “How to Travel Sober” or any of the aspirational, prescriptive self-help pieces that I built my career on. I'm more in the dark part of an experience and I'm writing from that underbelly.
People elevate you to be this person that's healed in some way and will never go through a dark period and has all the answers, which I'm not and have never claimed to be. It’s easy to put someone on a pedestal and expect them to behave in a certain way and when they diverge, it’s weird. I think that is what I have personally felt. It’s been a real thing of: what am I allowed and not allowed to do?
I can relate to the stages you’re describing. I’m a few years behind you and I’ve been thinking a lot about the transition from early sobriety to a steadier stage. In recovery, people talk about the “graveyard shift,” or years 5-10 of recovery. You’re not “high” on the novelty of sobriety anymore and you’ve settled into life with sober references under your belt. I think it’s natural to evolve, and at six years sober I’m not only thinking and writing about alcohol anymore. But I also know that people associate my writing with sobriety, so I always want to share about that aspect of my life, too. It’s a bit of a balancing act. You also had the added component of running an online sobriety school. Do you think that contributed to any pressure you felt to be this example of what a successful sober life “should” look like?
Yeah, I think it did. It goes back to the whole social media influencer ethos of the early 2010s and this idea of “be it” and then “teach it.” My philosophy has been about incorporating a softer, more forgiving, inclusive approach to recovery through harm reduction versus an abstinence-only lens. But I think when you have any kind of attention on you for one thing, you still internalize the need to be the model student, no matter how much you’re speaking about not needing to be perfect. So, yes, I really did feel that pressure.
Today I feel like I’ve broken up with it. And as I've broken up with it, so have other people. I think we’re going through a collective shift right now where we have a lot more awareness around parasocial relationships and gurus and self-care. And as I’ve gone through my own redefinition of what my work and role is, I think a lot of us have had the same questions.
I'm so proud of what I did, and I'm so proud of my book and the company that I started. I did good work. Would I do it again in that same way? Absolutely not. But that's kind of part of the deal, right? We do the best we can in the moment and we continue to evolve. That's the definition of being a human: try things, make mistakes, grow, learn. Try things again.
I love that. I want to talk a bit about different recovery modalities. I'm very open in my book, Drinking Games, about getting sober through a 12-step program. I tried to quit drinking multiple times on my own and it never worked. I ended up finding a community of women in New York and they really helped me navigate sobriety. Having women I could call from the bathroom at a wedding where everyone was drinking and I was feeling uncomfortable and say, “What should I do at this moment?” saved me.
I know that you didn't get sober through a 12-step group; I remember reading some of your early blog posts about your experience with meetings and how you didn’t resonate with some of the language they used. You also wrote an opinion piece for The New York Times about AA that went viral a few years ago and elicited a lot of emotional responses. What works for one person doesn’t work for everyone, and I’m always interested in hearing about different paths to recovery. On the subject of evolving, I’m curious if your perspective on 12-step programs is something that has continued to change and how you feel today about what you’ve previously written about them.
In my book and in all of my work, I've actually never said, “Don't go to AA” or that AA doesn't work. Most of my friends are in the program. My criticism has always been of the foundational understanding of recovery; who it is for and what tenets exist. I have consistently argued for an examination of what it means when our entire framework and understanding of recovery is suited toward one specific kind of individual. It upholds this idea of the alcoholic as the issue versus the cultural context and the society they exist in and the systems that they're a part of, like extractive capitalism and Big Alcohol. And so that has not changed.
In writing what I wrote about AA, I always knew it was going to be assumed that my position was that AA is bad. But I've written extensively about how important it is for there to be as many options as possible for every type of person. Most of the people that I'm close with are in recovery, and so I’m proximal to AA; it's part of my world. I don't really regret having made any comment that I've ever made about it.
I do probably regret the title of The New York Times article, but it was meant to be divisive, right? It was not to piss people off. It was to throw people a lifeline and give language to an experience a lot of people have had that isn't named, which is that this organization wasn't built for them. Because it’s a decentralized organization, your experience is going to vary widely. For example, you've lived in New York and Los Angeles. You have a million different meetings to go to and you have a community of people that are really accepting and probably really different from a really small town in, say, rural Alabama. The experiences that we have are shaped by that and I think that needs to be part of a discussion of who this was built for and what it means for us to still rely on this one system that still has, written into its code, what an alcoholic is and isn’t.
It doesn't mean that AA is not an incredible resource filled with wonderful people who want to save each other's lives. Someone who it wasn’t designed for can still walk through those doors and have their life saved by it. That can be true, and it can also be true that the default system of recovery that we have in the Western world is still built on principles that were established in 1930s America. And that might be disadvantageous to everybody who conceptualizes recovery and sobriety through the lens of AA.
You make some very interesting points. I remember how divisive your piece in The New York Times was when it came out, but I also remember that it started a lot of important conversations about recovery as a whole. What was the experience like for you after the piece came out?
To be honest, that was a defining moment. I was just, like, done with the space. And I don't think I ever fully recovered from the experience of writing something that was not meant to reduce any kind of access or take away anybody's definition or dignity but was met with backlash that was so severe, visceral, personal, and vicious. It just made me absolutely not want to talk about sobriety and recovery, you know?
I still think AA is a radical organization that promotes shared meaning and belonging and a support system. There are people I know that are in active addiction that I believe would really benefit from it, and then there are other people that I would never recommend trying it out. We have to remember nuance is such an important piece of this. The idea is to have more options and also to give vulnerable people more access and the words to object.
Thank you for being so candid on the subject. It’s obviously a very personal topic for so many and elicits a lot of impassioned reactions, and I can imagine it must have been incredibly intense to be on the receiving end of those criticisms.
I want to wrap on a positive note: I know you’re working on something new! Can you share anything about your forthcoming book or what you're most excited to write and talk about next?
My next book is called Lost Is A Place. I am trying not to talk about it at length just because I'm in the middle of writing it, but it's addressing this idea that there's a binary between addicts and non-addicts. The general audience for it is not just people in recovery. It’s looking at this specific period of time that we’re in and seeing how we might be able to apply some of what we know about how recovery works. It doesn’t matter what program it is or what it includes; we know people who struggle with addictions and use the container of recovery go on to thrive and have beautiful lives and do a lot better than the general public when it comes to navigating a lot of things.
Just like you said in your article for The Cut about being an awkward teenager when you were dating in early sobriety, you allowed the actual parts of you that existed in that state to come out. Wouldn't it be great if, instead of drinking our way through, we all did that? I like that I'm still an awkward teenager when I'm dating. You really are awkward when you meet somebody that you may or may not be romantically attracted to, and I think that’s a good thing. There is so much treasure in that experience of recovery that gives access to these experiences that we keep looking for through forced numbing and escapist means.
I'm writing about how to use the principles of recovery while we're going through such a transition and how to give that to a wider population than just people who stop drinking and doing drugs and gambling and watching porn. It's a limited set of people that get recovery and I think that if we viewed addiction differently and who qualified for recovery differently it would be a game changer.
It’s so true. Sobriety altered my perspective in so many areas, from wellness and social media to my career and mental health. I think so many people could benefit from that shift and from the permission to continue changing.
Yes! Some people will stay in a certain place forever, but it’s really sweet to be able to evolve.
This was such an interesting conversation, especially the part about access to different kinds of meetings and how because AA is decentralized a persons experience in LA or NYC is very different than in Alabama. I got sober at 28 through 12-step in 2007, so online sobriety wasn't a thing. In my early years I had to wade through the smoke filled rooms of mostly older men. I did what I was told and got a sponsor and worked the steps, but I never connected with any other women my age, but I stayed sober. I didn't really see it as a problem until I stared having kids. I was going through some pretty hard core PPA and I needed to connect with sober moms with young kids, but they didn't seem to be anywhere and the "mommy wine culture" was rampant. I think I was just lucky because I kept going to AA and still stayed sober. It's only been in the last five years that I've made real connections with other sober moms. AA for sure saved my life, but I don't make it my life, and i think that's what's saved me as i have continued to evolve over the last 15 years. Sometimes that means I get the side-eye from an oldtimer who "hasn't seen me in a while" but I don't let it bother me anymore. If another woman comes to me asking about sobriety I just focus on the primary purpose of staying sober and helping other alcoholics achieve sobriety (however that may look for that person) Thank you so much for sharing this story!
This was very interesting and raises interesting conversations. I've learned your moment of clarity comes when you face your fears. Sobriety gave me back me - my life. Self-medication kills you slowly. You can never get a handle on that. It's a highly destructive force that has to be dealt with on a spiritual level as much as a physical one.