Episode 67: How Self Trust Gets You To Sobriety

If you've ever promised yourself, "Today's the day I stop drinking," only to find yourself pouring another glass that evening, this episode is for you.

Lindsay breaks down why so many high-achieving women stay stuck in the stop-start cycle with alcohol and why the problem isn't a lack of discipline or willpower. The real issue? Self-trust.

In this episode, you'll learn why lasting sobriety isn't built by trying harder, but by becoming someone you can consistently count on. Lindsay shares her Identity → Practice → Trust framework, explains why slips are valuable feedback (not failure), and offers practical ways to build confidence one decision at a time.

You'll discover:

• Why willpower isn't enough to change your relationship with alcohol
• The hidden role self-trust plays in lasting sobriety
• How to stop viewing slips as failure and start using them as information
• Why practicing alcohol-free living matters more than consuming more information
• How identity shifts make staying alcohol-free feel natural—not forced
• Simple questions to help you identify whether you're struggling with identity, practice, or trust

If you're tired of negotiating with yourself, breaking promises, and wondering why moderation never seems to stick, this conversation will help you approach sobriety in a completely different way.

Remember: Information doesn't create transformation. Action does.

Transcript

Lindsay Hennekey (00:02.688)
So glad you're here today. I'm running a little casual today. It's hot. It's summer. I'm I'm here for it. It's I I don't know about where you live, but I live in the northeast of the United States and it gets pretty gloomy here in the winter. So I I am thriving in this heat, but it's also kind of making me dress a little bit more casual, I guess to say. and there's this element of like

The way we want to get what we want. And I very much believe that part of that is like presenting myself and showing up like where I feel good. And that often for me is related to my hair being done, and what I'm wearing. And so this, I promise there's a point to this. It's all really tied to sobriety and the habits that we keep and how when we

We kind of have to act as if we already have the thing in order to get it. And so in this episode, I want to walk you through the way I think about lasting sobriety and why smart, high-achieving women are like more prone to stay stuck in the stop-start cycle and why rebuilding trust is the real foundation for changing your relationship with alcohol. And I think that

Having self-trust and this ability to take action on a daily basis to build trust really starts with like how you take care of yourself first thing in the morning. And for me, that includes, like I was kind of saying, like getting dressed. And but in this heat, sometimes I just want to throw on a pair of shorts and a tank top. So, okay. The woman this episode is for.

I'm going to paint a bit of a picture for you. This is for the woman who knows she doesn't have just one glass. Maybe you've done a dry January or a sober September. You've taken some breaks. You're reading the books, you're listening to the podcasts, and maybe you've even had some long stretches without drinking, but somehow you keep ending up in the same place. Now,

Lindsay Hennekey (02:27.468)
You're successful in so many areas of your life, but this is the place where you keep breaking the promises to yourself. Now, I know this was me forever. Forever. I had so many. I'm going to start fresh on Mondays. I talk about this a lot where I would wake up on Sunday mornings feeling really angry with myself for drinking too much. And then I would.

Create this new fresh list of rules for the week. And I would do some things to make me feel productive and better about myself, you know, exercise even though I felt like garbage, do all the meal prepping, even though I didn't want to eat healthy food in that moment, you know, and I would I would start my week fresh. But usually, like it was pretty normal for me to have a solid Monday where I wouldn't drink, but by Tuesday,

The pressure would be building, and I would already be saying, F it, I deserve this. It's been a long day. Ugh, the rest of this week is gonna be so packed. And I deserve to like sit on my couch and just drink. And so this was that stop-start cycle for me. And then I would look too far forward, and there was always something that kind of told me, like, well, now's not a good time to take a break from drinking because

You have this thing where drinking is required. So I the stop-start cycle looks like basically not having the tools or the willingness to try the thing that you think requires drinking without drinking. And so because of that, you feel like you're just in a I'm never going to get there. This isn't a good time. I can't do this kind of state. But

I promise you, like when we have this emotional hangover of waking up thinking, like, why did I do this again? That is never going to end until you start like believing in yourself that you can try the thing that you think you need to drink at without alcohol. And here's the thing, like

Lindsay Hennekey (04:50.878)
We think we have to believe that we can do it in order to do it. But I'm gonna talk through today how it's actually backwards. It's actually the other way around. You know, I've coached hundreds of women through this for over three years, and I really do not believe that the issue is around willpower or having more discipline.

The deeper issue here is self-trust. It's not about believing if you can do it. It's about trusting yourself that you're going to follow through in the moment. And we have to just take the scary action. Otherwise, you stay in that stop start cycle. You know, I think a lot of the sobriety space or this world of becoming sober.

unintentionally keeps women stuck in this place of effort and shame and like short-term behavior change. And I really I disagree with this fundamentally because it's not actually how we work or how we create a life that is sustainable and feels good. I really believe that quitting drinking is about self-trust built through repeated follow through. So

It's not willpower because willpower is finite. Willpower is going to help you like stay up late and finish a presentation, but you're not going to be able to do that every single day on repeat. So like it's it just doesn't work. Willpower does not rebuild the belief that you can count on yourself. And when I say count on yourself, I mean when in the morning you say, I'm not going to drink today, and then at night, you don't drink today.

Like willpower is not going to get you there. The other thing that I think is really common when it comes to trying to quit drinking. And, you know, this is really specifically more, I think, prominent in the AA world. And is when having a drink equals failure. There is nothing that I want you to believe more than a slip.

Lindsay Hennekey (07:10.314)
Is actually just telling you something. It's telling you where your work still lies. It's feedback, it's information. And when we have this perfection mindset, which many high-achieving women have, that's when we look at having a drink as failure. And it's not. It's not. It's like, well, that is an area that I need to pay attention to now. And so

A lot of times, you know, I might have a client who they have a nice long stretch, 30, 40 days, and then they have a slip and they're like, I've just ruined everything. And they may even cancel a call with me or something because they're feeling really bad about it. And I really help them like reframe it. It's why it's so important for women when they're working with me to show up even on the days that they don't feel like it.

And you know, come to the call even when they've had a drink or something, because that's where we can like look through where how we learned where the system needs support. Like, okay, I'm gonna point out all of the amazing things that you've done in the last month, and we're gonna compare that to the month before and the month before, and really dig deep of like, okay.

This is what we need to focus on now. I want you to bring your attention to this so that that doesn't happen again. And you this is what I mean by getting more information. Another thing that is really common is like we can't just focus on don't drink. We can't say, I'm not drinking today. I love to like we have to rise up from that because it doesn't actually tell us what we're going to do instead.

I focus on building these internal skills and coping mechanisms so you're not just reaching for alcohol on autopilot. And so this is what I want you to think about. Like, what am I missing?

Lindsay Hennekey (09:14.85)
What am I missing in my day-to-day so that I can take care of myself and not use alcohol as my coping mechanism? And I help women do this because the tools are different for a lot of women. What works for one may not be useful for somebody else. And there's like so many women use wine to transition from like work mode to home mode. And I know that like you don't need

Some big lecture or inspirational speech to help you get through that. You need a replacement practice. So this is the other piece that is so important. We have to interrupt your autopilot of using wine to transition from work to home or to decompress and like actually create a practice that helps you take care of yourself and feel prepared and able to be present for your family or just.

For whatever it is that you have going on that night. So the next thing is that we feel like we need the information, like we're thinking ourselves into change. But again, when we think about believing if we can change and just like thinking about it, that's not actually gonna get us there. We I help women practice their way into change. You have to

practice the real life moments without drinking in order to get to the point where you don't drink anymore. Listening to 47 pat podcasts throughout the week, but not having a plan for Thursday or Friday o'clock or not having a plan for Thursday or Friday at five o'clock, that's not going to help you. This is why my work is not just about removing alcohol. It's about creating the coping skills.

Building the self-trust and that emotional resilience so that alcohol stops being the thing you reach for. You have to create your alternative practice. We can't wake up and say, I'm not drinking today. Your brain doesn't know where to go. Like you have to have the new thing ready for it to take on. So, you know, this work is deeply personal. And I think that.

Lindsay Hennekey (11:38.915)
When we hold on to this like double life that we have around our drinking, where this external version of ourselves that we put out into the world on paper, we look amazing, we're sharp, we're we always get everything done, we're successful, you know, that is the thing. But on the inside, we're just like a solid hot mess. We are scatterbrained. One of my clients told me.

I just always feel so scatterbrained. And it's so true. It's like we feel like we're not being this genuine person because we feel like a big fat liar. Like, this person thinks I'm amazing and so successful and I gave get everything done. But the reality is every night at 5 30, I'm on the couch ready to put down two bottles of wine and watch HGTV for five or six hours. Like, no.

Those that action doesn't match up with who we want to be and how we wanna be living. So I know what it feels like to break promises to yourself around alcohol. And I had like, I talk about this a lot in my coaching containers because it's so important so that the women it's important because the women need to see like how long this can actually take.

Remy, come on.

Lindsay Hennekey (13:11.342)
It's so important because I really want people to understand like how long it can take to go through all of these phases. Like I spent probably eight years trying to moderate my drinking. I remember thinking in my early 30s, like, okay, I'm realizing that drinking isn't really fun anymore. Like, I'm not just drinking.

when I'm out or when people come over to my house to spend time with me. Like I'm actually drinking alone. And I'm drinking alone a lot. Like it wasn't fun. And so that is when all those rules come into play because and that can last many, many years. Like I spent a long time trying to keep alcohol in my life. Like I I wanted to be the person who could just have a glass of wine on Friday nights and relax after work.

And then I would for years I tried to be that person and I never got there. And my gut says if you're listening to this podcast, you probably have been trying to do that for a long time too. Or I'm only going to drink on special occasions. I'm only going to drink on my birthday. Or it's my friend's birthday this weekend. We're gonna be celebrating. So obviously I have to drink. And like

That just keeps you in a place of always feeling like you're starting over because what happens is you make an exception for what is acceptable to drink. And that's the rule breaking. So this is now we're into broken promise territory. You well, I know. I I I know it was my friend's birthday and I went to her party and she turned 40 or she turned 50 and I drank and

Now I feel like garbage. So I'm just gonna, I'm just gonna start over tomorrow. And then now you're drinking again. And it's like that you always feel like you're starting over when you're living in moderation. And so I want you to really think about that. Like thinking about how many times, like how much evidence do you need? And how many times do you want to wake up in this like shame spiral over your drinking? And it's like

Lindsay Hennekey (15:28.546)
We weren't meant to keep trying to do the same thing that isn't giving us the results that we want. That's the signal of like, okay, I need to do something differently. I need to approach this differently. And I need to have an open mind about what might come up for me. And so there's this turns into that big identity shift of becoming somebody who doesn't drink. And so when I think about this, I look at like

The old version of me who drank like outwardly, socially, at work things, at social events. Like I was always the one who was like, you know, let's stay for another round, or I'll bring a couple of bottles. Like I was always bringing enough wine. Like there was never a circumstance where I was involved with something and there was going to be a wine shortage. Or like that became my identity, or like,

Let's Lindsay, do you want to hang out this weekend? And like the first thing would be like, let's go to a winery. Like that became my identity. And it's not that like the my identity now, I mean maybe outwardly on social media, like I am a sober person, but in my behind the scenes life over here, I'm not I'm just a person who doesn't drink. I'm a person who

has finally discovered how I want to be living, what's really important to me, and my actions now match up with those things that are important to me. Now, am I perfect? No, I still do things that are not like how I want to be living. For example, sometimes I lean into food, right? Like I'm I binge sometimes when I'm feeling stress and I'm not proud of it.

But it's different in that I'm able to bounce back from it faster than if I in the old version of myself who used to drink a bottle or two of wine when she was stressed out. And so I want you to just think about that, like your identity now versus your identity of who you want to become. And one little exercise that you can do through this is like quick, you know, personal core values. What's important to you? Like.

Lindsay Hennekey (17:52.64)
Is integrity important to you? Health and wellness, your mental what mental and physical well-being, is that important to you? Is connection important to you? Do you have a lot of acquaintances, but no deep friendships? And you're really craving somebody that you talk to on a deeper level? Like, really think about what the things that are important to you are. And then I want you to look at how your actions.

draw a direct line to those things. And I've shared this example many times on different areas of my when I give talks and workshops and such. And one of the things is like I used to work at a tech company where there were like lots of 30 somethings and I had

A lot of amazing friends when I worked there. And some of them I am still friends with now. They're some of my closest friends actually. But there was a specific little group of women that we would meet a few times a week and we would go running before work. We'd meet at like 6:15, we'd do a little three or four mile run. And then we had a locker room and everything at work. And so we would like get ready together. And then we would go to the cafe in the office and get a coffee or breakfast or whatever.

And we would go back to our, you know, respective desks or whatever for our work day. And it was like it was the best, honestly. I loved it so much. And as my career ramped up and the some of the demands from work were really a lot of pressure on me. And I was also going through a divorce. I was selling a house and buying a house on my own. It was like just a really kind of personally tumultuous time for me.

all while I was really excelling in my job. And so I my drinking ramped up. Like I started drinking to cope with stress. And as time went by, I became this person who was bailing on these women. I would send the text at six o'clock in the morning, like, I'm not gonna make it today. And it was because I was hungover. Like, who am I kidding? And then that was just this ripple effect. So like

Lindsay Hennekey (20:12.16)
This was just such a big thing and I just remember it so deeply. It really sticks with me because especially now, like my morning workout routine is something that I cherish and it took me a long time to get to the point where it became just something that is like a discipline. It does not occur to me to not work out in the morning. So I really just want you to think about like so the the direct tie here is that.

I loved this friend group. I loved the exercise. This activity of meeting this group of women in the morning and running before work ticked a lot of my core value boxes. Connection, friendship, you know, exercise, health and wellness, like all of those things. But my action of drinking to relieve stress was keeping me from it. So my actions were not matched up with this version of myself that I wanted to be. So, okay.

Before I started doing this work, I actually spent most of my career leading other people, like leading teams. I led global marketing teams at tech companies. I was the head of marketing at a credit union. And so I was I've spent a career developing high achieving professionals. And so we're talking about growth, accountability, follow through, leadership, and behavior change. Like

All of these identity shifts so that people can get to where they want to go. And so instead of helping people become better leaders at work, I now help women become better leaders of themselves. This is a game of self-leadership. And I know that you can lead yourself to the other side of alcohol. And you know.

I've actually like I've coached hundreds of women through this exact transformation enough times to see the patterns. And the pattern that I see over and over again is that alcohol is the place where deeper issues with follow through and coping and identity and self-trust show up. So the transformation that you're going through or that you desire isn't just I don't drink anymore. I want you to start thinking about how.

Lindsay Hennekey (22:31.842)
The transformation is actually, I trust myself again. I trust myself to not break promises to myself. Because right now you might be in a place where you're breaking promises, you're waking up with regret, you're overthinking, you know, social events or things that you have to go to. You question your discipline and you feel like you're always starting over more than you're moving forward. And it's like so many women.

Are living in like intention and then having a slip, shame, reset, repeat. Like that was my cycle. But I promise you, when you practice living alcohol free, doing the things on as much as possible, like then you experience follow-through, less mental noise.

you're feeling more grounded in the social situations that you find yourself in and you're trusting yourself in real time. So what happens is you're actually identifying as a woman who keeps promises to herself. Because right now my gut says the primary promise that you break to yourself is that you end up drinking when you say you're not going to. And so what I want you to look at is

What we're building here is intention around who you want to be, what what your core values are, what's really important to you, practicing the actions that line up with that, and then the follow-through. Like that's where you build self-trust. And then that is where stability from in sobriety comes. Like I can promise you this.

I had a client who I started working with her in I want to say September. It's been a while. We were working together for quite some time. And the very first thing that she said in our first session was Lindsay, if I had actually looked at my calendar, I probably wouldn't have signed up with you. And this is because and this is what I mean like people, we have.

Lindsay Hennekey (24:48.482)
These things coming up. And so we kick the can on trying to quit drinking or just trying to take a break from drinking. And she said, I have a work trip. Like she was literally flying to DC three days after our session for a work trip. And we created a plan for her about what success actually looked like on the work trip. And it wasn't even really about not drinking.

There were some tactics in place so that she wouldn't drink too much at the happy hour after the day of conferences. There were tactics in place so that she would say, I have to go and go to bed earlier than usual. Like we created a bit of a toolkit, but the punchline here is that we created a plan where she felt good enough and confident enough, where she

Went on to her airport, she went on to the airplane, she went on to a hotel, she went on to a conference, she had to socialize, which the key thing here is that she just didn't like these events. Like she's an introvert, she didn't want to be doing all of this. And she actually ended up getting through the entire work trip without drinking at all and surprised the crap out of herself. Like she could not believe it. And this is the thing.

We have to do it even when we don't believe it. And she just followed the direction of what she said she was going to do. And so this was just like a big green flag for her. Like, my gosh, this is what I need to keep doing. So she is now nine months alcohol free. Like I really want you to think about that. She had some slips in the first four.

To six weeks of us working together. But after that, she just continued to keep the self-trust thing going because it's about practicing. And when you have a slip and then you show up for yourself to figure out why, what was going on, that's the only way that you're gonna move on from it. Otherwise, you just look at it as failure. You know, she's in this time, she's also just really.

Lindsay Hennekey (27:06.402)
found the language that feels really good when she's around other people when it comes to like saying like yeah I don't drink anymore or I started with a little bit of a break and it just kind of snowballed from there and I feel really good. So my point is that when you start a break from drinking, you also don't have to have it figured out of like, I'm never drinking again. Like you don't have to have anything figured out. You just have to start

And as you collect the evidence of like, yeah, I feel better. yeah, I can do that. gosh, actually, people weren't even drinking that much there. I I'm the one who drinks the most, or all like quitting drinking is literally just a massive journey of self-discovery. And because when you're drinking, you we're so oblivious to what's going on. And when you're not drinking, you're paying attention. And so you get to this point where you're like,

I actually believe I can do this now. I'm seeing it. I'm seeing the path. And even when you see the path, it doesn't necessarily mean like you've made a decision of like I'm never drinking again. But you see that you are making progress and you can no longer deny that you feel your best, that you're sharper at work, that your marriage is improving, that your relationships are getting closer. Like that starts to happen. But it doesn't happen overnight, is the big thing here.

It takes time. So this is why my method works. Like this is why I created it. Identity, practice, trust. So every challenge I see with clients usually falls into one of those three buckets. It's identity, practice, or trust. So identity is who you are becoming and what no longer fits. Remember my running example.

So many women just focus on stopping drinking or needing to use willpower. I help you focus on becoming the woman who no longer needs alcohol to cope or celebrate or belong or relax and transition from that work to home life. So you go from being somebody who's like, well, I just drink on vacation. I I'm just I'm someone who drinks. Or I'm the fun one. I I'm expected to drink. Everybody's gonna be expecting me to drink or

Lindsay Hennekey (29:33.558)
Wine is how I connect with friends. Or my husband and I we always open a bottle of wine over dinner. Or one of the other things, I don't know who I am without alcohol, which is very common. None of us do because we've been drinking so long to shove down our feelings. And so when you know who you're becoming, your decisions and of what actions you need to take, those become a lot easier. So

Step two is practicing. Practice is building the skills and behavior that support that identity. This is where our actions start to line up with who we want to be. This is where change becomes real because self trust isn't built through just intentions. We have to practice it. You practice, you see, and then you have trust in yourself. So this looks like

Planning for the cravings. You know when the cravings start. You know when you start thinking about alcohol. We're gonna plan for that. Navigating, going on date night, going out to dinner, seeing friends. We create toolkits for you for those things. Setting boundaries. What time you want to leave? How long you want to stay at the party because you know that being around people drains you, or learning how to decompress after work.

without alcohol, handling a Friday night without defaulting to alcohol, practicing what to say when someone asks you why you're not drinking. Language is important and we have to feel good about where we're at in our journey so that we feel confident in our response to things like this. Also, by the way, not that many people are going to ask. So I

You know, I work with women who are going through this, they're putting this into practice, and then they might have a slip. And sometimes the slip can last a little while because they are like it's I call it the comfort zone. Like when you're quitting drinking, you're in the growth zone for a very long time. And like honestly, a couple of years. Things feel awkward for a long time. And so it's natural to just be like, ugh.

Lindsay Hennekey (31:57.357)
I don't want to think about this right now. I don't want to work on this right now. And so you're in the comfort zone. And oftentimes, like there's a couple of things that happen. You don't need more motivation in those moments. You don't need more information in those moments. You need to put action into practice. This is how you build self-trust. And when you do that, tiny little actions stacking up, that's where the motivation comes.

We need to put a little momentum behind us. So the third piece here is trust. I want you to trust the evidence that you can follow through on what matters to you. You know, a lot of women try to start with trust, like and belief. They want to believe that they can do it before they have evidence. So my method works in a different order because identity is what's going to give you the direction. It tells you where you want to go.

And practice creates the evidence, and then that trust is the result. And this ends up showing up in you know a sober work trip, a handled craving at 5 p.m., an honest conversation with yourself or with your partner, a morning where you wake up feeling so effing good and proud of yourself, and a slip that becomes data instead of a shame spiral. Trust is built, one action.

one decision at a time. So so many women are trying to trust themselves before they've built the evidence. It's backwards. That is backwards. Identity gives you your direction. Practice creates that evidence. And trust is the result. I really want you to hone in on that. I want you to say it as your mantra. And when your trust grows, sobriety becomes easier to maintain because you believe in yourself now.

But you're not gonna believe in yourself until you start collecting the evidence, okay? So I know this was a long one today. And I want you to know that, like, if you're stuck in this stop start cycle, I don't want you asking what's wrong with me. I want you asking, is this an identity problem, a practice problem, or a trust problem? And then define really quickly, okay, maybe it's identity.

Lindsay Hennekey (34:21.974)
I don't know who I am without alcohol. Maybe it's practice. I know what I want, but I don't have enough repetition or support to get there. Or trust. I don't believe I can follow through because I've broken this promise so many times. That was me. I was in the lack of trust category for so long in my journey. So you don't need to become perfect at this. You need to become somebody that you trust. That's where lasting sobriety begins.

As always, you know that I love giving you a little bit of an assignment. So this is the assignment. I really want you to see, like, have an honest conversation with yourself. Where where am I falling here? Do I know what I want, but I don't have enough repetition or support to get there? Do I just not believe any of this? Like, do am I sitting in a place of disbelief that I'm ever gonna get there? And trust me, I was in that space. I would have months go by where I would just say, I'm never gonna be there. I'm just a drinker.

It's not the case for you, just like it wasn't for me. So if you're feeling like you want support and you want to put this method into practice, send me an email. You can enroll online, you can hit my website, or just send me an email and we can get the conversation started about what working together would look like. Okay, have an amazing day. And remember, information does not create transformation. You've got to put action behind it. I love you and I believe in you.