Chapter Two: 20-Something Survival Guide from 'Almost 30'
Are you tired of feeling stuck in your 20s? Do you feel like you're not living up to your potential? In this episode, Madison, Ava and Elle sit down with founders, authors, and co-hosts of the popular “Almost 30” podcast Krista Williams and Lindsey Simcik about how to heal and overcome the struggles of your 20s before turning 30. From letting go of past traumas to building healthy habits and relationships, we'll dive into the most important lessons you need to learn to set yourself up for success in the next decade of your life (and beyond). Whether you're struggling with anxiety, depression, or just feeling lost, this video is for you.
In This Episode:
0:00 – Welcome to the 20 Something Playbook Setting the tone for navigating the decade of uncertainty, growth, and self-discovery.
3:40 – The Lie About Purpose & Your Career Krista and Lindsey break down the myth that your career must be your purpose — and what it means to choose your own path instead.
8:56 – Whose Voice Are You Listening To? Is it your dad? Society? Yourself? A conversation about questioning the motivations behind your decisions.
13:48 – Figuring Out Your Gifts How human design, astrology, and even your friends can help you understand what you actually bring to the table.
18:49 – The Portfolio Career Reality Why your twenties may look more like a patchwork of skills than a linear trajectory — and that’s okay.
23:00 – Serving Tables & Soul Growth From bartending to burning out — the jobs that humble you and the wisdom that comes after.
25:00 – When Life Falls Apart (and You Do Too) Lindsey opens up about cheating, shame, and how rock bottom became her greatest teacher.
29:37 – Being Single in Your Mid-20s Madison shares her fears around being single — and the rollercoaster of being deeply true to yourself while longing for connection.
31:45 – Are Your Standards Too High? (Spoiler: No) The girls unpack what “lowering your standards” really means and why soul-level connection over surface-level checklists.
34:15 – Dating in a World of Boys Who Aren’t Ready Krista keeps it real on the maturity gap, dating while fulfilled, and what the masculine can (and can’t) give you.
38:00 – Practicing in Your Friendships How strong female friendships — and even twinhood — become the training ground for honest communication.
41:30 – Rage, Illness & Survival Madison gets vulnerable about mental health, sickness, and the messy beauty of speaking the truth through it all.
44:10 – Mental Health & Substance Sobriety Krista opens up about depression, anxiety, and why sobriety helped her meet herself for the first time.
49:00 – Caffeine, Birth Control & Nervous Systems Tiny lifestyle tweaks that made a huge difference — and what they wish they knew sooner.
50:44 – Their Book, Your Journey Almost 30’s new book is a companion for your twenties — with tools, stories, and love on every page.
52:10 – You’re Not Lost. You’re Becoming. The most important reminder: you’re exactly where you’re supposed to be.
Order Krista and Lindsey’s book Almost 30: A Definitive Guide to a Life You Love for the Next Decade and Beyond NOW: https://static.macmillan.com/static/smp/almost-30-9781250327208/
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Transcript
Lindsey Simcik (00:00):
You couldn't pay me to go back to my twenties, to be honest.
Krista Williams (00:11):
Everyone said that your twenties and college were the best years of your life. And I was like, I'm waiting for that to happen.
Madison MacGregor (00:12):
What were the most character building moments of your twenties? Was there a moment where just shit hit the fan and you were like, where do I go from here? How did you navigate it?
Lindsey Simcik (00:23):
Oh yeah. There were so many
Krista Williams (00:29):
Especially when I'm with twenties. I'm like, parts work. You want to hear about parts?
Lindsey Simcik (00:31):
What do you want to do with your life?
(00:32)
I'm turning 26 and being single at this age is terrifying.
Krista Williams (00:38):
Every day you should ask me how I'm feeling 500 times a day. That's literally not how their brains are wired. This was so much fun.
Madison MacGregor (00:50):
Hey, it's Madison.
Ava MacGregor (00:52):
Ava
(00:52)
and I'm Elle.
Madison MacGregor (00:53):
And this is the 20 Something Playbook. And today we are joined by Krista Williams and Lindsay Simcik of Almost 30. Yay. We're so excited to have them on. Their podcast has over a hundred million downloads, which is just insane. And what they've accomplished is incredibly inspiring to us. Their book, Almost 30, A Definitive Guide to the Life You Love For the Next Decade and Beyond is out Now we're going to be talking to them about their book. Thank you so much for being here you guys.
Lindsey Simcik (01:21):
Thank you for having us, we've already had a chuck or two with you. I know. Honestly, that was
Krista Williams (01:26):
Nice. Feels weird to start. I'm like, I feel like we should start when we walked in.
(01:30)
Yeah.
(01:32)
Hi.
(01:33)
If you could describe your twenties in three words, what would you describe it as?
(01:36)
Oh, that's a good one.
Lindsey Simcik (01:37):
Oh man. Chaos, A mask and drunk. Honestly. Drinking a lot.
(01:51)
Good one. Frustrating. Confusing and like a letdown. I think everyone said where I grew up in Ohio and where I grew up, everyone said that your twenties and college were the best years of your life. These are the best years of your whole life. And I was like, I'm waiting for that to happen because it wasn't the best years of my life. My life has gotten so much better as I've gotten older and as I've gotten healthier and just more well and as I've become more of the person that I am. And I felt like the twenties was such a hard time for a lot of the reasons we talk about in almost 30 or the book, but it's just a really defining decade of time. You're finding your partner that you're going to be with for the rest of your life. Most people by 26 or 27 are having their first child. The average age of marriage is 28. A lot of people have a lot of student debt that they're really struggling with. 60% of Americans have student debt. You are figuring out where you want to live, what your career is, your friendships are changing, your body is changing. You're on your own. I just think it was something that we felt like wasn't being talked about enough and we wanted to really start a conversation around this really challenging time that was really defining for the rest of your lives. And I just honor you guys for being in this process. And I think with the last thing I'll say is with the information, hopefully that you guys can gather where you are, you can make it really beautiful.
Ava MacGregor (03:13):
Thank you. Thank you. Yeah, I mean that's the whole reason we started this. Maddie on her 25th birthday had a meltdown.
Madison MacGregor (03:18):
I had a breakdown on my 25th birthday, but it's exactly what you were saying, Krista. It was just this shit storm of expectations not being met. I was 25 single, my parents were married with a house at 25. So I was like, what's wrong with me? What am I doing? Okay, I have no idea. So yeah, this is the origin of the 20 something playbook. And what I love about what you guys are doing is just normalizing the twenties. Even hearing you say it gets better. That's just so real.
Lindsey Simcik (03:46):
So much better. My gosh, I can't even tell you. I was going to say you couldn't pay me to go back to my twenties, to be honest. It was such a formative time and I'm so thankful for all that I went through, but it gets so much better. And I think really if I think about it, why it got better, it's not necessarily what was happening around me, but once I got right with myself within then everything else,
Ava MacGregor (04:09):
I was listening to your podcast the other day and you said that you felt, you just said it now too, where you felt like you were wearing a mask in your twenties. How did you get through that? How did you, you find your true self and transform into a very authentic version?
Lindsey Simcik (04:21):
Yeah, yeah. And I mean when I say a mask, I felt like most of my life leading up to now was kind of a performance. I wasn't truly living my life. I was kind of waiting for the things to happen that I was told like Krista said, were going to happen for me. And I was trying to be someone that I wasn't to get there
(04:42)
And I was confused as to why things weren't happening, but the mask was so much of what I was told I should be in order to get to where I want to go, whether it's like the nice girl, the polite girl, or you should do this in order to be that famous actress or you should be this way in order to get the guy. I just had so many different narratives about what I should be. And so that pulled me so far from who I really was. So in my late twenties into my thirties, I really started this walk slow, treacherous, back to myself. And so once, I think for me, one of the first steps in removing the mask was finding my voice and my truth, and Krista talks about this a lot, but I struggled with a lot of vocal health issues and it was so connected to me being able to speak my truth. So where did that start? That started with really honest conversations with my family about what my true dreams were. It was about my desire to move away from home.
(05:57)
That also looked like being honest with guys I was dating about what I really desired or what I wanted to experience in a relationship. To be honest, I was putting up with really poor behavior all the time. And if I was honest with myself, I didn't want my relationships to feel like that. I didn't want to be treated like that. So in these little ways I started to hear my own voice and my own truth and that kind of helped me to recenter and be like, okay, what do I really want? Where do I want to go? Who do I want to be around? Where do I want to live? What lights me up? And so it's not this overnight thing. It's not this huge spiritual awakening. "I am enlightened." It's like these little moments where you choose to listen to the voice that's much softer and quieter than every other voice, but you get quiet enough to listen.
Elle MacGregor (06:51):
What did that conversation with your family look like when you wanted to go a different route? Was it difficult? Did they support you or advice for a 20 something who maybe wants to do something different than their parents maybe always imagined them doing?
Lindsey Simcik (07:03):
Yeah, yeah. I've been thinking a lot about that idea of the expired dream. I think a lot of us grew up with a dream. We're like, we want to be a lawyer, we want to be a doctor, we want to be an actress or whatever it is kind of the track we're put on. And then at some point you kind of realize that though you might be leveraging your gifts, they want to be expressed in a different way. And so with my parents, they've always been supportive. I'm really blessed in that way, always been supportive of whatever I want to do. But I think they had this vision of like, okay, she's going to become an actress. It's going to be a hard road, but she's going to get there. And then when I kind of veered off and I was a SoulCycle instructor and a fit model and then we started the podcast and all these other things started happening, still leveraging my gifts, they were a little disoriented. Is this okay? This is a big leap to move to LA and take a chance on this. And I think what I have found is that my family and people that love me always catch up.
(08:09)
I think it's about taking the action first as confidently as you can and trusting that your love between you and your family and friends and what have you will eventually it'll catch up to the moment and they will eventually get it. But by the way, that's not the point. Not everyone's going to get what you're doing. So I just trusted my family. I shared with them my plans. It wasn't a question. It was just like, these are my plans, this is what I'm going to do. And they were like, okay, that's what you feel. Then you go into it. I know they weren't totally bought in, but eventually they were.
Elle MacGregor (08:46):
Yeah. What did that look like for you, Krista? Because you talk about growing up in
Ava MacGregor (08:50):
Ohio,
Elle MacGregor (08:50):
It's the same thing. It was going to college, that was the best years of your life, how you rework that? Was your family supportive as well?
Krista Williams (08:57):
Yeah, so my situation was a little different because my family didn't really have any dreams or visions for me. They were just like, don't go to jail. They loved me, but they really were kind of just in their own experience and their own world. So they didn't have much attachment to me becoming anything or being anything. They were interested in me going to a great college. They were interested in me making good money, but it was nothing really beyond that. So I had kind of freedom in that way, felt a little lost because of it, but also a lot of freedom. And so it never felt like I was disappointing them or letting them down by doing what I was doing. I definitely think they were confused. They were like, what is this? Why do you keep talking bad about us? What's going on? And so in their confusion, but I had a relationship with my family where we struggled a lot.
(09:44)
There's a lot of mental health in my family. I love them deeply and we're very connected, but it wasn't a peaceful household. It wasn't really nice a lot of times. So I didn't have a sense where I was like, I want to make them happy or I want to make them proud. I'm not saying that there's not a part of me that wants to make my mom happy or proud. There for sure is. But my dominant parts were rebellious. I was like, oh, I don't even care what you guys think of me. I'm going to do whatever I want to do. I'm going to do this thing. And so my drivers were a little bit different and I didn't ever have that. So there's a positive to that that gives you a lot of freedom. And then there's kind of a sadness there where you're like, well, does anyone care about me? Type thing. So both are true. Yeah. And
Madison MacGregor (10:23):
You talked about parts work. Can you break down parts work a bit? I do parts work as well and it's been so transformative in my twenties. So can you share a bit about how that's helped your mental health?
Krista Williams (10:33):
I know this whole conversation, especially when I'm with twenties, I'm like, oh my God, all I want to do, I'm like, parts work. I'm like, don't talk about parts work yet. Don't say parts have to go ahead now you said it. I'm like, want to hear about parts? Okay, so parts, it is a psychotherapy technique called Internal Family systems and the founder is called Dick Schwartz. And he worked a lot with women that had eating disorders. And the way that it came about was that he was working with women with eating disorders and they would have binging for example.
(11:03)
And he noticed that the women would be having two concurrent experiences where they had the part of them that would be binging and overeating and eating till they were sick or eating till they were nauseous. And then they had this other part that would also come online that would say, tomorrow we don't eat, we restrict, we're going to eat perfectly, we're going to do all these things. And he's like, how could these two exist? And I think a lot of us can think about experiences and parts of ourselves where we have two concurrent experiences. I love this person, but I also feel like we need to break up and we can have these multiple experiences. So he was kind of like, I'm going to get curious about this. I'm going to break these experiences and feelings into parts. And he got to know them very well.
(11:40)
And what we can find is that the brain can really understand things and heal much better when we personify things. So personifying the part that's the binger. We can look at this part, the binger and say, Binger, what's going? How are you feeling? Why are you overwhelmed? Why are you binging? And then when we can really sit with that, we can understand that the binger is trying to soothe the binger is trying to help us feel better. The binger is really trying to give us a break from a stressful day. Then we can look at the other part in this case where it's telling us that we need to be perfect. We have to eat this many calories, we have to work out this much, we have to do all these things. What is the reason for doing that? Oh, I remember that mom really loved me when I looked perfect.
(12:21)
I remember that people gave me a lot of attention when I was thin. And I really like that. I really like getting attention. I like getting thin. Okay, great. Now where can we find the truth? And the truth is our soul is beyond any numbers, any labels, any love outside of ourselves. So the truth here is above these two parts and we want to get connected to that truth. So where I see parts work being really important for people in your twenties is because most of us in our twenties are still being driven by an unconscious part of us. So the unconscious part of you would be the part of you that's still programmed from your parents. So in the example with you, it's the part of you that still wants to appease mom and dad. For me, that was a part of me that probably wanted to appease something else and the part of me that wanted to prove them wrong.
(13:00)
And so instead of your soul leading the way in your twenties, you have a part that's a perfectionist. You have a part that's trying to do these things and that's not the real you. And that's the part that whenever you achieve the goal is never going to be happy. And we all know what that's like when we've had a goal and then we achieve it and we're not happy. So we know that that's a part leading us. It's going to keep us chasing all of the things. So the way that we work with that is really looking at that truthfully and honestly getting to know that loving, honoring and accepting it. But coming back to the truth, my soul knows that I'm worthy beyond achieving something. My soul knows that I'm worthy beyond money, beyond labels, beyond anything else. Yeah,
Elle MacGregor (13:38):
Beautifully said. Thank you. Seriously. Very well said. I can tell you wanted to talk about that. I'm so glad
Madison MacGregor (13:47):
That was great. And it's interesting hearing you talk about that because I've noticed that in the twenties with my peers, I went through this in my early twenties, I was diagnosed with a life-threatening health condition. So by the time I was 20, I enrolled myself in therapy and I was like, I got to get my shit together. It looks like my life's going to end soon. So I got to figure things out. And luckily as close as there is to a cure to, it came about a couple years ago. So that was a whole process of parts work for me of coming to terms with an early death and then being like, oh, okay, I got my life back again, my whole life ahead of me now what is going on? And I noticed that it's been a blessing and a curse because I had to face really dark things at a young age, but parts work really helped me face them and find my authenticity and true self amongst really dark, disturbing stuff. And I've noticed now with my peers, a lot of them, exactly what you said, Krista, they're following a part of themselves. They're not on an authentic path. So just talking about this now, it feels like parts work is actually one of the keys to an authentic path for someone in their twenties. Because then it's not taking over. The parts are taking over their path
Krista Williams (15:00):
That's my path and that's my journey and parts is my truth. And there's a lot of different ways people can find self. The truth, the soul, the self is the soul, whether it is parts or other. But I think it's really knowing ourselves well enough to know when we're in a story, when we're in a program, when we're in conditioning, and when we're in the freedom and liberation, you can use your body as a tool to tell, okay, when I'm thinking about this situation, how does my body feel contracted, stressed, anxious? How do I feel free, liberated, light. It's really powerful to go into therapy and do the work of unblending in parts. I've done a lot of different modalities and it's just been the part that been the thing that works for me.
Ava MacGregor (15:42):
And I find our audience, every kid we talk to, I mean kid, young adult these days, everyone wants to know how do you figure out what you want to do with your life? What did that look like for you two? Did you always know? Did you have a feeling or did it evolve over time?
(15:56)
Yeah, even I want to know. So speaking is something that really came naturally to Maddie and she's always wanted to do it. It did not come naturally to us, but now we're kind of in a space where we're doing that more and it's looking like this might be the path for us. Thank you. It took a lot of really scary work. But was that something that always came naturally to you too? What did that look like for you?
Lindsey Simcik (16:17):
Yeah, when I think about what do you want to do with your life, I feel like that's a question we get way too early. Yes, three years old, way too early. I remember feeling just a lot of pressure around that question and even though I had a very clear vision of I want to be a performer, I don't know what that's going to look like specifically, but I want to perform and that's what I want to do. The question as I just became a bit more in my body and conscious, it did feel like a lot. And I was actually confused by the question because I think, and I can imagine a lot of people listening maybe are too, because there's these two things tugging at you. What's the job that you're going to have that's going to provide a stable life or get you all the things that society says is success or markers of success? And then there's that pull of I really want to be doing something that fulfills me and I want to be doing something potentially that makes an impact or it's kind of less of the tactical or tangible and more of just that feeling. And I think it's very specific to the person. Some people are in their actual career living their purpose and some people have a career and then they are living their life outside of their career as their purpose. And then I'll pull up one other layer and what I realize now as a 37-year-old that the way that I show up for my life and are living my life on a daily basis is my purpose and where I want to be focused in terms of what am I doing with my life rather than, okay, what's the thing that I'm showing the world that I'm doing and how I'm making money that has always flowed. It's not been easy, but it's been on its own zigzag journey and I trust that that will be for the rest of my life. So I think for me it's like how do I want to feel in my life and in terms of my relationships make me feel fulfilled, my relationship with my body, how I'm rearing my child, how I have or my relationship with the community that I'm in or with nature. It's so many other things outside of the career path, but I do feel fulfilled in our career path. So I was at this moment in my life, I wasn't always, and I might not always be right, it's it's such a nuanced thing. So the answer felt a little all over because it is all over. I think we're stepping into a time and an era where that linear track of your career isn't going to hold as much intensity and pressure and all of your purpose and it's going to change.
Elle MacGregor (19:28):
We were very lucky, we saw our mom go through a huge career change at 40.
Ava MacGregor (19:32):
It was
Elle MacGregor (19:32):
Like she was in corporate and then she went to health and wellness and now she's doing something she loves. So for us, I always knew that whatever I embark on when I'm young, I can always change that.
Ava MacGregor (19:45):
So I
Elle MacGregor (19:45):
Important and I think that's something important for people to hear on this. If you're in your twenties, if you're younger or older, you can always change it. That's up to you. You're in control of that.
Madison MacGregor (19:54):
Yeah.
Elle MacGregor (19:55):
You worked in corporate.
Krista Williams (19:57):
I did. What was that like for you? Just thinking about what you were saying? One of the concepts I really love and the name is escaping me of who discovered it, so whoever can tell me in the comments, but it's called a career portfolio.
(20:09)
And I think people oftentimes think about a career path and they think about a linear career path. I'm a director and then I'm a VP and then I'm president and then I'm making a million dollars and I'm happy. And it's like actually careers don't work that way. And it's like if we can think about the way that we work as a portfolio where it's like I did this one job in photography and I really loved that. And what I loved about that was I loved working with people, creating a vision and storytelling. Okay, cool, my next job, I want to do something that has creative storytelling, working with people, all these things, but it's not going to be photography. What can I add to my portfolio of this more robust? And it just gives a little bit more freedom and flexibility of who you are and what you do. Instead of thinking you need to work up the corporate ladder because for a lot of people that doesn't make you happy. I think for me, I was in the corporate world, I lived in Chicago and New York and I was working in just various corporate jobs. I was very successful at the beginning because I thought that was my path. And then in the end when I discovered that I didn't want to be in the corporate world, I did fine, but I was not
(21:08)
The most, I was a personality hire to be honest. I don't think I was doing my thing. I was in meetings just like I gained a skill of tracking, how could I understand the least and just kind of float by. I was like, oh, I got to lean on this thing.
(21:23)
That would've been me, honestly.
(21:24)
Oh, I was like, I'm going to ask this one question and just see this and then I'm out. It was just crazy. But I felt like for me, I never really wanted to find purpose at my work. I just wanted money. I was really about money and status. I was like, oh, I want to be at the top and I want to be making so much money and all these things I didn't really even know why.
(21:42)
That's what I think in your twenties is being mindful of what's unconscious. Okay, why are you at that job in finance? Let's be truthful. Let's be honest. And then when you're speaking is that your dad's voice? Is that society's voice? Whose voice is that? Because you can be like, well, it's got great benefits. And it's like, are you caring about benefits? Truthfully, right now you are. That's great. Most of us are not.
(22:02)
Being mindful of whose voice is really speaking when you're thinking about your career and really just allowing it to unfold naturally. I think the biggest thing that I'll say, just as a takeaway for people, what I wish I would've done earlier was I wish I would've understood my gifts. I think astrology, human design, whatever tools you use, Enneagram, doing research on just various personality type studies can be helpful of figuring out what your gifts are.
(22:28)
Could even ask your friends. You guys could ask each other, what are three things I'm really good at? Where do you see me really shining? And by doing something like this, you can understand what you have to offer so much more deeply than just going around willy-nilly fitting yourself into every box. Like, oh, you need someone who's organized, I can be organized. Maybe you're not truly organized for me. I'm organized in a specific way. So I think understanding your gifts is going to be the biggest thing that's going to help you at any path and your career because then you can really figure out where you're fit and what you want to do based on that.
Ava MacGregor (23:00):
Love it. I love that. And I love the portfolio analogy because it makes it less this to this, this, it's less of a linear, like you said, linear path. It gives us more freedom. I think even I've actually never heard that before, so I really appreciate you saying that. And I feel like we can relate to that. Even in our early twenties, I do graphic design, I do social media, I do a podcast, serving job. Yeah, serving job. We were serving. We were serving. Yeah. You said you were a bartender. Bartender. Girl. Your thoughts on that?
Elle MacGregor (23:35):
You're like, yeah, is it legal to talk about it? Honestly, met great people. Oh, you guys, you were a bartender too.
(23:47)
I was not a bartender, but I had to sometimes go in the bar.
Madison MacGregor (23:54):
Well no, you better than me. I could not bartend to save my life. I literally was like,
Elle MacGregor (23:58):
You do the, you couldn't do much. I had to make machine. Did you guys have a restaurant? Just so you know, we all worked. This is actually, it's like then three as little girls at the plastic center. We do. I think everything together. There's only one thing I've done on my own serving. We did together, we worked every shift together, the three of us. And it was actually funny because we all look so similar that we would be serving a customer and then one of them would be like, Hey, you forgot this drink. And I'd be like, that was my twin sister actually.
Elle MacGregor (24:30):
But honestly, serving I think is one of the most humbling jobs you could ever have. And I honestly would not take it back.
Elle MacGregor (24:37):
Think that everyone should do listen if you get a good job before that. I'm not saying you should go and be a server, but it's something that is very character building. Character building is a great word.
Madison MacGregor (24:49):
Definitely. Speaking of character building, what were the most character building moments of your twenties? Was there a moment where just like shit hit the fan and you were like, where do I go from here? How did you navigate it?
Lindsey Simcik (25:00):
Oh yeah. There are so many. Where do I begin? I think in the relationship realm, I had just a total blow up in my long-term relationship. My college sweetheart who I thought I would marry, I would tell everyone, this is my person, I'm going to marry him, no doubt. And I was working in the bars at the time. I was running myself ragged. I was honestly just trying to survive. I could not, New York is very expensive. I could not hold onto money. It was all going to bills and rent and my whatever, partying habits on the weekend and we were drifting. We were drifting away from each other. I was losing the plot on, yeah, just what integrity feels like in relationship. Granted, my soul was kind of pulling me there because I think I know that he wasn't my person, but I didn't have the tools. I didn't have the communication tools to be like, Hey, listen, I'm feeling this way. So I ended up cheating on him and he ended up finding out and it was just my whole world fell apart. And even though I was the one that caused that, it just sent me into a really, really dark place because yeah, everything dissolved that I thought would happen in my life. And just dealing with the guilt of that and just what part of me would cheat on someone that I love. What part is that? It just felt so, just gross at the time really.
(26:37)
It was probably a reflection of where you were at in your life. Totally. It had no reflection of who you are as a person. And how did you get through the guilt of that?
Lindsey Simcik (26:49):
I had to come to terms with the fact that even though I loved him deeply, there were a lot of things that were not working between us and just parts of who he was that were not compatible with who I was, but I'm someone who kind of critiques myself before anyone else and is really hard on myself. So that's where a lot of my energy went in trying to make sense of everything. I was like, man, you fucked up. But really my soul was like, you actually haven't made a move on this for a while and you haven't communicated with him, and so we're going to take you on a ride right now.
(27:26)
And so it just took time in terms of the grief and just forgiving myself a lot of therapy. And on the other side of that was seven years of being single. So I learned a lot in terms of who I really was and what I really desired within relationship. I reconnected with the little girl inside of me that just was in, she was wanting to feel validated in ways that she didn't get when she was younger and it was kind of coming out in her dating life. So yeah, it was a process. It was certainly a process, but I think that where I thought my life was done, I was like, it's over. I don't know what my life's going to be. Really woke me up to so many more possibilities in my life. I think when we're young, especially in our twenties, we have this vision, we're like, this is what it is. Our blinders on we're like, this is what our life's going to be. And then when it blew up, it's like the aperture opened and I was like, oh wow, I could move anywhere. I want to move, I can pursue other things. I can meet other people. It just felt like my life opened up in a lot of ways. And so on the outside it was a total breakdown and I'll be cheesy the day, it was my biggest breakthrough of my life and really catapulted me into I think a season of coming back to myself. And I needed that. Because especially in the relationship realm, I wasn't meeting people as me. I was meeting people as who I thought they wanted me to be. And so at the end of that stint of being single for seven years, I did reconnect with my now husband and I just felt more me than ever. It wasn't about putting on a mask and hoping they choose me and like me, it was like, I'm good actually. If you don't choose me, I'm good with me and I'll be good with me for the rest of my life. And that was a different feeling than in my twenties.
Madison MacGregor (29:37):
That's a really powerful place to get to. I'm 25, I'm turning 26 and being single at this age is terrifying because I feel like, ooh, I'm almost getting closer to 30. When am I going to meet someone? Sorry, what does that mean? Biological clock? Yes. No, I'm scared of, yeah, I think I'm just scared of not meeting anybody. So I'm in a place of almost negativity that I'm moving through of feeling like I'm at that place of like, well, if I don't meet anyone, I don't meet anyone and feeling confident. And then I go back to, oh my gosh, I'm so scared. Oh my gosh, what if I don't find anybody? What should I do? The anxiety and panic. I had months where I would wake up with panic and being like, I'm not meeting anyone. And I also work from home and I do not like dating apps. I've been on them and they just have not served me well. So it's amazing to hear your journey, Lindsey, because it's inspiring to know that continuing to go my own way and stay on my authentic path will lead me to the right person. I am very true to myself and I'm proud of that. But it's also hard because there is a part of me that wants to be in a relationship and wants to move forward, but I'm not willing to sacrifice my sense of self for a relationship that isn't right.
Ava MacGregor (30:56):
And what are your thoughts on, I feel like at this age, especially as three single girls in our twenties, we hear a lot, someone's texting someone. What do you mean? Yeah, we hear a lot of lower your standards. Why are your standards so high? More to what Lindsey describes how she got to a point where it's like, this is me and if you don't like it, kind of like not f you, but in a way.
Elle MacGregor (31:28):
I think we've cultivated really great friendships in our lives and I think that fulfills me. And also even doing things career wise fulfill me a lot as well. And I think that's important to have focus on because in a way you can't really control when you're going to meet someone.
Krista Williams (31:45):
I have so much to say, oh my gosh, I'm trying to regulate. I'm trying to regulate. So what they'll start with the standards.
(31:53)
So there's a lot of nuance to that. And the nuance is I have standards. He needs to be a billionaire, he needs to be six four, he needs to be doing these things. He needs to be doing all these things. All of these things are surface level things that are ego-based. Not that I'm saying that I don't have my own list honey about what my man looks like and what's going on, but there's a difference between connecting with someone from your ego to ego and soul to soul. So when you meet someone at the soul to soul level, that's a whole different experience than my list matches your list. Does your list match my list? And that's why online dating can be hard. I have a box that I want you to fit into. Do you fit into my box check yes or no? And when we think about standards, there should be standards for how you're treated
(32:37)
And how you are in relationship to that person, how you feel, how you feel. And yes, of course you can have standards for other things, but I think we want to be a little bit more flexible with that. Me as an example in my process where I was in a relationship for 10 years and we were married and I'm now dating, which is so much fun and I love it. And my standards are more energetic and soul-based of how I feel in relationship, how they treat me, what they can teach me, and are we aligned from a values perspective. And so now that experience on the outside looks completely different, shapes, different sizes, different money levels, different success levels, different, completely different.
(33:15)
I'm really grateful for the experience of being able to get outside my box. I had quite the box I was like, needs to look just like this. I was like, this is my type mustache. Yes, yes. Literally I was like slam dunks, basketballs. And it feels so good to meet people at a heart level because I want to be met at that level. So we think about ourselves too. We don't want a man to be looking at us. How much do you weigh? What does your mom do for work? You want to be seen at the soul level how you make someone feel. And so your standards should be around that. And then when I think about the satisfaction that I think a lot of modern women have, modern women are just so incredible with what we've been able to do, cultivating the friendships, relationship satisfaction in our life. And I think there's a part of us that kind of is like, well, what is a man going to do? Or what are they going to add? And that's very normal and that's very true. And I do think in a lot of cases there are a lot of boys that don't have the capacity at this moment to be with you in a way that's going to be supportive of your life
(34:16)
And your phase of your age is really challenging because there isn't a lot of men that are mature enough to really meet you at the place that you're at. I'll be honest.
Elle MacGregor (34:26):
Preaching to the choir here.
Krista Williams (34:27):
I'll be honest. It is real and it's true. And I'm not saying I don't love men. I love men. I have so many men, friends, I've had great relationships with men dating, I love men. But it is challenging at that time. But what I'll say is that I think for me, I had to really learn that just because I'm fulfilled by my friends and my work doesn't mean that a man can't add to that. And I think it's almost like when you're like, okay, everything's really good, nothing's going to change this. It's like how can we make it bigger? How can we expand our capacity and possibility? How could a man add to your life?
(34:57)
How could he bring more to your life? And just the last thing a man, the texture of the masculine of a man is not going to be the same as a woman. He's not going to talk to you like a woman. He's not going to relate to you like a woman if you're in a hetero relationship is what I'm talking about. So accepting that and honoring that and being appreciative of that instead of being like, you don't cry when I cry. I used to approach every one of my men and be like, every day you should ask me how I'm feeling 500 times a day. And it's literally not how their brains are wired. And so not expecting that from them can really help you.
Elle MacGregor (35:28):
Amazing. I love that. Two things I want to say that I loved about that one was the addition. We always say that a partner should be an addition to your life. It's something that should enhance it, not bring it down or change. It's going to change, but it's an addition. I love that you said that. And then also the values piece. I think that, would you say that the most important thing that you're looking for in a relationship is shared values? One thing that I, there's the soul connection as well, but I feel like shared values needs to be involved in that needs to be involved in a way.
Krista Williams (35:58):
I agree. I agree it needs to be there, but a lot of people say they have values but aren't living in alignment to them. So that's my whole thing is if I was to ask even myself maybe, I don't know if I was to ask someone, any man on the street, what are your values? Family growth and whatever. It's like how often do you see your family? Twice a year Growth. Okay. What are you doing for growth? Well, I'm trying to get a promotion. Okay. Are we talking spiritual growth? Mental growth, emotional growth? There's a range, but I do feel like having clarity on what yours are and even being in conversation, what does it look like for you to be in deep relationship? What does that mean? How much are you seeing each other? Being curious about that I think can be helpful.
Lindsey Simcik (36:39):
Yeah. And I think your female friendships that you mentioned that are so strong and something you've cultivated and love, Krista talked about this too, where you can use those relationships as a model where you practice certain things, whether it's clear communication, it's not going to have the same texture, but there is a way in which I feel like I was able to practice before stepping in a long-term committed relationship where I had that felt sense and that body sense of, yeah, it feels really good when I have a story in my head where I can actually speak it out loud to the other person.
(37:25)
So I was able to bring that to my relationship with Sean where I was like, the story I'm telling myself is, and I had practiced that with my friends, so while it's not the same and they will be an addition to that and enhance all of that, but you have opportunities to practice and it's not just kind of this thing where you get in relationship, really what do I do? You've been deep, intimate relationship with your girlfriends.
Madison MacGregor (37:48):
I really like that. I, that's actually approach, I've been taking the past couple of years in therapy and I literally had a moment a couple of years ago where I was like, I'm just going to practice my communication skills with my family and my friends. That's great to hear like, okay, I'm on the right track.
Lindsey Simcik (38:03):
Because it's a standard where you meet someone and you can kind of feel into where they're at. They're not going to be at the same level most likely. However, I think what's really cool about being in a romantic relationship, one of the coolest things is growing together. Maybe not at the same pace and time, but there is a commitment to growing together. And so your communication style, the clarity, the honesty might call that person up, might really inspire them and liberate them to be honest. So it's a really a great thing to cultivate now.
Elle MacGregor (38:42):
Yeah, okay. I love that. That's really reassuring. A little joke that Ava and I joke about we're twins is that this was our practice. We've been married for 22 years. We share a room, we share share a chair.
Krista Williams (38:58):
I want to do a documentary on twins. The experience of being a twin is so unique.
Elle MacGregor (39:03):
It's actually funny too. Our best friend is a twin as well. I mean they're a boy and a girl, so it's definitely a little different, but there's similarities that I just think wild. But again, we grew up with a lot of twins, strangely enough, and a lot of them didn't like each other. We had
(39:17)
I literally was just thinking I would fucking be shut up. I dunno. It's my time. Get out of here.
(39:24)
Well, I mean we have our moments. Trust me for sure. I think, I don't know why. I don't Know why we like each other.
Madison MacGregor (39:29):
Their interpersonal skills. Their interpersonal skills are off the charts. They are above and beyond. We took a self-compassion test and I was like, my therapist, my therapist, we were a little too high. You're like, I failed. I literally, mine was seven out of 10. Ava and Elle took it. I was like, guys, why don't you take it always? I love all those tests. Think were lower than a seven out of 10. Okay, yeah.
Elle MacGregor (39:51):
Maybe a five, maybe I'm judging. No, I have to literally tell her. I'm like, dude, Ava and I are like, you have to love yourself. We are always like, girl, we love you.
Krista Williams (40:00):
It's so crazy. Just a minute. Two minutes before you said that, I was thinking I was thinking about you because I was like, I feel how hard you on yourself and it hard. It's hard. You're incredible. And I was thinking how important you guys are to balance that. Yes,
Ava MacGregor (40:14):
You are very insightful. Very insightful. I'm the perfectionist. That's intense. And they're chill. And their self-compassion score was almost a hundred percent.
Lindsey Simcik (40:23):
Wow. It was
Krista Williams (40:24):
Incredible.
Madison MacGregor (40:25):
I
Elle MacGregor (40:35):
Yeah. And then also I think, I don't know, there's a certain level of confidence of growing up with sisters, I don't know if you've seen, there's a TikTok where it was like, oh, if people don't like me, it's about sisters. Oh, if someone doesn't like me, I got my sister. She's my best friend. So I don't know if it's that kind of thing too where it's you almost have a level of confidence of like, oh, I don't need a best friend. I have one here. Things like that. I don't need to go externally to find anything.
Ava MacGregor (40:59):
And you're never alone. I had to go through school alone
Elle MacGregor (41:02):
And they went through it together. We were both together. Even your health issues we went through together. It was the support angle where we kind of supported each other to support her.
Elle MacGregor (41:14):
I think maybe that's also why we like each other. We've been through a lot, but I don't know. I don't know. It's an interesting dynamic also working together. You were saying Krista, she is very hard on herself and that's I think one of the biggest things. We joke it comes from the child prodigy, but we were talking about earlier. I think it's also too,
Madison MacGregor (41:32):
I was bullied a lot in school and then I had a health condition. So there were moments in my life where I was so depressed I was almost suicidal. And living through that with them, I think they were honestly my saving grace. I'm not even saying that to be genuinely. They have gotten me through some of the darkest moments of my life
Elle MacGregor (41:59):
And I'm very grateful that I could have helped. I think as a supporter, I mean I'm sure you have experienced this as well, but as a supporter, you don't always know what to say. You don't always know what to do. I feel like you communicated with us, again, back to communication. You communicated with us, you told us,
Madison MacGregor (42:15):
But it's a learning curve.
Elle MacGregor (42:16):
You communicated though what you needed and because I love you, I did that. I did what I needed to do to get you through that time.
Madison MacGregor (42:24):
But even talking about feeling guilt, I felt so much guilt on how I communicated because I was so fucking angry because I was dying. So it was like there's some sick children talk about this a lot. Sick kids, no, this is funny because we can laugh about it now because I'm healthy and I'm okay. But I was like, there's the image of a sick person is this warrior spirit angel never complains and they're calm. And I was like, I was fucking mad and angry and I was almost suicidal, mad, angry. And I would sometimes take that out on my family. And the guilt of that and the weight of that for me was a lot to move through because it would make me be even harder on myself. And so that was a huge learning curve, those years of learning how to communicate. And they were so patient with me, which I'm so grateful for, but they were the angels in this situation because I was losing my shit. We talked about female rage, I just had rage.
Elle MacGregor (43:21):
We joke, she has male rage. It's
Madison MacGregor (43:22):
Not feminine, it's just rage. Because I couldn't believe I couldn't come to terms with the fact that I was in my early twenties. My life is supposed to be starting and it feels like it's literally ending. So that situation taught me how to communicate with them, but it was really rough. But if there's anything I could say to anyone, whether you're a supporter or you're going through your own mental health issues, communicate, I know it's scary to say exactly what you're feeling,
Elle MacGregor (43:52):
I think that's what got you through.
Madison MacGregor (43:54):
And it also is what enabled you guys to support me properly.
Elle MacGregor (43:59):
I did want to ask Krista, because you mentioned that you experienced a lot of mental health struggles in your family. Was that you supporting someone or was that you going through it yourself? And how did you navigate that with whichever, or was it
Krista Williams (44:12):
Both? It was both. So my experience was both. So I think being younger, me as a child, doing what I could to support, not really knowing what I was doing or what I needed to do.
(44:25)
And so really using a lot of my energy and my life force to help them for things that I wasn't understanding or I wasn't privy to or I wasn't really aware of. And then that caused me to be depressed from a young age. I remember I was diagnosed with depression when I was young, and then it kind of came and went throughout my life. Struggling with anxiety and depression has been something that I've really worked with and been with. I feel the most well at this point in my life than I ever have. But it doesn't mean it doesn't ever come back. I think mine now more comes through as I see things more in the parts. So it's kind of more I'm able to be with it more and it's truth and kind of see it clearly rather than having it consume me.
(45:10)
I think in my twenties it was consuming and I didn't really realize how much I was struggling until I kind of hit my rock bottom. When I was in my twenties, I was living in Chicago and I remember I had my best friend staying over and she was sleeping in the living room. And I remember waking up in the morning. I remember just having a split second before the anxious thoughts started going. And I just remember a second and then they started looping again and I was like, fuck. And I was like, oh no, they're back. And it was just every morning and I was like, I can't do this anymore. And I just walked down. I was like, dude, I can't do this anymore. I was at my lowest and she was like, I've never seen you like this. And we had been friends since I was 12, so she's like, I've never seen you like this.
(45:51)
It's just so bad. And that was at the point where I needed to quit my job. I needed to leave my relationship. I needed to change the way I was relating to myself. I needed to stop drinking. There was so many changes I need to make. And so at that point I was like, okay, what can I do? So I'm so grateful. The one thing I'm so grateful for in myself is that I never really quit. I'm never someone that gives in. I think we have to keep living, I guess, but I always kind of seek to feel better and seek to do better. And so that's when I stopped drinking.
(46:20)
That was the first thing I did in my twenties to really support my mental health with stopping drinking. That was instrumental. I don't drink now. I haven't drank for a while. And I think for anyone that struggles with your mental health, you have to be really mindful about your substances. I was even talking to one of my clients recently who has been partying and I'm like, you have to be mindful about how it's impacting your brain chemistry, how it's impacting your mood, how it's impacting your sleep. And I feel like when we can really be truthful about that, we can really see our mental health more clearly. And I think it was impacting me in a way that I wasn't seeing. So yeah, it's been a through line of my life and my journey. And I think it's kind of the plight of someone that is a seeker, someone that wants for more, someone that's deeply spiritual, someone that's really sensitive, someone that takes on a lot. And I think what we can do is just figure out ways to be with it in the best way possible.
Madison MacGregor (47:13):
Love that. And I appreciate you talking about being mindful of substances. We all don't drink either. And we recently had a conversation,
Elle MacGregor (47:25):
Saying it's funny, the colder it is, the more it's like our whole thing is we got stronger beer. It's a big drinking culture in Canada. But I think thankfully in this day and age, it's a bit more normal to not drink. We actually, it was weird. I feel like it's almost like a movement right now. People are kind of stopping, but we grew up without it. Neither of our parents drank. There was just never alcohol in the house. They never drank. My parents I think were aware they didn't know it was mental health, but I think in some way they were aware that it made them feel not as good as they could be. But we're very lucky to have had that.
Ava MacGregor (48:04):
But a lot of people, a lot of our friends in their twenties have talked about cutting out alcohol and managing their substance use and how much it's transformed their mental health. So I appreciate you sharing that
Krista Williams (48:12):
Big time. It's huge. I remember there was a night, I did some drugs and I remember in my twenties and it was like 7:00 AM and I had the covers over me and I was just like, and I just heard this thought, it was like, I should kill myself. And I was like, where does that come from? And it was outside of me. It was just this dark, dark, intrusive thought that I heard. And I was like, oh, that's very interesting. I was like, that's not me. Not that I've had my own share of darkness and dark thoughts, but I was just like, oh wow, this, I don't want to be up at 7:00 AM just stressed in my bed, anxious. You have to be really honest with yourself about the pros and cons of these. And honestly, I'm sober all the time. I go out all the time. I'm out at night. I have the best time. And also I'm able to show up as myself. I'm able, and if you're a control freak myself, I can control the conversation. I can control. You know what I mean? I don't know how I was doing it before when I was drunk it, you're just like, see you tomorrow. Hopefully I end up in my bed. It's just crazy. So yeah, in your twenties, quitting drinking is huge.
(49:14)
In the book we talk about just the power of nourishment. So we talk about alcohol, we talk about things like coffee in your every day that are like, yeah, that's another thing. Your nervous system, your anxiety. I mean, the amount of people or friends of mine even that are like, I've been so anxious lately and dah, dah, dah. And usually, eventually I'll get to the simple question of how much coffee are you having?
Madison MacGregor (49:42):
That was me a couple of weeks ago. I cut out caffeine and I'm not stressed.
Krista Williams (49:46):
There's so many little things that we put in the book that are just the little things that we learned where was like, caffeine is going to make you anxious. It's going to make you not sleep. Drinking, birth control was another thing that really supported us that we wrote a lot about in the book too. There's just things that we've learned in this process that if we would've known when we were in our twenties would be so much happier and so much more satisfied. And that was our hope with the book, was to share this resource of everything that's really helped us become the people that we are and support us. When you feel this way where you feel lost, you feel confused, you feel like you don't know where you're going,
Krista Williams (50:18):
You feel like you just want to feel like you're here for purpose and that you're here to do what you came here to do.
Lindsey Simcik (50:26):
And I feel like you both are living your purpose and it's beautiful to see and to see how far you've come. You started this pod, you're almost 30 in your twenties. So it's been so inspiring for us to see that. And I know for our audience can see that too. For our audience Who wants to get your book, where can they find it?
Lindsey Simcik (50:44):
Well, it's out now. Everywhere books are sold and on every platform online, you can go to almostthirty.com/book. It's kind of an easy way and you can grab it there. But yeah, this has been, it's really a culmination of our life's work thus far. And our hope is that when people read this book, they feel just the support, the comfort, and the confidence to take the next step. And honestly, for us, that's what it's been. It's like one step. We don't lay out the blueprint for your life. It's like this is how you can come back to yourself so that you feel really confident taking that next step, whether it's in your relationships, within your career, whatever it is. It's funny, lots of personal stories. You'll learn a lot, lots of wisdom from our past podcast guests. It's a 333 page book that you'll have for the rest of your life to help you navigate change.
Elle MacGregor (51:41):
I love it. Yeah. I love that love. And as someone who's listened to your podcast, actually listened to the one you did recently about your book,
Elle MacGregor (51:47):
And I love the angle you're coming from, it's inspiring. I feel like as a 20 something, part of the reason we were so excited to have you guys on is because it's a positive angle. Yes. You're going to go through tough times, but it's going to be okay. I feel like there's a lot of doomsday stuff out these days, especially with social media. It was just really nice to hear such a positive angle, so we appreciate it.
Krista Williams (52:10):
Oh yes. We just believe you're not behind. You're just becoming, and it's just all a part of the process. And if I would tell my younger self anything, it would be that you're not lost. It's all for purpose and you're on your way.
Elle MacGregor (52:23):
I love that. I think we can end there. Yes.
Madison MacGregor (52:26):
Thank you guys. Thank you. This was so much fun. Was so
Elle MacGregor (52:38):
We stayed in the beautiful Westgate, New York Grand Central for the duration of our stay, and it was really fun. The Westgate treated us to a cozy room
Elle MacGregor (52:48):
And a beautiful boardroom to film in, and the location was just spectacular. If you're headed to New York and want a place that brings both comfort and charm, hit the link in our show notes and treat yourself to a stay at Westgate New York Grand Central.
