I've been doing a lot of reflecting lately on the moments that have shaped who I am today. Not just the highlight-reel stuff, but the real, sometimes messy experiences that fundamentally shifted something inside me.
As I was putting this list together, I noticed a pattern: so many of these moments were about having a rude awakening or losing some kind of innocence. I know that sounds heavy, and I don't want this to read like "10 Major Negative Life Events" (though let's be honest, some of them were pretty rough). But the thing is, each one taught me something important and pushed me to grow in unexpected ways.
Some of these are specific, defined moments I can point to on a calendar. Others are more like overarching experiences that built up over time until something clicked. But all of them changed my personality in ways I'm still unpacking.
1. My Uncle Donald's “Visit”
After my parents' best friend Donald passed away (we called him Uncle Donald), I had an incredibly vivid dream the night of his funeral. Unlike past dreams with deceased loved ones where they seemed alive in the dream, this time I knew he was dead and questioned him the moment I saw him… “What are you doing here? I thought you just died.” I've heard that when you see someone who's passed and you register in your dream that they shouldn't be there, it's actually a “visitation.” In the dream, he told me that he'd be around for another 10 years and would be at my wedding. (He died when I was in my late teens, but I did, in fact, get married in that 10-year window.) The following day, I told his wife about this visitation and she revealed that she, too, had been “talking” to him in her head at the funeral, and that he'd told her the exact same thing (that he’d be around for another 10 years). This story goes on and on, but on the 10th year after his death, on the morning of Uncle Donald’s birthday, I woke up to a positive ovulation test and got pregnant with Milo that day. I am confident that Milo was a gift from Uncle Donald before he officially departed. This initial visitation opened me up spiritually and made me realize that there might be more to life than we can understand.
2. Leaving Refinery29
This was a full-on plunge moment. I walked away from a successful, stable job and from multiple thriving video franchises to start my own media company. Immediately, my perspective shifted. That first year, I entered a contract with Refinery29 to create a handful of videos for them. That contract alone paid me more than my entire previous salary—for a fraction of the work. It completely unlocked how I saw my own value and changed how I price myself. It was also a major turning point, carving out my own path away from a well-known series and guiding my audience into the unknown with me.
3. Moving in With Michael
Yes, moving in with a boyfriend is a big deal. But for me, I had been dating Michael for so long (and we’d had many sleepovers before), so moving in with him wasn’t the biggest change. This one is actually about living apart from my twin sister, Allie, for the first time in my life. We literally lived together from the womb through college, being roommates the entire time (only splitting up for two months during a study abroad program—and even then, we were in the same city in London). Moving in with Michael meant establishing my own separate life for the first time ever.
4. The Tabloid Article
When I was 19, I had been appearing on a live morning show in New York City regularly. After one of these appearances, a tabloid published an article about me and one of the (very famous) male hosts, making claims that just weren't true—claims that were potentially career-damaging. Remember, this was before my career had even begun… so it was a very scary time. Before the article was officially published, I was given some advanced notice from the network’s PR team that something would be coming out. I was living in NYC that summer, and I remember going out to dinner with a friend and realizing that the person who was sitting next to us was actually a writer, listening in on our conversation and trying to “find” a story where there truly was none. It was my first real experience with the potential dark side of the media industry and a scary realization that people can just write whatever they want about you whether or not it’s true. It made me much more cautious as I built my personal brand.
5. “The Creator Catch”
After years of accumulating internet commentary on everything I posted, I came to a major realization a couple of years back: if you're going to do this job, you literally cannot win. And that’s okay… you can still enjoy showing up every day and being vulnerable, but the world will always have something to say about it. Shop at a high-end store? You're not relatable. Buy from a fast fashion brand? You're ruining the environment. Move to the suburbs? How can you afford that? Stay in the city? How can you afford that? Share your kids online? You’re exploiting them. Hide your kids online? Are they even a part of your life? Have a clean house? You’re unrealistic. Have a messy home? You’re disgusting. Work full-time? Why even have kids? Stay home with your kids? Must be nice. Making no money? Get a real job. Making lots of money? Eff you. Talk about the hard stuff? You’re oversharing. Never share the hard stuff? You’re inauthentic. Never get a brand deal? You’re failing. Get a brand deal? You’ve sold out. Create polished content? It’s too curated. Create casual content? You have no talent. Evolve your content? We miss the old you. Stay the same? You’re boring AF. Talk about privilege? That’s performative. Never mention privilege? Out of touch. And the best comment that seems to come in every time a young woman has a successful job on the Internet (which, by the way, is a highly female-dominated field)… “Since she’s ‘doing nothing,’ her husband must be making a lot of money.” Ultimately, you're damned if you do and you’re damned if you don't. This realization helped me start showing up with more of an unapologetic energy.
6. Getting Married
Michael and I dated for 10 years before getting married, but something shifted after our wedding. It was the first time I truly understood that you create your own family from scratch. You take people who weren't part of your past and make them your new nuclear family. The moment we got married, things changed from him feeling like a “boyfriend” who I loved, to me feeling this protectiveness over him and his well-being as I would a family member. Michael jokes that he felt this way about me the whole time we were dating, and of course, I’ve always loved him to bits. But call me crazy… I genuinely felt a different kind of love for him after marriage. He went from boyfriend to family in a way that felt profound and new.
7. My Gallbladder Removal
This was my first health scare and first surgery, likely caused by my birth control pills which listed “gallbladder disease” as a direct side effect. Even though this wasn't directly related to my diet, what I ate worsened the gallstones and caused gallbladder “attacks” or flare-ups. I'd never really cared (or been educated) about food and health before, so this was a wake-up call that just because you might look healthy on the outside doesn't mean your organs are healthy on the inside. It completely changed how I think about caring for my body.
8. Becoming a Mom
As much as I love motherhood, the experience of having a baby (at least in those early days) was absolutely nothing like what I had expected it to be. It was a jarring shift of expectations. I don’t think I fully grasped just how much having kids would change my life overnight, and I think in those first few months I was so lost in the “baby blues” that the entire experience of coming home from the hospital and having a baby just felt very heavy. It highlighted an ongoing issue I have in my life when it comes to expectations versus reality. For example, I always expect holiday events to feel like they did when I was a child, and I often go into my kids’ birthday parties with sky-high expectations and end up feeling let down. I'm working on managing my expectations better, but motherhood has been the biggest teacher here.
9. Getting Kicked in the Head
When I was young (around 9), we were on a family vacation in the Caribbean, and I was playing on the beach at night with my older brother and his friends. It was dark and I was hiding behind a stack of pool chairs as we played dodgeball. A drunk American teen wandered over to where I was hiding and (very suddenly and extremely aggressively) drop-kicked me in the head. I went flying across the beach and then looked up to find him running away. I ran to my brother who then found a security guard, and the teen was ultimately found, but the entire experience was terrifying and really shattered my glorified vision of reality. I think this experience potentially led to some anxiety down the road in my life. It certainly made me more vigilant about my surroundings everywhere I go. Nothing like that had ever happened to me in my hometown, and then I went out into the world and experienced that violence. It was a defining loss of innocence.
10. Being Catfished
As many of you may recall, a follower catfished me, pretending to have cancer when she didn't, and then pretending to be her dad and faking her own death. I've told the full story in a podcast episode (a must-listen if you missed it), but this experience was about the shattering of internet innocence and the realization that not everything is what it seems. Although this was a negative experience, it came with important lessons about being more discerning. And in telling the story publicly, I was able to raise money for actual cancer research, so something positive came from it. Additionally, after opening up about this story online (and keeping her anonymous), the girl did ultimately reach out to me and apologize. Even though it doesn’t take away the scar of the experience, it definitely helped me feel a bit of closure.
These are some of the defining moments that have made me who I am today. Some were painful, some were beautiful, but all of them taught me something I needed to learn.
As always, keep scrolling for more good stuff!
IN CASE YOU MISSED IT
I had a special episode of the podcast last month where I sat down with my brother Rob and his two best friends and bandmates, Lukas and Alex, who together make up the band East Love.
We walked through their entire origin story, from meeting in elementary and middle school (including a hilarious hair-braiding incident that got them in trouble in fourth grade), to how they've managed to keep the band going for 20 years while all having full-time jobs, kids, and lives on the East Coast.
We covered a lot during our conversation, but these were a few of my favorite parts:
On why they've lasted 20 years: Lukas perfectly captured why they've been able to sustain this for so long: "The very worst case scenario is we get a chance to hang out with our friends." Even when a practice or writing session doesn't go as planned, they're still spending quality time together, which makes all the hard work worth it.
On the cheating story behind "Never Mine": Rob opened up about their newest single and the wild story behind it. He explained, "I fell head over heels in love with this girl who, only a few months into the relationship, cheated on me." He showed up unannounced at her apartment to end things and walked in on her in bed with her ex-boyfriend. But here's the thing—the song isn't angry at all. As Rob says, "I totally forgive this person and have no negative feelings toward her at all. It's just something that happened to me that played a role in who I became."
On choosing stability over stardom: They actually sat down together and seriously considered quitting their jobs to tour full-time. Rob shared some wisdom from our dad, who's been in the music industry his whole life: "Regardless of how much money you make...it's more about the lifestyle." They chose family time and keeping music as something they love rather than something they have to do to survive. Lukas summed it up perfectly: "I don't think we could do this indefinitely if we had chosen to go out and do it 100%. I think the way we chose to approach it, we'll be able to do it forever."
On their unexpected reach: The numbers are pretty incredible. Rob pointed out that "at any moment, there are tens or even hundreds of people listening to us" on Spotify alone, 24/7. They've had fans from Australia recognize them on a food tour in Peru, been asked to play at proposals, and had their songs chosen as first dances at weddings—all while doing this independently on the side.
On the gift of creative friendship: Alex said something that really stuck with me: "If anybody listening has a chance to get together with friends who have similar interests and just make something, I think it's just an incredible gift to give yourself." The way these three guys talk to, support, and show up for one another is genuinely inspiring.
Not only do these guys make great music, but they’re also just great people and an inspiration to anyone who's trying to balance creative passion with real-life responsibilities.
You can listen to the full episode of The Real Stuff on Spotify, Apple Podcasts, or watch on YouTube. Also, go follow @eastlovemusic on Instagram!
BE MY NEXT GUEST
A couple of times a month, instead of a celebrity guest, I’m handing the mic to YOU. I’m inviting members of my audience (anonymously if you’d prefer) to join the show and talk about ALL the real stuff: sex, money, mental health, and everything in between. If you’re ready for a deeply personal conversation on a public platform or have a wild life story to share, apply here.
WHAT YOU SAID
Last week, I asked what YOUR goals were for the new year. Here’s what you told me:
I'm fascinated that systems and health tied for first place at 31% each. It makes sense, though… they're kind of two sides of the same coin. Building better routines is often how we actually prioritize our health, and vice versa. We know what we want to do (eat better, exercise more, get enough sleep), but we need the systems to make it sustainable.
What surprised me was how low “spending quality time with loved ones” ranked, at just 9%. Maybe it feels like a given, or perhaps, as many of us come out of the holiday haze, that cup is already full (or even overflowing) and we need time to ourselves. I’d love to hear your thoughts on this.
And 18% of you are taking it one day at a time. No judgment here, that's where I'm at right now, too.
ASK ME ANYTHING
Q: “What does your exercise routine look like? (from a fellow mom trying to figure it out!)”
A: I have a virtual trainer who I used to meet with virtually twice a week. However, she’s in the midst of a job change and won’t be offering training sessions soon, so I’m in a transition phase when it comes to working out. I just joined a local gym and I’m starting to get into a routine a couple of times a week with Michael.
Have a question for me? Reply and ask away!
QUESTION OF THE WEEK
Earlier, I shared some personal moments that shaped who I am today. Now, I want to hear yours.
What's been your biggest catalyst for personal change?
The results will appear immediately after you vote! Check next week's issue for the final numbers.
UNTIL NEXT TIME
I'm not going to lie. Writing today’s issue hit harder than I thought it would. Some of this stuff I haven't thought about in forever, and other parts still feel pretty fresh.
But even the really hard moments taught or gave me something I needed. Whether it was perspective or resilience or just a better sense of who I am and how the world actually works.
Thank you for being here and for always letting me share the more personal side of things. This is the reason I created this newsletter in the first place, and I’m so happy to see it becoming the space I’d hoped for.
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