← My So-Called Midlife with Reshma Saujani
My So-Called Midlife with Reshma Saujani
Getting Comfortable with Being Uncomfortable with Lilly Singh
00:45:23
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- [00:01]
Reshma Sajani
Today's episode is supported by what Should I Do with My Money? An original podcast from Morgan Stanley. This podcast pairs real people with experienced financial advisors. You'll hear candid conversations from people just like you with questions just like yours. Questions like can I retire early? Like really early. How do I leave a financial legacy for my special needs child? Menopause is making me feel wacky and it's shifting how I think about money. Help. These conversations can get emotional, but they're always practical. I checked out the episode about money, motherhood and menopause on what should I do with my Money? And I loved hearing from other women who are also committed to setting their kids up for success and hearing how menopause plays into work and money and just everything. It's so on brand with what we talk about every week on the show. Search for what Should I Do with My Money in your podcast player. We'll also include a link in the show Notes. Thank you to what Should I Do with My Money? And Morgan Stanley for their support. Ever feel like you're navigating life's biggest changes alone? Well, you're not. I've been there too. I'm Tamsen Fadal and on the Tamsen Show I'm tackling the conversations we all need to have Midlife, menopause, career, invention, relationships and more with expert advice and real unfiltered conversations. This is your go to guide for living better, feeling stronger and taking charge of your well being. No topic is off limits. No conversation is too big. It's time to own it. Listen to the Tamsen show wherever you get your podcasts. Lemonada hey midlifers, Just a quick message before we get started. You can now listen to every episode of My Soul Cloud Midlife ad Free with Lemonada Premium on Apple Podcasts. You'll also get ad free access to and exclusive bonus content from shows like Wiser Than Me with Julia Louis Dreyfus, Fail Better with David Duchovny and so many more. It's just $5.99 a month and a great way to support the work we do. Go ad free and get bonus content when you hit subscribe on this show. And Apple Podcasts make life suck less with fewer ads with Lemonade Premium. Welcome to my so Called Midlife a podcast where we figure out how to stop just getting through start actually living it. I'm Reshma Sajani. So are you comfortable being uncomfortable? I'm gonna guess that most of you aren't, but you know who is. Lilly Singh. Lilly Singh is An author, an actress, a creator. You may know her from YouTube, where she got her start way back in 2010, or when she hosted A Little Late with Lilly Singh on NBC or as a gender equality advocate. But I hope you've caught her in her brand new movie doing it, because it was hilarious. Here's the thing about Lily. She is a busy woman. And I had the chance to talk with her recently, and there was something that she said that has really stuck with me. She told me that she has a high threshold for being uncomfortable. And you see, that's different than being just resilient. Being uncomfortable is about putting yourself in spaces and places where it doesn't always feel good to see what you're actually going to learn. And I thought, wow, that is like a really, really powerful and important lesson that Lily literally taught me on this conversation. Lily is stepping into midlife. She turned 37 literally two days after I spoke with her. So it was pretty interesting to hear her reflect on the beginning of the middle, if that makes sense. She's young, and she's had so many ebbs and flows in her career and a lot of obstacles. So she's kind of like an old, young person. She's a really great reminder that, like, life is long, so go out and live it right now. All right, so now that we're all pumped up to hear from her wisdom, let's hear from Lilly Singh. So I don't want to freak you out, right? This show is called My so Called midlife. And you're 36, so you're probably like, am I in midlife?
- [04:25]
Lilly Singh
Feels like, really?
- [04:27]
Reshma Sajani
Okay, good. Because. And so I want to know, how.
- [04:30]
Lilly Singh
Does it feel like, well, I'm actually turning 37 in a few days, and that feels.
- [04:35]
Reshma Sajani
Happy early birthday.
- [04:36]
Lilly Singh
Thank you. That feels very daunting to me. I do feel like the age of 36 was a little bit of a revolutionary one. I do feel like a lot of things in my life kind of fell apart and unraveled, and I was forced to rebuild a lot of things. And one of my friends who's very into the planets and stars and whatnot, was like, looking at my chart and she's like, no, this is 35, 36. This is the time when things are supposed to fall apart. And 37, she says, is the year where you rebuild. But the one thing is you cannot rebuild using any of the old bricks. That's what she told me. And so I do feel like I'm a little bit of in a midlife crisis. I don't know, I feel like in 36, some career stu fell apart. Some personal relationships really fell apart. I had to look in the mirror a lot of, you know, what are the lessons I, like, finally need to learn? What are the things I need to unlearn? It was a big year for me, for sure. So I do feel that way.
- [05:26]
Reshma Sajani
That's. So when that happens, because I feel like I had that kind of year in my 40s. I kind of like every three. Three years, I'm like, what the fuck's going on? My life isn't where it needs to be. Like, this isn't it. Is this how it's gonna. You know? And I feel like. And you get all these disappointments. Cause I feel like you like me. Like, you go for it. Like I go for it. Which means when you go for it, you get a lot of rejection because most people don't really go for it. So when you're in that period, what do you do to get. So make sure you just don't get in a really deep, dark hole.
- [06:00]
Lilly Singh
Yeah. So I'm a really, for better or for worse, pragmatic type A person, and that's how I deal with most things in my life. Like, if I have a therapy session, my therapist is like, I. I think this is something we need to work on. Problem A here and whatever. I'm now blocking three hours in my calendar to journal about it, to reflect on it, to meditate on it. You know what I mean? So I really do go inward, maybe to a detrimental extent. Even sometimes where I'm very, like, problem solving mode, like trauma, I can fix that. You know what I mean? Like, this trust issue, I can fix that. So I'm not saying it's a great quality, but I'm saying I do really go inward.
- [06:33]
Reshma Sajani
So over the course, you do the assignment. You do the assignment.
- [06:36]
Lilly Singh
I do the assignment. I really, really do. In my entire year thus far, I've been very adamant on journaling almost every day. I've been very adamant on doing a monthly check in. I've been very adamant on, like, certain prayers and rituals that I do because of things I've learned and unlearned about myself this year. So that's me as a person. And the reason I say it sometimes to a detriment, is I treat most things like a problem that can be fixed. But as we know, not everything is like that.
- [07:04]
Reshma Sajani
That's right. That's right. Like, some things can't be fixed and you just have to move on. So I don't know if you remember this, but I met you way back. We were both at a Google conference. It must be like 2012, 13. And you were first getting started, but you were like. I mean, you were big enough that the people are like, I was trying to get my way to, like, shake your hand. Like, it was just great. And you were young, you know, you were young. Like, it's like. Could you tell us a little bit about, like, when you first started making content and, like, what drew you to YouTube? Because it was pretty new back then. Like, you got in the inside track.
- [07:43]
Lilly Singh
Yeah, I made my first YouTube video in 2010, which was pretty, pretty early. And not a lot of people knew what YouTube was or that you could make a living off YouTube. I didn't even know at that time you could make a living off YouTube. What drew me to is I vividly remember being in university and one of my friends being like, have you heard of this platform, YouTube? People are uploading videos. And I. I remember thinking, that sounds dumb. I was like, why would people do that? That sounds like a waste of time. And during that time in university, I remember feeling quite lost in the sense of, thus far in my life, everything I've done, I just followed my sister's, my older sister's footsteps. She got a degree in psychology. I got a degree in psychology. I went to the same university she went to. Not necessarily because my passions laid in any of that was just like, my older sister's doing it, I'm going to do it. And this linear life has been mapped out for me that, you know, my immigrant parents are very adamant on where you go and you get a degree and you get married and you have kids. And I was like, and that's life. That really was unsettling for me. I always felt like I wanted to do something different. I always felt like that was not right for me. And so around that time, I discovered YouTube. And, you know, as a kid, I always loved entertainment. I was like in the middle of the dance circle at parties. I was like, always the one trying to make people laugh. But, you know, I'm just in a small town in Toronto, not ever thinking that that could be pursued as a career in any type of way. You know, there's no auditions in Toronto, there's no casting age in Toronto. And so when I. When I finally did check out YouTube, I was like, wait, people are just expressing their opinions without a gatekeeper to other people that are just sitting in their rooms. And that's so cool. And so when I uploaded my first Video. I think what I was really looking for was just a sense of like, freedom to do what I want to do and talk about what I want to talk about and connection more than anything else. And I think that's why my first couple videos really hit. I think especially at that time, other brown girls were like, this girl's talking about relationships and.
- [09:30]
Reshma Sajani
Right.
- [09:30]
Lilly Singh
Taboo subjects and we're connecting in a way we never got to connect to. So I just like got addicted to this idea of like, this can be mine. This doesn't have to follow the linear path. No one's going to tell me how to do this or what to do here because it's brand new and I can just invent whatever I want to do myself. And that was really intriguing to me.
- [09:48]
Reshma Sajani
Did your first couple videos really hit? Did you like. Or did you have to do a.
- [09:51]
Lilly Singh
Bunch before, you know, they didn't hit at all? I mean, my first video got 70 views, which at that time I thought was phenomenal. You're like, wow, I don't know, 70 people, so. But no, it took. You know, I'm not, I don't. I'm not the product of a viral video. I think every video I've ever made has garnered views and garnered subscribers. I'm not like an overnight success by any means. And I really have to figure out what works for me. Like the first couple of videos I did were spoken word and then maybe it was a tutorial. And then finally I tried comedy and I tried this like direct to camera style rant that I used to do and like these sketches and that really started to hit. So it took a second for me to figure out what I wanted to do, what people wanted to do. Because I'm not trained in any of this, right? I'm not trained in writing or comedy or shooting or editing or anything. And so it took a second for me to teach myself all that also.
- [10:36]
Reshma Sajani
And the analysis, right? Because you don't have a bunch of people watching you be like, all right, when you're standing by the board like this, you know, I mean, you end up getting 100 more likes. Or if you, you know, do an educate like, so how. So you. How did you have to do and look at the content yourself, do the analysis? Like almost like self critique yourself to figure out what works well based on.
- [10:57]
Lilly Singh
Everything I just told you about me being type A. It will not shock you that I had multiple Excel sheets up on my bedroom wall because back then we didn't even have the analytics really on the back end. Of YouTube like we do now. So I used to like track my subscribers and views manually.
- [11:10]
Reshma Sajani
That's incredible. Incredible.
- [11:12]
Lilly Singh
Which videos hit? Why did they hit what comments? I used to like send people surveys. Like what did you like about this? What didn't. So of course it was a lot of self criticism. A lot of like learning how to market things myself. Learning like simple, simple things. When I'm doing a rant style video, if I cut out the music here or more people engage versus if I cut out the music there. Like just learning all these small things to keep people engaged and to get them to click on the video. Yeah, that was all self, just research and analysis. Look a huge nerd.
- [11:42]
Reshma Sajani
But Lily, it's so. But it's very against the way we're raised as girls, right? Because we are not raised to. Part of what I tell I teach all the time is like ask for critical feedback, get rejected. You know what I'm saying? Because if you don't, if you want to be great, you have to have that feedback loop. But like you're like, I don't know, how old are you at this time? Like, like you're 18, 19?
- [12:03]
Lilly Singh
No, I'm probably my early 20s.
- [12:05]
Reshma Sajani
Early 20s. So. So were you raised to be comfortable getting that kind of feedback and rejection in order to like allow yourself to kind of hear it yourself and solicit it?
- [12:16]
Lilly Singh
No, it's been terrible from the very beginning. I wasn't raised that way. I was raised of course be very like soft spoken and very obedient and I always went against the grain, for better or for worse, my parents sake. But it's always been scary. It's scary for me even now to be critical of myself and like look how I can do better, not do better to hear people's feedback. It's really uncomfortable for me and it's always been. But I somehow some way I think I have a very high threshold for being uncomfortable. I think that's the one thing I'm very grateful for when the amount of times I've stepped out of my comfort zone every once in a while I have to like wake up on a Sunday morning to be like, can you just do something easy today? Just do something easy today. You don't need to do anything that's crazy today. But like I think, yeah, my threshold for feeling uncomfortable and my threshold also with like being able to work hard, they're very high.
- [13:03]
Reshma Sajani
And so Lily, I love that I live, I love that because people don't talk about it in terms of having a high threshold, you know, for uncomfortability. They talk about it often in terms of resilience, but that what you're talking about is different. It's different, right?
- [13:19]
Lilly Singh
Yeah, yeah, it's different.
- [13:20]
Reshma Sajani
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- [18:40]
Lilly Singh
Yeah, I agree. I think the greatest joy and pride of my life is when brown girls come up to me and they say that they really resonate with my stuff. And they grew up. Grew up with me, and they've supported me for, you know, all these reasons. That's amazing, because that's literally why I create things, because I wish I had it when I was younger. You know what I mean? And so for other girls to say that they found that in me is really special.
- [18:58]
Reshma Sajani
So I want to ask you something about being authentic, because I think part of your brand is this genuine, sincere authenticity. I mean, I really saw it when I watched your movie this weekend, doing it.
- [19:10]
Lilly Singh
Thank you.
- [19:10]
Reshma Sajani
You are like, you are you. But I have to imagine, as you've gotten more famous and, like, the stakes have gotten harder, it's got to have been even harder to stay authentic.
- [19:24]
Lilly Singh
It has, and, you know, it is. I'll tell you, my journey with authenticity is not linear. It is definitely up and down. I feel like when I first started on YouTube, I was very authentic. And then I think, like, three years ago, four years ago, I went through a little bit of, like, okay, now I have to be like this, because everyone has all these expectations of me being like this. And online, I wasn't as open. I wasn't as vulnerable. I was, like, doing just the pretty photo shoots and just, like, posting of the accolades. And I think now I'm back into a spot where I'm really vulnerable again. And so I think it kind of ebbs and flows with the amount of pressure I feel at the time, the amount of pressure I'm putting on myself. What I feel personally about my success at the moment, because success is also not a linear feeling. It's also something that ebbs and flows. And so I think when people talk about authenticity, they think of it like a destination. Like, you are. You're not. But I think there's a lot of factors that play into that, and I find it easier to be authentic on some days and less easy to be authentic on others.
- [20:21]
Reshma Sajani
Do you feel like you've made it?
- [20:23]
Lilly Singh
Oh, that is the question, isn't it? I've done a lot of work over this year for the answer to that question to be yes. If you had asked me this a year ago, I don't think I would have said yes. And I think it's because I being a very rigid thinker, which is one of the things I'm trying to unlearn. But I am a very rigid thinker. I'm very, like, black, white, this, that, right, wrong. And I know the truth lies somewhere in the middle. And. And so the reason I bring that up is because when people would ask, have you made it? I would automatically be like, well, there's so many things I still want to do. There's so many projects I still want to come to life. There's so many people I still want to meet. So I couldn't have possibly made it if I still want to do all those things. But I think what I've learned over the past couple months is that two things can be true at once. And you can be so thrilled with where you are, but also be so incredibly ambitious. And so that's where I am. I've made it in the sense that I've done a lot of incredible things I'm super proud of. And I know in my heart that every little thing Little Lily wanted to accomplish, I've actually done at the same time. There's a ton of things I still want to do.
- [21:22]
Reshma Sajani
Yeah, it has to be that way. I mean, I interviewed Julia Louis Dreyfus for this podcast, and she said it. The queen, right? And she's just like. Her whole philosophy on this was like, yeah, every. It's never done, like, in a good way. Like, I keep feeling like there's more, there's more, there's more. There's more I wanna do. There's more I'm excited about. And I think you have to, because then what's the point? You might as well just die, right?
- [21:43]
Lilly Singh
Like, but I think that ambition can exist with you still being so proud of where you are right now. And that's the distinction I didn't have before.
- [21:49]
Reshma Sajani
That's right. That's right. And, like, not feeling and being able to say that, like, I work with a spiritual coach, and he's like, you know, I always sometimes feel uncomfortable when people come up to me and say, thank you. You know, Reshmitta, you so much for your work. And I think part of. We've been raised to be very humble, right? So I want to be. Oh, no, I haven't done. I haven't done anything. But, like, you almost have to take that love in and feel it, right? And there's nothing wrong with it. And that. That helps you be able to say, I have accomplished something. Yeah, it's.
- [22:18]
Lilly Singh
It's super interesting you say that because, you know, over this past weekend, I've been promoting the movie and I've had a lot of people come up to me and say really nice things, and I have to, like, be really present in those moments because my first instinct is exactly what you said to be like, don't take it in. Just like, yes, nod. Thank you so much. But, like, I'm like, no, let me actually listen, right? Like, what are you saying? Like, take it into my body and, like, feel it in my nervous system, what you are saying, because we are so bad, especially as women, especially as brown women, taking in that positive feedback. We're so used to taking in the negative. So I'm trying to get equally good at taking in all types of feedback.
- [22:50]
Reshma Sajani
For sure. That's right. It's a practice. So I want to. Let's talk about your incredible movie. Doing it. I watched it this weekend and I loved it. I'm still giggling as I, like, think about different scenes.
- [22:59]
Lilly Singh
Thank you.
- [23:00]
Reshma Sajani
What. What inspired you to create this film? I mean, you wrote the script. Tell us about the process.
- [23:05]
Lilly Singh
Yeah, I mean, I've been working on this for seven years, which is a long, long time. Wow. I know. And again, going back to. I wanted to create something that little Lily really needed when she was growing up. And when I think about me and as an adult, one of the most daunting things in my entire life has been sex, sexuality, feeling comfortable around that conversation. Because growing up, I was never given the talk, didn't really have sex at. In school. You know, I think as. As kids and teenagers, we all kind of feel awkward about sex. But it has followed me into my adult life in the sense of, like, every relationship I've ever had. It's been the stress point for me. And I've never known how to talk about sex. I've never believed truly in my soul that women should even enjoy sex, because no one taught me that. I never was taught about consent, about boundaries. And I was like, how tragic is that? That's something that can be so beautiful and feel so safe. I feel so traumatized around. And I think part of that is just the conversation has never felt like it's for me. And so I thought, how cool would it be for there to be a sex comedy that features a South Asian lead where we can normalize this conversation because I cannot be the only one. And through talking to some of my other adult female friends, it seems that at any age, 30s, 40s, 50s, women in particular, and probably all people, but I'll focus on women. Still feel fear and awkwardness and uncomfortable around the subject. And I feel like we need to correct that. You know, we're 50, 50% of the population, and we deserve to feel empowered and safe and comfortable when it comes to sex.
- [24:27]
Reshma Sajani
Yeah, I want to come back to that because I, I, I was kind of had a similar experience growing up. So. So for what is the process? So you have this film, you're working on it for seven years. Like, what's the next process as, like, to create it? Like, what's the obstacles you encountered? Like, how'd you do it?
- [24:45]
Lilly Singh
Totally. So actually, the first draft of the script entered my inbox seven years ago by the original writer, Neil Patel, and the director, Sara Zandia. We all co wrote it together. But 70 years ago, when it came to my inbox, you know, there was years of us workshopping. It takes a long time to workshop a script, and that was a few years we tried to get it sold, you know, to a big studio. That didn't happen because I was told it's too niche. I'll let you all deduct why that is. It's about sex, which is a pretty universal concept, but, you know, it features myself and a South Asian mom, and it's told to the South Asian perspective. So feedback was it was too niche. And that's the struggle with these types of stories, especially in the time we live in now. Telling these types of diverse stories is next to impossible in Hollywood. It is truly, truly next to impossible.
- [25:29]
Reshma Sajani
So sad.
- [25:29]
Lilly Singh
Yeah. Yeah, it is. It is. We've taken major steps backwards in, in this way, for sure. And so after that, we were like, all right, we're gonna get it independently financed. It took years for us to find a financier, years to raise the money. This all Covid happened throughout this as well. So, you know, that was a big pause button. Then we were chasing the writer strike and the acting strike, and so there's just every possible obstacle that could have hit us during this movie. We actually shot the movie in its entirety during the writers strike, which means, as.
- [25:58]
Reshma Sajani
You're kidding.
- [25:59]
Lilly Singh
I could not make a single tweak to the script. We only had one draft of the script that we shot with, which is unheard of when shooting a movie. Wow. And we did it on a very, very tight budget in Toronto. And then we premiered at south by Southwest and took a year or two years to figure out distribution. And now finally, it's in theaters now. So when I tell you that all of my hair is white and my therapist is intimately familiar with every point of this movie, it has really, truly killed me. I mean, I Love it. I'm so proud of it. It's my baby. But it has truly been a labor of love.
- [26:30]
Reshma Sajani
Wow. It's so powerful. You know, I've been thinking a lot about content. Cause you're right. We're in this moment right now where nobody wants to fund, you know, content from women, from people of color, from lgbtq, Right. Et cetera, et cetera, et cetera. Like, you know, that moment lasted for like a second. And we're in this moment where so many of, like, the networks and the companies are quite frankly, owned by the people who don't want to see that content. So, like, what did you learn in this process in terms of, like, what's your advice you would give to somebody? Would you say, don't do it. It's just too fricking hard. It's impossible. Or would you be like, yep, this is exactly what we have to do. And we need these set of things to be able to make this kind of content and movies and stories.
- [27:16]
Lilly Singh
So I get this. This question of, like, would you recommend other people do this? I wish I could sit here and tell you that Hollywood is going to change. I wish I could sit here and tell you that it's. It's okay, it'll get easier and it'll get fine, and you just have to fight for your seat at the table. I genuinely don't know if that's true. I feel like the system of Hollywood is so powerful that there's so many people at the top. It's really hard to infiltrate. I do feel like me doing this as an indie was the only way it would have happened. It is so hard to make an indie movie. It is so hard. When I tell you my sanity, my money, the amount of resources I put into this money is vast. But I wouldn't tell people not to do it. I think it is one of the only ways to do it. Do it in a way where it actually feels diverse, where it's not being watered down, where you can actually have somewhat of your vision on the screen. Because when you do go through the Hollywood system, I. I've had it happen with a ton of my other projects. This is beautiful, nuanced piece of art that a bunch of execs come in and they make it something totally different. They make it something super watered down. They make every love interest white. They make it so that there's no nuance whatsoever. And so the advice I'd give people is, it's so hard, it's going to be next to impossible. But you absolutely have to do it. And the number one thing I learned during this process is, you know, I'm a big believer of I can work my way through anything and I can work hard enough and accomplish anything. And I can have a certain degree of being a control freak to figure out everything. This movie was like, hold my beer. The amount of things I've not been able to control and I've just had to go with God, let go, but.
- [28:50]
Reshma Sajani
Let go in a really scary way.
- [28:51]
Lilly Singh
Like, I'll give you an example. You know, my, my film is in theaters right now and clearly anyone listening knows I'm a. I'm a type a control freak by now. I think we've established that. But you don't know which theaters your movie's gonna be in until two days before the release. What, so someone like me that wants to go to all the cities and do the Q and A's, like you don't know until two days before every Monday they'll tell you which theaters continue having your money. So right now we're taping this as Monday. I don't know which theater my movie's still gonna be in this week until they email me whenever they choose to email me today. And so it's impossible. So I have all these ways I wanna help the movie succeed. I can have my friends do buyouts.
- [29:29]
Reshma Sajani
But you can't do them.
- [29:30]
Lilly Singh
But I cannot do that.
- [29:31]
Reshma Sajani
That would drive me frickin nuts.
- [29:32]
Lilly Singh
And that is just this entire process. This is one example I'm giving you with everything. There's like, I have all these amazing resources I can use to make this movie win. Don't have any of the information or any of the ability to use any of them. So it's, it's a lot. It's a lot.
- [29:48]
Reshma Sajani
Can I ask you a question? Do you think today you could have done what you did at YouTube in 2010?
- [29:54]
Lilly Singh
I genuinely don't. No. And I don't think so. I think where I am in my life right now, I don't know if I would have had the same level of like, energy and love of risk.
- [30:05]
Reshma Sajani
Yep.
- [30:06]
Lilly Singh
Love of risk at this age. I mean, where I am right now, I'm fully able to be 100% the person I need to be now. But if I had to start from scratch now for two reasons. One, because of where I am in my life. And also, number two, because of the landscape of the digital space, which is so super saturated and so, so tough to navigate now, in 2010, there was a lot less. There was a lot less people. And so my honest answer is I don't think so. I think everything happened exactly when it was supposed to happen.
- [30:32]
Reshma Sajani
Yeah, I don't know if you could fight the algorithm in the same way. Right. I don't know about you, but I've always struggled with burnout and focus. This is such a common experience for so many of us, but what we don't realize is that sometimes the difficulties you go through might be something deeper. It might be time to explore what it means to be neurodivergent. If that's where you're at, I want to tell you about another podcast you should check out. It's called Hyperfocus with Ray Jacobson. Each episode Ray speaks with a different expert, whether they're a scientist, doctor or researcher, to dive into some of the big questions and headlines around mental health and well being from an ADHD lens. They talk about things like can you really hack your dopamine? And what parents need to know about the MAHA Report. I checked out a few episodes and was so impressed by how they broke down adhd. I thought I knew what ADHD was. But hyperfocus taught me the misconceptions, what to look out for with kids with adhd, and even trace back the history of how women have been underrepresented in ADHD diagnosis. As a parent and midlifer, I feel better equipped to understand what it really means to have ADHD and how to support those around me who are neurodivergent. If you're curious about adhd, make sure to listen to Hyperfocus with Ray Jacobson. Search for Hyperfocus with Ray Jacobson in your podcast app. That's Hyperfocus with Ray Jacobson. Sometimes I wish I had a personal sommelier to guide me to find the best wines I normally wouldn't be able to access. I get so overwhelmed at the store trying to pick the right wine when so many feel like a complete wrong fit to my palate. Nothing beats a quality wine, but where do I find them? Don't settle for ordinary wine. We deserve better. That's why I use Sumpsation. Sonsation's expert team seeks out incredible wines from top independent producers. Bottles you won't find in stores and shelves. These aren't mass produced wines. They're handcrafted with care, using pure ingredients and meticulous winemaking. Their team of sommeliers curates the selection. So you're getting wines that redefine what exceptional tastes like, whether you want a single bottle, a guided tasting experience, or an Entire wine club membership. Somme Station makes it easy to elevate your wine experience. You're not just giving wine, you're giving their next favorite bottle. Plus, they have a massive online wine shop with hundreds of hand selected bottles plus curated wine club options. If you love discovering new favorites, want to go deeper? Somsation offers virtual tastings, private tastings, and even sommelier services. To make your experience even more special, shop their wines@ sumsation.com mysocalledmidlife.
- [33:33]
Lilly Singh
Hey, it's me, Steve Burns. And I'm so glad you're here because you and I go way back, right?
- [33:39]
Reshma Sajani
Yeah.
- [33:39]
Lilly Singh
And look at us now, like we're all grown up. We've got this new podcast where we.
- [33:43]
Reshma Sajani
Talk about all this grown up stuff.
- [33:44]
Lilly Singh
And there's special guests like Jamie Lee.
- [33:47]
Reshma Sajani
Curtis and Bill Nye, but for the.
- [33:49]
Lilly Singh
Most part, it's about you. I mean, it's always been about you. From Lemonada Media Alive with Steve burns.
- [33:56]
Reshma Sajani
Is coming September 17th.
- [33:57]
Lilly Singh
Wherever you get your podcasts or you can watch every episode on YouTube.
- [34:14]
Reshma Sajani
I want to talk about the film again. So what are you hoping that people. I'm going to tell you what I took away from it, okay?
- [34:18]
Lilly Singh
Please.
- [34:18]
Reshma Sajani
What are you hoping that people take away from this film?
- [34:21]
Lilly Singh
I think, listen, I'm hoping that they laugh and they feel seen and they have a great time with their friends. But if none of that happens, which I'm hoping it does, but if none of that happens, just to normalize the conversation around sex, I think it's so important for, I mean, it's, it's such a big part of our lives and for people, especially young girls, to not feel safe and feel like they can have this conversation is really unhealthy to me. And so at the very least, I hope people just leave being like, yo, did you feel like that about sex? Like, I don't know, should I talk to my parents about this? You know, I'm encouraging people to take their parents. And I know that sounds crazy because the sex comment, I watched it with my parents and for the first time ever, we had the top and we talked about these things. And I think that's the step towards healing. It's like we need to normalize this conversation around sex so we can all be safer and not to get super dark. But in many communities, the South Asian community is definitely not an exception. There's so many issues around sexual abuse and consent and violence. And I'm like, if we normalize this conversation around sex and sexual health, I do think there will Be a massive positive ripple effect in people's lives. Yeah.
- [35:22]
Reshma Sajani
Not to do any spoiler alerts, but like that, you know, one of the scenes that really stuck with me was the end, right, where you're there in the school. You know what I mean? Council meeting. And, you know, you're talking about both your internalized shame and the fact that you've denied yourself pleasure in many ways, but not knowing your body and then everyone's kind of standing up and sharing their stories. And similar to, like, my mom never had a sex talk with me. I was told to stay away from boys. You know, my mom would peek out, you know, at 10 o', clock, see who was in the car. And it really created, like you said, this almost disconnection. Like, I don't feel like I know at 50, I'm about to be 50 this year. I don't feel like I know my body.
- [36:06]
Lilly Singh
Right.
- [36:07]
Reshma Sajani
And what do you hope, you know, by really centering that conversation, especially kind of in this moment where they're getting rid of sex education in schools, like, we're actually going backwards. That's what you're seeing more pregnancy. The, you know, the woman in Kentucky. Right. Like, there's. You're seeing almost like a return to shame. So what? How could this film be like a spark in this moment to change that?
- [36:37]
Lilly Singh
Yeah, I mean, that's the hope of it. Fortunately and unfortunately, the attack on women is pretty consistent. So I feel like everyone's like, this film is so timely. And I'm like, unfortunately, if it released any time within the past five years, it probably would have been timely for better or for worse. I mean, that makes me sad to say, but that is the truth. I just hope it, like, kind of holds a mirror up. I feel like comedy is such a good vehicle to have these types of awkward conversations, especially conversations where people otherwise are really defensive. I think that's a superpower of comedy, and I've always used it that way. It's the best for people to lower their defense mechanisms and actually look at themselves in the mirror. And I was shocked. You know, when I was researching for this movie, I talked to a lot of teachers and one of the most, my first cousin. And I was not expecting her to say the things she said. She was like, till this day, like, in 2025, parents pull their kids out of sex. Wow. They do not want their kids to learn about any. And I was like, really? And I listen, I don't have kids, but I personally cannot understand why I would not want my kid to learn about safety with sex, about sexuality, about, like how to be comfortable talking about sex and talking about your body, what you like and don't like that. I don't know why you would not want that.
- [37:42]
Reshma Sajani
No.
- [37:42]
Lilly Singh
Or your child. It makes no sense to me.
- [37:45]
Reshma Sajani
No. I mean, my 10 year old asked me about sex and I had a conversation with my mother that has still not ever had with me. Not the full thing, but because I know that boys as young as 10 are get exposed to porn all the time. And so while he's online playing his Robloxes video games, I want him to more hear about it from me. But yeah, I mean, we are in this big, big, big moment in this culture around shame. And it's really, it's interesting. But then we kind of romanticize Bonnie Blue, you know what I mean? And so it just creates so much, I think, complexity and dichotomy of like, what's the message that we're actually sending in this society right now?
- [38:27]
Lilly Singh
I think not allowing your kids to be educated and deprive of them of information is a massive disservice to them. And so I hope that's what people take away from the movie is like information and knowledge. So that kids can actually have the tools and resources is really important. And if you believe that they're. Oh, if I don't talk to them about sex or not having sex, that is a level of delusion that you. That needs to really be worked on. Because look around social media, music, movies, like, they're gonna learn it from somewhere and you would probably want them to learn it from an accurate source.
- [38:59]
Reshma Sajani
Yeah. What was the second theme in the film that was important to you or that you were trying to get across?
- [39:05]
Lilly Singh
You know what? There's a lot of themes in the movie that are really important to me. Of course, the first one being, you know, I think the first theme is a woman's journey unlearning shame. I think from the day a girl is born, she's just bombarded with messaging about you should be ashamed and you should do this and you shouldn't do this. And it's just a system of control. And so the first theme was like a woman very genuinely unlearning shame. Of course there's commentary around sex ed and sex education. There's also a through line between the character, the main character, Maya, and her mother, which is really sweet, powerful, which is. Yes. So the mother is a single mother who also, she's like operating in a system of shame because her husband cheated on her. And now she's like, I can't date anyone else. I can't love again. I can't feel pleasure, I can't be happy. And I think throughout the movie we see this mother character, through her daughter also learn that like, wait, I also am allowed to enjoy life and experience intimacy again. And it's another person unlearning shame. And so I wanted to show all these parallel stories of women just going through real stuff and collectively unlearning it. And another last theme I'll talk on, which I think is really special, is in the movie, Maya is learning from her students as well. And I think something we are bad at as we get older is learning from younger people. Especially as a South Asian woman. My whole life I was taught, respect your elders. They know better. Older people know better. I think there's a lot of value to looking to younger people because when you're older, you start treating your opinions as facts. You believe that everything you know is word. And that's what it is. Younger people still question things. They still are like, well, why is this like that? Why isn't this like that? Is there another way to do that? Why should I believe that? And there's a lot to be learned from that level of like, curiosity and questioning.
- [40:51]
Reshma Sajani
Yeah, I love that scene where they're gathered around her and she's like, what's wrong with me? And they're like, don't worry miss, you're fine. And I think that's right. It goes back to this point of also just connection and being able to break down the boundaries that we have. Whether it's age, whether it's how you're supposed to act or be. I thought that that was. Well, listen, you got all of those points across in a really beautiful way in the film and I really loved it. I want to talk a little bit about some of the projects and your journey of like going through these careers and projects as you're young and entering into midlife. Tell me about your experience hosting A Little Late with Lilly Singh. I mean, I can tell you from like when you got that gig and you did that, we were just like, ah, like it was just. It was a big deal.
- [41:45]
Lilly Singh
Yeah, it was a big deal. You know, it's definitely one of the biggest things that ever happened in my life in terms of my career. And when I reflect back on it, I can tell you it was the wildest two year ride of my life. Like, the amount of things I learned in those two years is like a ten year crash course. Truly. It was A really exciting time. I'm really grateful for what I learned, but it was definitely the most. One of the most difficult things I've ever done in my life.
- [42:09]
Reshma Sajani
Tell me more.
- [42:11]
Lilly Singh
Well, you know, I did not grow up with late night. My parents didn't watch the late night, probably because they couldn't relate to it, which is why, you know, they wanted someone like me to be host. And so I wasn't as familiar with the prestige of late night. So actually, the first time they asked me to do it, I said no, because I was like this. I didn't grow up wanting to be a late night host. I didn't like, this is not my dream. And then a month went by and they circled back again. And I'm a big believer of the universe bringing things to you for a reason. So I was like, okay, okay, let me look at this properly. Now I say it's difficult because that was one of those decisions that I didn't make solely because of my own authentic desires. Like I said, I did not grow up with late night. But my team and everyone around me was explaining to me the historic nature of something like this. Like, you would be the first in so long and, like, this would be really meaningful to help pave the path. And I was like, okay. So really the decision was made from a place of pressure, obligation, and responsibility. Right? Not so much like, oh my God, I can't.
- [43:07]
Reshma Sajani
My dreams come true. Exactly, yeah.
- [43:09]
Lilly Singh
And so that's a very difficult place to operate from, especially when you're stepping into the machine of late night. So late night to begin with is already extremely difficult to do. Right. It isn't a daily show, but when you're a new show and a new host and you're trying to, you know, you're following Jimmy and Seth and those, those audiences are used to those two people. Now you're trying to get them to stay at a really late hour to watch me, someone who's fundamentally quite different. That's really hard when you're doing it with a fraction of their budget. That's even harder when you're doing it on the schedule we did it on. That's more difficult. So the first season of my show, we shot 96 episodes in three months.
- [43:45]
Reshma Sajani
Wow. Yes, wow.
- [43:47]
Lilly Singh
It was extremely difficult to do. Extremely difficult to do from a physical, mental, spiritual, emotional standpoint. Like, absolutely. Just torment. And then the pandemic hit. So the first season of my show aired during the pandemic. And so I'm the only late night show that has a live audience that's talking about traveling and parties and all that type of. So already I've lost the game because.
- [44:09]
Reshma Sajani
Like, no one's doing those things, right.
- [44:10]
Lilly Singh
Because late night's all about being timely. But if the. The schedule and the budget doesn't allow you to be timely, that's the spark of late night. So you've already lost that. So the first season was very difficult for that reason. The second season, I shot in its entirety in the Pandemic. So I shot all the interviews over zoom. Same, you know, budget, same, same issues. And I think when you expect a new show to find its voice, find its audience in two seasons during a pandemic, like, that's. That's kind of asking for failure, in my opinion. You know what I mean? I think with a thing like that, you need to dedicate at least, like, five years of proper resources to actually let a show thrive.
- [44:46]
Reshma Sajani
Were you sad when it ended, or were you just kind of like, yep, I didn't. Like, I didn't real. I tried this. It's not. It wasn't my dream. It's fine.
- [44:54]
Lilly Singh
You know, one of my friends said something to me that could not be more true. She said, I'm so happy that this show ended because I know if the universe didn't do this for you, you would not do this for yourself. Because she saw just the degree to which I was unwell. Like, I was truly in the worst shape physically, mentally, spiritually in my life. And she's like, I know you care so much about paving this path. If they let you do this for 10 years, you would torture yourself for 10 years. And so, of course, there was part of me that was like, oh, man, this. The show didn't work out, but there was a big part of me that was massively relieved as well, for sure.
- [45:30]
Reshma Sajani
So you're also the host and producer of a popular game, Battle of the Generations. You host your shameless digitals. I mean, you got a lot of projects going on. What brings you joy in terms of which one of them really bring you joy and a sense of real pride in your work. When you're like, are you. Like, when I'm doing standup, I'm like, I guess I'm a speaker or writer. And I know, like, when I'm on stage, I'm like, I am home. I am present. Like, where's the place where you feel the most amount of joy, the most amount of flow, the most amount of presence?
- [46:04]
Lilly Singh
It's funny you ask this, because I just spent a long time telling you that this recent movie, doing it was so difficult to do. But my answer would be that movie. And the reason is because that is a story that I so deeply needed growing up. It is a story that I worked so hard to get made. You know, I love the game show and I love all the other projects I do. But I always think about, like, there's so much noise in the world already. And my number one thing for my production company is like, I don't want to add noise to the world. I want to add commentary. I want to add, like, messages into the stories I do. And this is the best example of that I can think of as doing it, which is like, every day when I was on site, I'm like, this really matters. This really, I think, is going to make people feel very seen. And this feels like I'm living out my purpose.
- [46:48]
Reshma Sajani
Yeah, you're also. You're a great actor. Thank you so much.
- [46:51]
Lilly Singh
I appreciate that. And I will say we were doing it challenged me in ways that really helped me grow. I mean, for my first feature to have so many intimate scenes to steps, I said the threshold for comfortability for me to, like, really do the things I did. I think, like, as an actress, as a storyteller, as a human, really was meaningful to me. And another thing I'll tell you is, like, all acting aside, all movie aside, that experience of playing Maya and doing it healed so much within me. Before I shot this movie, I was not able to talk about sex. I would whisper the word sex. It has, like, made me feel quite confident and liberated and healed something within me. So I think that when you talk about what brought me the most joy, it's definitely projects like that where I can be like, not only am I proud of what this project is, but it has changed some part of me fundamentally as well.
- [47:34]
Reshma Sajani
I saw a cute video you did with your parents. Was it really the first time you guys had this, The S E X conversation?
- [47:39]
Lilly Singh
Yes. It's the first time I've ever heard my dad say the word sex was a week ago.
- [47:42]
Reshma Sajani
Oh, my God.
- [47:42]
Lilly Singh
When he watched tv. I know. I have headphones on. I'm like. I put my ears over them. I know. And you know what's crazy about that video? So, yes, I made my parents react to some of my intimate scenes in doing it. The reason is one, they're gonna watch the movie. They've watched them. There's no world where my parents are not. So they're see these scenes anyways. Right. And every interview I do feel like, well, what Are your parents think, what do you have something like, mom, dad, can you just react to this so we can just get this out of the way? And, you know, they were so happy to do it. And my parents actually really loved the movie. And the comments on. If you look at the comments under that post, they show you why this movie is important. Honestly, I was not anticipating. Like, some people are like, oh, my God, I wish I could have this conversation with my parents. Like, this is goals in terms of, like, parents and addressing Taboo. There's so many comments that I was not expecting that were so disappointed and for a very particular reason. It was. It's one thing to talk about sex or show this to your mom, but it's so disrespectful to show it to your dad. Dad, there's so many comments that are like, how dare you put your dad through that?
- [48:43]
Reshma Sajani
What is that? What is that about?
- [48:46]
Lilly Singh
That is essentially the patriarchy, which is basically like, hey, you can, as a woman, have this conversation with other women, but for you to think as a woman, you can have this conversation with men and especially the man who raised you is. Is a shame on you. And that's fundamentally a huge issue. A huge issue, because, you know, it's. It's putting men on this pedestal again of like, my dad doesn't have to talk to me about sex. My mom can handle that, and my dad doesn't have to make me feel comfortable when it comes to sex. My mom has to do that. And, like, when we take a step back and you look at abuse and you look at all the issues that face our community, you're like, you should absolutely want women to feel empowered to talk about sex with men.
- [49:25]
Reshma Sajani
That's right. And you want men to actually be able to talk to their daughters about sex in the same way.
- [49:30]
Lilly Singh
Correct. It shouldn't be. Yeah, a huge red flag for me. And I was like, that's why this movie's important.
- [49:35]
Reshma Sajani
That's powerful, huh? So as we close, like, how do you find space to, like, rest and recharge? Like, so, like, after you're doing this, are you going on. Going to Mexico or something? Like, you want to make. What do you do?
- [49:49]
Lilly Singh
That is the plan whenever my schedule allows. Listen, I've come to terms with the fact that my life is one that operates in seasons. I know the concept of work life balance gets thrown around a lot. That cannot happen every day. My schedule is one where it's like, okay, this is the season for rest, and this is the season for hustle and I knew with this movie. I knew very well. Yeah, it was going to be a lot. And it is a lot. Like, I won't lie. I'm super exhausted. I just got off a flight. I don't know what day it is. I don't know what time it is. My body doesn't know what country I'm in right now. But after this kind of slows down, I will absolutely be horizontal on a beach somewhere. Not doing a single email in that. Such as the seasons.
- [50:23]
Reshma Sajani
Yeah, it's such good advice. I'm kind of the same way. And then you can anticipate it, right? You're like, okay, I'm doing a tour of a book coming out or this big project. Projects coming out, or we ought to go lobby comic. So it's going to be three months of this, you know, and you're just going to be on a plane.
- [50:35]
Lilly Singh
And you lock in.
- [50:36]
Reshma Sajani
Yeah, and you lock in. And then you take the time to really rest. Do you know how to rest, though? Like, when you. When you go horizontal, do you really go horizontal?
- [50:45]
Lilly Singh
I do now. I do, yes. Back in my YouTube days, I didn't because everything was content and I was like, da, da, da, da. But now I do. Now I'm very good at being like, nope. And I'm really good at saying no. I never used to be good at saying no. If I go on vacation now for a week, I'm like, whatever the ask is, it's no. Whatever the email is, it's not getting response. Like, I need to.
- [51:03]
Reshma Sajani
Like, even if it's like, the biggest thing ever, it's no.
- [51:06]
Lilly Singh
I mean, don't put me on the spot like that, because maybe. But what I'm saying is I'm a lot better. I'm a lot better at really, like, prioritizing rest. Because I know it makes me better. It makes me better when I'm rested. Also, when your mind is quiet, that's when you have the best ideas. I've learned.
- [51:21]
Reshma Sajani
Yeah.
- [51:22]
Lilly Singh
Anytime I'm bored, quote unquote, suddenly I'm like, I have an idea for a movie.
- [51:25]
Reshma Sajani
It's so true.
- [51:26]
Lilly Singh
Because I actually have space.
- [51:28]
Reshma Sajani
I was bored this summer and I'm like, now I'm like, oh, there's a documentary and another book and this course, I'm like, it's so true, you know, to close, like, okay, so what's next? Because you had this thing for seven years. If I'd asked you five years ago, you'd be like, I'm working on this thing.
- [51:42]
Lilly Singh
Yeah.
- [51:42]
Reshma Sajani
What do you got in the hopper.
- [51:44]
Lilly Singh
I have two more scripts, feature scripts that I've written that are almost good to go that I want to torment myself in the exact same way that I've done with doing it. Hopefully it's a little easier this time because I know a little more and I've learned the and maybe, who knows, maybe there will be a big studio that, you know, buys them. But this is what I want to do. I want to tell the types of stories that I wish I had growing up that otherwise we haven't seen before. And I want to normalize all the conversations that I wish were normalized.
- [52:08]
Reshma Sajani
Well, listen, I mean, I hope you feel good that you put something out there that is excellent and funny and good and like changes the world. And I do feel like it is going to help open up doors that you know that you'll even do great things. So I hope everybody watches it and let us know how we can help you. But it was beautiful. It was really good.
- [52:28]
Lilly Singh
Thank you and I appreciate your support and you watching it.
- [52:43]
Reshma Sajani
Thank you so much Lily Singh for talking with me today. Her new movie is called Doing It. One last thing, thank you so much for listening to my so called Midlife. If you haven't subscribed to Lemonada Premium yet, now's the perfect time. Because guess what? You can listen completely ad free. Plus you'll unlock exclusive bonus content like even more from my conversation with Anna Malika Tubbs, who gives you tips for finding time to write. When you're juggling all the things we juggle, just tap that subscribe button on Apple Podcasts or head to lemonadapremium.com to subscribe on any other app that's lemonadapremium.com don't miss out. Thanks and we'll be back next week. I'm your host Rashmi Sajani. Our associate producer is Isara Acevez and our senior producer is Chrissy Pease. This series is sound designed by Ivan Kurayev. Ivan also composed our theme music and performed it with Ryan Jewell and Karen Walter Tuck. Our VP of New Content is Rachel Neal. Special thanks to our development team, Oja Lopez, Jamila Zara Williams and Alex McGowan. Executive producers include me, Reshma Sajani, Stephanie Whittles Wax and Jessica Cordova. Kramer. Series consulting and production support from Katie Cordova. Help others find our show by leaving a rating and writing a review. And let us know how you're doing in the you can submit your story to be included in this show@speakpipe.com midlife. Follow my so Called Midlife wherever you get your podcast or listen. Ad free on Amazon Music with your prime membership. Thanks so much for listening. See you next week. Bye. Want to listen to your favorite Lemonada shows without the ads? Subscribe to Lemonada Premium. On Apple Podcasts, you'll get ad free episodes and exclusive bonus content from shows like Wiser Than Me with Julia Louis Dreyfus, Fail Better with David Duchovny, the Sarah Silverman Podcast, and so many more. It's a great way to support the work we do and treat yourself to a smoother, uninterrupted listening experience. Just head to any Lemonada show feed on Apple Podcasts and hit subscribe Make Life Suck Less with Fewer Ads with Lemonada Premium, are you looking for ways.
- [55:11]
Lilly Singh
To make your everyday life happier, healthier, more productive, and more creative? I'm Gretchen Rubin, the number one bestselling author of the Happiness Project, bringing you fresh insights and practical solutions in the Happier with Gretchen Rubin podcast. My co host and happiness guinea pig is my sister, Elizabeth Craft.
- [55:28]
Reshma Sajani
That's me, Elizabeth Craft, a TV writer and producer in Hollywood. Join us as we explore ideas and.
- [55:34]
Lilly Singh
Hacks about cultivating happiness and good habits. Check out Happier with Gretchen Rubin from lemonada Media.