Highest Self Podcast 432: How To Go From Lost To Getting Your Life In Shape with Lilly Singh


Do you ever look at your life and while it seems like you have everything, you still feel overwhelmed, empty and wondering “Is this really it?” This happened to Lilly Singh, who you may know from her hilarious Youtube channel and TV show, and for the first time she shares how while she was making the world laugh – her mental health was crumbling. In this conversation we share the challenges faced being first generation with immigrant families, as well as the blessings, how to bring up therapy to your parents if they’re resistance, what is means to “Be a Triangle,” our relationship with social media, what she would and wouldn’t have been differently in her career and so much more. Get ready for a good one!

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Episode 432: How To Go From Lost To Getting Your Life In Shape with Lilly Singh
By Sahara Rose

[00:12] Sahara
Namaste, it’s Sahara Rose and welcome back to The Highest Self Podcast, a place where we discuss what makes You, Your Soul’s Highest Evolvement.

[00:19] Sahara
If it’s your first time listening, welcome, I am so grateful to have you here, this is an amazing first Episode to listen to, and you may be listening to it because you’ve heard the guest – Lilly Singh.

[00:29] Sahara
So, she is a hilarious, fierce, first-generation queen, who really has won our hearts and our laughter, over from her decade plus, of creating hilarious YouTube content, that’s how I first discovered her. And she shares, for the first time ever, really, her journey of feeling lost despite the success; feeling burned out; feeling like she needed to get to the next thing and the next thing; the issues with her family; the intergenerational trauma that is often passed down until we become aware of it; and how she was able to build this framework around being a triangle, that she’ll share in today’s Episode, to get your life back into shape.

[01:11] Sahara
So, this is such an amazing conversation, whether your parents, or your family, are immigrants, we really share how we both have that in common and how, sometimes, there can be a lot of pressure to be successful, or a hard time understanding your family, or shame around going to therapy and healing, and how to really overcome that and have compassion for your family.

[01:31] Sahara
This is also a really great conversation if you’re someone that wants to be a content creator. So, Lilly, not only created her YouTube channel, but has gone onto to have her own late-night show, A Little Late Night with Lilly Singh, her own scripted show that she’s on, called Doll Face, which is hilarious, and so much more. So, she has been able to really create a life for herself and her entertainer archetype, really rocking it!
But then also, just for someone, who feels maybe a little bit overwhelmed and goes into lots of plat-spinning, and things going on in your life, and it feels like everything is so important, that you just don’t know how to chill, how to have fun, and we really share about that in this Episode – our addictions with social media, especially when we’re on a social world, and her career was built off of social media (as was mine), how do we find balance in that.

[02:18] Sahara
So, there is just so much realness in this conversation, too. What I really love about Lilly is, yeah, she keeps it really grounded and doesn’t give you some fluff advice, and tells it to you as it was, that it was a lot of hard work for her, and I ask her what she would’ve done otherwise, if she knew what she knew today, and the answer might surprise you.

[02:39] Sahara
So, wherever you are, in your life, in your career, I think all of us can relate to being a little bit thrown off track, with Covid and everything else that has been happening in the world, and this is really a time to get your foundation in place, so we can bridge and co-create with our highest selves.

[02:57] Sahara
So, with that, let us welcome Lilly Singh, to The Highest Self Podcast.


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[04:04] Interview

[04:04] Sahara
Welcome Lilly, to The Highest Self Podcast, it’s so great to have you here!

[04:07] Lilly
I’m ecstatic to be here! Thank you for having me!

[04:10] Sahara
And the first question I’d love to ask you is what makes you your highest self?

[04:14] Lilly
Hitting me with the hardest questions right off the bat! I think this answer has definitely evolved over my life. Right now, what is making me my highest self is, really understanding and behaving in a way that knows that myself has already complete without all the accolades and all the external validations that is out there.
My highest self, right now, is knowing that all of this cool stuff I get to do, writing books and having a job and having relationships and going places, are cool and awesome experiences, but they’re not my definition, and they are not what make me my higher self. My higher self, I’m already a complete human being and all the stuff is extra. So, that’s what’s making me my highest self, right now!

[04:55] Sahara
So true! It’s always like we’re going to more, to come back and remember that we already were enough. And I just have resonated with your story so much, over the past, many, years, that I’ve been watching your YouTube videos and watching your show and following you, and you’re just such an inspiration, especially for brown chicks everywhere. And I just so resonate with, almost like that first-generation burden on your shoulders of like “My parents struggled and sacrificed so much to be here in this country, so I need to make them proud”, but then also, being a creative person, and what’s making you come alive and all of that drive and ambition and hard-workingness that you got from them, is being placed towards something that they’re not in alignment with. And the struggle of that, like “I so resonate with the hustle and what I wat to put my hustle towards”, you don’t like.
So, how were you able to, kind of, overcome and balance that? And then also, write about it in your book?

[05:51] Lilly
Yeah, it’s a really great question, and I’ll also just add a little more flavor to say, for me, it wasn’t only “Oh, what I want to hustle on is something that my parents don’t understand”, but it’s also something, growing up, culture in general didn’t understand, school didn’t understand, society didn’t understand, because, I talk about a lot now, all the things that I really have learned to value now, which is who I am as a person, how I treat people, how I’m growing mentally, how I’m mentally healthy, how I’m spiritual, none was that was considered success in school, you know what I mean? And for me, it wasn’t just that my parents were like, “We were hustlers, and we were immigrants and we worked really hard so you have to do the same”, it was that, they taught me how to follow rules and how to follow a system, and that system doesn’t reward things like mental health, or spirituality, or compassion, or patience. And so, it was really tough for me to not only reconcile with my parents like “Hey, I want to do something that I know you’re not familiar with, and making YouTube videos”, and I know that different from – my dad, still, to this day, believes that I’m going to go to law school, I’m pretty sure, to this day, he’s like “My daughter could possible go to law school”. It was also just that school that also told me I had to pick a career and do things, and school also got me to think about things in a way that was never looking inwards, and so, I never considered those things successes, for just an array of reasons.

[07:07] Sahara
And now, writing about it in your book, I know for me, sharing that story of my family, and writing it in a way that felt fair to them, but also fair to me, and how I feel, but they’re going to read it, how is that balance for you?

[07:21] Lilly
It is one of the greatest challenges, through my book, through my videos. A lot of people ask like “How do you write about these very vulnerable things that happened with other people?” I have a rule that is, don’t throw anyone else under the bus, in storytelling. That becomes tricky when you’re talking about your own experience, but it involves other people. You know, in the book I talk a lot about my coming out experience, and that was really tough for me to talk about because I’m retelling the story of me telling my parents. And for a long time I didn’t want to do that, because I didn’t want to tell someone else’s story, I didn’t want them to get mad, to be straight up, didn’t want them to get mad, I didn’t want them to think – my parent’s biggest fear is other people knowing our business, and so, it was really scary for me to do that. And so, I had to do it in a way, that honestly required me to do the work, to not be lazy about it. I think the issue with talking (re-talking) about experiences is that you talk about them from your perspective, and in the book, I tried to do the work to tell all three sides of the story (my side, their side, and what actually happened), and that was really scary for me but I was true to my experience and I felt like I had to do it, but it is definitely a constant fear in my mind, of like “Are people going to get upset?”, and it’s just a line I have to constantly balance. And also, I hope that my parents trust me enough to know where my intentions lie. I’ve had a lot of conversations with them about me talking about them in my stuff, and they know where my intentions lie, and I think that’s an important conversation to have. I think a lot of people skip that step.

[08:50] Sahara
Did you have them read the book before it came out?

[08:53] Lilly
I did not have them read the book before it came out, which was an active choice I made, because part of me was thinking “Do I want to get their sign off on this?” And the danger with that is, I didn’t want them tweaking what I was talking about, I had to trust my gut of knowing that where my intentions lie. It was like that decision where it’s like, there is a chance that people are going to read this and think my intentions were to drag them, think my intentions were to frame them in a certain way. But I actually did a lot of the hard work to point out my own flaws in those experiences. So, if anything, I hope my parents read it and they actually gain more love and respect for me than – I probably haven’t even told them those things in person, the things that were said in the book. I really talk about my own flaws, so I think that’s why I didn’t get them to read it.

[09:45] Sahara
Totally! And it’s such an active healing too, to be able to write about something from a neutral place, to see all of the perspectives and be a step away from it.

[09:54] Lilly
And to be honest. And I’ve learned that these two things can exist simultaneously. You can have the utmost respect for people and love and want the best for them, but you can also draw that boundary and say “But for myself, I need to be true to who I am, and I need to talk about my experiences.” For so much of my life, I’ve had this battle of, I want to be able to talk to people about things happening in my life, but I’m from a culture that loves secrets and they don’t like to talk about things. And so, I’ve always had to, kind of, tether this line, I’ve just come to the point in my life, now, where I believe that communication and community is medicinal, and I don’t think that means you have to expose everything everyone said. I think being together and having a sense of togetherness is really powerful. So, I challenge that culture of secrets a little bit.

[10:39] Sahara
Totally! And I think they grew up in a time that, if someone knew the family issues, it could be a potential threat to the family’s safety, the reputation, their stance in society, whereas, right now, authenticity is all about being vulnerable and sharing your shadows, and they’re like “Wait, what?! Why don’t you share that we sent you to summer camp?”

[10:58] Lilly
Exactly! I think, also, a lot of me writing this book, has been me unsubscribing to, or at least, recognizing and doing the work to unsubscribe to generational trauma. Because a lot of my decisions with this book were me looking at the behaviors and thought patterns I have and questioning where those come from, and the what do people think, and all that type of stuff that my parents have passed down to me.
As a teenager, I think I used to be mad at them about that, like “You care so much about what other people think, you don’t actually love me”, it’s more complex than that, it’s like, you’re absolutely correct, that was a survival tool for them, where they had to care what people thought, because that was their community and support system and those people had to think well of them.
And so, the issue is that we use those patterns in places and realities that are not that. Now we’re online, thinking what will people think, now we’re on dating apps thinking what will people think. So, I’ve tried to do the work to really see where those thought patterns come from and question whether or not that’s beneficial in my actual environment right now, which is different than my parents.

[11:57] Sahara
And it gets passed on! Totally, and they learned it from their parents and their parents, and here we are, the first people in a new country, where there’s a totally new culture and set of beliefs. And sometimes it’s like, imagine we all moved to China right now, we would totally be figuring it out, we don’t know all the nuances of the culture.
So, with that, what do you think are some of the blessings of growing up first-generation?

[12:19] Lilly
So many, so many! And I love that you ask that this question because I think, very often, people can think, from watching my videos, it’s all jokes and comedy, but the best parts of me are because my parents were immigrants. I think I have a layer of resilience that it so impenetrable because of them. I’ve seen them go through things, whether it’s working multiple jobs or having to learn a whole new set of rules or way of life. I think that really puts something special in your DNA with when you deal with what the life throws your way.
But on top of that, I’ve seen my mom, specifically, had to, she’s had to unlearn and learn new things over and over again. Especially as a woman, she’s had to unlearn things she was taught when she was brought up, about what women should and should not do. I’ve seen her blossom into someone, now, who does meditation every day, who really values her mental health. And that’s a big leap and bound from where she started, which was “I don’t have time for that, it’s too late for me, I can’t learn new things, I don’t know how to meditate, my life is just to take care of people”, that’s a huge leap. And so, just to see her adapt and make decisions for herself and learn that she can do that was really inspiring for me, and kind of gave me the permission to do the same. Because I think for a long time, I felt I had to be something because I saw my mom be that something, she was the mother and the wife and the caregiver and the person who kept the house together. And recently, I’ve seen her give herself permission to be her higher self, like we’re saying, and that has been really liberating for me to see. And that’s a hard thing for her to learn because I’m sure there’s probably a million voices in her head telling her that that wasn’t the right thing to do.

[13:55] Sahara
Yeah, it’s a whole multiple generations of women who have been brought up that your worth was defined by how much of a nurturer you are to other people, how much can you serve me, give to me, take care of the kids and everyone else except for you. And they’ve grown up thinking it’s selfish to take care of themselves, which has been passed down to us.

[14:14] Lilly
Right! Absolutely! I think some of the times, and I write about this in the book, where I have butt heads with my parents the most – I want to make it clear to everyone listening, my mom will publicly roast me on the internet, she has no shame when doing this. So, I once wrote a caption that was like “Sometimes you need to be selfish, you need to focus on self-love”, and my mom was like “Must be nice”, in the comments, fully roasting me. But I have learned that you can respect and where they come from and their reality, and still unsubscribe to the ideas that don’t serve you, those two things can exist. It doesn’t mean you’re disrespectful, it doesn’t mean you hate your parents, it means that we have to one up in accordance to our reality.

[14:51] Sahara
Yeah, and in every generation, it stands upon the shoulders of the next, and hopefully the next generations is like, “You guys are so hard working, you don’t enjoy life enough”, and we get to be inspired by them.

[15:01] Lilly
I think, even to truthfully answer your question that you asked me about, was I scared that my parents would read the book? I think I, deep down, had a belief that they are, too, evolving into their highest selves. And so, I just feel like, through the work we have done, the conversations we have had, the honesty we have shared, especially over the last couple years, I have full faith that they are able to also talk about those experiences. I think they are actively unsubscribing from the ideas that don’t serve them well as well. So, I believe that to my core.

[15:31] Sahara
How were you able to start that process? If someone has parents who are totally not into healing or therapy, or any of this, how do you begin that journey?

[15:39] Lilly
Well, I think, first and foremost, it is to respect where that is coming from, and that is what I really struggled with. I used to not understand, at all, when my mom was so hesitant towards therapy. I used to really judge her harshly for that, like “How can you be against something that is good for you? It is good for you, mental health is real, how do you not understand that?” And for so long I would approach it from a judgmental lens, until I actually took a seat and I was like “Let me actually get to – what is it that you don’t believe or like about therapy?”, really understanding the reasons for those types of decisions and thoughts is important, because you’ll realize it’s rooted a lot in those survival instincts from back in the day, my mom’s fear of, I was surprised to know, it’s not that she doesn’t believe in therapy, it’s that she’s really concerned, again, about what will the therapist think, what if she tells someone, what if, it is all of these things that my brain just doesn’t operate that way.
And so, I think, first and foremost, it’s, actually listen and get to know why your parents think the way they do and kind of honor that and give value to that, don’t judge it, know that it’s valid to them. Even though it might be absurd to your upbringing, it is valid for them.
So, I think addressing that helped me to get to the root of “Okay, mom, what if I found a therapist that I will show you all the ways in which you are protected, but with privacy? And what if I give you a therapist that has a similar upbringing to you, so you know the person is not going to judge you?” And then you start to tackle it from a place of progress as opposed to judgment.
So, I actually found the therapist that was South Asian, that I worked with, I got some sessions, I got my mom involved, and she was totally able to relate to my mom. And more than anything, I just stopped making it a fight and more of a conversation. I know that sounds very, it’s easier said than done, but it’s true, stop making everything black and white, this or that, wrong or right, progress is in the middle, and two people that have different viewpoints can still have a conversation. And the point isn’t for you to then see eye-to-eye, at the end of a session or at the end of a conversation, it’s just to at least know that the other person’s coming form.
I think that is the goal, is to know where the other person’s coming from. And the biggest thing that has changed between me and my parents is not that we see eye-to-eye on every single thing, it’s that they know why I think the way I think, and I know why they think the way they think.

[17:53] Sahara
So true! Just to have that compassion and understanding. And yeah, I think they think a therapist is a sign of weakness, and we can also look at the gift of they’re used to the family solving everything, not asking for outside help. So, it’s like, if we need someone from the outside our family, or therapy is for broken homes, we’re not from a broken home, so it’s like all of these, what does it mean if I’m a person who goes to therapy?

[18:15] Lilly
I think that’s true for a lot of things. Growing up, we think of a lot of things are weaknesses, again, because we’re not taught that they could be strengths, and I don’t want to pin this just on parents, I also want to pin this on society and the school system because I have this issue now, where as an adult, if I have a day where maybe I don’t do work or I don’t do emails, or I don’t do something associated with numbers, but instead I was just like a really great friend or I really listened to someone, it feels like an unproductive day, it feels like a not successful day. And I have grown to have a big issue with that because I found myself in a place where I was good at all of the things I was told to be good at, but I was a bad friend and I was mentally unhealthy, and I kept being lost and thinking “Why don’t I have this clarity and this happiness and this fulfillment like I was supposed to have being good in all of those things I was told to be good at”, and that has been a hard pill to swallow. And it’s because of things like therapy not being valued, mental health not being valued, and all these other things not being valued.

[19:22] Sahara
So, you share this concept about being a triangle, in your book. What does that mean?

[19:27] Lilly
Okay, so, let’s dive into this. So, during the pandemic, I, like a lot of people, I’m sure can relate, had a really tough time, but it wasn’t a tough time in the way I thought it was going to be. When it first got announced that we’re going into lockdown, everything shutting down, everything’s going away, I thought “Oh man, I’m going to be really bored and I’m not going to know what to do with my day”, and that’s what I thought I was going to experience. What I actually experienced was a lot sadder than that, to be honest.

[19:52] Sahara
I wish I was bored! I miss saying that.

[19:55] Lilly
Yeah, it was more so that when the work went away, and the gigs went away, and the projects went away, I didn’t even feel like a worthy human being, I just had the feeling of “What is my value? what can I do today, to feel valuable, if I can’t do these things? And why am I even here, what is my purpose?” That really bothered me because I thought, that means that you don’t actually value yourself in any other way, and you don’t have any other purpose in life, except for all of these external things, and what does that make you as a human being, what is that going to make you years from now, if the stuff disappears, and does that mean that up until you got those things, you were worthless? That really was a hard thing to come to terms with. And so, I concluded that it was because, I felt that way because I had never actually done the work to have a foundational set of beliefs of who I am and what I want out of life, and what’s important, because I was always just told what that should be, I was told what to do and what to value, without ever actually giving it original thought on my own. And that left me feeling pretty empty and lost. And so, I wanted to build a place in my mind, a safe place in my mind, that was not tied to anything external, not tied to external relationships, not tied to work, not tied to what I did and didn’t have. And so, when I decided that was the goal, to create a strong foundation, a safe place in my mind, I hopped onto Google and put ‘strong foundation, how to build a strong foundation’, and the triangle popped up, because, structurally, the triangle is the strongest shape in existence because of its strong foundation.
And in the book, I write about, and if you’re a visual learner, I’ll kind of paint you this picture, but a triangle doesn’t change over time. When you add to a square, it becomes a rectangle, when you add to a circle, it becomes an oval, the fundamentals of those shapes change, when you add to a triangle it just becomes a bigger triangle, it’s still a triangle. And I thought that’s how I want to live my life where I have the set of beliefs, the foundation, where, if tomorrow I won 15 Oscars or I fail 15 times, that foundation doesn’t change, it is just being built upon. And so, that was what my goal was with the triangle.

[22:01] Sahara
So beautiful! And I love that visual that we can see just its sturdy foundation and how that needs to come first, and you’re not able to – you share that you were an upside-down triangle at the beginning.

[22:12] Lilly
I really was, I was upside-down triangle because I feel like I change from my core, very often, depending on what was happening in my life. I know it sounds like a common sense statement of like “Of course your attitude and your thoughts are going to change with what’s happening in your life, but to such a degree”, but one day I’m so grateful and I’m so happy, and I have such a great outlook on life and then something can happen and now suddenly I’m like “Life sucks and why am I even doing this?”, and I started to spiral and I thought, I’m literally just swaying whatever direction of life events put me and have nothing ever to fall back to. At least, physically, when you have a hard day, you can come back home and it feels like a safe place, a little bit, but what is that place mentally; was the job I was trying to set off to do?

[22:59] Sahara
Yeah, having that home base. So, what were the practices for you, that allowed you to recalibrate?

[23:05] Lilly
So, I, while writing this book, looked at every conflict and struggle in my life and thought “What are the set of pillars I can create where everything I can look at through this lens?” And I came up with four, and this was the hardest part of the book, coming up with this framework of “What actually makes this foundation?”, because that’s a fluffy word (foundation), what does it actually mean, I’m a very practical person. So, I came up with four things, and they are:
1) a relationship to yourself; 2) a relationship to the Universe; 3) understanding distraction; and 4) implementing design.
And these four things, I chose because, like I said, I could look through every problem through those four pillars, but also, they’re not tied to anything that will ever change, they’re not tied to my job, to any relationship outside of myself, to where I live, to what life stage I’m in. No matter where I go in life, I will always have a relationship to myself; I’ll always have the relationship to the Universe; I will always have distractions I need to understand and I will always be able to implement design into my life and change things. Those four things will always be constant.
And so, that’s why I made them the pillars, because my goal is to never write a book, and I’m going to be honest with you, I never want to write another book again, I’m hoping that this thing can be the blueprint for years to come. So, I had to design it in a way where it’s like, even the things you don’t know life is going to throw your way, because we always think we have it figured out, like “Oh this is the worse! This is the worse pain I’m ever going to be in! It’s always going to get worse; it’s always going to get better; it’s always going to surprise you in new ways”, the Universe is a master artist it will keep throwing things at you. these pillars have to withstand even the things you don’t know about, and I’m confident that these four things can.

[24:43] Sahara
So good! And you share such great stories about you practicing meditation and overcoming the monkey mind. And I love what you wrote about how we sometimes have that expectation of like “Well, life shouldn’t be so unfair”, and how, really, life doesn’t owe us anything.
So, can you share a little bit more about that?

[25:00] Lilly
Yeah, this has to do with our relationship to the Universe. And I think it’s the relationship that most people ignore the most, but whether or not you want to acknowledge it, it does exist, your connection is something bigger to you. And I want to be clear that this is not me coming at things from a religious mindset, whatever you believe in, whether it’s science, power, God, whatever it is, there is something bigger at play than just you, and I think that’s an important thing to remember, because it also gives us permission to not try to control everything. We should know that, as much as we try to control everything, there are things out of our control.
So, I think that’s just a little humbling reminder for everyone. But also, the relationship with the Universe, I think we have this picture painted in our mind of what life should be, and when life doesn’t match that picture, instead of questioning our expectations, we question life and the Universe. And that’s a really illogical thing to do because that’s make-belief, we’ve made up this idea in our mind, this is not based on facts, this is based on our ideas. And so, we need to see a relationship with the Universe for what it is. It is that we are in this experience, nothing is owed to us, and therefore, when something wonderful happens, it’s actually a great thing the Universe having your back, nothing is against you.
And another way I challenge people to think about their relationship to the Universe is that, every single person listening, I will die on this say, I am confident in saying this, no matter what has happened in your life, think of the worst thing that has happened in your life, the worst thing, the most painful thing, not a single one of you can tell me that something positive did not come from that. The Universe is an exchange, it is a beautiful design, whether you lost a loved one and now you have a greater appreciation of life, whether it’s, your house got broken into, but now you have a better security system, whether it is, you had to suffer through a horrible break up and now you have a better relationship with someone that actually empowers you, the Universe is in constant exchange and we need to think of our relationship with the Universe like that.
And so, I end by saying, the only way to be in a relationship with the Universe is to be of service, because we take and take, and ask and ask and ask, but what are we actually giving back into the Universe is an important part of the relationship.

[27:04] Sahara
I love that so much! And I feel like manifestation is such a buzz word, but people think about it as like “How do I get the car and the boyfriend and the dollar bills and all these things? Universe, be my sugar daddy”, but we forget that we’ve got to give to the sugar daddy of the Universe, we are the sugar daddy of the Universe, and we are the creatrixes of it all.

[27:23] Lilly
And that’s why I love the word relationship with the Universe, because, when you think of the word relationship, you think of two beings and how they interact with each other. It’s not one way, no relationship should be one way. And so, you have to ask yourself, are you the type of partner to the Universe you would want? Do you listen back? Do you give back? Do you love back? And would you be in a relationship with someone that didn’t do those things?
So, when you ask for things from the Universe, you really have to ask yourself “Are you a good partner to the Universe?”, and then, the flip side of that, being the first pillar, are you a good partner to yourself? Again, relationship to yourself, do you listen to yourself, do you love yourself, are you patient with yourself, are you a good partner to yourself, do you give yourself the time of day? And that’s why I, specifically, worded these pillars with relationships, so that we can think about them through that framework.

[28:10] Sahara
I love that! And it is a constant listening and what’s showing up, and those things that are showing up are the obstacles that are preventing you from having that whatever thing is, instead of feeling like it’s unfair, like “Oh, this is showing up, so this is my next lesson to learn.”

[28:25] Lilly
Yeah, absolutely. I also think that we are, as human beings, and another reason why I like the word relationship is because we are so all or nothing, as human beings. Or at least we become very all or nothing, in some regards.
I know when I talk about relationship to self, and I talk about meditation, and I’m sure you’ve experienced this as well some people will respond saying “That doesn’t work for me, I don’t know how to do that, I can’t turn my thoughts off”, and my response to them is always “Who says that’s wrong? Maybe what you need to do, during meditation is to hear all of those thoughts, maybe you need to listen to yourself, maybe you’ve not been listening to yourself and this is your brain’s chance of actually getting you to listen to some of these thoughts that you’ve been ignoring.”
I think we treat mindfulness and people and situations and conversations very all or nothing. We have to label them, we have to find them, it has to be this or it has to be that. Progress is in the middle and so, we just have to remember that when it comes to our relationships, that it doesn’t have to be all or nothing, progress is in the middle.

[29:20] Sahara
And there are so many forms of meditation, so you share that you use dance as form of meditation, which I love! Can you share a little bit more about just how you use dance to unwind?

[29:29] Lilly
Yeah! I think, we were talking before this, about how we’re friends with some mutual people, and I’m friends with a lot of people that wake up at 6:00 AM and meditate for 3 hours, and I’m like “You’re so cool, I could never do that!” And I think we need to know that meditation can look different for everyone. Sometimes, after a long day, I come home, play some Bob Marley, close my eyes and just move my body and dance, not to be a good dancer, not to perform for anyone, but just to feel my body move and just express and be free. For some people going on a walk can be meditation, writing music can be meditation.
I also, in the book, talk about the difference between meditation and being present with yourself, because when I talk about being present with yourself, people will say “Isn’t that meditation?” I have a little bit of a distinction between the two. I think meditation is intentionally making time to isolate yourself and do something that’s a safe place for you. I think, throughout the day, though, without meditating, you can still choose to be present with yourself. And what I mean by that is, I mean a lot of it has to do with social media and our reality, it’s not the only way we distract ourselves, but it’s probably the biggest way, which is, when you’re alone in an elevator, do you pull out your phone because you can’t even hear your own thoughts? We do with it other people in an elevator, I guarantee, anyone listening to this, if you walk into an elevator with two other people, every single person is going to pull out their phone, because they don’t want that awkward interaction, but do you do that when you’re alone in an elevator? You already know you don’t have service in that elevator, but you’re still going to do it as a crutch because you don’t even want to be alone with yourself for those 20 seconds in an elevator. While you’re waiting for a flight, when you have a spare second, how do you spend that time? Is it to then dive into something else, into noise and let noise into your world, or do you actually sit and think “How do I feel right now? How do I think about this thing right now? What is important to me right now?”, those are the ways that we present with ourself. And the best example of this, I write in the book that I deleted social media off my phone for 6 months, during the pandemic, and it was exhilarating and terrifying, all at the same time, because I had phantom hand for a while and my phone kept trying to go onto social media and it wasn’t there, but I kept trying, which was scary to me, to know how much of a response it just is, without us thinking about it. But something wonderful happened, I was in the airport and I was waiting to board a flight, and usually when I’m waiting to board a flight I’m just on social media, waiting to board that flight. Every other person in the terminal was on their phone. And so, I was just looking around and I thought “You know what, no! Let me try something different. Let me think about the trip I’m about to take, let me think about what I want, the intention I want for this trip, what I want to feel during this trip, how grateful I am to be going on this trip.” And it sounds kind of silly to say, but I felt so important in that moment, of listening to myself and giving myself the time of day to have just some thoughts and to hear them out. And I think we don’t do that enough; we don’t treat ourselves well like that enough.

[32:20] Sahara
So true! It’s almost like you seem like a psycho to not be on your phone, just standing in the line, staring out into the distance, because we’re so used to every single person head down. And I think we also feel like we’re falling behind, so, every spare second I get, maybe I can get ahead of responding to those emails or WhatsApps or texts, and it even affects the quality of our relationships, our friendships.
I feel like so many friendships are, I send a voice note back at point of time and like three days later they send a voice note back, and is that really connection?

[32:50] Lilly
Connection is one of the things I fear – there’s a few things I fear are becoming extinct with social media, and that’s connection, context and accountability. I think all of those three things are really important to have meaningful conversations, and those things are very hard on social media. And I want to make it clear, if anyone who doesn’t know me, I have a career because of social media, I started on YouTube, so I understand it’s kind of strange for me to be saying this, but I think we need to understand our relationship with social media. It is a tool for us to use, it should not be using us, we should be getting used by social media.
And the reason I put social media back on my phone after those 6 months, is because I did the work with just my relationship with it, and to understand what purpose it should serve in my life. It is a tool to express, to learn, it is not a tool to validate and to define a purpose with, it is not a tool to only have conversations on, because you cannot have conversations with context and accountability on social media, those are still better in person, face-to-face, with real people, and we should not make the mistake of thinking otherwise.
And so, social media is great, as long as we understand how it should be used.

[34:03] Sahara
So, now, coming back to social media, how do you use it?

[34:06] Lilly
Now, I very much so, put it in the category of work and expression. It is work because I want to uphold my brand, I want to talk about my projects, I want to make sure that I have a connection with my audience. Notice I said audience, very specifically, it is not where I have a connection with my friends or family, it is for my audience. And if I need to express and I want to build a community of worldwide people, yes, sharing thoughts about mental health and all that stuff, I still do. However, I’ll be really honest and say this, and I think some people are a little scared to say this, but I’m going to say it, we still have to understand there is a level of performativeness, even when we do those things. Me making a post about my mental health, I could mean every single word and I could really mean for it to help people, but it is still quite an unnatural thing to do, to say “I just had an experience, now I’m going to write a caption about it and I’m going to share it, and I’m going to do this post where I’m going to blend to the caption.” I’m not saying that it’s fake, it’s just still, there’s a level of performativeness that I have deemed okay for what it is, but I’m not going to make the mistake into thinking that is a complete reality now. And I think that’s where we need to draw the line between social media and reality.

[35:15] Sahara
Totally. And it’s almost like our brains are changing that hat, is becoming a normal. I remember I was in Costa Rica and I’m about to jump into this beautiful waterfall and I had to stop to take a bunch of stories, and I’m like “Wow, I can’t even be here, I need to tell other people that I’m here.” And then, how many times are you with friends, but it’s like, people see a picture of you and your friends at dinner but little did they know, 30 minutes was spent just trying to get everyone their own individual photo. So, it’s that performativeness.

[35:42] Lilly
I think, the way I’ve reconciled that is, instead of being jaded about that reality, because, realistically, my job requires that to some degree, instead of thinking “Oh, I hate that”, I’ve just accepted that definition of social media.
So, now, jumping into the water, for me, I will dedicate five minutes doing the thing I need to do and then I will put my phone away and be like “That was for work and for my audience and to share, but now I can choose to live that experience for real.” So, it’s not like I’m saying you have to pick one or the other, it’s just, know that that’s the tool and what it’s used for, instead of believing that that actual, whole, experience can only be lived through social media.

[36:20] Sahara
Totally, yes! And I think there’s just so many benefits of social media as well, that there are people who are like “Screw it, I’m just getting off this app”, and they create realities in a different way. But for us, I’ve built my whole career based off of social media, as well, so, you’ve just got to pick, it’s a mixed bag, everything in life.

[36:37] Lilly
One hundred percent! And I think you can also subscribe to the ideas that serve you best. I love social media, I hate Twitter. I haven’t been on Twitter for months and months, and I’m okay with that, it’s not good for me or my mental health and I’ve decided that that’s just what it is and that’s how I live my life.

[36:52] Sahara
Totally, yeah. And it’s knowing which ways you want to show up. I think creating art out of it too, which I have seen you’ve been doing around your book, and it’s like, these are art pieces, they’re forms of expression and letting it come from that place.

[37:05] Lilly
Absolutely! Definitely!

[37:06] Sahara
So, if someone is thinking “You know what, Lilly and Sahara, you guys are already successful, so easy for you to say, to have work-life balance, not be on social media, but I still got to get the shit off the ground”, what would you have to say to them?

[37:20] Lilly
I’m going to give this a really real answer, I’m going to say I totally agree with that person! It is very easy to preach about work-life balance when you’ve gotten to a place where you actually have it. And I’m going to be real, I, in 2010, when I started making YouTube videos, I did not have work-life balance, I pulled many and all-nighters, I hustled very, very hard, and I’m also going to say I regret no part of that. I do not think I would be where I am right now, if I did not spend those years hustling. However, to that I say this, I hustled so hard those years with the goal of one day I’m going to earn my stripes and be able to do what I really care about, and I’m going to be able to have the life I want, and I have to just earn my stripes.
We get so caught up in that race, that we forget that goal sometimes. And I think I’ve caught myself in that place this year, where I thought “Are you not now in that position where you can have work-life balance but you’re not doing it is, because you’ve convinced yourself that this race of always wanting more and always getting more, is where you want to be”, but no, the goal was always to be able to say yes to your passion project, do what you wanted to do, because, yes, I had to the things I didn’t care about, I had to do projects I wasn’t passionate about, but I did all of that to earn stripes. So, this is, again, where I go back to saying, it does not have to be all or nothing, in the sense of, now, I still work really, really hard, but now, I believe I’ve earned my stripes to have some work-life balance. But, and this could be an unpopular opinion, and I’m a happy if people disagree with me, I think it’s unrealistic to tell people who are early on in their career that they can start saying no to their bosses and they can start taking vacations all the time and that they will get to where they want to get. I think you absolutely have to have that race and you have to work really, really hard to work to a place where you can get that.

[39:04] Sahara
I mean, I agree with that, I’ve pulled so many all-nighters in my career and I wouldn’t be where I am, I wouldn’t have been able to write my books and everything, had I not. And I do think, knowing what I know now, there could’ve been a different way of doing it, but I didn’t know, so I had to do what I had to do.

[39:20] Lilly
A hundred percent! If I could go back, would I prioritize my mental health a little more? Yes! Would I avoid doing all-nighters? No! Would I avoid working really hard? No! I probably would still say no to people’s birthday parties and focus, I would probably still do all of that. The one thing I would implement is meditation and mental health practices, but it would be naïve to think that all of the greatest people I know, that have all the things on their vision boards, you do have to make some sacrifices, you do. I don’t want to lie to people and say that from the jump you can just have work-life balance, but the goal is hopefully that you can work to a place where you do. And so, I hope that when I say that, people don’t take it in a way that’s negative or meant to be disheartening, but I want to be real, that you can work very hard but also be mentally healthy, but you still have to work really, really hard, that’s not going to change. And I think, again, people think that’s the all or nothing, either you’re going to meditate 10 hours a day or you have to say no to your boss and punk your boss, or you hustle really hard. No, I encourage us to find that balance, but working hard is always going to be part of the recipe, that is not going to go away.

[40:24] Sahara
Yes, a hundred percent. And that meditation can support you in not burning out, and being able to come from a more creative place, and not come across different blocks. Going back, I would’ve not been as anxious as I was the whole time, because you have that trust, but at the same time, I do think we learn these things, you earn your stripes and you figure it out along the way. And I guess, my question for you is, how did you know when you could come to a place to be able to chill a little bit? I guess people don’t really – it’s sometimes, that day never comes.

[40:55] Lilly
Right. For me, it was less about chilling and more about fun, and I’ll explain this. I think, for a lot of my career, when I should’ve been having fun doing what I was doing, I was too stressed to be having fun. I was too obsessed with the outcome, to have fun; I was too obsessed with perfection, to have fun. I would do these amazing things, go to amazing events, meet amazing people, and at the end of it, I wouldn’t reminisce and think “Oh, what a great memory that was”, I would think “Why didn’t I do that better? Why didn’t this turn out perfect? How can I get more of this?” It was always just more, more, more, but, but, but, never “That was awesome.” And the final straw for me was, I had two seasons of the late-night show on NBC and that was one of the hardest things I have ever done in my life, it was after Seth Myers and it was…

[41:47] Sahara
And you looked amazing in every outfit! Your hair!

[41:49] Lilly
Oh my God, thank you, you’re sweet for saying that! But it was a very tough experience for me because it was so physically, mentally, spiritually, emotionally taxing, in a way that I’ve never experienced before. And I remember coming home after shooting 18 hours and thinking “That was horrible! I actually did not have fun doing that!” and I had to do that every day for many, many months. And that was such a crushing feeling because after years and years of climbing the ladder, I remember thinking to myself “Why aren’t you in the place you said you were going to be where you were able to do things that were fun and that you’re passionate about, and you were going to live this dream life?” All the pieces are there, but you still don’t have the feeling you wanted. And I discovered it was because, I tell people, I never wanted to be a late-night host, the reason I said yes to that was because – I actually said no to it first, I said no to it the first time it came to my desk, and then it came back around and it was expressed to me how historic it could be, and then of course, my ego got the best of me in thinking “I want to be involved in this moment”, but then my responsibility and duty also got the best of me of thinking “If I say no to this and it goes to someone else, this historic moment could never happen and I could not be paving this path.” So, the responsibility and pressure and ego are the things that got me to say yes to that, not passion, not genuine desire, and I was naïve to think those feelings would help me get through those long hard nights of shooting. And so, after the late-night show, the second season, I vowed to myself that now, an important part of every decision I make is going to be “Are you going to have fun?” My definition of success now has changed, it’s not just numbers, it’s not just the paycheck, it’s not just the historic nature, it is “Are you going to have fun?” That is in the center of my vision board, it is my definition of success now. So now, literally, when a project comes my way, me and all my agents will be on a call, and we’ll talk about the money and we’ll talk about the time commitment, we’ll talk about the contract, but then I’m going to ask the question “Do I like this? Is this something I’m passionate about? Is this going to be fun for me? Are these people going to be nice to work with?” These are things that I really care about now. So, I learned through the late-night show, through literally being, kind of, tortured, I learned that, I valued that because I had to learn the opposite, I had to experience the opposite first.

[44:06] Sahara
Fun is one of my core values as well. And I think, too, the beauty of back to social media, is, you have that experience of being your own creative producer and director and everything, whereas, when you go to TV, it’s an older paradigm, that you lose some of that freedom, some of that spontaneity and that fun. And I think right now, so many of us, we think “Oh, the pinnacle of success is being on TV”, but in today’s landscape, is that actually, we’re reaching so many more people on social media, so I think it’s just, you had that freedom in a way, already, and you had to realize maybe how much freedom that you already had and now be able to use it in your own expression.

[44:44] Lilly
Right. And I love that you brought this up because when I agreed to do the late-night show so many people joked saying “So, you want to get paid less and have less people watch than what you’re doing right now?” And I had to really ask myself the question, you’ll realize the theme with me is, I always ask myself the why, what is the real reason of why you’re doing what you’re doing? And that is serving me well in life, to dive deep and to go beyond the surface. The why is simple, I grew up, still, with television and movies, I did not grow up in the generation of social media, so I adored movie stars and pop stars, and people are on TV. And so, I know, in my heart, there’s still a part of me that ties success to that, to the red carpet, to that big screen, even though it’s less people, it’s less relevant. And I have allowed myself to be human in that way, I’ve embraced that and said “Okay, it’s that’s important to you, then chase it. It’s okay, maybe the relevancy doesn’t matter, if it’s something the inner child of you wants, I give you the permission to chase that.” So, it’s been kind of an interesting thing to chase TV and movies, even though, yes, the digital work I do, gets way more views and is way more relevant than all of those things, but I’m kind of fulfilling the dream of the inner child.

[45:57] Sahara
Yeah, and I loved you in Doll Face, where you had a scripted role and it was so good!

[46:00] Lilly
Yes, and it was so much fun doing things like that. And so, like I said, and I understand anyone listening to this might be rolling their eyes because it’s such a privileged conversation, I get it, to be like “I now make decisions based on fun and I don’t have to think about money”, but I think that everyone needs to do that chase and that climb to get to that place. And when you get to that place, recognize that. I think so many of us, my parents, don’t even recognize they’re in that place. I talk about this in my book as well, about how so many of us are surviving, not because we need to survive but because survival is a habit, it is a habit now we cannot shed. My parents and relatives, my mom is on a vacation right now, and I’m so proud of her because they never take vacations, they’re saving money for this abstract thing that is never going to need it, I’m like “Mom, I am well off, I’m not going to get married, let that ship sail, you don’t need to save money for this anymore.” But their answer to everything is always “Happiness will be later. That stuff is later, it is not for us.” Why is it not for you? If you have the means and your kids are grown up, why can you not spend your money on whatever you want to spend it on? Why can you not try new things? Why can you not have hobbies? Because they are always surviving, but they don’t need to survive.
So, I encourage all of us to really question ourselves in needing to survive right now.

[47:20] Sahara
I so resonate with that, yes! And having more fun and that brings in more ideas, more drive, more creativity and everything else.

[47:28] Lilly
I wouldn’t go as far as saying, and I say this in my book, that, not living a fulfilling life is selfish. I think one of the best ways to be of service to the Universe is to live a fulfilling life, because when you live a fulfilling life, you bring your best version of yourself to the Universe and to relationships. And not bringing the best version of yourself, that only you can uniquely bring, is selfish.
I think living a happy, fulfilling life that is fun is actually an act of service, I really believe that. And since writing this book on the best version of myself, my relationships have gotten better, I’m a better daughter, I’m a better friend, I’m a better everything. And I feel like I would not have been able to do that if I didn’t focus on fun and fulfillment.
And so, I encourage us to think about our relationship with those ideas and questioning why we think they’re selfish.

[48:16] Sahara
Totally! And it’s that replacing the old paradigm of “Me to be of service, I need to sacrifice”, but rather, it’s from a place of joy because you have so much more to give.

[48:26] Lilly
Yes! Absolutely!

[48:28] Sahara

[48:28] Lilly
Yes, I love all of it!

[48:31] Sahara
So much incredible wisdom!

[48:32] Lilly
So much vibes!

[48:35] Sahara
So, where can people get your new book “Be A Triangle”?

[48:38] Lilly
Yes, you can get my new book at lillysinghbook.com or in your local bookstore if you want to support a local bookstore, no one’s mad about that. But I really believe it could be a gift to the world.
I truly mean this, and I’m going to be really honest, and I hope you’ve gathered I’m a pretty honest person, if you don’t want to get the book, don’t get the book, who cares, who cares about the book! But I can tell you, in my life, I have never worked on something that has helped me as much as this book, no project, no movie, no event has helped me, I use the things I talk about in this book in my meditation, almost every day, I’m in the best physical, mental, spiritual, emotional shape of my life. It is a short, concise read and I do believe, even if you don’t agree with every part of it, maybe your pillars are different from mine. More than anything, what I want this book to serve is, as I want it to be a light in the world and remind people that you are never too old, you are never too far gone, you are never too set in your ways, to not work on yourself. I think we need to work on yourselves like we are the most important project of our life, even school didn’t tell us that, even though our parents didn’t tell us that, even though society and culture didn’t tell us that, I’m telling you that now, in case you’ve not heard it, that you can work on yourself like you are the most important project and you should and you deserve that!

[49:47] Sahara
So good! And it’s such a good book to listen to on audible as well because you narrate it and it’s just so funny.

[49:51] Lilly
I do narrate it, so you’ll hear this goofy, over the top voice narrating this book!

[49:56] Sahara
Oh yes! alright, well thank you so much for being here today, we deeply appreciate it!

[50:00] Lilly
I appreciate it, thank you!

[50:01] End of Interview

[52:02] Sahara
Oh yes! How amazing was that conversation! I love chatting with Lilly and I love how real she is because I feel like what happens sometimes in the spiritual space is, everyone just pretends like “Oh, I just manifested my whole career and I quantum leaped into it and here I am, with zero work”, and it’s just not true!
Anything that you create, even creating this podcast, it takes work. I’m here, recording an outro for you guys, so, sometimes we get dissuaded because people paint to us a false reality that we’re like “Oh my God, this is really hard! So, is this not my Dharma? Is this not my path?”, but it’s like, no, it’s going to be hard and you get to grow through it and you get to take care of yourself, so it’s a little bit easier. And have your practices so you’re able to tolerate a lot more than you would’ve if you didn’t have these practices.

[50:48] Sahara
So, I love Lilly’s practical and grounded, and of course, joyful approach, and I think that fun, laughter, celebration, is really what it is so needed!

[50:58] Sahara
So, thank you so much for tuning in! Please share this Episode on your stories, if this resonated, this Episode may help someone out there who wants to be a content creator or create their project off the ground, and it may inspire them to really be able to do so from a place of the heart, as well as heal our relationship with our families.

[51:18] Advertisement
So, if you loved this Episode, I would love for you to leave a review. So, please share a review with me, if you’re listening to this on iTunes and take a screenshot of that review so I can send you a free gift as my thank you.
You can email that free gift over to [email protected], take a screenshot of your review and I will send you a free gift of my unreleased book “Eat Right For Your Mind-Body Type” which is a deep Ayurveda book all about eating right for your Dosha.
So, again, take a screenshot of your review and send it over to [email protected] and I will send you over my free E-Book.

[52:00] Sahara
I hope you loved this conversation, share it with people that you think it may resonate with, and I’ll see you in the next one. Namaste!

Episode 432: How To Go From Lost To Getting Your Life In Shape with Lilly Singh
By Sahara Rose


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