My So-Called Midlife with Reshma Saujani

Episode: “Getting Comfortable with Being Uncomfortable with Lilly Singh”

Air date: October 1, 2025

Episode Overview

In this candid and energetic episode, host Reshma Saujani sits down with trailblazing comedian, actress, author, and filmmaker Lilly Singh. The theme centers on embracing discomfort and unlearning shame, both in life and creativity—especially as women and people of color navigating midlife, identity, and societal expectations. The conversation dives deeply into Lilly’s journey from early YouTube days to mainstream fame, her personal and professional evolution, creative risks, and the making of her new film, Doing It, a coming-of-age sex comedy challenging taboos in the South Asian community and beyond.

Key Discussion Points & Insights

1. Redefining (Mid)Life Crisis and Personal Growth

• Lilly Reflects on Transitioning Into Midlife
  • Lilly just turned 37, sharing that her mid-30s were marked by significant upheaval and forced personal growth.
    • “A lot of things in my life kind of fell apart and unraveled, and I was forced to rebuild a lot of things… [My friend] said, ‘37 is the year where you rebuild, but you cannot rebuild using any of the old bricks’.” – Lilly Singh (04:36)
  • Both Reshma and Lilly discuss how life doesn’t unfold in a linear or tidy way, and recurring questions of “is this it?” open the door to new lessons at any age and stage.

2. Embracing Discomfort vs. Resilience

• Self-Improvement as an Ongoing Practice
  • Lilly describes her pragmatic, type-A approach to handling adversity—journaling, rituals, and treating personal growth as daily “assignments.”
    • “Trauma? I can fix that. You know what I mean?” – Lilly Singh (05:59)
• Discomfort as a Superpower
  • Distinguishes her high threshold for discomfort from generic ‘resilience.’
    • “My threshold for feeling uncomfortable and my threshold with being able to work hard—they’re very high.” – Lilly Singh (13:02)
    • “People don’t talk about it in terms of having a high threshold for uncomfortability. They talk about it as resilience, but what you’re talking about is different.” – Reshma Saujani (13:02)

3. Pioneering Digital Content and Learning on the Job

• Early YouTube Years

  • Lilly started in 2010, drawn to the freedom and connection the platform offered—especially for a young South Asian woman.
    • “It was pretty early... Not a lot of people knew what YouTube was or that you could make a living off it. I didn’t even know.” – Lilly Singh (07:43)
  • She self-taught, analyzed feedback, and embraced critical self-review to refine her style—contrary to how girls are socialized.
    • “I had multiple Excel sheets on my bedroom wall… I tracked subscribers and views manually… I’d send out surveys: what did you like about this video, what didn’t you?” – Lilly Singh (10:56)

• The Importance of Feedback, Especially for Women

  • Both discuss how girls are not raised to seek or process criticism, and how entering new territory means getting comfortable with rejection.

4. Authenticity: Maintaining It as Stakes Rise

• The Evolution of Being "Real" Online
  • Lilly admits authenticity fluctuates, and as pressure and public profile increase, it’s easy to slip into performativity.
    • “My journey with authenticity is not linear—it’s up and down… People think of authenticity like a destination, but I find it easier to be authentic some days and less so on others.” – Lilly Singh (19:24)
• Success and Ambition Can Coexist
  • After a big year of change, Lilly now recognizes she’s accomplished much, but still has more she wants to do—and that’s okay.
    • “You can be so thrilled with where you are, but also be so ambitious. That’s where I am.” – Lilly Singh (21:22)

5. Breaking Taboos: The Making and Impact of Doing It

• A Film to Normalize Sex and Unlearn Shame

  • The idea was sparked by her own discomfort—growing up without open conversations about sex, consent, or pleasure in a South Asian household.
    • “I've never believed truly in my soul that women should even enjoy sex, because no one taught me that… How tragic is that?” – Lilly Singh (23:05)
  • Seven years in the making, the film almost died at multiple stages because Hollywood viewed it as “too niche”—reflecting wider industry bias.
    • “Telling these types of diverse stories is next to impossible in Hollywood… But I wouldn’t tell people not to do it. Do it your way, even if it’s hard.” – Lilly Singh (27:16, 28:49)

• Film Themes: Shame, Sex Ed, Mother-Daughter Dynamics, and Intergenerational Learning

  • The movie threads together several journeys of unlearning shame—across ages and generations, particularly between mother and daughter.
    • “From the day a girl is born, she’s just bombarded with messaging about you should be ashamed… I wanted to show women learning to unlearn shame together.” – Lilly Singh (39:05)
  • A key theme: adults need to learn from young people too; curiosity and questioning can drive change.

• Cultural Resistance and Backlash

  • Lilly describes reactions to her sharing the film (and sex talk scenes) with her parents:
    • “There’s so many comments that are like, ‘How dare you put your dad through that?’… That is the patriarchy. You can talk to your mom, but if you talk to your dad, it’s shameful.” – Lilly Singh (48:43)

6. Navigating Burnout, Rest, and Seasons of Hustle

• Work-Life Balance as “Seasons”
  • Lilly embraces the idea that life comes in seasons: some for intense work, others for rest.
    • “My life operates in seasons. This is the season for hustle, and after, it’s the season for rest. After the movie stuff slows down, I will absolutely be horizontal on a beach somewhere.” – Lilly Singh (49:48)
  • She’s now comfortable saying “no” and truly offloading when resting; this was a skill hard-won from her earlier, always-on YouTube years.

7. Looking Ahead & Purpose

• Future Projects Rooted in Representation
  • She teases having more scripts in the works, again centering stories she wishes existed when she was young.
    • “I want to tell the types of stories I wish I had growing up… and normalize all the conversations I wish were normalized.” – Lilly Singh (51:44)

Memorable Quotes & Moments

• On Rebuilding After Loss

  “The one thing is you cannot rebuild using any of the old bricks.”
  — Lilly Singh (04:34)

• On Learning from Failure

  “Some things can’t be fixed and you just have to move on.”
  — Reshma Saujani (07:04)

• About the High Threshold for Discomfort

  “Every once in a while I have to wake up on a Sunday morning and be like, can you just do something easy today? But yeah, my threshold for feeling uncomfortable and my threshold also with being able to work hard, they’re very high.”
  — Lilly Singh (13:02)

• On The Indie Filmmaker’s Paradox

  “I’m a big believer I can work my way through anything… This movie was like, hold my beer. The amount of things I’ve not been able to control… I just had to let go.”
  — Lilly Singh (28:49)

• On the Power of Comedy for Change

  “Comedy is such a good vehicle to have these types of awkward conversations… it lets people lower their defense mechanisms and look at themselves in the mirror.”
  — Lilly Singh (36:36)

• On Shameless Digital Work

  “My number one thing for my production company is, I don’t want to add noise to the world. I want to add messages.”
  — Lilly Singh (46:03)

Timestamps for Key Segments

• [04:30] Lilly’s "midlife crisis" at 36–37; themes of loss and renewal
• [05:59] “Problem-solving” trauma and journaling as self-care
• [07:43] Early days of YouTube and breaking the Asian family mold
• [10:56] On self-critique, analytics, and learning by doing
• [13:02] The discomfort advantage; redefining resilience
• [19:24] The non-linear nature of authenticity
• [21:22] Reconciling ambition and self-acceptance
• [23:05] The inspiration and challenges in making Doing It
• [27:16] – [30:05] The realities of Hollywood for diverse creators; would YouTube success be possible today?
• [34:20] Hopes and intended impact of the film—normalizing sex, dismantling shame
• [39:05] Multi-layered themes: shame, consent, and learning across generations
• [41:44] Reflections on A Little Late with Lilly Singh – successes and struggles
• [46:03] Work that brings joy and the impact of Doing It
• [48:43] The parental backlash scene and cultural taboos
• [49:48] Seasons of rest vs. hustle; now prioritizing recovery
• [51:44] What’s next: more scripts, more trailblazing

Notable, Personal, and Culturally Resonant Moments

• Reshma’s Authentic Reaction to “Doing It”:
  “I loved it. I’m still giggling as I think about different scenes.” (22:59)
• Lilly’s first ever “sex conversation” with her father, prompted by her film. (47:38)
• Lilly’s reflection on the backlash:
  “There’s so many comments that are like, ‘How dare you put your dad through that?’ … That’s fundamentally a huge issue.” (48:43)
• Lilly on letting go:
  “If they let you do this for 10 years, you would torture yourself for 10 years. So when my show ended, I was also massively relieved.” (44:54)

Listen If You Want…

• Real talk on professional transitions, creative risks, and midlife reinventions
• A vulnerable look at what it takes to break cultural and industry taboos
• Honest discussion of activism, self-healing, and staying true to one’s purpose under pressure
• Insight into building a digital and entertainment career as a woman of color in a system stacked against you

Final Thought from Reshma (52:08):

“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…”

Guest: Lilly Singh
Host: Reshma Saujani
Podcast: My So-Called Midlife (Lemonada Media)
Episode: “Getting Comfortable with Being Uncomfortable with Lilly Singh”
Date: October 1, 2025

Note:
For more, watch Lilly Singh’s new movie Doing It and follow her latest projects for stories that don’t just add noise, but create real dialogue and change.