Maybe Someday | A podcast for people on the fence about having a baby

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Quirkyalone and childfree


More about Sasha:

Sasha Cagen is the author of the cult favorite book Quirkyalone: A Manifesto for Uncompromising Romantics, a landmark book putting a new twist on being a discerning single that got attention everywhere from the New York Times to CNN.

Sasha is a life coach for women and men who are drawn to the quirkyalone philosophy of not settling in life or love, helping her clients work with loneliness and that “there’s something wrong with me” feeling if they’ve been single a while, divorces and new singlehood, romantic obsession, low self-worth and codependency. She also helps clients to create quirkytogether partnerships, unique career paths and businesses and next steps at 30, 40, 50 or 60. Sasha has helped women sort through their ambivalence about motherhood, especially if they have "social infertility." Key to Sasha's perspective is the acknowledgement of each person's quirky individuality and that life can be hacked creatively with fun and pleasure.

Sasha also focuses on empowering women through travel and sensuality, which she offers through her self-guided Solo Chica Travel Adventures. Solo Chica means the Itineraries are designed to support women to feel comfortable and confident to travel alone. The first Solo Chica offering is the Tango Adventure Itinerary in Buenos Aires.

Sasha is at work on a memoir which tells her own story of transformation and healing through travel adventures and sensuality in South America. The working title for the memoir is Wet.

Connect with her here:


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In 2004, Sasha Cagen wrote a book called Quirkyalone: A Manifesto for Uncompromising Romantics, based on a term she’d created to describe people who are comfortable being single but who want to be in a relationship and won’t settle for something (or someone) that doesn’t allow them to be who they truly are.

I first found Quirkyalone probably 10 years ago, and like most people who are drawn to Sasha’s book, I felt like someone finally understood me. Aside from a few short-lived relationships with guys who’d started out as friends, I’d spent most of my adult life single - not happily single, exactly, but happi-ER single than dating indiscriminately, which seemed like what I was supposed to be doing. Dating just didn’t make sense to me. I felt like there was something about it that I just didn’t get. And because I was bad at dating, because I didn’t get it, I felt like there was something broken in me. I just wasn’t interested in dating just to avoid being lonely or just to have someone to sleep with. I wanted to find my person, and I had zero problem being alone until I met them. 

So when I found Sasha’s book and I took her quiz to figure out where I landed on the quirkyalone spectrum, I wasn’t surprised at all to find that my quirkyalone score was pretty much off the charts. 

Finding Sasha’s work helped me to understand and accept myself in ways I hadn’t been able to before. Being quirkyalone is about accepting yourself as you are, ignoring societal expectations that don’t work for you in any area of life, and above all - choosing yourself first.

So having Sasha on the show meant a lot  to me. Even though Sasha’s work has taken her in different directions in the 15 years since she wrote the book, and even though her association with the quirkyalone concept has sometimes felt like a burden, Sasha opened up about her perspective on quirkyalone now, and how it relates to choosing to become a mother. 

In this episode Sasha and I talk about being quirkyalone, wisftulness about having children, confronting our fertility expiration date, climate change, and not settling for anything less than what you truly want.


Discussed in episode 36 with Sasha Cagen

  • Sasha’s quirkyalone evolution

  • The vast difference of age and perspective on relationships

  • Shedding the shame that comes with being single

  • Facing your biological clock

  • How motherhood ties in with quirkyalone

  • Struggling with the lie that you’re missing out if you don’t choose motherhood

  • Why Sasha decided to leave everything behind and go to Brazil

  • The impact of climate change on the choice to be childfree

  • The importance of doing work that is meaningful to you

  • Having compassion for women between 35 and 40

  • An inside look into Sasha’s newest work


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