The Generalist's Dilemma

Rahil Shah
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The Generalist’s Dilemma is for anyone who refuses to be just one thing. Hosted by Rahil, each episode spotlights modern-day generalists — people who embrace change and variety and have built (or are building) lives out of many passions. Through open and vulnerable conversations, we explore how they navigate ambition in many directions, challenge a world built for specialists, and redefine what fulfillment can look like. If you’ve ever felt pulled between your talents and struggled to “choose one lane,” this show is for you.

Episodes

  1. Feb 26

    George Hearn ON: How To Overcome The Region Beta Paradox And Adopt a “Live To Work” Mentality

    How does one strive for their ideal 10 out of 10 life when things in life are not horrible but “fine”? In this episode, Rahil sits down with George Hearn, a Sydney based life coach helping young professionals answer this very question. Having many different interests of his own, George and Rahil talk about the origins of the fixation on the question “So what do you do?”, his shift in mindset from “working to live” to “living to work” and key decisions he makes and has made to live a life more aligned to his full self. If you want an honest view on what it is truly like to make decisions that are against the grain but more in line with the life you want to lead, this episode is for you. Find George on Instagram: @georgehearn_ Emilie Wapnick’s book (mentioned in the episode)- How To Be Everything: A Guide for Those Who (Still) Don’t Know What They Want To Be When They Grow Up

    1h 7m

  2. Feb 12

    Charlie Rogers ON: How The Undefinable Can Lead A Life Of Fulfilment And Alignment

    When there is so much to who you are, how do you fit in and connect deeply with others whilst also authentically present your full self? In this episode, Rahil sit down with Charlie Rogers - a speaker, coach, community founder and life design strategist. Most recently, he is also an author of the book "Undefinable Life Design - how to design a unique life that sustains your energy and income" (coming out on 4th March 2026). They talk about what it means to be an "undefinable" and going beyond conventional labels, the importance of finding like-minded people when navigating your many passions and how to design a life that is aligned with all that you are (the focus of the upcoming book). This conversation is the sneak peak to a framework that one can use to find their "thing" and tailor their life around it. If you feel like you can not be defined with traditional labels and want to embrace the journey of doing beyond that, this one's for you. Learn more about the book and Charlie's work at https://www.undefinablelifedesign.com/

 Find Charlie's writing at https://undefinablelifedesign.substack.com/

    1h 3m

  3. 12/25/2025

    Wendy Kriz Evans ON: Rediscovering Creativity Alongside Being An Actuary

    Where is the space for creativity when you have dedicated decades to a job focused on statistics, numbers and calculations? In this episode, Rahil sits down with Wendy Kriz Evans- an actuarial principal and emerging artist. They discuss how Wendy rediscovered her love for art and painting after decades of being in the actuarial space, how the skills built in forging her art business have helped her in a seemingly unrelated day job and how she navigates the balance of two demanding pursuits. For anyone trying to make sense of seemingly conflicting hobbies and interests, this episode is for you. Check out Wendy's work at https://wendykrizevans.com/ or on Instagram- @wendykrizevans

    55 min

  4. 12/11/2025

    Kishan Shah ON: How Eastern Philosophy Helps Those Pursuing Their Purpose In Many Ways

    How does one make sense of wanting to pursue many different things? In this episode, Rahil sits down with Kishan Shah- co-founder of the educational organisation New Heights Academy as well as a speaker, spoken word artist and published author.
 They discuss how spirituality has helped Kishan identify his North Star, how said North Star has acted as a compass for all that he has pursued and the power of seeking and experimenting in one's search for purpose and meaning. It is an eye-opening conversation on how teachings from eastern wisdom can help bring clarity to the confusion that generalists in the western world face. Find more about Kishan's work on Instagram: @spokenthiiird and @new.heights.academy. His Light In My Darkness: https://www.amazon.co.uk/His-Light-Darkness-Spoken-Thiiird/dp/9358317043 Diary of a Pilgrim: https://www.amazon.co.uk/Diary-Pilgrim-Spoken-Thiiird/dp/1999967100

    1h 4m

  5. 11/27/2025

    Ace Blake ON: How Curiosity Can Help Find What Fulfils You

    In this episode, I sit down with Ace Blake - a PhD student at the University of Oxford working in AI Drug Discovery in the field of biological ageing and age-related diseases. From industry experience as a software engineer to obtaining an undergraduate degree and TWO Masters degrees (MSc Computing and Machine Learning at Imperial and MRes Biosciences and Biogerontology at UCL), the story that leads to his current position at the intersection of machine learning and biology is one of many turns and pivotal moments. We talk about how being exposed him to many ideas and concepts influenced his journey into academia and each pivot that came after as well as what it means to pursue fulfilment in the world of research. If you find yourself innately curious about lots of different topics and want to see how this can translate into what you study, this episode is for you.

    49 min

  6. 11/13/2025

    Sharvani Sivakumar ON: How To Pursue Your Passions Without Losing Yourself Along The Way

    Who are you - really - when there are so many things you are passionate about? In this episode, I sit down with Sharvani Sivakumar - once a natural sciences student and documentarian and now balancing her job as a sales representative at a climate technology company alongside being a qualified yoga instructor. We talk about the transferable skills that are build through different pursuits, the importance of a "core sense of self" in all that you pursue and the varying "types" of generalists that exist. This conversation is an honest reflection on what it means to be multi-faceted and how it impacts one's relationship with themselves and those closest to them. Check out her content on Instagram: @sailingwithsharvani

    1h 1m

  7. 10/30/2025

    My Why: The Story Behind This Podcast

    Welcome to The Generalist's Dilemma podcast! For the very first episode, we start with a solo episode, where Rahil expresses his motivation for starting this podcast and what listeners can expect from what is to follow.

    22 min
  • 7 Episodes

About

The Generalist’s Dilemma is for anyone who refuses to be just one thing. Hosted by Rahil, each episode spotlights modern-day generalists — people who embrace change and variety and have built (or are building) lives out of many passions. Through open and vulnerable conversations, we explore how they navigate ambition in many directions, challenge a world built for specialists, and redefine what fulfillment can look like. If you’ve ever felt pulled between your talents and struggled to “choose one lane,” this show is for you.

Information

  • Creator
    Rahil Shah
  • Years Active
    2025 - 2026
  • Episodes
    7
  • Rating
    Clean
  • Copyright
    © Rahil Shah
  • Show Website
    The Generalist's Dilemma