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The Generalist's Dilemma

Podcast by Rahil Shah

English

Personal stories & conversations

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About The Generalist's Dilemma

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.

All episodes

7 episodes

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

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

26 Feb 2026 - 1 h 6 min
episode Charlie Rogers ON: How The Undefinable Can Lead A Life Of Fulfilment And Alignment artwork

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

12 Feb 2026 - 1 h 3 min
episode Wendy Kriz Evans ON: Rediscovering Creativity Alongside Being An Actuary artwork

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/ [https://wendykrizevans.com/] or on Instagram- @wendykrizevans

25 Dec 2025 - 55 min
episode Kishan Shah ON: How Eastern Philosophy Helps Those Pursuing Their Purpose In Many Ways artwork

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 [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 [https://www.amazon.co.uk/Diary-Pilgrim-Spoken-Thiiird/dp/1999967100]

11 Dec 2025 - 1 h 4 min
episode Ace Blake ON: How Curiosity Can Help Find What Fulfils You artwork

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.

27 Nov 2025 - 49 min
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