GUEST:Christina Wallace is a Harvard Business School faculty member, entrepreneur, author and Broadway producer who has built a career across business, technology and the arts. Her own journey has moved across seemingly different worlds, giving her a deeply personal perspective on what it means to build a career and life that does not fit neatly into a single identity. In this conversation, we explore Christina's idea of a Portfolio Life and why it may be useful to think beyond the traditional model of building one linear career. She introduces the idea of the Human Venn Diagram — the different skills, interests, experiences, perspectives, passions and pursuits that come together to make each of us unique. Christina then breaks down the four pillars of a Portfolio Life: identity, optionality, diversification and flexibility. She explains why our identity needs to be broader than our current job title, how seeing ourselves more expansively can create optionality, and why recognising that we have multiple doors available to us can help us navigate disruption and change. We also explore the idea of diversification and why it does not mean simply doing more. Christina argues that we need to begin with the needs and wishes of the particular season we are in and then consciously decide where to allocate our time and attention. Just as a financial portfolio is rebalanced as circumstances change, our life portfolios can also be reconstructed and rebalanced across different chapters. The conversation goes deeper into the idea of Explore and Exploit over the long game. We discuss how the early decades of a career can often be about experimenting, discovering our strengths and finding talent-market fit, while later chapters can allow us to bring different parts of our Venn diagram together in more intentional ways. Christina also shares her perspective on creating a bespoke scorecard for life. While money, promotions and other conventional measures of success are easy to track, many of the things that matter most — relationships, happiness, health, creativity and meaning — are harder to measure. The question, therefore, is not simply what are we measuring, but whose definition of success are we using? Throughout the conversation, Deepak connects Christina's ideas with his own FLAVOUR framework and the idea that we may need different flavours for different seasons of our lives. The conversation ultimately explores how we can remain open to the different parts of who we are while consciously deciding what deserves our time and attention in the chapter we are currently living. This episode is for anyone thinking about career transitions, reinvention, identity, or how to design a life that allows different parts of who they are to find expression. Published in October 2026.ABOUT THE PODCAST:The podcast has been functional since 2016. We are one of the (if not the only one) podcasts that break a conversation down into small pieces of content and reorganise them by theme. To know more you can visit www.playtopotential.com and see the Curated Playlists section. While the full conversations on Apple, Spotify and other platforms are open access, the curated insights require membership. HOST:Deepak Jayaraman, the host of this podcast series, works with Leaders and Organizations with a growth mindset and helps them play to their full potential. He strives to spend significant upfront energy in understand the nuances of the context and then armed with the mutual trust and understanding of the context, strives to be of value as a (behind the scenes and discreet) Coach / Sounding Board for their journeys. LinkedIn profile here. OTHER GUESTS:1.Vijay Amritraj 2.Amish Tripathi 3.Raghu Raman 4.Papa CJ 5.Kartik Hosanagar 6.Ravi Venkatesan 7.Abhijit Bhaduri 8.Viren Rasquinha 9.Prakash Iyer 10.Avnish Bajaj 11.Nandan Nilekani 12.Atul Kasbekar 13.Karthik Reddy 14.Pramath Sinha 15.Vedika Bhandarkar 16.Vinita Bali 17.Zia Mody 18.Rama Bijapurkar 19.Dheeraj Pandey 20.Anu Madgavkar 21.Vishy Anand 22. Meher Pudumjee 23.KV Shridhar (Pops) 24.Suresh Naraynan 25.Devdutt Pattanaik 26.Jay Panda 27.Amit Chandra 28.Chandramouli Venkatesan 29.Roopa Kudva 30.Vinay Sitapati 31.Neera Nundy. 32.Deepa Malik 33.Bombay Jayashri. 34.Arun Maira 35.Ambi Parameswaran 36.OP Bhaat 37.Indranil Chakraborty 38.Tarun Khanna 39. Ramachandra Guha 40. Stewart Friedman 41. Rich Fernandez 42. Falguni Nayar 43. Rajat Gupta 44. Kartik Hosanagar 45. Michael Watkins 46. Matt Dixon 47. Herminia Ibarra 48. Paddy Upton 49. Tasha Eurich 50. Alan Eagle 51. Sudhir Sitapati 52. James Clear 53. Lynda Gratton 54. Jennifer Petriglieri. 55. Matthew Walker 56. Raj Raghunathan 57. Jennifer Garvey Berger 58. BJ Fogg 59. R Gopolakrishnan 60. Sir Andrew Likierman. 61. Atul Khatri 62. Whitney Jonson 63. Venkat Krishnan 64. Marshall Goldsmith 65. Ashish Dhawan 66. Vinay Sitapati 67. Ashley Whillans 68. Tenzin Priyadarshi 69. Ramesh Srinivasan 70. Bruce Feiler 71. Sanjeev Aggarwal and T. N. Hari 72. Bill Carr 73. Jennifer Wetzler 74. Sally Helgesen 75. Dan Cable 76. Tom Vanderbilt 77. Darleen DeRosa 78. Amy Edmondson 79. Katy Milkman 80. Harish Bhatt 81. Lloyd Reeb 82. Sukhinder Cassidy 83. Harsh Mariwala 84. Rajiv Vij 85. Dorie Clark 86. Ayse Birsel 87. Ravi Venkatesan E2 88. Pradeep Chakravarthy 89. Dan Pink 90. Alisa Cohn 91. Ayelet Fishbach 92. Thomas Wedell-Wedellsborg 93. Raghu Ananthnarayanan 94. Tarun Khanna EP2 95. Manjari Jaruhar 96. Ethan Kross 97. David Bradford 98. Jeffrey Pfeffer 99. Michiel Kruyt 100. Christopher Clarey 101. Stephen M.R. Covey 102. David Noble & Carol Kauffman 103. Ricardo Sunderland 104. Neeraj Aggarwal 105. Jaspreet Bindra 106. Bill Burnett 107. Roopa Kudva EP2 108. Jennifer Garvey Berger EP 2 109. Hitendra Wadhwa 110. Viral Doshi. 111. Wendy Smith DISCLAIMERAll content and opinions expressed in the podcast are that of the guests and are not necessarily the opinions of Deepak Jayaraman and Transition Insight Private Limited. Views expressed in comments to blog are the personal opinions of the author of the comment. They do not necessarily reflect the views of The Company or the author of the blog. Participants are responsible for the content of their comments and all comments that are posted are in the public domain. The Company reserves the right to monitor, edit, and/or publish any submitted comments. Not all comments may be published. Any third-party comments published are third party information and The Company takes no responsibility and disclaims all liability. 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