Summary Jonathan Clements is the founder and editor of Humble Dollar and brilliant free blog site that is dedicated to providing articles, guides and resources from some of the greatest thinkers in the world of finance. The goal of Humble Dollar is to tell you everything you need to know about money – all in one place without the hype and hollow promises that characterises so much financial writing. Jonathan was born and educated in England before moving to the states and prior to semi-retiring and launching humble dollar in 2014, Jonathan spent almost 20 years as The Wall Street Journal’s personal finance columnist and six years at Citi group where he was director of financial education for the banks US wealth management arm. He is also the author of 9 personal finance books. In this episode, Jonathan and I discusses the challenges and risks in retirement, both from a financial and human standpoint. He focuses on the need to have sense of purpose and identity in retirement, which he believes can be overcome by continuing to work in some fashion. Jonathan also explores the concept of embracing a second childhood, allowing for childlike curiosity and exploration. He emphasises the importance of experimenting in early retirement to discover what truly makes one happy. Jonathan also discusses his work with Humble Dollar and the ventures that provide him with a sense of purpose. Takeaways Longevity risk is a significant financial challenge in retirement, and individuals should consider guaranteed income options such as annuities. Investing in the stock market can help retirees combat inflation and grow their wealth over time. Working in retirement provides not only financial benefits but also a sense of purpose, identity, and social interaction. Retirees should focus on their own financial goals and avoid comparing themselves to others. Retirement can be a time of exploration and curiosity, allowing individuals to embrace a second childhood and pursue new interests and passions. Transitioning to retirement can be a unique experience depending on one's life circumstances. Early retirement is a period of experimentation to find activities that bring fulfilment. Financial stability and a sense of purpose are key factors in enjoying retirement. Chapters 00:00 Introduction and Background 04:05 Financial Challenges and Risks in Retirement 11:02 Investing in Retirement 21:28 The Importance of Working in Retirement 28:36 Generating Income in Retirement 38:02 The Importance of Identity and Purpose in Retirement 45:45 Avoiding Comparisons in Retirement 48:12 Embracing a Second Childhood in Retirement 48:30 Transitioning to Retirement 49:23 Experimenting in Early Retirement 50:35 Finding Fulfilment in Retirement 52:03 Humble Dollar and Jonathan's Work 53:16 Closing Remarks Episode Links & Resources Humble Dollar Jonathan’s book My Money Journey: How 30 people found financial freedom – and you can too Jonathan’s book From Here to Financial Happiness: Enrich Your Life In Just 77 Days Connect with Jonathan on LinkedIn Connect with Jonathan on X WealthGPS – Lifestyle Financial Planning by TFP Download My FREE Retirement Toolkit Subscribe to my Super Sunday Retirement Roundup Newsletter