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THE RETIREMENT YOU DIDN'T SEE COMING
You planned the finances. You counted the days. But no one warned you about the identity shifts, the awkward Tuesdays, or the strange feeling of freedom.
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This isn’t a book about pensions or portfolios.
It’s a guide to the human side of retirement, full of reflection exercises, gently provocative insights, simple but powerful sketches and the kind of real talk you won’t hear in a financial review.
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Whether you’re just retired, nearly there, or wondering why it feels off, this book will help you rethink, rebuild, and reignite the next chapter of your life.
A guide to the human side of retirement nobody warns you about
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See what global pioneers in behavioural finance and retirement well-being are saying about the book
What You'll Learn
Retirement isn’t just a financial shift, it’s a full-body, full-life plot twist. Here’s what you’ll take away from The Retirement You Didn’t See Coming.
Understand the emotional stages of life after work
Challenge the myths holding you back
Build purpose, structure, and rhythm into your days
Redefine who you are beyond your job title
Strengthen the relationships that matter most
Give yourself permission to spend, and enjoy it
Craft a personal manifesto for the next chapter of life
Praise for The Retirement You Didn't See Coming
Dr Daniel Crosby
Behavioral Finance expert, Psychologist, Author of The Soul of Wealth & The Behavioural Investor
In The Retirement You Didn't See Coming, Dan delivers a compassionate, funny, and deeply insightful guide to the part of retirement no one talks about: the emotional rollercoaster that starts the moment the novelty wears off. With the heart of a coach and the clarity of a behavioral scientist, Dan dismantles the ten illusions we’re sold about retirement and replaces them with something far more useful: honest questions, practical frameworks, and soulful reimaginings of what life after work can be. Whether you’re 6 months into retirement and feeling off, or 6 years away and wondering what all the fuss is about, this book is your roadmap for designing a life that’s rich in meaning, rhythm, and joy.
Dr Meghann Lurtz
Leading global expert on the psychology of financial planning & Partner at Shaping Wealth
This book is classic Dan: wise, warm, and wonderfully useful. Drawing on years of experience as a financial advisor, Dan brings together a hive mind of client stories, insights, and gentle humor to guide readers through the retirement transition. What I love most is how approachable the book feels—full of simple, thoughtful exercises that invite readers to start, stop, rethink, or try something new, all with a sense of support and possibility. And yet, beneath the friendliness, there’s rigor. These aren’t just good ideas—they’re grounded in real research. As someone who works in financial psychology, I appreciate how seamlessly Dan blends science with humanity. This is a generous, credible, and genuinely helpful guide for anyone that is or will be navigating retirement.
Christine Benz
Head of Personal Finance & Retirement at Morningstar and author of How To Retire
Dan has made it his life's work to help people get the most out of their retirements, and it shows in this lovely book. Filled with personal stories, humor, and empathy, The Retirement You Didn't See Coming is a valuable guide to troubleshooting the psychological challenges that can catch retirees off guard. I came away with many new ideas about how to make retirement more joyful and purposeful, and readers surely will, too.
Roger Whitney
Founder of The Rock Retirement Club & Host of The Retirement Answer Man Podcast
Retirement isn't just about numbers, it's about navigating one of life's most profound transitions. Dan Haylett, host of the acclaimed podcast Humans vs. Retirement, reveals what years of one-on-one client work have taught him about the emotional and psychological challenges retirees face. Drawing from real conversations and lived experiences, Dan addresses the questions that matter most: Who am I without my career? How do I find purpose when every day is Saturday? With the wisdom of a practitioner who has truly listened, he offers practical strategies for creating a retirement worth living. This isn't another retirement calculator disguised as a book, it's a compassionate guide to the human side of life's third act, providing the roadmap traditional planning books miss: how to build not just financial security, but a life rich with purpose and joy.
Ashley Quamme
Founder of Beyond the Plan®
Dan delivers the truth about retirement—that it's not all golf and grandchildren, that freedom without purpose feels like floating, and that 'the most dangerous day' isn't your last day at work. Haylett's compassionate, real-world approach helps readers navigate the unexpected emotions and identity shifts that come with this profound life transition. This book doesn't just help you retire from something; it helps you retire into something meaningful.
Brian Portnoy
Founder of Shaping Wealth & Author of The Geometry of Wealth
Dan Haylett has quickly emerged as a significant voice in financial life planning. I can’t think of anyone who brings more perspective into every element of what we might simply call “retirement” but what is actually more broadly a massive transformation in one’s identity and purpose later in life. In this punchy volume, Dan has unlocked a remarkable set of insights both practical in their application and inspirational in their word.
Neil Bage
Behavioural Finance Expert & Award-Winning Fintech Founder
This is the retirement book we've been waiting for. The Retirement You Didn't See Coming is a deeply human guide to the most overlooked transition in modern life. Dan writes with warmth, wit, and rare insight into what really happens when the noise of work falls away and the questions get louder. I've worked in behavioural science for years, and this is one of the most emotionally intelligent and practical resources I've read. Every adviser should read it. Every retiree deserves it.
Dr Mary Bell Carlson
President, Financial Behaviour Keynote Group
“Hands down, one of the most impactful books on retirement I’ve ever read. Dan captures what so many miss—the human side of life after work. This book offers comfort, clarity, and the courage to reinvent what’s next. It’s not just a book—it’s a companion for life's second half.”