Don't Do What I Did

Most business books are written by people who want you to believe they figured it out early. That the success was inevitable, the strategy was always clear, and the mistakes were minor detours on an otherwise straight path. This one is different.
"Don't Do What I Did" is a candid, practical guide to the lessons that only come from actually living them. From making avoidable mistakes, paying the tuition nobody warns you about, and coming out on the other side with a clearer, harder-earned understanding of what actually matters in business and in life. It is not a book about how to be perfect. It is a book about how to be better, faster, than the people who had to figure all of this out the hard way.
Jason Kestler spent more than three decades building, scaling, and selling organizations in one of the most relationship-driven industries in financial services. Along the way, he got things wrong. Sometimes in ways that were costly, occasionally in ways that were spectacular, and always in ways that taught him something he could not have learned any other way. This book is his attempt to hand you the map he wishes he'd had earlier; not a map that guarantees the destination, but one that at least shows you where the expensive wrong turns tend to be.
"Don't Do What I Did" covers the terrain that matters most to anyone building a career or leading an organization: What separates real leadership from the title that comes with it, and why the version of you that got you here is not necessarily the version that will get you there. Why culture is the operating system everything else runs on, and what it actually costs when you get it wrong. How strategy works in a world that refuses to hold still while you execute your plan. The negotiation frameworks that actually shift outcomes, and the ones that only feel like they do. How to sell by listening instead of talking, and why the best salespeople operate more like doctors than pitchmen. What ethical blind spots look like before they become legal and business problems. And the personal habits of mind that either accelerate your growth or quietly work against you when you are not paying attention.
The lessons throughout are grounded in real examples, both celebrated and humiliating, drawn from companies and leaders who got it right and those who got it spectacularly wrong. Each chapter translates decades of hard experience into something immediately applicable, anchored by a direct, no-pretense voice that respects the reader's time and intelligence.
This book was written for anyone standing at the beginning of something―a new role, a fresh start, or simply a moment when they have decided it is time to figure out how to do this better. It was written for the new manager who was excellent at their job and is now discovering that leading people requires an entirely different skill set. For the mid-career professional who has been at it for twenty years and quietly suspects there are things they never quite learned. For the parent who wants to hand their kid something useful before the world gets to them first.
It was written for anyone who has ever felt like the odds were not exactly stacked in their favor, and who is willing to learn from someone who took the long road, made the avoidable mistakes, and came back with a notebook full of things worth knowing.

Jason Kestler is a Harvard Business School alumni and recognized leader in the annuity and insurance distribution industry, with more than three decades of experience building organizations, advancing distribution strategy, and driving product innovation across some of the most consequential platforms in the retirement planning space.
His career spans the full arc of financial services distribution, from founding and scaling independent marketing, distribution, and securities organizations to leading distribution operations at major broker-dealer and brokerage platforms. He currently serves as Head of Sales at a financial distribution company purpose-built for third-party distributed registered index-linked annuities in the institutional markets.
His work across these organizations reflects a consistent philosophy: that the most enduring competitive advantages in financial services are built through trust, alignment, and relationships developed over time, not through short-term tactics.
Beyond company-building, Jason has been a consistent voice in industry advocacy and leadership. He has served two terms on the board of directors of the National Association for Fixed Annuities and is a co-founder of NAFA's Annuity Distribution Summit―one of the industry's most respected forums for collaboration and thought leadership. His involvement reflects a long-held belief that the industry rises or falls together, and that the most meaningful contributions extend beyond any single organization.
Stepping into the world of publishing, he authored "Don't Do What I Did: Lessons Learned," a business and leadership book written for early-career professionals and anyone navigating the realities of building something meaningful without a roadmap. The book draws directly from Jason's career, offering practical frameworks, candid personal reflection, and hard-won lessons across leadership, culture, strategy, and professional growth.