The Exit Kit - Resources for a Major Life or Career Change
Here are my favorite resources for navigating a founder's exit, a career change, or another major life event
There’s no instruction manual for navigating a significant life change. After selling my business at the end of 2020, I navigated a common period of transition uncertainty and found the books and articles linked below to be invaluable.
Books to Read
The Psychology of Money by Morgan Housel. Housel’s book, which has become an overnight sensation, is a persuasive exploration of a better definition of wealth—freedom and flexibility—and why more money won’t make you happier. This book fundamentally changed my perspective on what is enough and explains the importance of a wealth strategy that mitigates risks and volatility. It also highlights the value of consistency, the hidden cost of trying to time the market, and the uncomfortable truth that, in investing, our emotions are often in the driver’s seat and need to be managed with discipline.
Die With Zero by Bill Perkins. This is a good counterweight to the financial discipline Housel preaches. When you successfully exit a business, you’ll have two things almost everyone else in the world wants more of: time, and money. However, most people don’t capitalize on either; rather than using their resources to impact the people and causes they care about during their lifetime, they make those contributions as part of an estate plan executed after they’re gone. Perkins encourages using the majority of your resources during your lifetime while mitigating your largest risks. He also makes a compelling case to consider investing in experiences, not things.
From Strength to Strength by Arthur Brooks. If your work or business has been your identity, stepping away can leave a void that’s hard to fill. Brooks, the HBS professor of happiness, tackles this phenomenon with insight and compassion, offering a roadmap for the second half of life. He explains why the skills that brought early success often fade and shares how to embrace a different kind of growth rooted in wisdom, connection, and service. This book helped me reframe aging not as a decline, but as a transition into a more fulfilling chapter, one where we use our hard-earned wisdom as a tool to create greater impact. More than anything I read, this is what kept me from falling into the trap of immediately launching another business or chasing a 10X investment in startups.
The Second Mountain by David Brooks. Exiting a business is often the summit of your first mountain. But what comes next? Brooks offers a deeply thoughtful guide to finding purpose beyond achievement. He explores the four commitments that give life meaning: to a spouse or family, to a vocation, to a community, and to a philosophy or faith. This book helped me think differently about legacy, which is not something you leave behind, but something you live out daily through service and connection.
Articles to Read:
Transparently, these are much more targeted at exited entrepreneurs than the books, which are more generally applicable.
What’s Next? The Entrepreneur’s Epilogue and the Paradox of Success:
Nearly every founder I’ve talked to post-exit has said the same thing about this report: it’s the most accurate description of the experience they’ve seen.
Published by the Yale School of Management, the research was led by two entrepreneurs—Matthew Guilford and Jacob Donnelly—who partnered with Yale to study what really happens after a successful exit. They interviewed dozens of founders and uncovered a clear pattern: achieving the goal you’ve worked toward for years can often lead to confusion, disorientation, and a loss of identity.
But they don’t stop at naming the problem. The report explains why this happens, shows the impact of timing, and offers a thoughtful roadmap for navigating what comes next. It’s essential reading for anyone nearing or moving through an exit.
The report also has two valuable follow ups:
A Dozen Questions To Consider After Selling Your Business: A great list of questions to prompt deep thinking on what you want from the next stage of life after exiting a business.
Exploring Six Key Decisions Post-Exit Entrepreneurs Will Have To Make: This third Yale case guides exiting founders through detailed tactical decisions, such as how to manage their newfound wealth, how to find a sustainable level of spending, structuring a new routine, and even approaching philanthropy.
This is part of the Friday Forward Resource Vault, where Robert Glazer shares the best resources and frameworks leaders can use to keep raising their game. Join Friday Forward Premium for access to the full vault.