Root Talks: How to Get Past the Fear of Retiring Even When You Have Enough

You've run the numbers. You have enough saved. Your spreadsheet says you can retire comfortably. So why can't you pull the trigger and leave your high-stress, high-paying job behind? This struggle represents one of retirement planning's most challenging psychological hurdles. After spending decades accumulating wealth and building a career identity, many successful professionals find themselves paralyzed when the time comes to actually step away—even when financially prepared to do so. Our conversation explores this common predicament through the lens of a Root Collective member who knows they're financially ready but can't seem to make the leap. We dive into how our brains process major life transitions, why we tend to see future versions of ourselves as different people, and how this affects our decision-making. Just as starting preschool, college, or a new job feels intimidating, retirement represents a significant unknown that naturally triggers hesitation. The discussion moves beyond simple financial calculations to examine what we're really sacrificing by postponing retirement. While the opportunity cost of leaving unvested compensation on the table is obvious, the opportunity cost of continuing in a high-stress position—measured in health, time, relationships, and experiences—remains harder to quantify but potentially more valuable. We share perspectives from community members who've successfully made this transition, including practical advice on how to structure your finances and mindset for a fulfilling post-career life. Connect with our Root Collective community to learn from others navigating similar transitions and discover resources to help make your own retirement decision with confidence. What would your 85-year-old self advise you to do today? Create Your Custom Early Retirement Strategy Here Get access to the same software I use for my clients and join the Early Retirement Academy here Ari Taublieb, CFP ®, MBA is the Chief Growth Officer of Root Financial Partners and a Fiduciary Financial Planner specializing in helping clients retire early with confidence.