What to Do Before You Retire: Making the Most of Your 59½ Rebellion

In this episode of Empty Nest Full Pockets, Matt Meline and Will Schroeder continue their conversation about the 59½ Rebellion and explore what people can actually do during the years between 59½ and retirement. For many people, 59½ isn't a finish line. It's a window of opportunity—a chance to test drive retirement, make strategic tax decisions, rethink Social Security, prepare for future required minimum distributions, and figure out what life after work will actually cost. Matt explains why retirees often have more control over their tax situation during these years than they realize, including opportunities around capital gains, charitable giving, Roth conversions, and taxable assets. He and Will also discuss why Social Security shouldn't be treated as a simple “wait until 70” decision and why every family's circumstances can lead to a different answer. The conversation also tackles one of the biggest barriers to early retirement: healthcare before Medicare. Instead of assuming you have to work until 65, Matt encourages listeners to find out what healthcare will actually cost and consider whether alternatives could create more freedom. For those approaching their late 50s, the episode offers concrete steps to start taking now—from establishing spending guardrails and understanding your retirement income needs to test driving retirement and preparing for the years ahead. Empty Nest Full Pockets: How to Emotionally and Financially Prepare for Your Family's Future As your children prepare for their next chapter, it's time to prepare for yours. In Empty Nest Full Pockets, Matt Meline offers practical guidance for navigating the emotional and financial realities of becoming an empty nester, including college planning, retirement preparation, housing decisions, family relationships, and creating a meaningful future after the kids leave home. Learn how to build financial confidence while embracing the opportunities that come with this new season of life. Get your copy here: https://prairiefirewealth.com/book/ Episode Topics Covered What the 59½ Rebellion Really Means How to “Test Drive” Retirement Before Fully Retiring Why You May Have More Control Over Your Taxes Than You Think Managing Capital Gains During the Transition to Retirement Using Charitable Giving as Part of Your Tax Strategy Donating Appreciated Stock Roth Conversions Before Required Distributions Begin How Social Security Fits Into Retirement Planning Why Waiting Until 70 Isn't Always the Right Answer Spousal and Survivor Social Security Benefits The Potential Surprise of Large Required Minimum Distributions Using Qualified Charitable Distributions Establishing Retirement Spending Guardrails Why Retirement Spending May Not Immediately Drop Planning for Healthcare Before Medicare How Healthcare Costs Can Affect Early Retirement Decisions Checking Your Social Security Record in Your 50s Taking a Sabbatical or Part-Time Work as a Retirement Test Drive Why the Years Before Retirement Can Be a Valuable Planning Window Turning the 59½ Rebellion Into a More Intentional Second Half of Life — I sincerely appreciate your support. Thank you for being a part of our podcast journey. If you haven't already, please subscribe to stay updated with the latest episodes. Your subscription means the world to me! Want to dive deeper into the 59½ Rebellion? Check out our 59½ Rebellion playlist on YouTube for more conversations, insights, and practical guidance on making the most of the years leading up to retirement. I’d love to hear from you; here are some ways to connect: Web: https://www.prairiefirewealth.com/ Email: [email protected] Get a copy of my book: Empty Nest, Full Pockets: How to Emotionally and Financially Prepare for Your Family’s Future at https://amzn.to/3PovUWM