Are you ready to cross the goal line into retirement? Josh dives into the critical five-year period before retirement, guiding you through essential strategies to secure your financial future. He kicks off with the importance of mapping out retirement goals and emphasizes the benefits of catch-up contributions for those aged 50 and above. Josh then explores the advantages of rolling over old 401(k) plans into IRAs for better investment flexibility, along with the triple tax benefits of Health Savings Accounts (HSAs) for healthcare expenses. Josh tackles Medicare, breaking down the different parts and explaining when to sign up to avoid penalties. He also shares tax-smart strategies like Roth conversions to optimize your retirement savings. Later in the episode, Josh plays a game of "Head to Head," putting retirement strategies to the test. Then in "Extra Points," he compares the best and worst states to retire in based on Bankrate’s latest rankings. Can't get enough of the Financial Quarterback? Click 'Subscribe' to never miss a play. New episodes touchdown right here! Loving the playbook? Drop us a 5-star rating and share your thoughts in a review. Your feedback fuels the game plan!