Planning for Healthcare in Retirement

Today, Jesse is joined by Spencer Reese—Air Force veteran, financial educator, and creator of the Military Money Manual—for a conversation about the surprising overlap between military transitions and civilian retirement. Together, they explore why the only constant in retirement is change, how life evolves through “go-go, slow-go, and no-go” phases, and Jesse’s framework for a “Retiree’s Financial Decathlon,” covering everything from building a sustainable paycheck to tax efficiency, healthcare, estate planning, and even learning to spend with intention. Spencer shares lessons from his own service and separation, highlighting the financial quirks of military life—like government-covered housing, allowances that incentivize marriage, and the all-too-common trap of buying too much car—as well as the importance of communication and systems for long-term success. Beyond the dollars, they discuss the identity shifts that come with leaving the military or workforce, the challenge of replacing purpose and community, and how preparation and adaptability ease the transition. Throughout, Jesse and Spencer remind listeners that whether you’re a veteran or a civilian, financial independence is as much about mindset and meaning as it is about math.

Key Takeaways: • Retirement is not a fixed point in time but an evolving, decades-long transition. • Purpose, meaning, and social connection are as critical as financial stability in retirement. • Jesse’s “Retiree’s Financial Decathlon” framework highlights ten essential planning areas, including building a paycheck, taxes, healthcare, estate planning, and spending. • Many military families struggle not from lack of will, but from lack of financial skills and role models. • Transitioning out of the military often brings a loss of identity, community, and structure, similar to civilian retirement. • Preparing early—whether through classes like TAP for veterans or retirement workshops for civilians—eases major life transitions.

Key Timestamps:(00:00) – The Only Constant in Retirement: Change (07:59) – The Retiree's Financial Decathlon (20:09) – Interview with Spencer Reese: Military Financial Planning (31:20) – The Importance of Financial Vision and Communication (35:24) – Creating Financial Systems for Deployment (38:17) – Behavioral Traps and Financial Resources for Military Families (43:19) – Opportunities During Deployment (47:07) – Transitioning to Post-Service Life (50:18) – The Importance of Purpose and Meaning in Retirement (01:00:52) – Resources and Recommendations for Financial Success

Key Topics Discussed: The Best Interest, Jesse Cramer, Wealth Management Rochester NY, Financial Planning for Families, Fiduciary Financial Advisor, Comprehensive Financial Planning, Retirement Planning Advice, Tax-Efficient Investing, Risk Management for Investors, Generational Wealth Transfer Planning, Financial Strategies for High Earners, Personal Finance for Entrepreneurs, Behavioral Finance Insights, Asset Allocation Strategies, Advanced Estate Planning Techniques

Mentions: Website: https://militarymoneymanual.com/ LinkedIn: https://www.linkedin.com/in/spencer-c-reese/ Mentions:  https://bestinterest.blog/your-only-retirement-constant-will-be-change/ https://bestinterest.blog/the-retirees-financial-decathlon/ https://bestinterest.blog/e108/ https://bestinterest.blog/e106/ https://bestinterest.blog/when-should-i-take-social-security/ https://bestinterest.blog/retirement-withdrawal-order-of-operations/ https://bestinterest.blog/planning-for-your-healthcare-costs-to-and-through-retirement/ https://www.militaryonesource.mil/ 

More of The Best Interest: Check out the Best Interest Blog at https://bestinterest.blog/ Contact me at jesse@bestinterest.blog Consider working with me at https://bestinterest.blog/work/

The Best Interest Podcast is a personal podcast meant for education and entertainment. It should not be taken as financial advice, and is not prescriptive of your financial situation.