Why do so many retirees struggle to spend money they’ve spent decades saving? Don and Tom explore the psychology behind retirement spending, including the fear of running out of money, the reluctance to touch principal, and how guaranteed income sources like Social Security, pensions, and even simple immediate annuities can make retirees more comfortable enjoying their wealth. They discuss practical strategies for creating spending confidence, the importance of comprehensive retirement planning, and why delaying meaningful experiences can be riskier than spending. The episode also answers a listener question about setting up a Roth IRA for a teenager and examines the latest uncertainty surrounding 529-to-Roth transfers.

0:05 Introduction: Why retirees struggle to spend money they can afford to spend
1:36 Fear of running out versus fear of missing out in retirement
2:52 Why even millionaires worry about spending their savings
3:51 The saver mentality and the challenge of switching to spending mode
4:47 Research shows many retirees barely touch their nest eggs
5:29 YOLO, aging, and the reality of declining mobility later in life
6:02 Why retirees prefer spending Social Security, dividends, and interest over principal
8:04 Travel, aging, and the danger of postponing experiences
8:49 Creating confidence through retirement planning
9:56 Using Social Security and RMDs to cover essential expenses
10:12 Flexible withdrawal strategies for retirement spending
11:39 Could a simple immediate annuity help retirees spend more confidently?
12:42 Healthcare costs, aging, and changing spending patterns
13:30 Recency bias and how it distorts retirement decisions
14:48 Why lifelong savers have trouble becoming spenders
16:27 Summer slowdown and a request for more listener questions
17:58 Listener question: Setting up a Roth IRA for a 19-year-old daughter
19:16 Evaluating Avantis ETFs and M1 Finance for a young investor
19:48 Why a single-fund solution may be better for small accounts
20:56 The importance of emerging markets exposure
22:40 Understanding 529-to-Roth IRA transfer rules
24:33 The unanswered question of beneficiary changes and the 15-year rule

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