Don and Tom tackle some of the most common retirement planning mistakes, with a particular focus on taxes and the danger of becoming overly obsessed with them. They discuss taxable Social Security benefits, the importance of diversifying across account types, Roth conversion considerations, tax-loss harvesting, and why most retirement decisions ultimately fall into the category of “it depends.” They also answer a listener question about navigating poor 403(b) plan options and the advantages of a 457 plan for educators. Finally, they dive deep into a thoughtful challenge from a listener regarding Avantis and Dimensional factor funds versus traditional Vanguard index funds, examining the evidence for factor tilts, the role of risk premiums, costs, and whether higher expected returns justify modestly higher expense ratios.

0:05 Retirement planning mistakes, taxes, retirement income, financial independence, retirement readiness
1:58 Tax obsession, retirement taxes, income planning, financial priorities, wealth management
2:43 Social Security taxation, taxable benefits, retirement income, Social Security myths, tax planning
5:14 Tax diversification, traditional 401(k), Roth accounts, brokerage accounts, retirement savings
7:57 Roth IRA, young investors, compound growth, retirement investing, tax-free income
9:11 Tax-loss harvesting, brokerage accounts, capital gains, tax strategy, investment management
10:03 Roth conversions, Medicare IRMAA, retirement taxes, financial planning, tax efficiency
12:03 Inherited IRAs, heirs, estate planning, retirement accounts, legacy planning
13:35 403(b) plans, 457 plans, retirement savings, school employees, listener question
15:29 403(b) Wise, 457B Wiser, educator retirement plans, high fees, retirement options
18:35 Roth IRA investing, small-cap funds, emerging markets, diversification, asset allocation
19:38 Avantis funds, Dimensional funds, Vanguard funds, factor investing, index investing
23:55 Fama-French research, small-value premium, indexing, active management, factor premiums
26:08 Rules-based investing, passive investing, factor tilts, portfolio construction, diversification
27:02 Small-cap value investing, fund performance, index comparisons, advisor value, investment returns
30:25 International small value, emerging markets, factor premiums, diversification, expected returns
32:55 Academic investing research, Nobel Prize economics, risk premiums, value investing, factor investing
35:18 Portfolio construction, asset allocation, diversification, retirement planning, investment strategy
36:16 Free portfolio review, financial advice, portfolio allocation, retirement readiness, fiduciary planning

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