When people think of what could haunt their retirement, they often imagine running out of money, facing unexpected expenses, or living too long. But as we discuss in this episode, there's a more insidious villain: sequence of return risk.

Sequence of return risk refers to the threat of poor investment returns occurring early in your retirement years, just when you start withdrawing funds. Even if the average returns over your retirement are sufficient, early losses can irreparably damage your nest egg and dramatically increase the odds of running out of money.

To bring these concepts to life (with a Halloween twist), we walk through a scenario featuring Jamie Lee Curtis's iconic character, Laurie Strode, imagining her retirement through 25 years of market ups and downs. The outcome all depends on her initial withdrawal strategy and, crucially, how her portfolio is allocated.

• [00:00] A Halloween retirement survival tale, ft. Laurie Strode.
• [03:16] Retirement withdrawal scenarios analysis.
• [07:30] Optimizing financial asset allocation.
• [11:47] Diversification protects retirement portfolios.
• [15:16] Retirement portfolio stress testing.
• [16:41] Retirement planning for stability.

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Tax planning often slips to the bottom of our financial to-do lists—until a surprise bill or missed opportunity crops up. But behind the scenes, the right process for an ongoing tax strategy can put you leagues ahead, reducing uncertainty and helping you capitalize on changes. On the show this week, we'll walk through the seven stages of tax planning, highlighting key insights and practical actions you can take.

• 00:00 Holistic Tax Planning Overview
• 01:56 Understanding clients' overall current situation and future goals
• [03:11] Importance of staying up-to-date for maximizing client opportunities
• [05:05] Importance of gathering detailed, current financial information:
• [06:50] Identifying tax planning opportunities and potential pitfalls by life stage
• [09:53] Adjusting withholding, making estimated payments, and managing expectations
• [13:19] Identifying and quantifying strategic tax planning actions
• [18:34] Examples of in-year tax planning

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📰 See the full show notes here

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Planning for retirement isn't just about hitting your savings targets and hoping for the best. It's about getting creative, asking new questions, and challenging your own assumptions.

We follow the retirement planning journey of a fictional couple, Dwight and Angela, who are three to five years from retirement, using the SIFT framework shared by Rohit Bhargava and Ben duPont in their book "Non-Obvious Thinking", to shed light on hidden financial opportunities.

• [00:00] Broadening perspectives on retirement strategies.
• [03:11] Making time to reflect to get better clarity on retirement plans.
• [07:05] Expand your perspective by looking for alternative experiences and advice beyond typical financial practices.
• [11:05] Focus on solving the right problem to combat overwhelming options.
• [14:58] Explore other investment opportunities like a business 401k, HSA, or brokerage account.
• [17:35] Coordinated financial planning strategies for our case study couple.

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📰 See the full show notes here

🌐 Sign up here to receive a detailed pre-retirement checklist to ensure you are positioned to experience your ideal retirement.