The Personal Finance Podcast: "21 Things to Do Before You Retire" (Part 2)
Host: Andrew Giancola
Episode Date: November 12, 2025
Episode Overview
In the second installment of his "21 Things to Do Before You Retire" series, Andrew Giancola continues his comprehensive guide to navigating the essential action steps leading up to retirement. Building on part 1 (which covered tips 1–10), Andrew details steps 11 through 21, focusing on crucial financial planning elements such as healthcare, debt elimination, housing, withdrawal strategies, estate planning, and designing a work-optional retirement. His energetic, practical advice is aimed at making retirement less stressful, more flexible, and aligned with personal goals.
Key Discussion Points and Insights
1. Plan for Healthcare — The Big Wild Card in Retirement
[02:10]
- Healthcare costs are unpredictable and often underestimated in retirement.
- Key components to understand:
- Medicare Parts A, B, D, Medigap, and Medicare Advantage (Part C): Learn the differences, premiums, and coverage.
- Plan for pre-Medicare years: If retiring before age 65, explore COBRA, ACA marketplace, spouse's employer plan, or private insurance.
"It is worth... getting a ton, and I mean a ton, of different quotes because you could be saving yourself thousands of dollars every single year." – Andrew [06:55]
- Long-term care (LTC):
- 70% of retirees will need LTC; plan now.
- Options: Traditional LTC insurance, hybrid life+LTC insurance, self-funding.
- Family conversation: Discuss your LTC wishes and funding so children know your intentions and conflict is minimized.
2. Build a Cash Buffer to Manage Sequence of Return Risk
[12:33]
- Drawing down your portfolio during market downturns can derail retirement.
- Solution: Maintain a "cash runway" of 2–3 years worth of expenses in liquid, safe accounts (high-yield savings, laddered CDs, T-Bills, money market funds).
- "This is your sleep-well-at-night fund, your 'swan number'… to give you that buffer." – Andrew [13:40]
- "It turns a market crash into an inconvenience instead of a crisis." – Andrew [14:55]
- Practical Tips:
- Decide on the buffer amount (1–3 years of living expenses).
- Use high-yield, easily accessible accounts for this reserve.
- Refill the buffer during strong markets.
3. Eliminate All Debt Before Retirement
[19:19]
- Aim to have zero debt (including mortgage, car loans) in retirement for peace of mind, flexibility, and lower risk.
- "Every dollar you owe is a claim on your future income." – Andrew [19:59]
- "Peace, control, flexibility: that's what you get when you're completely debt-free." – Andrew [21:43]
- Don’t prioritize low-interest debt payoff over investing, but gradually work toward full debt freedom before retiring.
4. Max Out Your Health Savings Account (HSA)
[23:07]
- HSAs offer "triple tax advantage" (tax-free contributions, growth, and withdrawals for medical expenses).
- Andrew’s advanced strategy: Invest HSA funds and let them grow for retirement healthcare/long-term care.
- After age 65, HSA behaves like a traditional IRA for non-medical expenses.
- "It's a supercharged, triple-tax advantage retirement account that I absolutely love to use." – Andrew [24:43]
5. Know and Stress Test Your Retirement Number
[26:10]
- Calculate your needed retirement savings and run it through stress tests (e.g., Monte Carlo simulations) for market downturns, inflation, and lifestyle changes.
- "Most people go into retirement guessing… you need to stress test your retirement number and figure out if this is actually going to work." – Andrew [26:49]
- Adjust if your probability of success is low (save more, spend less, delay retirement).
6. Decide on Housing and Location Strategy
[29:42]
- Your housing can either empower or hinder your retirement.
- Will you stay in your current home, downsize, or move to a lower cost-of-living area?
- The sooner you decide, the more options you'll have.
- "Housing for most is typically the largest expense. It can either support your goals or it can drain your freedom." – Andrew [30:15]
- Weigh family, friends, lifestyle, and cost considerations.
7. Establish Your Guaranteed Income Floor
[32:19]
- Social Security, pensions, annuities, and rental income form your "guaranteed income."
- "For most retirees, [Social Security] only covers about 40–50% of what they actually need… where are you building a guaranteed income floor?" – Andrew [32:35]
- Calculate essential expenses and identify the gap to fill with investments or additional income streams.
8. Craft an Estate and Legacy Plan
[35:14]
- Create a will and (as net worth grows) consider a revocable trust to avoid probate.
- Regularly review and update documents and beneficiaries.
- Clearly communicate your wishes to heirs to avoid family strife.
- "Clarity over conflict should always be your goal." – Andrew [38:23]
9. Plan for Inflation
[39:29]
- Test your retirement projections using higher inflation rates (3–4%) to ensure sustainability.
- "You can't get a cheeseburger for 25 cents anymore… so what's going to happen over the next 30 or 60 years?" – Andrew [40:05]
10. Prepare for Required Minimum Distributions (RMDs)
[41:27]
- Starting at age 73, you're required to withdraw from tax-deferred accounts, adding to taxable income.
- Not planning RMDs can create tax headaches and increase Medicare premiums.
- Solutions: Roth conversions, charitable distributions, early spending from tax-deferred accounts.
11. Design a Phased or Work-Optional Retirement Plan
[43:39]
- Retirement doesn’t have to be a hard stop; consider phasing out, consulting, or part-time work to maintain income, purpose, and a flexible transition.
- "Even a modest part-time income can make a big difference." – Andrew [45:02]
- "I think this is a graceful way to retire… tapering down before you retire." – Andrew [46:07]
Notable Quotes & Memorable Moments
-
On LTC planning and family:
"Sit down with your children... say, these are my long-term care wishes. This is how it’s going to get paid for. This is the money I have set aside for this." – Andrew [08:36]
-
On leveraging your HSA:
"Most people put money in their HSA and spend it every year. No, no, no... You can invest the money in the HSA. This is going to allow you to grow your money." – Andrew [24:10]
-
On eliminating debt emotionally:
"Light, secure, and in control. That’s how I want you to feel in retirement." – Andrew [21:07]
-
On housing choices:
"If you don’t enjoy your life or… where you live, consider moving and looking at a lower cost of living area. That may help you tremendously." – Andrew [31:42]
-
On estate surprises:
"Don't make it a big old grand opening surprise where everybody's sitting around the table... Have a conversation with everybody." – Andrew [38:10]
-
On phased retirement:
"I think ripping the Band-Aid off and going from 40+ hours per week to zero is what causes a lot of retirees to spiral… If you actually had a plan to slowly taper down, that is going to help you tremendously." – Andrew [44:29]
Timestamps for Key Segments
- [02:10] – Planning for Healthcare in Retirement
- [12:33] – Building a Cash Buffer for Sequence of Return Risk
- [19:19] – Why and How to Eliminate All Debt
- [23:07] – Using the HSA as a Retirement Weapon
- [26:10] – Stress Testing Your Retirement Number
- [29:42] – Housing/Lifestyle Strategy
- [32:19] – Understanding Your Guaranteed Income Floor
- [35:14] – Estate and Legacy Planning Basics
- [39:29] – Inflation’s Long-Term Effects on Retirement
- [41:27] – RMDs: Required Minimum Distributions
- [43:39] – Designing a Phased Retirement/Work Optional Plan
- [46:07] – Final Thoughts and Parting Advice
Final Takeaways
Andrew wraps up with encouragement to seriously plan each step rather than leaving them to chance. The episode empowers listeners to confront major retirement unknowns—healthcare, debt, housing, and income stability—while providing actionable frameworks to reduce stress and maximize fulfillment in retirement.
"Peace, control, flexibility." That’s the retirement Andrew wants listeners to achieve.