Five reasons why the MONTH you retire MATTERS episode artwork

EPISODE · May 1, 2026 · 34 MIN

Five reasons why the MONTH you retire MATTERS

from Playbook of the Wealthy · host Playbook of the Wealthy

Retirement timing matters more than most people realize. The right month to retire can be worth six figures in bonus, RSU, pension, and tax savings.In this Playbook of the Wealthy episode, financial advisors Dave Grant of Retirement Matters and Heather Townsend of Townsend Financial break down 5 things you must lock in before you hand in your notice, using a case study of Jeffrey, a $400k-a-year executive with a base salary, bonus, RSUs, and a pension. They cover 401K and HSA frontloading, the NUA strategy, COBRA vs marketplace healthcare, IRMAA Medicare planning, zero-income years for Roth conversions, and pension service credit timing.▶ Listen on Apple, Spotify, or visit https://playbookotw.com★ WHAT YOU'LL LEARN ★▸ How to max out your 401K and HSA in 2-3 months and capture a full year of tax-deferred savings▸ The NUA (Net Unrealized Appreciation) strategy for company stock inside a 401K▸ Why leaving one month before your bonus or RSU payout could cost six figures▸ Clawback provisions, where to find them, and how they change your exit timing▸ The real cost of COBRA, marketplace alternatives, and how income unlocks premium tax credits▸ IRMAA: how Medicare premiums in retirement are based on your income from two years earlier▸ Why a zero-income year is the ideal window for Roth conversions▸ When Roth conversions are oversold online, and when a lopsided pretax portfolio makes them essential▸ Pension service credit: how six months can mean thousands per year for life▸ What to do when your bonus, RSU, 401K match, and pension credit all fall in different months★ CHAPTERS ★00:00 Cold open: losing an 11-month bonus and Roth conversion traps01:26 Why retirement month planning beats retirement year planning02:26 Case study: Jeffrey, $400k total comp executive03:47 Point 1: Max out 401K and HSA in the first 2-3 months06:21 The NUA strategy: company stock in a 401K explained07:37 Point 2: Capture your prior year bonus and RSU payout08:55 Clawback provisions in your employment agreement10:43 Point 3: Healthcare coverage from retirement to Medicare11:06 COBRA vs marketplace insurance costs compared13:09 IRMAA explained: Medicare premiums based on income from two years ago16:50 Point 4: Zero-income years for tax-free Roth conversions19:48 Pension and Roth: convert before your pension sets your tax bracket20:33 Point 5: Pension service credit timing23:44 The 5-point retirement timing checklist25:02 Q&A: Bonus in April, pension credit in October, when do I retire?27:15 Q&A: Wife retires at 62, I'd lose pension. Should I delay?28:41 Q&A: 401K match spread monthly, retire in spring or year-end?30:21 Highlights33:58 Wrap up★ LISTEN ON ANY PLATFORM ★Apple Podcasts: https://podcasts.apple.com/us/podcast/playbook-of-the-wealthy/id1787630097Spotify: https://open.spotify.com/show/21LrI3IB2wMsOOJLiGsRJKWebsite: https://playbookotw.com★ WATCH NEXT ★The 5 DIY Money Mistakes That Quietly Cost You Years | EP065: https://www.youtube.com/watch?v=s4zprAatOtoDividends Are Lying To You: The Outdated Retirement Income Strategy | EP066: https://www.youtube.com/watch?v=P3B5rw6VPSU★ CONNECT ★Submit a question for a future episode: https://playbookotw.comEmail: [email protected] Grant on Instagram: https://www.instagram.com/davegrant82Heather Townsend on Instagram: https://www.instagram.com/heather.townsend.financial★ ABOUT THE SHOW ★Playbook of the Wealthy is a podcast that makes wealth planning and retirement simple, clear, and approachable. Hosted by financial advisors Dave Grant of Retirement Matters and Heather Townsend of Townsend Financial, the show covers Social Security, tax strategies, IRAs, 401(k)s, Roth conversions, RSUs, executive compensation, job changes, inheritance, and more.#RetirementPlanning #RothConversion #PlaybookOfTheWealthy

Retirement timing matters more than most people realize. The right month to retire can be worth six figures in bonus, RSU, pension, and tax savings.In this Playbook of the Wealthy episode, financial advisors Dave Grant of Retirement Matters and Heather Townsend of Townsend Financial break down 5 things you must lock in before you hand in your notice, using a case study of Jeffrey, a $400k-a-year executive with a base salary, bonus, RSUs, and a pension. They cover 401K and HSA frontloading, the NUA strategy, COBRA vs marketplace healthcare, IRMAA Medicare planning, zero-income years for Roth conversions, and pension service credit timing.▶ Listen on Apple, Spotify, or visit https://playbookotw.com★ WHAT YOU'LL LEARN ★▸ How to max out your 401K and HSA in 2-3 months and capture a full year of tax-deferred savings▸ The NUA (Net Unrealized Appreciation) strategy for company stock inside a 401K▸ Why leaving one month before your bonus or RSU payout could cost six figures▸ Clawback provisions, where to find them, and how they change your exit timing▸ The real cost of COBRA, marketplace alternatives, and how income unlocks premium tax credits▸ IRMAA: how Medicare premiums in retirement are based on your income from two years earlier▸ Why a zero-income year is the ideal window for Roth conversions▸ When Roth conversions are oversold online, and when a lopsided pretax portfolio makes them essential▸ Pension service credit: how six months can mean thousands per year for life▸ What to do when your bonus, RSU, 401K match, and pension credit all fall in different months★ CHAPTERS ★00:00 Cold open: losing an 11-month bonus and Roth conversion traps01:26 Why retirement month planning beats retirement year planning02:26 Case study: Jeffrey, $400k total comp executive03:47 Point 1: Max out 401K and HSA in the first 2-3 months06:21 The NUA strategy: company stock in a 401K explained07:37 Point 2: Capture your prior year bonus and RSU payout08:55 Clawback provisions in your employment agreement10:43 Point 3: Healthcare coverage from retirement to Medicare11:06 COBRA vs marketplace insurance costs compared13:09 IRMAA explained: Medicare premiums based on income from two years ago16:50 Point 4: Zero-income years for tax-free Roth conversions19:48 Pension and Roth: convert before your pension sets your tax bracket20:33 Point 5: Pension service credit timing23:44 The 5-point retirement timing checklist25:02 Q&A: Bonus in April, pension credit in October, when do I retire?27:15 Q&A: Wife retires at 62, I'd lose pension. Should I delay?28:41 Q&A: 401K match spread monthly, retire in spring or year-end?30:21 Highlights33:58 Wrap up★ LISTEN ON ANY PLATFORM ★Apple Podcasts: https://podcasts.apple.com/us/podcast/playbook-of-the-wealthy/id1787630097Spotify: https://open.spotify.com/show/21LrI3IB2wMsOOJLiGsRJKWebsite: https://playbookotw.com★ WATCH NEXT ★The 5 DIY Money Mistakes That Quietly Cost You Years | EP065: https://www.youtube.com/watch?v=s4zprAatOtoDividends Are Lying To You: The Outdated Retirement Income Strategy | EP066: https://www.youtube.com/watch?v=P3B5rw6VPSU★ CONNECT ★Submit a question for a future episode: https://playbookotw.comEmail: [email protected] Grant on Instagram: https://www.instagram.com/davegrant82Heather Townsend on Instagram: https://www.instagram.com/heather.townsend.financial★ ABOUT THE SHOW ★Playbook of the Wealthy is a podcast that makes wealth planning and retirement simple, clear, and approachable. Hosted by financial advisors Dave Grant of Retirement Matters and Heather Townsend of Townsend Financial, the show covers Social Security, tax strategies, IRAs, 401(k)s, Roth conversions, RSUs, executive compensation, job changes, inheritance, and more.#RetirementPlanning #RothConversion #PlaybookOfTheWealthy

NOW PLAYING

Five reasons why the MONTH you retire MATTERS

0:00 34:30

No transcript for this episode yet

We transcribe on demand. Request one and we'll notify you when it's ready — usually under 10 minutes.

No similar episodes found.

No similar podcasts found.

Frequently Asked Questions

How long is this episode of Playbook of the Wealthy?

This episode is 34 minutes long.

When was this Playbook of the Wealthy episode published?

This episode was published on May 1, 2026.

What is this episode about?

Retirement timing matters more than most people realize. The right month to retire can be worth six figures in bonus, RSU, pension, and tax savings.In this Playbook of the Wealthy episode, financial advisors Dave Grant of Retirement Matters and...

Can I download this Playbook of the Wealthy episode?

Yes, you can download this episode by clicking the download button on the episode player, or subscribe to the podcast in your preferred podcast app for automatic downloads.
URL copied to clipboard!