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[Should I Roll Over My Roth 401(k) to a Roth IRA When I’m About to Retire?] – Clear, tax-smart guidance for people close to retirement

About to retire – or recently retired – and wondering if you should move Roth 401(k) dollars into a Roth IRA? In this episode of The Perfect Retirement Plan?, Phillip Smith explains why a Roth 401(k) is great while you’re working, but why the rules at retirement can change taxes, timing, and flexibility.

We cover the different 5-year clocks, plan withdrawal limits, pro-rata taxation on non-qualified plan distributions, the 2024 RMD update for designated Roth accounts, and the Roth IRA ordering rules that can make a withdrawal fully tax-free.

What you’ll learn
00:00 Intro – 59½ milestone, plan “gotchas”
01:00 Today’s roadmap
01:27 Why Roth 401(k) shines during accumulation
02:17 The 5-year rule & non-qualified distributions
03:12 Plan constraints, menus, costs – plus the 2024 RMD change
05:06 When keeping money in-plan still makes sense (age-55 rule, low costs, creditor protection)
05:57 Why a Roth IRA often wins in retirement
06:29 One IRA 5-year clock and the contribution → conversion → earnings ordering rules
08:23 Coordinating MAGI for Medicare IRMAA; creditor-protection caveats
09:36 Case study – $50k withdrawal: plan vs IRA tax impact
12:46 Action steps
13:55 Closing

Action step
Verify your Roth IRA’s 5-year status, request your plan’s distribution rules, and choose a path that protects tax-free flexibility.

More resources: TidepoolWealth.com and our YouTube channel @TidepoolWealth.
#RetirementPlanning #Roth401k #RothIRA #FiveYearRule #AboutToRetire #RecentlyRetired #TaxPlanning #MedicareIRMAA

Thanks for tuning in to this episode of The Perfect Retirement Plan, and remember: it's not about having the smartest financial advisor, the most money saved, or the highest probability of retirement success. The perfect retirement plan, for you – is the one you act on.

Phillip Smith, CRPC AIF | Financial Planner
Tidepool Wealth Strategies
450 Country Club Road, Suite 350 | Eugene, OR | 97401

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Additional Disclosures:
The opinions contained in this material are those of the author, and not a recommendation or solicitation to buy or sell investment products. This information is from sources believed to be reliable, but Cetera Wealth Services, LLC cannot guarantee or represent that it is accurate or complete.
All investing involves risk, including the possible loss of principal. There is no assurance that any investment strategy will be successful.

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Medicare IRMAA can blindside people who are about to retire - and especially those who have recently retired. In this episode of The Perfect Retirement Plan?, Phillip Smith (Financial Planner with Tidepool Wealth Strategies breaks down IRMAA in plain English and shows how smart retirement planning in your low-tide tax window can lower lifetime premiums and taxes.

You’ll learn about the 2025 IRMAA income thresholds, the 2-year lookback, how Roth conversions and one-time income can trigger the surcharge, and practical ways to set income buffers, time conversions, harvest gains on purpose, and appeal to Social Security with SSA-44 after qualifying life events. If you are an Oregon PERS retiree or OPSRP member, we cover how IRMAA fits into a PERS strategy so your Medicare costs don’t erode your income plan.

00:00 IRMAA shock: why your Medicare bill jumped
00:24 Who this helps and how IRMAA shows up
00:55 Today’s roadmap
01:19 IRMAA basics in plain English
01:43 Two-year lookback and 2025 premiums
02:29 Cliffs, thresholds, and single-filer halves
02:50 The low-tide tax window
03:13 Strategy playbook overview
04:02 Set bracket buffers for Roth conversions
04:25 When to convert: early, throughout, year-end
04:50 Harvest gains and pair with deductions
05:21 SALT cap timing and coordinated deductions
06:01 Muni interest counts; SSA-44 appeal option
06:25 Common pitfalls to avoid
07:12 The widow(er) tax bomb
07:41 Case study: results and lessons
08:16 Action steps this week

Subscribe for more retirement planning content, and explore additional videos at @TidepoolWealth or visit TidepoolWealth.com.

Thanks for tuning in to this episode of The Perfect Retirement Plan, and remember: it's not about having the smartest financial advisor, the most money saved, or the highest probability of retirement success. The perfect retirement plan, for you – is the one you act on.

Phillip Smith, CRPC AIF | Financial Planner
Tidepool Wealth Strategies
450 Country Club Road, Suite 350 | Eugene, OR | 97401

____________________________________________________________________________________________
Additional Disclosures:
The opinions contained in this material are those of the author, and not a recommendation or solicitation to buy or sell investment products. This information is from sources believed to be reliable, but Cetera Wealth Services, LLC cannot guarantee or represent that it is accurate or complete.
All investing involves risk, including the possible loss of principal. There is no assurance that any investment strategy will be successful.

Send us a text

Running a consultancy, LLC, or S-Corp in the Pacific Northwest and getting close to retirement? This episode of The Perfect Retirement Plan? is built for you. Phillip Smith, Financial Planner with Tidepool Wealth Strategies, shows late-career small business owners how a Solo 401(k) can cut today’s taxes, accelerate savings in your final 5–7 working years, and stay flexible when income is lumpy.

We cover 2025 Solo 401(k) contribution limits, stacking employee deferrals with employer profit sharing, age-50 catch-ups and the enhanced 60–63 super catch-up, plus pretax vs Roth vs after-tax dollars (including when a “mega backdoor Roth” makes sense). You’ll also hear Solo 401(k) vs SEP IRA vs SIMPLE IRA trade-offs for Oregon/Washington owners, S-Corp wage considerations, key setup and funding deadlines, plan loans, rollovers, and practical SECURE 2.0 updates. If you’re searching “Solo 401k for consultants,” “SEP vs Solo 401k,” or “late-career retirement planning for business owners,” start here.

Chapters
00:00 Intro and why this matters when you're nearing retirement
00:29 Solo 401(k) overview for sole proprietors
01:13 Roadmap for the episode
02:07 Solo 401(k) basics and eligibility
02:39 2025 contribution limits, catch-ups, deadlines
04:19 Pretax vs Roth vs after-tax, mega backdoor Roth
06:28 Solo 401(k) vs SEP IRA vs SIMPLE IRA
11:42 Loans and rollover considerations
12:26 SECURE 2.0 updates to note
14:18 Action steps for this quarter
15:08 Closing and disclosure

Subscribe for more on retirement income, tax efficiency, and investment strategy. Explore additional content on our YouTube channel @TidepoolWealth and visit TidepoolWealth.com.

Thanks for tuning in to this episode of The Perfect Retirement Plan, and remember: it's not about having the smartest financial advisor, the most money saved, or the highest probability of retirement success. The perfect retirement plan, for you – is the one you act on.

Phillip Smith, CRPC AIF | Financial Planner
Tidepool Wealth Strategies
450 Country Club Road, Suite 350 | Eugene, OR | 97401

____________________________________________________________________________________________
Additional Disclosures:
The opinions contained in this material are those of the author, and not a recommendation or solicitation to buy or sell investment products. This information is from sources believed to be reliable, but Cetera Wealth Services, LLC cannot guarantee or represent that it is accurate or complete.
All investing involves risk, including the possible loss of principal. There is no assurance that any investment strategy will be successful.