Paying taxes on purpose sounds backwards...until you understand why Roth conversions are one of the most talked-about retirement planning strategies for people nearing retirement.

In this episode of The Perfect Retirement Plan?, Phillip Smith explains what a Roth conversion actually is, why some retirees use them to reduce future taxes, and when they make sense (and when they don’t). This is a no-hype, plain-English walkthrough designed for people getting close to retirement (and those recently retired) who want clarity, not pressure.

We cover how Roth conversions work, how they show up on your tax return, the five-year rules that confuse almost everyone, and how conversions fit into a broader retirement income, Medicare, and legacy planning strategy. This episode is especially relevant if you’re retiring in Oregon (or another state with income tax) and are thinking about RMDs, Social Security timing, or tax diversification.

If you’ve searched “what is a Roth conversion,” “should I do a Roth conversion,” “Roth conversion explained,” or “how to reduce taxes in retirement,” this episode is for you.

Episode Chapters

00:00 – Why paying taxes on purpose feels wrong
01:48 – What a Roth conversion is and is not
02:44 – How Roth conversions actually work
03:24 – Paying taxes now vs later
04:51 – The five-year rules explained clearly
06:12 – Why retirees use Roth conversions
07:35 – RMDs, Medicare, and tax control
09:16 – When Roth conversions may not make sense
10:13 – The best timing windows for conversions
11:04 – Transfers vs rollovers vs conversions
13:17 – How to execute a Roth conversion correctly
14:19 – A real-world tax example
16:32 – Common Roth conversion mistakes
18:14 – How to think about conversions long-term
18:43 – Action steps and next moves

More resources at TidepoolWealth.com and on YouTube @TidepoolWealth.

#RothConversion #RetirementPlanning #TaxPlanning #RetirementTaxes #howtoretire #OregonRetirement #RothIRA #RMDPlanning #MedicarePlanning #TidepoolWealth

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.

The hardest part of retirement isn’t saving the money. It’s knowing how to withdraw income for 30+ years without constantly worrying about market swings, taxes, or running out too soon.

In this episode of The Perfect Retirement Plan?, Phillip Smith breaks down retirement withdrawal strategies that work in real life, not just on paper. We unpack why the popular 4% rule became so appealing, where it falls short, and how dynamic withdrawal strategies with guardrails can help retirees adapt through market volatility, changing tax rules, and different phases of retirement.

This conversation is especially relevant if you’re about to retire, recently retired, or retiring in Oregon, and wondering:
• How much can I safely withdraw each year?
• What happens if markets drop early in retirement?
• How do taxes and account types affect withdrawals?
• Is there a better approach than a fixed withdrawal rate?

Rather than relying on rigid rules, this episode shows how flexibility, planning ahead, and behavior-aware strategies can create more durable retirement income.

Episode Chapters

00:00 – Why withdrawing money is harder than saving it
02:07 – The rise (and limits) of the 4% rule
05:13 – Sequence of returns risk explained simply
08:21 – What dynamic withdrawal strategies really mean
09:42 – Income guardrails and how they work
13:18 – Why guardrails can support higher starting income
15:49 – Taxes, account types, and income sourcing
17:17 – Adjusting withdrawals through retirement phases
18:16 – Practical action steps for retirees

More retirement planning resources at TidepoolWealth.com and on YouTube @TidepoolWealth.

#RetirementWithdrawalStrategies #RetirementIncome #SequenceOfReturns #RetiringInOregon #RetirementPlanning #DynamicWithdrawals #GuardrailsStrategy #AboutToRetire #RecentlyRetired

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.

You can do all the math and still miss retirement if the pieces are out of order. In this episode of The Perfect Retirement Plan?, Phillip Smith explains why retirement success is less about formulas and more about coordination, timing, and rhythm. Using a simple layup analogy, we explore how Social Security timing, IRA withdrawals, pensions, Medicare, and housing decisions need to work together, not in isolation.

This conversation is built for people who are about to retire, or who have recently retired, especially those who feel confident about their savings but uneasy about how everything fits together. You’ll learn why good decisions made in the wrong order can increase taxes, inflate future RMDs, raise Medicare premiums, or create unnecessary stress. We also connect the dots to recent episodes on retiring before 65 and the psychology of retirement income, showing how emotional readiness and income sequencing go hand in hand.

If you have searched “retirement income sequencing,” “when should I take Social Security,” “how to withdraw from retirement accounts,” or “retirement planning Oregon,” this episode brings clarity without complexity.

Key takeaways
• Why coordination matters more than clever math
• How timing affects taxes, Medicare, and income stability
• Questions to ask before making any retirement move
• How to build rhythm instead of chasing perfection

More resources at TidepoolWealth.com and on our YouTube channel @TidepoolWealth.

#RetirementPlanning #RetirementIncome #SequenceOfReturns #SocialSecurityPlanning #MedicarePlanning #AboutToRetire #RecentlyRetired #OregonRetirement #TidepoolWealth

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.

If you’re about to retire (or already retired) and relying on the Affordable Care Act for health insurance, you’ve probably seen the headlines: “The ACA subsidy is going away.” In this episode of The Perfect Retirement Plan?, Phillip Smith cuts through the noise and explains what is actually changing in 2026, what is not changing, and why this matters so much for retirement planning between ages 62 and 65.

You’ll learn the difference between the original ACA premium tax credit and the temporary enhanced subsidy created during the pandemic. We break down how the American Rescue Plan and Inflation Reduction Act expanded subsidies through 2025, what happens with those enhancements now expired as of December 31, 2025, and how income planning affects ACA premiums. This episode is especially relevant if you are planning to retire before Medicare, considering Roth conversions, selling a business, or starting Social Security during the pre-65 years.

If you have searched “is the ACA subsidy going away in 2026,” “ACA subsidies and early retirement,” or “how to plan income before Medicare,” this episode gives you clarity without politics or panic.

What you’ll learn
• What the ACA premium tax credit really is
• What changes in 2026 if the enhanced subsidy expires
• How income affects ACA premiums for retirees ages 55 to 64
• Why Roth conversions and capital gains matter more than ever
• How to plan retirement income without relying on headlines

More resources at TidepoolWealth.com and on our YouTube channel @TidepoolWealth.

Thanks for tuning in to The Perfect Retirement Plan?, brought to you by Tidepool Wealth Strategies.

Tidepool Wealth Strategies website
Phillip Smith, CRPC AIF LinkedIn

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.

How to Retire Without Chasing Hot Investing Trends
Practical, tax-smart guidance for people about to retire or recently retired

Hot stock trends are like pumpkin spice season: loud, overhyped, and gone before you finish your latte. In this episode of The Perfect Retirement Plan?, Phillip Smith of Tidepool Wealth Strategies explains why chasing the latest investment craze can sabotage your retirement confidence. Learn how to avoid FOMO-driven decisions, focus on what really builds wealth, and retire in Oregon with a calmer, more disciplined plan.

Phillip breaks down why “can’t-miss” investment tips trigger our psychology, how herding bias leads to costly mistakes, and what long-term consistency actually looks like in practice. You’ll hear why excitement fades but confidence lasts, and how to design a plan that lets you enjoy your life — not just your portfolio.

Perfect if you’ve searched “should I follow stock tips before retirement,” “how to invest before retiring,” or “Oregon retirement planning for market volatility.”

Chapters

00:00 Cold open – the danger of “pumpkin spice” investing
00:25 The allure of the hot tip
02:20 The psychology of FOMO and herding bias
04:56 Why consistency beats excitement
06:28 The difference between excitement and confidence
07:15 Building a plan that actually works for real life
09:18 Action steps to stay grounded and avoid the noise
10:20 Closing and reminder to stay focused on your plan

Action Step:
Pause before chasing the next “can’t-miss” trend. Review your plan, refocus on your long-term goals, and build consistency instead of chaos.

More at TidepoolWealth.com and on our YouTube channel @TidepoolWealth, where we help Oregon professionals retire with clarity, confidence, and purpose.

#RetirementPlanning #InvestingMistakes #FOMO #RetireInOregon #MarketVolatility #AboutToRetire #FinancialPlanning #TidepoolWealth

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.

You spent decades saving. Now you have to start spending. Why does that feel so hard? In this episode of The Perfect Retirement Plan?, Phillip Smith explains the psychology of retirement income for people about to retire or recently retired in Oregon and the Pacific Northwest. Learn why the paycheck-to-withdrawal shift triggers anxiety, how couples can stay in sync, and how to design a simple income system you can trust. We cover predictable cash buffers, automated “paychecks,” behavioral tools, and a practical retirement rehearsal you can run before Day One. If you have searched “how do I start spending in retirement,” “retirement withdrawal anxiety,” or “retirement income plan Oregon,” this is for you.

Chapters

00:00 Intro and why spending feels wrong after a lifetime of saving
00:42 Today’s roadmap
01:33 Paycheck as security and the stress response to withdrawals
02:29 When good saving habits backfire in retirement
03:21 Couples and communication about money, safety, and joy
04:12 Make withdrawals feel like income with simple systems
05:04 Retirement rehearsal you can try before you retire
05:57 Build predictable income with cash buffers and automation
06:23 Withdrawal anxiety and market volatility
07:13 Behavioral tools: purpose accounts and small “fun” money
08:11 Stewardship mindset over scarcity
09:04 Action steps you can take this month
09:24 Closing

More resources at TidepoolWealth.com and on our YouTube channel @TidepoolWealth.

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.

You’ve hit 62 and you’re ready to clock out, but Medicare doesn’t start until 65 and COBRA coverage costs more than your first car. What now? In this episode of The Perfect Retirement Plan?, Phillip Smith of Tidepool Wealth Strategies explains how to bridge the gap between early retirement and Medicare without draining savings or triggering surprise taxes.

You’ll learn how to blend your three retirement money buckets (pre-tax, Roth, and taxable) for maximum flexibility, keep your ACA subsidies intact, and avoid income traps that can shrink them. Discover how smart Roth conversions, capital-gain timing, and debt decisions can lower both health-care premiums and lifetime taxes. Phillip also shares a detailed case study of “Tom and Lisa,” showing how coordinated withdrawals and ACA planning can save tens of thousands in pre-Medicare years.

Perfect if you’re searching “retire before Medicare,” “ACA subsidy strategies,” or “early retirement health insurance options.”

Chapters

00:00 Teaser
00:18 Intro
00:48 Roadmap for today’s episode
01:15 The 3-to-5-year health-care gap explained
02:04 The three retirement money buckets (tax buckets)
03:23 How to balance pre-tax, Roth (tax-free), and taxable income
05:13 ACA subsidies and the modified AGI “sweet spot”
06:03 COBRA coverage vs. marketplace options
07:31 Avoiding subsidy clawbacks and “bear traps”
08:23 Social Security timing and Roth conversions
09:42 The debt payoff dilemma
10:29 Smart ways to bridge health coverage before Medicare
12:25 Case study: Tom and Lisa retire at 62
18:02 Using HSAs as stealth tax-free income
20:18 Action steps to smooth income and stay subsidy-friendly
21:17 Closing and key takeaways

Action Step:
Estimate your pre-65 health costs, coordinate withdrawals from all three tax buckets, and plan your income window before Medicare begins.

For more insights, visit TidepoolWealth.com and subscribe on YouTube @TidepoolWealth for more retirement planning content created for professionals in Oregon and the Pacific Northwest.

#RetirementPlanning #RetireBefore65 #MedicarePlanning #ACASubsidies #AboutToRetire #TaxPlanning #TidepoolWealth

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.

Cash feels safe—until it quietly starts working against you. In this episode of The Perfect Retirement Plan?, Phillip Smith of Tidepool Wealth Strategies explores why “cash is king” can be both comforting and costly for people about to retire or recently retired. You’ll learn how too much cash can lose value to inflation, trigger extra taxes, and delay smart decisions like investing or Roth conversions. Phillip explains how to find your personal “sleep-well number”—the right balance between liquidity, growth, and peace of mind.

Using a simple tidepool analogy, he shows how cash acts like still water: it protects you during low tide but stagnates if it never refills. Whether you just sold a business, rolled over a 401(k), or are sitting on a large savings balance, this episode helps you build a plan that keeps your money working for you. Perfect for searches like “how much cash to keep in retirement,” “inflation and retirees,” or “retirement income strategy.”

Chapters

00:00 Cash is king… until it’s not
00:23 Why retirees love cash—and why that’s risky
00:45 Three key ideas for a healthy cash balance
02:07 Inflation: the quiet thief of purchasing power
03:05 The tax drag dilemma—when 4.5% becomes 3.5%
03:33 The liquidity trap: waiting for “the right time”
04:20 How much cash is enough? A simple framework
05:12 The tidepool analogy—balance vs. stagnation
06:01 Large cash positions and redeployment planning
06:51 Three action steps to optimize your cash flow
07:42 Closing: make your cash serve your plan

Action Step:
Review all your cash accounts, calculate your “sleep-well” number, and put the rest to work through a thoughtful, tax-smart income strategy.

Explore more at TidepoolWealth.com and watch companion videos on our YouTube channel @TidepoolWealth, where we help professionals in Oregon and the Pacific Northwest retire with clarity, confidence, and purpose.

#RetirementPlanning #CashInRetirement #Inflation #AboutToRetire #RecentlyRetired #TaxPlanning #TidepoolWealth

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.