In this episode of the Financial Harmony™ Podcast, Dr. Preston Cherry explores why so many smart financial decisions still feel heavy — and why the answer has less to do with optimization and more to do with control.

These conversations aren’t about tactics. They’re all responses to the same question: what actually reduces dependency when financial decisions start to matter more.

The conversation moves across three seemingly different topics that all point to the same truth:

Bitcoin, mortgage decisions, and even everyday preferences are all responses to uncertainty.

Dr. Cherry unpacks:

• Why Bitcoin decentralized rails, not power
• How the original decentralization belief shifted from ideology to utility
• What people misunderstand about “digital gold”
• Why paying off a mortgage isn’t about interest rates, but about buying flexibility
• How housing decisions shape retirement timing and healthcare planning
• Why accumulation matters — and why accumulation without direction creates anxiety
• How cultural signals, like the return of wired headphones, reflect a deeper desire for reliability over convenience

This episode isn’t about tactics.

It’s about understanding what actually reduces dependency, restores clarity, and supports well-being as financial decisions become more consequential.

If you’ve ever felt torn between “what pays more” and “what feels right,” this conversation helps explain why.

👉 Take the Retirement Readiness Scorecard:
https://concurrentfp.typeform.com/genx-scorecard

Explore more:
Financial Harmony™ Membership
https://www.concurrentfp.com/financial-harmony-membership/

Flat-fee, life-aligned financial planning
https://www.concurrentfp.com/

Subscribe for weekly episodes on money, meaning, and alignment.
Follow: @DrPrestonCherry

Gen X followed the rules.

Work hard.
Max the plan.
Delay gratification.
Trust the system.

And yet retirement feels fragile, spending feels wrong, and confidence in institutions keeps eroding.

This episode isn’t about interest rates.

It’s about what happens when a generation does “everything right” and still ends up boxed in. When retirement accounts solved accumulation but killed flexibility. When policy feels political, not procedural. When spending feels irresponsible even when money exists.

We unpack:

• Why Gen X feels hustled by the promise of high achievement and retirement accounts
• Why institutional trust is breaking down and what that signals beneath the surface
• Why gold, policy theatrics, and market behavior reflect confidence erosion, not panic
• Why spending guilt persists and what it reveals about control, identity, and choice

This is a conversation about money, culture, and judgment.
Not tactics. Not fear. Not hot takes.

If you’ve ever thought, “This wasn’t the deal,” this episode is for you.

👉 Take the Retirement Readiness Scorecard:
https://concurrentfp.typeform.com/genx-scorecard

Explore more:
Financial Harmony™ Membership
https://www.concurrentfp.com/financial-harmony-membership/

Flat-fee, life-aligned financial planning
https://www.concurrentfp.com/

Subscribe for weekly episodes on money, meaning, and alignment.
Follow: @DrPrestonCherry

High earners are often told they’ll be in a lower tax bracket in retirement.
For executives and business owners, that promise rarely holds up.

In this episode of the Financial Harmony™ Podcast, Dr. Preston Cherry breaks down why retirement taxes are often higher—and more complex—than people expect. While income may decline, taxable income often doesn’t, due to RMDs, taxable Social Security, Medicare IRMAA surcharges, and capital gains.

In this episode:

• Why “lower” doesn’t always mean low for high-income retirees.
• The hidden tax layers most retirement plans underestimate.
• Why retirement income is often lumpy, not smooth.
• Practical strategies for lifetime tax smoothing and withdrawal sequencing.

Segment highlights:

• The Wealth Word: Why the “low-tax retirement” idea persists
• The Signal: Cutting through noise, headlines, and false certainty in retirement planning
• The Money Move: How tax brackets really work in retirement and what to plan for instead
• Financial Harmony™: The financial and emotional investment we make in adult children—and how to audit it without guilt
• Culture Corner: Why this podcast paused, and how alignment—not hustle—brought it back

🎯 Start here:

Take the Gen X Retirement Readiness Scorecard
https://concurrentfp.typeform.com/genx-scorecard

Go deeper:

• Join the Financial Harmony™ Membership: https://www.concurrentfp.com/financial-harmony-membership/
• Explore flat-fee fiduciary planning with Concurrent Wealth Management: https://www.concurrentfp.com

Subscribe for weekly conversations on money, meaning, and life alignment.
@DrPrestonCherry

🚨$250k+ household income and $500k+ assets...? You’re ready for a personalized plan! Book your FREE retirement readiness call 👉 https://www.concurrentfp.com/

Want confidence that your retirement plan ACTUALLY works? Get it inside my Financial Harmony™ membership ($115/month) 👉 https://www.concurrentfp.com/financial-harmony-membership/

Take the Gen X Retirement Readiness Quiz...📊 https://concurrentfp.typeform.com/genx-scorecard
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You can make six figures, max your 401(k), and still feel broke inside.

A 2024 NerdWallet poll found 47% of Americans lack financial confidence — and even high earners say they “should be further along.” But your problem might not be income. It might be alignment.

In this episode, Dr. Preston Cherry shares the Five Permissions of Wealth™ — a powerful framework that replaces guilt, comparison, and confusion with clarity, confidence, and control. You’ll learn how to rewrite limiting money beliefs, align your spending with meaning, and plan from your story — not just your spreadsheets.

Ready to stop feeling behind and start living your wealth, your way? Take the Retirement Readiness Quiz, join our Financial Harmony™ membership, or schedule your no-cost good fit meeting below.

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Ready to align your wealth with your well-being? Here’s where to start:

1️⃣ Take the Financial Harmony™ Quiz - See your Retirement Readiness Scorecard and discover where your plan and purpose meet. https://www.concurrentfp.com/financial-harmony-membership/

2️⃣ Join the Financial Harmony™ Membership - Go deeper with group-based fiduciary guidance, interactive workshops, and community support built for high-income Gen X professionals. https://www.concurrentfp.com/financial-harmony-membership/

3️⃣ Explore all-inclusive flat-fee financial planning services - If your needs require customized 1:1 planning, schedule a no-cost good fit meeting to see how Concurrent Wealth Management can help you design a personalized plan aligned with your values and goals. https://www.concurrentfp.com/

4️⃣ Subscribe & Stay Connected for weekly episodes that help you live your wealth, your way. @DrPrestonCherry
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TIMECODES:
00:00 - Introduction
00:13 - Feel Guilty About How You Spend Your Money?
00:34 - Why You Don’t Feel Financially Confident
01:05 - Mindset & Money Shifts Which Help You Feel Confident
01:49 - How To Stop Feeling Financially Stuck
04:19 - The Framework That Aligns Your Money With Your Mindset
05:24 - How to Build True Financial Confidence
06:35 - Align Your Money To Your Purpose
07:20 - Moment to Check In
07:47 - Align Spending With What Actually Matters to You
09:19 - Adapt Your Finances to Life’s Changing Seasons
10:27 - Your Story Shapes Your Financial Strategy
11:51 - Outro

financial harmony, Gen X retirement, money psychology, wealth and well-being, retirement planning, tax planning, investing for gen x, money mindset, financial wellness, personal finance

#FinancialHarmony #MoneyMindset #FinancialConfidence #WealthMindset #FinancialTherapy #GenXWealth #BehavioralFinance #MoneyBeliefs #PurposeDrivenWealth #FinancialPlanning

🚨$250k+ household income and $500k+ assets...? You’re ready for a personalized plan! Book your FREE retirement readiness call 👉 https://www.concurrentfp.com/

Want confidence that your retirement plan ACTUALLY works? Get it inside my Financial Harmony™ membership ($115/month) 👉 https://www.concurrentfp.com/financial-harmony-membership/

Take the Gen X Retirement Readiness Quiz...📊 https://concurrentfp.typeform.com/genx-scorecard

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Over 50? Watch This — You’ll Catch Up on Your Retirement

Starting in 2026, if you earn $145,000 or more, your 401(k) catch-up contributions MUST go into a Roth - not pre-tax like before.

That’s not just a big tax change - it’s a huge opportunity for late starters in their 50s and early 60s.

If you’re between 50 and 63, this video walks you through the 5 exact steps to turn this new law into a retirement catch-up plan that works - even if you feel behind.

You’ll learn how to use super catch-ups (up to $34,750/year!), layer in Roth and brokerage savings, build a “retirement bridge” before Medicare or Social Security kicks in, and invest with confidence - not confusion.

Forget feeling late. This is your decade to win.

In this episode, Dr. Preston Cherry (Financial Planning Ph.D., CFP®, Top 10 Investopedia Advisor, and Founder of Concurrent Wealth Management) breaks down the 2025-2026 contribution limits, smart Roth planning, tax-efficient savings buckets, and how to actually retire on your terms.
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What You’ll Learn in This Video 👇
✅ The 2026 Roth catch-up rule for high earners (and why it matters)
✅ How to contribute up to $34,750/year - even if you’re starting late
✅ How to sequence savings across 401(k), Roth, HSA & brokerage
✅ Why tax diversification beats “just save more” in your 50s
✅ The “brokerage bridge” strategy to retire before Medicare
✅ How to smooth your income in early retirement without tax spikes
✅ How to build a 90-day and annual rhythm that compounds confidence

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Who Is This Video For?
📌 Gen X (50s - early 60s) professionals preparing for retirement
📌 High-income households earning $145K+
📌 Couples wondering if it’s “too late” to catch up
📌 Anyone confused by Roth rules, catch-ups, and tax strategy
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🚨 Gen X, older millennials & pre/early retirees, with $250k+ household income and $500k+ assets... Ready for a personalized plan? Book your FREE retirement readiness call 👉 https://www.concurrentfp.com/

Want clarity & control around your plan - without $6K+ annual advisor fees? Join my Financial Harmony™ membership for $115/month 👉 https://www.concurrentfp.com/financial-harmony-membership/

Take the Gen X Retirement Readiness Quiz...📊 https://concurrentfp.typeform.com/genx-scorecard

👉 Subscribe for weekly, values-aligned wealth insights: @DrPrestonCherry

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Keywords linking to this topic:
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#Roth401k #RetirementPlanning #GenX #CatchUpContributions #SecureAct2 #PrestonCherry #FlatFeeFiduciary #FinancialHarmony #LifeMoneyBalance #RetirementOver50 #TaxSmartRetirement #BrokerageBridge #RothConversion #TaxBuckets #ClarityConfidenceCadence #SmartRetirementSteps

🚨 Gen X, older millennials & pre/early retirees, with $250k+ household income and $500k+ assets... Are you ready for a personalized plan? Book your FREE retirement readiness call 👉 https://www.concurrentfp.com/

Want confidence that your retirement plan ACTUALLY works - without paying $6K+ a year? Get it inside my Financial Harmony™ membership for just $115/month 👉 https://www.concurrentfp.com/financial-harmony-membership/

Take the Gen X Retirement Readiness Quiz...📊 https://concurrentfp.typeform.com/genx-scorecard
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Most people think retirement plans fail because of the market, taxes, or not saving enough. Those are big - but not the real reason most plans quietly fall apart.

In this episode, Dr. Preston Cherry (Financial Planning Ph.D., CFP®, Top 10 Investopedia Advisor, and Founder of Concurrent Wealth Management) reveals the real breakdown point in most life and retirement plans: misalignment.

When your money no longer supports your actual life - your values, time, and energy - everything starts to fray. You’re doing all the “responsible” things, but feeling stuck in decision fatigue and endless money tweaks that never feel done.

This episode shows you how to re-center your plan using Clarity, Confidence, Cadence, and Control - and introduces the 90-second reset that’s already helped dozens of Gen X professionals feel peace around money again.

If you’re juggling careers, kids, aging parents, and still trying to “optimize” retirement in the background - this one’s for you.

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What You’ll Learn in This Video 👇
✅ Why most plans fail before the market drops - and what to watch for instead
✅ How financial noise (media, pressure, “rules”) paralyzes decision-making
✅ The silent tax of decision fatigue - and how it shows up in everyday finances
✅ The 3 major drifts that derail your rhythm: cash, calendar, and cognition
✅ A 90-second reset to align your season, values, and spending with zero spreadsheets
✅ Two tiny tweaks that boost clarity & control (fun card + automating the boring)
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Who Is This Video For?
📌 Gen X (40s - 50s - early 60s) professionals preparing for retirement
📌 High-achieving households juggling multiple financial priorities
📌 Couples trying to align money conversations with actual life
📌 Anyone tired of advice that feels like pressure instead of peace

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🚨 Gen X, older millennials & pre/early retirees, with $250k+ household income and $500k+ assets... Are you ready for a personalized plan? Book your FREE retirement readiness call 👉 https://www.concurrentfp.com/

Want confidence that your retirement plan ACTUALLY works - without paying $6K+ a year? Get it inside my Financial Harmony™ membership for just $115/month 👉 https://www.concurrentfp.com/financial-harmony-membership/

Take the Gen X Retirement Readiness Quiz...📊
https://concurrentfp.typeform.com/genx-scorecard

👉 Subscribe for weekly, values-aligned wealth insights: @DrPrestonCherry
-

Keywords linking to this topic:
retirement plan failure, financial alignment, Gen X retirement planning, decision fatigue, cash flow planning, retirement clarity, values-based planning, money mindset, 90-second reset, money cadence, spending buckets, financial harmony, retirement rhythm, financial therapy, retirement stress, automate finances, clarity and control, plan vs real life, fiduciary flat-fee planner

#RetirementPlanning #GenX #FinancialHarmony #MoneyMindset #DecisionFatigue #FinancialAlignment #CashFlowPlanning #LifeMoneyBalance #FlatFeePlanner #RetireOnTime #ClarityConfidenceCadence #ValuesBasedPlanning #FinancialTherapist #PrestonCherry #WealthInTheKeyOfLife

Ready for a personalized plan? Book your FREE retirement readiness call 👉 https://www.concurrentfp.com/

Take the Gen X Retirement Readiness Quiz 🚨 https://concurrentfp.typeform.com/genx-scorecard
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Healthcare is the sleeper cost that can quietly delay retirement by 3+ years. In this episode, Dr. Preston Cherry (Financial Planning Ph.D., CFP®, Top 10 Investopedia Advisor, Founder of Concurrent Wealth Management) breaks down the real price of healthcare in retirement - and how to plan for it before it hijacks your date.

Fidelity’s 2025 estimate puts a 65-year-old’s average lifetime healthcare spend at ~$172,500 after tax (up ~4% YoY), and MarketWatch notes it’s more than doubled since the early 2000s. Meanwhile, Advisor Perspectives highlights Gen X confidence gaps and competing pressures that make this easy to overlook. This video turns those numbers into a clear plan you can use now.

This isn’t about fear. It’s about building a healthcare-aware retirement plan - so your life drives your money, not the other way around.

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What You’ll Learn in This Video 👇
✅ The hidden line items Medicare doesn’t cover (dental, vision, LTC) and why premiums/deductibles still matter
✅ The $172,500 reality: why healthcare inflation outpaces wages/savings - and how to budget it proactively
✅ The costly “62 - 65 bridge”: options (spouse plan, ACA, COBRA, private) and how to avoid subsidy/IRMAA surprises
✅ Five smart Gen X moves: HSA strategy, Roth conversions with IRMAA awareness, catch-ups, stress-testing LTC, annual guardrails
✅ A simple 90-second audit to add a healthcare line to your plan and set annual IRMAA/tax checkpoints
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Who Is This Video For?
📌 Gen X (40s - 50s - early 60s) building a healthcare-aware retirement plan
📌 DIY planners who want clear guardrails (IRMAA/ACA/social security tax interactions)
📌 Couples coordinating pre-Medicare coverage and Social Security timing
📌 Professionals who prefer transparent, values-first planning over guesswork

-
Ready for a personalized plan? 👉 Book your FREE retirement readiness call: https://www.concurrentfp.com/

Subscribe for weekly, data-driven retirement strategies 👇
YouTube: @DrPrestonCherry

Take the Gen X Retirement Readiness Quiz 🚨
https://concurrentfp.typeform.com/genx-scorecard
-

Key Words linking To This Topic:
retirement healthcare costs, Fidelity $172,500 estimate, Medicare gaps, IRMAA surcharges, ACA subsidy cliff, pre-Medicare coverage 62 - 65, Gen X retirement planning, long-term care planning, HSA strategy, Roth conversions and Medicare, healthspan vs lifespan, retirement budget healthcare line item, premiums deductibles out-of-pocket, MarketWatch healthcare cost, Advisor Perspectives Gen X confidence, retirement date delay healthcare

#RetirementPlanning #GenX #HealthcareCosts #Medicare #IRMAA #ACASubsidies #HSA #RothConversions #LongTermCare #FinancialPlanning #TaxSmartRetirement #PreMedicareBridge #RetireOnTime #WealthInTheKeyOfLife #MoneyMindset

Ready for a personalized plan? Book your FREE retirement readiness call 👉 https://www.concurrentfp.com/
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Roth conversions can be a tax win - or an expensive mistake.

In this episode, Dr. Preston Cherry (Financial Planning Ph.D., CFP®, Top 10 Investopedia Advisor, Founder of Concurrent Wealth Management) shows exactly when conversions work, when they don’t, and how to size yours without tripping Medicare IRMAA, ACA subsidy cliffs, or phaseouts.

You’ll learn the “retirement tax valley” timing, how to calculate your conversion room, and the guardrails that keep a smart move from turning costly.

This isn’t about hacks. It’s about aligning taxes, timing, and your life- so you build durable, tax-free income with confidence.

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What You’ll Learn in This Video👇
✅ The 3 rules for a winning Roth conversion (rate arbitrage, income smoothing, no surcharge surprises)
✅ “Retirement tax valley”: the window after work, before SS/RMDs when conversions shine
✅ How to calculate this year’s conversion room (“fill, don’t spill”) and pay tax without penalties
✅ Law changes to watch: wider lower brackets vs. hidden phaseouts that raise your effective rate
✅ IRMAA & ACA tripwires: how $1 over a tier can add $3,000 - $6,000 in premiums next year
✅ Pro-rata rule (Form 8606), asset location after you convert, and the Dec 31 hard deadline
✅ Case study: multi-year plan → lower lifetime taxes, fewer surcharges, bigger ending Roth
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Who Is This Video For?
📌 Gen X & Boomers in their 50s - 60s eyeing conversions in the gap years
📌 High earners with RSUs/bonuses who don’t want to overpay by converting in peak years
📌 DIY planners who want a clear formula and simple guardrails
📌 Couples planning Social Security/RMD timing and survivor tax exposure

-
Ready for a personalized plan? 👉 Book your FREE retirement readiness call: https://www.concurrentfp.com/

Subscribe for weekly, data-driven retirement strategies👇
YouTube: @DrPrestonCherry

Take the Gen X Retirement Readiness Quiz 🚨
https://concurrentfp.typeform.com/genx-scorecard
-

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#RothConversion #TaxFreeRetirement #RetirementPlanning #GenXMoney #IRMAA #MedicarePremiums #TaxStrategy #RMDPlanning #SocialSecurityTiming #ACACliff #Form8606 #BracketManagement #TaxBracketArbitrage #AssetLocation #FinancialPlanning #PersonalFinance #InvestingTips #RetireSmart #AvoidOverpaying #WealthPlanning #TaxTips #MoneyMatters #RetirementStrategy #PortfolioPlanning #CFPAdvice