Retiring after age 65 changes the math and the priorities. You have fewer high-energy years, shorter tax planning windows, and RMDs much closer than most people realize. But you also often have higher Social Security, clearer spending needs, and more flexibility if the plan is built the right way. 

This episode breaks down how retirement strategy shifts when you retire later. Traditional withdrawal rules are built for 30–40 year retirements. If your timeline is closer to 10–20 years, blindly following those rules can lead to significant underspending and missed opportunities in your healthiest years.

Tax strategy becomes more compressed. Roth conversion windows are shorter. Medicare premiums and IRMAA surcharges matter more. Required minimum distributions arrive faster. Planning mistakes are harder to unwind, which makes coordination between income, investments, and taxes far more important.

Market risk looks different too. Higher Social Security and other income sources can reduce pressure on your portfolio, even though recovery time after downturns is shorter. The goal is not extreme conservatism. It is matching investments to real cash-flow needs while protecting against inflation and future healthcare costs.

The episode also covers survivor planning, charitable giving strategies like QCDs, Medicare surcharge planning, and why prioritizing health becomes one of the highest-return investments you can make when retiring later.

Retiring after 65 is not a disadvantage. It simply requires a different plan, tighter execution, and more intentional use of the years that matter most.

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Advisory services are offered through Root Financial Partners, LLC, an SEC-registered investment adviser. This content is intended for informational and educational purposes only and should not be considered personalized investment, tax, or legal advice. Viewing this content does not create an advisory relationship. We do not provide tax preparation or legal services. Always consult an investment, tax or legal professional regarding your specific situation.

The strategies, case studies, and examples discussed may not be suitable for everyone. They are hypothetical and for illustrative and educational purposes only. They do not reflect actual client results and are not guarantees of future performance. All investments involve risk, including the potential loss of principal.

Comments reflect the views of individual users and do not necessarily represent the views of Root Financial. They are not verified, may not be accurate, and should not be considered testimonials or endorsements

Participation in the Retirement Planning Academy or Early Retirement Academy does not create an advisory relationship with Root Financial. These programs are educational in nature and are not a substitute for personalized financial advice. Advisory services are offered only under a written agreement with Root Financial.

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Christian thought he was ready for retirement. He just didn’t realize how heavy the weight had been until he finally set it down.

After more than 30 years in a high-stress, always-on role at a global chemical company, Christian retired and discovered something he didn’t expect: the stress didn’t disappear all at once. It slowly melted away, like taking off a 30-pound jacket he didn’t even realize he’d been wearing. 

In this episode of Retirement Reality, Christian shares what the first 18 months of retirement have really felt like, both different and deeply liberating. He opens up about realizing work had become optional years before he actually left, navigating the mental shift from “always on” to fully unplugged, and why retirement gave him permission to finally live healthier and slower.

But the heart of this conversation isn’t spreadsheets or withdrawal strategies. It’s about priorities. Christian reflects on watching his father delay retirement, losing his mother too soon, and making a conscious decision not to repeat that pattern. For him, retirement became less about maximizing wealth and more about maximizing time with his wife — cooking together, spending unstructured days side by side, and building a life rooted in presence instead of pressure.

If you’re financially prepared but emotionally unsure, Christian’s story offers a steady, honest look at what actually happens after you step away, and why the freedom on the other side often feels lighter than you imagined.

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Christian is not a client of Root Financial Partners, LLC and received no compensation for participating in this video. His statements reflect his own opinions and experience and are not indicative of any specific client’s experience and are not a guarantee of results. No cash or non-cash compensation was provided, and no material conflicts are known.

Advisory services are offered through Root Financial Partners, LLC, an SEC-registered investment adviser. This content is intended for informational and educational purposes only and should not be considered personalized investment, tax, or legal advice. Viewing this content does not create an advisory relationship. We do not provide tax preparation or legal services. Always consult an investment, tax or legal professional regarding your specific situation.

The strategies, case studies, and examples discussed may not be suitable for everyone. They are hypothetical and for illustrative and educational purposes only. They do not reflect actual client results and are not guarantees of future performance. All investments involve risk, including the potential loss of principal.

Comments reflect the views of individual users and do not necessarily represent the views of Root Financial. They are not verified, may not be accurate, and should not be considered testimonials or endorsements

Participation in the Retirement Planning Academy or Early Retirement Academy does not create an advisory relationship with Root Financial. These programs are educational in nature and are not a substitute for personalized financial advice. Advisory services are offered only under a written agreement with Root Financial.

Create Your Custom Strategy ⬇️

Get Started Here.

Join the new Root Collective HERE!

Some of the most damaging financial advice doesn’t look shady at all. It looks responsible. It looks optimized. And it looks great on a spreadsheet. This episode breaks down one of the most unethical practices James sees in financial planning, not selling high-fee products, but using projections and tax strategies to justify an advisor’s fee while ignoring the life those numbers are supposed to support. 

The problem starts when advisors lead with “value creation” instead of purpose. Tax savings, Roth strategies, and optimized projections can be manipulated to look impressive, especially when spending is kept artificially low and retirement is delayed by default. The math may be correct, but the outcome can quietly cost years of freedom, experiences, and time.

Using a real case study, James shows how the same tax strategy looks wildly different once spending actually reflects the life someone wants to live. When travel, generosity, and earlier retirement enter the plan, the projected tax “value” shrinks, not because the strategy is bad, but because the goal changed. That’s the point most people miss.

This episode reframes what good advice should look like. Financial planning should start with how you want to spend your time, who you want to be with, and what matters most in your life. The tax strategy, investment strategy, and cash-flow plan exist to support that, not replace it.

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Advisory services are offered through Root Financial Partners, LLC, an SEC-registered investment adviser. This content is intended for informational and educational purposes only and should not be considered personalized investment, tax, or legal advice. Viewing this content does not create an advisory relationship. We do not provide tax preparation or legal services. Always consult an investment, tax or legal professional regarding your specific situation.

The strategies, case studies, and examples discussed may not be suitable for everyone. They are hypothetical and for illustrative and educational purposes only. They do not reflect actual client results and are not guarantees of future performance. All investments involve risk, including the potential loss of principal.

Comments reflect the views of individual users and do not necessarily represent the views of Root Financial. They are not verified, may not be accurate, and should not be considered testimonials or endorsements

Participation in the Retirement Planning Academy or Early Retirement Academy does not create an advisory relationship with Root Financial. These programs are educational in nature and are not a substitute for personalized financial advice. Advisory services are offered only under a written agreement with Root Financial.

Create Your Custom Strategy ⬇️

Get Started Here.

Join the new Root Collective HERE!

Retirement doesn’t always arrive on your schedule. Sometimes it shows up early, uninvited, and forces you to rethink everything you thought you knew.

For Jim, that moment came at 5, four years before the retirement date he’d carefully planned for. One unexpected layoff, and suddenly the identity he’d built over decades in big tech was shaking underneath him.

In this episode of Retirement Reality, James shares the stress, the fear, and the sense of disorientation that came with having the rug pulled out from under him… and the surprising clarity that followed once the dust settled. What started as panic slowly revealed itself as a turning point — a chance to reexamine what he really wanted from his next chapter, not just what he thought he should do.

He opens up about reevaluating his timeline, rebuilding confidence, and discovering that being forced off the treadmill early didn’t break his plan, it accelerated it. The layoff he once dreaded became the sharpening moment he didn’t know he needed.

As you listen, consider this:
Sometimes the moments you fear most end up freeing you the most.

Want to be a guest on James’ show to help others by sharing your story? Complete this form: https://vwo3759x8i7.typeform.com/to/IwyScIeR 

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Jim is not a client of Root Financial Partners, LLC and received no compensation for participating in this video. His statements reflect his own opinions and experience and are not indicative of any specific client’s experience and are not a guarantee of results. No cash or non-cash compensation was provided, and no material conflicts are known.

Advisory services are offered through Root Financial Partners, LLC, an SEC-registered investment adviser. This content is intended for informational and educational purposes only and should not be considered personalized investment, tax, or legal advice. Viewing this content does not create an advisory relationship. We do not provide tax preparation or legal services. Always consult an investment, tax or legal professional regarding your specific situation.

The strategies, case studies, and examples discussed may not be suitable for everyone. They are hypothetical and for illustrative and educational purposes only. They do not reflect actual client results and are not guarantees of future performance. All investments involve risk, including the potential loss of principal.

Comments reflect the views of individual users and do not necessarily represent the views of Root Financial. They are not verified, may not be accurate, and should not be considered testimonials or endorsements

Participation in the Retirement Planning Academy or Early Retirement Academy does not create an advisory relationship with Root Financial. These programs are educational in nature and are not a substitute for personalized financial advice. Advisory services are offered only under a written agreement with Root Financial.

Create Your Custom Strategy ⬇️

Get Started Here.

Join the new Root Collective HERE!

Roth conversions can save thousands in taxes, but they can also trigger Medicare IRMAA surcharges that quietly add up to more than $5,000 a year. Most retirees never see it coming, because the rules for Medicare premiums don’t line up with the tax brackets everyone focuses on.

In this video, James breaks down how Roth conversions interact with Medicare Part B and Part D premiums, why modified adjusted gross income matters more than taxable income, and how crossing a threshold by even one dollar can change your costs for an entire year. The case study shows how a couple could save nearly a million dollars in lifetime taxes… but lose tens of thousands to unnecessary IRMAA charges if they convert without a plan. A small adjustment (converting up to the right tier instead of the wrong bracket) boosts their long-term wealth and avoids surprise premiums.

If you’re planning Roth conversions before RMDs begin, evaluating a 401(k)-to-Roth strategy, or trying to minimize taxes in early retirement, understanding Medicare thresholds is essential. A smart conversion plan balances tax savings with premium costs so you don’t give back what you worked so hard to save.

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Advisory services are offered through Root Financial Partners, LLC, an SEC-registered investment adviser. This content is intended for informational and educational purposes only and should not be considered personalized investment, tax, or legal advice. Viewing this content does not create an advisory relationship. We do not provide tax preparation or legal services. Always consult an investment, tax or legal professional regarding your specific situation.

The strategies, case studies, and examples discussed may not be suitable for everyone. They are hypothetical and for illustrative and educational purposes only. They do not reflect actual client results and are not guarantees of future performance. All investments involve risk, including the potential loss of principal.

Comments reflect the views of individual users and do not necessarily represent the views of Root Financial. They are not verified, may not be accurate, and should not be considered testimonials or endorsements

Participation in the Retirement Planning Academy or Early Retirement Academy does not create an advisory relationship with Root Financial. These programs are educational in nature and are not a substitute for personalized financial advice. Advisory services are offered only under a written agreement with Root Financial.

Create Your Custom Strategy ⬇️

Get Started Here.

Join the new Root Collective HERE!

Steve spent more than two decades building video games, working with a team that felt more like family than coworkers. By all measures, he loved his work. But a heart attack in 2021 changed everything, and it became the moment that pushed him to rethink the one thing he’d always said he wanted someday: an early retirement.

In this episode, Steve sits down with James Conole, CFP®, to share how a health scare, a divorce, and years of slowly learning how to budget and invest turned into the freedom he now wakes up to every day. He didn’t leave work because he hated his job. He left because he finally understood how valuable his time had become and how much life he still wanted to live.

Steve talks about losing 70 pounds, rebuilding his health through trial-and-error fitness routines, and the joy of discovering things he never had energy for during his career: jazz bands, improv lessons, spontaneous travel, and even acting classes. He also opens up about moving back to Arizona just in time to support his mom through a cancer diagnosis, a moment that revealed exactly how meaningful this new freedom is.

His story is a reminder that retirement isn’t just a math problem. It’s a life problem that you can solve by knowing what you value and experimenting until your days feel like your own again. And for Steve, these last two and half years have been better than he imagined.

Watch this episode of Retirement Reality — where real retirees share the wake-up calls, reinventions, and surprising joys that define life on the other side of work.

Want to be a guest on James’ show to help others by sharing your story? Complete this form: https://vwo3759x8i7.typeform.com/to/IwyScIeR

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Steve is not a client of Root Financial Partners, LLC and received no compensation for participating in this video. His statements reflect his own opinions and experience and are not indicative of any specific client’s experience and are not a guarantee of results. No cash or non-cash compensation was provided, and no material conflicts are known.

Advisory services are offered through Root Financial Partners, LLC, an SEC-registered investment adviser. This content is intended for informational and educational purposes only and should not be considered personalized investment, tax, or legal advice. Viewing this content does not create an advisory relationship. We do not provide tax preparation or legal services. Always consult an investment, tax or legal professional regarding your specific situation.

The strategies, case studies, and examples discussed may not be suitable for everyone. They are hypothetical and for illustrative and educational purposes only. They do not reflect actual client results and are not guarantees of future performance. All investments involve risk, including the potential loss of principal.

Comments reflect the views of individual users and do not necessarily represent the views of Root Financial. They are not verified, may not be accurate, and should not be considered testimonials or endorsements

Participation in the Retirement Planning Academy or Early Retirement Academy does not create an advisory relationship with Root Financial. These programs are educational in nature and are not a substitute for personalized financial advice. Advisory services are offered only under a written agreement with Root Financial.

Create Your Custom Strategy ⬇️

Get Started Here.

Join the new Root Collective HERE!

Most retirement advice quietly assumes you have a partner: two incomes, two Social Security checks, someone to split expenses with, someone to catch the slack if something goes wrong. But for singles, the margins are tighter and the freedom can be much greater. Planning alone means every decision carries more weight, but it also means you have full control over the life you want to build.

This video centers on Tina, a 62-year-old single woman with roughly $2.2 million across investment accounts, employer stock, a 401(k), and a Roth IRA. Her situation highlights something many single retirees face: the rules for married couples don’t apply. There’s no second Social Security benefit, no shared expenses, no fallback income — just her plan, her goals, her decisions. Once her “freedom number” becomes clear, the entire plan shifts. Reliable income fills part of the picture, but the rest depends on how her portfolio supports the exact life she wants to live. Simple choices — retiring sooner, traveling more, inviting friends on those trips, or designing a lifestyle that actually reflects what matters — completely change her projections and expand what’s possible.

The heart of this conversation isn’t about budgets or perfect withdrawal rates. It’s about giving singles permission to build lives that match their values, not someone else’s template. When the numbers align with the life you want, confidence follows naturally.
If this perspective helps you rethink how retirement looks when it’s just you, tap like and share what resonated. Your retirement doesn’t need to look like anyone else’s, it just needs to support the version of life that feels right to you.

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Advisory services are offered through Root Financial Partners, LLC, an SEC-registered investment adviser. This content is intended for informational and educational purposes only and should not be considered personalized investment, tax, or legal advice. Viewing this content does not create an advisory relationship. We do not provide tax preparation or legal services. Always consult an investment, tax or legal professional regarding your specific situation.

The strategies, case studies, and examples discussed may not be suitable for everyone. They are hypothetical and for illustrative and educational purposes only. They do not reflect actual client results and are not guarantees of future performance. All investments involve risk, including the potential loss of principal.

Comments reflect the views of individual users and do not necessarily represent the views of Root Financial. They are not verified, may not be accurate, and should not be considered testimonials or endorsements

Participation in the Retirement Planning Academy or Early Retirement Academy does not create an advisory relationship with Root Financial. These programs are educational in nature and are not a substitute for personalized financial advice. Advisory services are offered only under a written agreement with Root Financial.

Create Your Custom Strategy ⬇️

Get Started Here.

Join the new Root Collective HERE!

Retiring at 50 sounds bold, almost unthinkable for most people, but for Kent, it was the only decision that made sense once life, loss, and perspective pushed everything into focus. In this conversation, he sits down with James Conole, CFP®, to share the honest story behind leaving work two decades earlier than expected.

Kent talks about saving from age 18, building a plan long before he knew what retirement would look like, and the complicated mix of discipline, luck, and family legacy that helped him reach this moment. He also opens up about the emotional side: the guilt of inheriting wealth after losing both his father and grandfather, the fear of telling coworkers and his mom, and the surprising relief when everyone responded with encouragement instead of judgment.

Nine months into retirement, Kent describes the freedom that comes from being fully present with his daughters, traveling on his family’s terms, rediscovering community through pickleball, and learning how to redefine productivity when your time finally becomes your own. And he doesn’t sugarcoat the harder parts — the identity shift, the loss of workplace validation, and the work it takes to build purpose outside of career.
This is what early retirement looks like when you stop planning only with your brain and start planning with your heart: more time, more presence, and a life shaped by intention instead of inertia.

Watch this episode of Retirement Reality — where real retirees share the highs, lows, and turning points that helped them choose a life they don’t want to postpone.

Want to be a guest on James’ show to help others by sharing your story? Complete this form: https://vwo3759x8i7.typeform.com/to/IwyScIeR

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Kent is not a client of Root Financial Partners, LLC and received no compensation for participating in this video. His statements reflect his own opinions and experience and are not indicative of any specific client’s experience and are not a guarantee of results. No cash or non-cash compensation was provided, and no material conflicts are known.

Advisory services are offered through Root Financial Partners, LLC, an SEC-registered investment adviser. This content is intended for informational and educational purposes only and should not be considered personalized investment, tax, or legal advice. Viewing this content does not create an advisory relationship. We do not provide tax preparation or legal services. Always consult an investment, tax or legal professional regarding your specific situation.

The strategies, case studies, and examples discussed may not be suitable for everyone. They are hypothetical and for illustrative and educational purposes only. They do not reflect actual client results and are not guarantees of future performance. All investments involve risk, including the potential loss of principal.

Comments reflect the views of individual users and do not necessarily represent the views of Root Financial. They are not verified, may not be accurate, and should not be considered testimonials or endorsements

Participation in the Retirement Planning Academy or Early Retirement Academy does not create an advisory relationship with Root Financial. These programs are educational in nature and are not a substitute for personalized financial advice. Advisory services are offered only under a written agreement with Root Financial.

Create Your Custom Strategy ⬇️

Get Started Here.

Join the new Root Collective HERE!

Think waiting until 70 is the gold standard for Social Security? We dig into the real math behind delayed retirement credits and the hidden trade-offs that rarely make it into the headlines. Drawing on years of planning experience and two vivid case studies, we show how the “bigger check later” can either amplify your lifetime income or quietly drain the resources you need to feel secure.

We start with the promise of delayed credits and then zoom out to the full picture: how bridging years are funded, how portfolio withdrawals reduce compounding, and why taxes can swing the outcome. You’ll hear about Greg and Michelle, a couple who used low-income years to convert IRAs to Roth, trimmed future RMDs, and paired those moves with higher benefits at 70. Then meet Linda, who spent down her savings to wait for a larger benefit and ended up with a thinner cushion and more anxiety. Along the way, we break down longevity assumptions, the importance of survivor benefits, and the outsized impact of sequence risk when markets fall during your withdrawal window.

By the end, you’ll have a practical framework to compare claiming ages on an after-tax basis, stress test market downturns, and decide whether you value maximum lifetime income, early-retirement flexibility, or a blend of both. If you’ve ever wondered whether to file early, wait until full retirement age, or push to 70, this is your roadmap for choosing the path that fits your health, taxes, investments, and lifestyle.

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Advisory services are offered through Root Financial Partners, LLC, an SEC-registered investment adviser. This content is intended for informational and educational purposes only and should not be considered personalized investment, tax, or legal advice. Viewing this content does not create an advisory relationship. We do not provide tax preparation or legal services. Always consult an investment, tax or legal professional regarding your specific situation.

The strategies, case studies, and examples discussed may not be suitable for everyone. They are hypothetical and for illustrative and educational purposes only. They do not reflect actual client results and are not guarantees of future performance. All investments involve risk, including the potential loss of principal.

Comments reflect the views of individual users and do not necessarily represent the views of Root Financial. They are not verified, may not be accurate, and should not be considered testimonials or endorsements

Participation in the Retirement Planning Academy or Early Retirement Academy does not create an advisory relationship with Root Financial. These programs are educational in nature and are not a substitute for personalized financial advice. Advisory services are offered only under a written agreement with Root Financial.

Create Your Custom Strategy ⬇️

Get Started Here.

Join the new Root Collective HERE!

Retiring with a pension changes everything about your retirement math.
Most people think about retirement in terms of net worth—how close they are to a million, two million, or more. But if you have a pension, that old framework can send you down the wrong path. In this episode, James explains why retirees with pensions need to think in terms of cash flow, not balances on a statement.

James begins with a simple shift: a pension that pays $60,000 a year acts like the income from a $1.5 million portfolio under a traditional 4% withdrawal rule. That perspective alone can reduce the pressure many people feel when they compare their savings to generic benchmarks or to friends who rely entirely on investments.

He then walks through real scenarios—showing how a couple aiming to spend $80,000 per year may only need $600,000–$750,000 in savings if pension and Social Security cover the first half of their income needs. And in cases where the pension plus Social Security fully replaces spending, a retiree might not technically need any portfolio withdrawals at all. Cash flow drives the plan; the portfolio simply becomes optional support.

James  also covers the nuances most retirees overlook:
• How to plan for pensions without cost-of-living adjustments
• Why survivorship options can make or break a spouse’s long-term security
• How investment strategy changes when you don’t need to pull from your portfolio
• Why being 60 or 65 doesn’t automatically mean you need a conservative allocation

Retirees with pensions often have far more flexibility than they realize. The key is understanding how the pension slots into the income puzzle, how it affects withdrawal rates, and how it should guide investment decisions—especially for couples.

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Advisory services are offered through Root Financial Partners, LLC, an SEC-registered investment adviser. This content is intended for informational and educational purposes only and should not be considered personalized investment, tax, or legal advice. Viewing this content does not create an advisory relationship. We do not provide tax preparation or legal services. Always consult an investment, tax or legal professional regarding your specific situation.

The strategies, case studies, and examples discussed may not be suitable for everyone. They are hypothetical and for illustrative and educational purposes only. They do not reflect actual client results and are not guarantees of future performance. All investments involve risk, including the potential loss of principal.

Comments reflect the views of individual users and do not necessarily represent the views of Root Financial. They are not verified, may not be accurate, and should not be considered testimonials or endorsements

Participation in the Retirement Planning Academy or Early Retirement Academy does not create an advisory relationship with Root Financial. These programs are educational in nature and are not a substitute for personalized financial advice. Advisory services are offered only under a written agreement with Root Financial.

Create Your Custom Strategy ⬇️

Get Started Here.

Join the new Root Collective HERE!