Ready For Retirement

James Conole, CFP®
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Nov 30, 2025 • 9min

Don’t Wait Until 70 for Social Security Unless You Hear This First

Think waiting until 70 for Social Security is the best choice? Discover the hidden trade-offs that could impact your finances. Delayed credits promise higher checks but may affect your investments and taxes. Meet Greg and Michelle, who smartly navigated their low-income years for better benefits, versus Linda, who faced anxiety after spending down her savings while waiting. Learn how to evaluate your options based on health, taxes, and lifestyle, to find the right claiming strategy for you.
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Nov 23, 2025 • 12min

Retiring With a Pension? Here’s How It Changes Everything About Your Retirement Math

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 allocationRetirees 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.-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 endorsementsParticipation 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!
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4 snips
Nov 20, 2025 • 16min

When Saving Becomes a Habit You Can’t Turn Off | Root Talks

Many retirees struggle with spending, even after achieving financial success. Some lifelong savers feel guilty buying simple pleasures, like $5 M&Ms. The hosts share stories of individuals who find it hard to transition from saving to spending. They discuss how a scarcity mindset can linger even in retirement and offer strategies for intentional, guilt-free spending. Practical exercises are suggested to help retirees clarify their desires and invest in experiences that enhance life, emphasizing health and joy over mere numbers.
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Nov 19, 2025 • 32min

The Wake-Up Call That Made Him Retire 10 Years Early | Retirement Reality

A cancer diagnosis changed everything. When Michael’s wife began chemo, time took on a new meaning. The long-term financial plan suddenly felt secondary to the years they still had together. That wake-up call led Michael, then 57, to retire a full decade earlier than planned, trading more income for more life.In this conversation with James, Michael shares the mindset shift that made him walk away from a thriving career and a team he loved leading. He opens up about the guilt of leaving, the relief that followed, and the realization that a company replaces you faster than you think.They also explore how a lifetime of small, consistent choices (early saving, investing through dividend reinvestment plans, and living below his means) gave Michael the freedom to say yes when life demanded it most. Now, his days are wide open: hiking sections of the Appalachian Trail, rediscovering old hobbies, and savoring the quiet moments that used to rush by.It’s an honest look at what happens when money finally becomes a tool for time, not the other way around.Want to be a guest on James’ show to help others by sharing your story? Complete this form: https://vwo3759x8i7.typeform.com/to/IwyScIeR-Michael 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 endorsementsParticipation 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!
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Nov 16, 2025 • 14min

The Secret Cost of Claiming Social Security Too Early (or Too Late)

Explore the nuances of claiming Social Security and how timing impacts retirement plans. Learn about the effects of early versus delayed claims on taxes and benefits for survivors. Discover the importance of aligning Social Security decisions with personal finances and investment strategies. Understand the role of 401(k)s and IRAs in optimizing tax efficiency. Dive into the pros and cons of different claiming ages, including how choices affect both income and long-term growth. Prioritize a coordinated approach for a successful retirement.
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Nov 12, 2025 • 31min

Retiring at 54: Why Darren Says It Feels Surreal | Retirement Reality

In this episode of Retirement Reality, Darren shares what it’s really like to walk away from work at 54 and why it still feels surreal. After decades of saving, hitting his number, and paying off the house, a company reorg gave him the push he needed to finally make the leap.He talks about how it feels to go from structure to freedom overnight, what surprised him about early retirement, and why he refuses to see it as a “forever” decision. For Darren, this season isn’t about stopping life — it’s about living it on his own terms.The conversation dives into what so many retirees quietly wrestle with: the emotional side of letting go, the fear of spending after years of saving, and the question of who you are without a job title. It’s honest, grounded, and a reminder that retirement isn’t an ending, it’s just a different kind of beginning.Want to be a guest on James’ show to help others by sharing your story? Complete this form: https://vwo3759x8i7.typeform.com/to/IwyScIeR-Darren 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 endorsementsParticipation 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!
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10 snips
Nov 8, 2025 • 16min

How to Maximize Social Security Spousal Benefits (Even if you Collect Your Benefit Early)

Understanding Social Security spousal benefits can save couples thousands. The spousal benefit is based on the primary earner’s full retirement age, not when they file. Learn how eligibility differs between current spouses and ex-spouses. Discover the critical differences between spousal and survivor benefits, and how early or delayed filing impacts them. James shares strategies to maximize spousal benefits and warns against common pitfalls that could reduce lifetime income. Make informed decisions to enhance your retirement planning.
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Nov 6, 2025 • 15min

I Threw the First Pitch at a Padres Game—Here’s the Real Lesson | Root Talks

What if the “smart” money choice isn’t the choice that builds your best life?This Root Talks episode starts with a bucket-list moment for James—throwing the first pitch at a Padres game—and turns into a bigger lesson: money is a tool to create meaning, not a score to keep. It’s a look at the Five Types of Wealth (financial, time, social, mental, and physical) and why the spreadsheet answer isn’t always the human answer.James and Ari share real examples: paying for time to be with family and friends, choosing health over “perfect” returns, even saying yes to a once-in-a-lifetime trip when it matters most. It’s practical retirement planning and financial planning through a different lens—purpose-driven wealth, money mindset, peace of mind.If the goal is a life well lived, optimization means aligning dollars with values: relationships, adventure, and the stories you’ll keep telling. That’s true retirement lifestyle design... building a life you don’t want to retire from.Watch to rethink “financially optimal,” and learn how to use your money to buy back time, reduce stress, and live on purpose.-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 endorsementsParticipation 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!
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Nov 4, 2025 • 11min

Retirement Benchmarks by Age: 40, 50, 60 (And What If You’re Behind?)

Those “3x by 40, 6x by 50, 10x by 67” charts feel official—until your life doesn’t match the average. In this episode, James shows why age-based savings benchmarks miss the mark and replaces them with a simple, four-step method that fits you.First, get clear on spending in retirement (inflation-adjusted, lifestyle-aware). Then credit guaranteed income, like Social Security, pensions, annuities, part-time work, help to size the real gap. Applying a conservative withdrawal rate to turn that gap into a target portfolio, and back-solve to today with reasonable returns and annual contributions can help you find security. No fluff. Just a plan you can update every year.Real-life cases make it concrete: an early retiree whose “confident” multiple falls short, two teachers whose pensions shrink the target, and a late-career saver who unlocks home equity to close the gap.What you’ll learn:Why age-based benchmarks exist—and where they can misleadHow timing (early retirement vs. later) changes the numberThe role of Social Security and pensions in lowering your targetWhen home equity or windfalls can bridge shortfallsThe four-step method: expenses → income → gap → portfolio mathUsing a withdrawal rate (e.g., 4%) to set a clear targetHow to back-solve to today’s balance and savings planStress-testing returns, inflation, and timing choicesIf generic multiples leave you anxious or overconfident, this conversation trades guesswork for clarity. Translate goals into numbers, see which levers actually move the needle, and build a plan that funds a life you enjoy.-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 endorsementsParticipation 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!
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Nov 1, 2025 • 45min

The Unexpected Exit at 55 — Finding Freedom, Purpose, and Identity

Donovan Volk, a 55-year-old semi-retired former corporate leader, transformed an unexpected job exit into a journey of self-discovery and newfound purpose. He discusses how the power of choice shaped his retirement journey and emphasizes the importance of financial preparation. Donovan reflects on the emotional shifts that accompany retirement, tackling fears about identity and spending. He also introduces the four retirement buckets—finances, health, relationships, and purpose—offering guidance for embracing this new chapter of life.

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