Ready For Retirement

James Conole, CFP®
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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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Oct 28, 2025 • 19min

3 Steps to Build a Retirement Paycheck That Lasts

Navigating early retirement income can be simpler than it seems! A flexible withdrawal strategy may allow for a 5% starting point instead of the traditionally conservative 4%. Learn how taxes significantly impact retirement income and can lower your overall tax bill. Discover how coordinating different income sources like Social Security and IRA withdrawals can create a streamlined paycheck. Plus, there’s insight on managing big costs and the concept of the retirement spending smile across different life stages!
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Oct 25, 2025 • 21min

Your Tax Planning Window Won’t Last Forever | Top 3 Strategies to Prioritize

Discover how tax strategies can unlock early retirement freedom. Explore the key levers like Roth conversions and health subsidies, and learn how small income shifts can have a major financial impact. A case study reveals the importance of account mix and spending habits. Find out when Roth conversions are advantageous or detrimental, and understand the benefits of harvesting capital gains at the 0% federal rate. By prioritizing long-term strategies, you can effectively manage your tax planning for a more secure financial future.
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6 snips
Oct 23, 2025 • 16min

Will Low Returns Ruin Your Retirement? (How to Interpret Goldman Sachs 3% Forecast) | Root Talks

What if the next 10 years bring just 3% returns from the S&P 500?In this episode, we turn that forecast into a real-world retirement plan—not panic. You’ll learn how to stress test your portfolio, build flexibility into your spending, and design a withdrawal strategy that can survive tough markets.Listen as James and Ari break down:Sequence-of-returns risk — why bad early years hurt more than bad averages.The modern 4% rule — how to use it as a guardrail, not a guarantee.Diversification that actually works — adding small caps, value, international, and bonds to reduce risk from overexposed tech-heavy portfolios.Tax-smart moves — Roth conversions, cash buffers, and dynamic withdrawal rules that adapt to changing markets.Whether you’re planning to retire early or just want peace of mind through an uncertain decade, this guide gives you a clear, flexible framework—so your lifestyle isn’t dictated by Wall Street’s forecasts.-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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8 snips
Oct 21, 2025 • 12min

3 Investments That Should Never Go In Your Retirement Portfolio

Discover why relying on gold, concentrated stocks, and home equity can jeopardize your retirement. Gold often fails to provide reliable inflation protection, while single-stock bets can increase risks significantly. Plus, home equity, though cherished, doesn’t translate into steady income. Learn about a framework that focuses on growth and reserve sleeves for sustainable withdrawals, along with rebalancing strategies to ensure a consistent paycheck for life. Say goodbye to shiny distractions and hello to financial security!
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Oct 18, 2025 • 13min

We're 62 with $2M: Retire Now or Wait?

A couple contemplates retirement at 62 with an impressive $2M savings. Insightful strategies demonstrate how timing and travel can bolster financial security. The discussion highlights the 'income canyon' — the gap between retiring and receiving Social Security benefits. By prioritizing travel in early years and planning a strategic downsizing in their mid-70s, they can enjoy retirement without extending their working years. Listeners learn about the pitfalls of the 4% rule, creating a sustainable spending plan, and maintaining flexibility in the face of shifting expenses.

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