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PODCAST

Ready For Retirement

James Conole, CFP®

Ready For Retirement is the podcast dedicated to helping you learn the tips and strategies that will help you achieve your retirement goals. When it comes to retirement planning, it can quickly become overwhelming and easy to not take action. I designed this podcast because I want you to have the knowledge and confidence to create your secure retirement. My ultimate goal for all of my clients (and listeners) is to create peace of mind and that starts with having a strategy. I want you to spend more

business investing

All Episodes

16:03

How to Maximize Social Security Spousal Benefits...

Ready For Retirement ·

2025/11/08

A single misunderstanding about Social Security spousal benefits can cost couples thousands over retirement. This episode unpacks the real math behind how Social Security treats spouses, ex-spouses, and survivors, so you can make smart claiming decisions that protect both cash flow and long-term security. Listen to learn how the spousal benefit actually works: it’s based on 50% of the primary earner’s full retirement age benefit, not when they file. We walk through clear examples showing who ...

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14:52

I Threw the First Pitch at a Padres Game—Here’s the...

Ready For Retirement ·

2025/11/06

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 an...

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10:30

Retirement Benchmarks by Age: 40, 50, 60 (And What If...

Ready For Retirement ·

2025/11/04

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 ga...

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44:57

The Unexpected Exit at 55 — Finding Freedom, Purpose,...

Ready For Retirement ·

2025/11/01

In this episode of Retirement Reality, meet Donovan, a 55-year-old retiree who turned an unexpected career exit into an opportunity for freedom, reflection, and new purpose. Donovan shares how one defining word, choice, shaped his journey before, during, and after retirement. From years of disciplined saving and intentional living to facing an unplanned exit from corporate life, Donovan opens up about how preparation, mindset, and adaptability transformed what could have been a setback into ...

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19:17

3 Steps to Build a Retirement Paycheck That Lasts

Ready For Retirement ·

2025/10/28

Early retirement income can feel complicated, but a steady paycheck from savings starts with a simple framework. This episode reframes withdrawal decisions, explains why a fixed 4 percent rule can be too conservative in some cases, and shows when a 5 percent starting point may fit with the right allocation and ongoing adjustments. A million dollar case study turns rates into an annual paycheck while addressing sequence risk and flexible spending guardrails. Taxes do the heavy lifting. Retirem...

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21:28

Your Tax Planning Window Won’t Last Forever | Top 3...

Ready For Retirement ·

2025/10/25

Retiring early isn’t just about having enough money, it’s about using the right tax moves in the right years. This conversation between James and Ari maps the three biggest levers for early retirees: Roth conversions, ACA health insurance subsidies, and 0% long-term capital gains. A real-world case study shows how account mix and spending levels can flip what’s “best,” and how small income shifts can change the math in a big way. The episode breaks down when Roth conversions pay off versus wh...

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16:17

Will Low Returns Ruin Your Retirement? (How to...

Ready For Retirement ·

2025/10/23

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. Diversificat...

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12:08

3 Investments That Should Never Go In Your Retirement...

Ready For Retirement ·

2025/10/21

Think your retirement’s safer with a little gold, a favorite stock, and a home full of equity? Time for a reality check. In this episode, we put three “sacred” retirement assets to the test and show how they can quietly derail the one outcome that really matters: a steady paycheck for life. You’ll learn how to define your retirement portfolio’s real job, growth that beats inflation and protection that funds your lifestyle through market swings. We unpack gold’s myth versus math, why concentra...

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13:27

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

Ready For Retirement ·

2025/10/18

The real question isn’t “Can we retire?”, it’s “On how much, and when do the big costs fade so our savings can breathe?” In this episode, James walks through one couples' retirement plan to show how timing, travel, and housing choices can turn a shaky forecast into a confident glidepath. He highlights the income canyon most people miss (the stretch between retiring and starting Social Security) where withdrawals rise sharply, then ease once benefits begin and the mortgage is gone. By front-...

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11:32

10 Ways Retirement Has Completely Changed in 30 Years

Ready For Retirement ·

2025/10/14

Forget the gold watch and glide path to the couch. Retirement has been rewritten. In this episode, James walks through the 10 biggest shifts redefining life after work—and how to replace outdated rules with a plan that’s practical, human, and built for how people actually live today. From the mindset shift away from Depression-era scarcity to using money as a tool for a richer life, this episode explores how to align spending with values so every dollar supports health, connection, and meanin...

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16:48

$10M+ Net Worth Case Study: What to Do First

Ready For Retirement ·

2025/10/11

What if the real financial risk isn’t running out of money, but running out of time to use it well? In this episode, listen as James and Ari unpack a $14 million case study with concentrated inherited stock, sizable retirement accounts, and big questions about spending, portfolio risk, taxes, and legacy. See how a single allocation decision can swing outcomes from an eight-figure estate to running out of money by age 75. Learn why $25,000 a month versus $50,000 a month can change the end bala...

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12:25

The 3 Worst Retirement Mistakes I See All the Time

Ready For Retirement ·

2025/10/07

Think your tax bill disappears in retirement? Think again. It may drop for a few quiet years, until RMDs, Social Security taxation, and Medicare IRMAA kick in. That “low-tax retirement” dream can close fast. Learn the retirement tax arc and how targeted Roth conversions during low-income years can cut lifetime taxes by six figures, reduce future RMDs, and give you more control over when you realize income. In this episode, you'll learn to tackle the silent retirement killer: underspending. Fe...

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11:36

The BEST Retirement Advice (From 909 Real Retirees)

Ready For Retirement ·

2025/10/04

What if the riskiest move isn’t retiring too early, but waiting so long your best years pass by? This episode unpacks the real regrets of 909 retirees and the practical steps they wish they’d taken sooner. Design purpose. Spend on what matters. Do it while health and energy are on your side. Beat the “one more year” trap. Working longer can look safer on a spreadsheet, but life isn’t a spreadsheet. Learn how to prototype purpose before day one, shift your identity from saver to spender withou...

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19:47

The Cliché Advice You Should Finally Pay Attention To

Ready For Retirement ·

2025/10/02

We’ve all heard the clichés: focus on what you can control, embrace the pain not the suffering, fight for what you want. Easy to dismiss, right? But the truth is, those sayings stick around for a reason. They hold the kind of wisdom that can change how you approach life, work, and even setbacks. What often gets missed is that clichés aren’t about perfection, they’re about perspective. They remind you that regret comes from the chances you didn’t take, that discipline lasts longer than motivat...

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12:59

5 Signs You Should Fire Your Financial Advisor

Ready For Retirement ·

2025/09/30

Most people stay with the wrong financial advisor far too long: out of loyalty, inertia, or fear of starting over. But the cost of sticking with the wrong person can be measured in dollars, stress, and lost years you can’t get back. 5 Signs You Should Fire Your Financial Advisor 1. They always say “ask your CPA” instead of doing proactive tax planning (advisors don’t file returns, but tax planning is inseparable from investing and retirement decisions). 2. They only talk about investme...

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18:39

Advice from Retirees: What They Wish They Knew in...

Ready For Retirement ·

2025/09/27

Ever wish your 80-year-old self could give you a nudge today? After years working with clients in their 70s and 80s, three lessons rise to the top: treat wealth as money, time, and health, know your financial independence number, and prioritize what money can’t buy while you still can. In your 50s–60s, many people hit a rare “sweet spot” where financial security, free time, and decent health overlap. Too many keep grinding until that window closes. A clear FI plan turns work from mandatory to...

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12:32

Roth vs. Traditional IRA – Which One Really Saves You...

Ready For Retirement ·

2025/09/23

Is a Roth IRA really better than a traditional IRA? The truth is... it depends on your tax situation. In this video, you’ll learn why your current tax bracket versus your retirement tax bracket should drive your decision, not blanket advice. Most retirees pay less in taxes later in life, which creates opportunities for smart strategies like tax arbitrage and Roth conversions. By contributing to traditional accounts during high-earning years and converting in lower-tax years, you can potentia...

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21:25

You Could Spend WAY More Than the 4% Rule Suggests...

Ready For Retirement ·

2025/09/20

Financial planning’s most famous guideline just got an upgrade. In this exclusive interview, James speaks with Bill Bengen—the MIT-trained engineer turned financial advisor who created the 4% rule—about his updated research and what it means for retirees today. Bengen reveals that diversification alone can raise the safe withdrawal rate to 4.7%, and under certain market conditions, retirees may be able to withdraw 6%, 7%, or even 8% annually. The original 4% rule was never meant to reflect av...

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18:18

How to Know You’ve Found the Right Financial Advisor...

Ready For Retirement ·

2025/09/18

What makes you trust someone with your financial future? In this episode of Root Talks, James and Ari unpack the powerful role of intuition in building lasting relationships with financial advisors, business partners, and even loved ones. They explain how what we call a gut feeling is actually condensed pattern recognition, your brain quietly scanning countless experiences to guide your decisions before you can put words to it. This is why many Root clients engage with our content for months ...

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13:42

What’s the Smartest Investment Mix for Retirees Right...

Ready For Retirement ·

2025/09/16

Navigating market volatility in retirement requires more than the traditional 60/40 portfolio. This episode explores three critical risks every retiree must address to maintain financial security through changing market conditions. The first is sequence of return risk, which can devastate a portfolio if early withdrawals align with a downturn. Listen to James share his concept of "Root Reserves", setting aside five years of stable investments to provide protection during turbulent periods wit...

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335 results

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