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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

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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6:55

The Real Reason Most People Struggle in Retirement...

Ready For Retirement ·

2025/09/15

Retirement planning is often framed as a numbers game where you can get lost in focusing on maximizing your 401(k), minimizing taxes, and chasing investment returns. But financial security alone doesn’t guarantee fulfillment. The bigger challenge many retirees face is psychological, not financial. The transition from decades of work into retirement often sparks an identity crisis. A career provides structure, purpose, and community—when it’s gone, retirees can feel adrift. Without clarity on ...

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13:19

How Much Can I Spend In Retirement with a $2 Million...

Ready For Retirement ·

2025/09/13

A retirement story that challenges everything you thought you knew about what’s possible in your golden years. Meet Michael and Lisa: a couple in their early sixties with $2 million saved who are worried about running out of money too soon. Their initial plan looked bleak, but three simple adjustments reshaped their retirement outlook without working longer or cutting back on their lifestyle dreams. The shift came from questioning assumptions. Instead of projecting first-year expenses forever...

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12:19

Top 5 Social Security Secrets Every 60-Year-Old Needs...

Ready For Retirement ·

2025/09/09

The hidden complexities of Social Security could cost retirees tens of thousands over a lifetime. While it may seem like a simple income source, the right strategy can dramatically improve your financial security. Claiming isn’t one-size-fits-all. Protecting a spouse, guarding against longevity risk, or maximizing investments each call for a different approach. Traditional breakeven analyses often miss key factors like the opportunity cost of using investments while waiting for benefits. Spou...

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9:37

Retiring at 65 Might Be Too Late (Here’s Why)

Ready For Retirement ·

2025/09/05

Most retirement plans focus on money alone, but the equation is incomplete without factoring in healthspan. Lifespan is how long someone lives, but healthspan is the number of years spent in good physical and cognitive health. The gap is significant. The average American lives to 77, but healthspan often ends around 66. This creates a retirement paradox. Many professionals work into their mid-60s to maximize Social Security and retirement accounts, only to discover declining health limits the...

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17:47

Inside Root’s Growth Plan (And the Promise Refuse to...

Ready For Retirement ·

2025/09/04

What happens when growth changes a company? We’ve all seen it—your favorite restaurant expands and suddenly the quality slips. The connection feels lost. But does growing always mean losing what made you special? At Root, we think about growth differently. We use “anti-goals” to define what we never want to become, with checks in place so expansion never overshadows client experience or team wellbeing. That’s why we recently lowered our minimum investment from $2M to $1M. It wasn’t a quick de...

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17:30

How to Avoid the Widow’s Tax (Before It’s Too Late)

Ready For Retirement ·

2025/09/02

When one spouse passes away, the survivor often faces what is known as the “widow’s tax.” It is not an official IRS tax, but the impact of moving from married to single tax brackets. A couple earning $120,000 in the 12 percent bracket can see the surviving spouse pushed into the 24 percent bracket with the same income. This tax bracket compression happens at the most vulnerable time. Watch as James outlines three strategies that help protect a surviving spouse from this financial burden. Stra...

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38:39

They Gave Up the ‘Traditional’ Retirement to Live the...

Ready For Retirement ·

2025/08/26

Redefining retirement with purpose and adventure John and Bev retired at 55, sold almost everything, and traded their dream home for two backpacks, golf clubs, and a life of full-time travel. Since then, they have visited 107 countries and all 50 states as “The Retirement Travelers.” Their journey began during COVID, when cancelled plans led to an Airstream trip across America’s national parks. Living in 220 square feet showed them how little they truly needed—freeing them to downsize, travel...

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17:43

The Hidden Cost of Financial Optimization (And How to...

Ready For Retirement ·

2025/08/21

What if the “financially optimal” choice doesn’t actually lead to your best life? This conversation explores the balance between optimizing money and optimizing happiness. We break down the Five Types of Wealth—financial, time, social, mental, and physical—and show why sometimes the decision that looks inefficient on paper may actually be the smartest for your overall wellbeing. From real-life examples like paying for time-saving conveniences or investing in health, to reflections on why pe...

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21:24

When Money Isn’t Enough: The 5 Types of Wealth You...

Ready For Retirement ·

2025/08/19

When the numbers say you can retire, but you can’t step away. Many people with the financial means to retire keep working, telling themselves one more year will make the plan even stronger. But at what cost to your time, health, and relationships? This episode explores “the good pickle,” where chasing more financial security comes at the expense of other forms of wealth like time freedom, social connection, and well-being. You will learn why money gets prioritized, how to rebalance, and...

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17:13

Here's How Early Retirement Will Impact Your Social...

Ready For Retirement ·

2025/08/12

Thinking about retiring early and worried it might hurt your Social Security benefits? Good news: it probably won’t. A common myth is that you have to work into your 60s to get the most out of Social Security. In reality, benefits are based on your 35 highest-earning years—not the age you stop working. This episode breaks down how benefits are calculated, what “bend points” are, and why even part-time income in semi-retirement can make a difference. There’s also an important distinction betwe...

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16:48

Does Your Spouse Really Know the Financial Plan? Why...

Ready For Retirement ·

2025/08/07

Money conversations fall short when only one spouse is at the table. It’s easy to treat financial planning like another household task to divide and conquer, but unlike errands, your financial plan is the blueprint for your shared future. What we’ve seen time and again is that the person sleeping next to you often holds the key to your blind spots. They know what stresses you out, what brings you joy, and what dreams you’ve stopped saying out loud. That’s why the best financial plans aren’t j...

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16:36

Can You Retire Without $1 Million? The Truth Might...

Ready For Retirement ·

2025/08/05

Forget the myth that you need a million dollars to retire. What really matters is creating sustainable cash flow—not hitting a magic number. Retirement success comes down to three things: your expenses, guaranteed income (like Social Security or pensions), and the gap your savings need to fill. For some, that gap is smaller than expected. Real examples—like a couple living comfortably on $300K in investments—show it’s possible. Small lifestyle changes, like cutting $1,000 in monthly expenses,...

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7:11

The #1 Way to Ruin Your Retirement (Most People Do This)

Ready For Retirement ·

2025/07/29

Can a children’s poem change how you think about retirement? In this episode, we unpack the hidden wisdom in Shel Silverstein’s “Smart” and how it reflects a common retirement planning mistake: trading time and well-being for wealth you may no longer need. We explore why it’s hard to step away from accumulation mode—even after reaching financial independence—and how this mindset can cost you more than it earns. The real risk isn’t running out of money. It’s not recognizing when you have enoug...

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17:07

How to Know If You’re Ready to Retire (Hint: It’s Not...

Ready For Retirement ·

2025/07/24

The hardest part of retirement isn’t always financial, it’s psychological. For many, stepping away from work isn’t a light switch, but a dimmer that adjusts over time. This episode of Root Talks unpacks what makes the retirement decision so complex, especially for high-achieving professionals whose identity is tied to their careers. Through a real-life case study, the conversation explores how severance offers can become powerful “test drives” for retirement, offering space to reimagine life ...

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11:51

This Is Why Financially Ready People Struggle to Retire

Ready For Retirement ·

2025/07/22

Even with a strong financial plan in place, many professionals find themselves hesitating at the retirement decision—stuck in the cycle of “just one more year.” The numbers say it’s possible, yet the fear of leaving behind a paycheck, a title, or a sense of purpose keeps them working long past the point of “enough.” This episode reframes retirement readiness through the lens of the five dimensions of wealth: financial, time, physical, social, and mental. Financial wealth is just one piece. Ti...

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16:25

What Should You Do With Your 401k When You Retire?

Ready For Retirement ·

2025/07/15

Your 401(k) is likely your largest retirement asset—so the decisions made about it can have a lasting impact. This episode explores the pros and cons of keeping a 401(k) versus rolling it over to an IRA. Learn when it makes sense to stay in a 401(k), especially for those retiring between ages 55 and 59½, when a special IRS rule allows penalty-free withdrawals not available in IRAs. Keeping pre-tax funds in a 401(k) may also support more efficient backdoor Roth strategies. Six key factors infl...

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20:11

DIY vs. Financial Advisor: How to Know When It’s Time...

Ready For Retirement ·

2025/07/10

If you’ve ever found yourself wondering whether you really need a financial advisor, this episode is for you. James and Ari unpack the deeper reasons people seek financial guidance—and why the decision often goes far beyond dollars and cents. Much like seeing a doctor for preventative care, working with the right advisor is about protecting your future, reducing stress, and reclaiming your most precious resource: time. From saving 20+ hours a month of DIY management to gaining peace of mind, ...

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9:37

5 Signs It’s Time to Retire - Right Now

Ready For Retirement ·

2025/07/08

At 90 years old, will you remember that final bonus or the time you didn’t spend with the people you love? This powerful question reframes how we think about retirement timing beyond the numbers. Yes, financial readiness matters. But delaying retirement for "just one more cycle" or "just one more raise" often leads to a dangerous pattern—constantly moving the goalpost while trading away your most vibrant, healthy years. In this episode, we explore the critical difference between lifespan and ...

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19:28

Watch Me Stress Test a $1 Million Retirement Plan

Ready For Retirement ·

2025/07/01

A seven-figure portfolio can feel like a green light for retirement—but the numbers don’t always tell the full story. In one case study, a couple with over $1 million saved faced a withdrawal rate close to 14% based on their desired lifestyle. That’s nearly three times higher than what’s typically considered sustainable. This story is a reminder that retirement success isn’t just about hitting a number, it’s about how your money is structured to support your life. A solid plan makes the diffe...

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336 results

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