Ready For Retirement

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Ready For Retirement

James Conole, CFP®

308 episodes

1 day ago

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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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...

Show more...

Episodes (20/308)

Ready For Retirement

How to Know If You’re Ready to Retire (Hint: It’s Not Just About Money)

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 ...

4 days ago

17 minutes

Ready For Retirement

This Is Why Financially Ready People Struggle to Retire

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...

6 days ago

11 minutes

Ready For Retirement

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

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...

1 week ago

16 minutes

Ready For Retirement

DIY vs. Financial Advisor: How to Know When It’s Time to Get Help │ Root Talks

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, ...

2 weeks ago

20 minutes

Ready For Retirement

5 Signs It’s Time to Retire - Right Now

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 ...

2 weeks ago

9 minutes

Ready For Retirement

Watch Me Stress Test a $1 Million Retirement Plan

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...

3 weeks ago

19 minutes

Ready For Retirement

Why Brokerage Accounts Might Be the Most Underrated Tool in Your Financial Plan

Retirement accounts like 401(k)s and IRAs often get all the attention, but there’s another tool that can play a powerful role in your long-term strategy: the humble brokerage account. Unlike retirement accounts with age restrictions and penalties, brokerage accounts offer flexibility. You can access funds at any time, for any purpose without early withdrawal penalties. That kind of control can be incredibly valuable, especially if your goals include retiring early, helping family, or funding ...

1 month ago

18 minutes

Ready For Retirement

5 Things Retirees Regret - And What You Still Have Time to Get Right

After working with hundreds of people navigating retirement, we’ve seen a clear pattern: the biggest regrets aren’t about money. They’re about meaning. Too often, people retire from something—but never toward something. They solve the financial side without planning for the life side. And that leads to some common regrets: No clear purpose after work: Retirement without direction quickly turns from freedom to restlessness.Neglecting health too long: Wellness is what fuels the retirement you’v...

1 month ago

13 minutes

Ready For Retirement

Stop Worrying About Running Out of Money: Here's What You Need to Do

The biggest question I hear from people planning for retirement is this: Am I going to run out of money before I run out of life? But here’s the thing, no matter how much you’ve saved, that fear doesn’t automatically go away. In this video, I walk through what the data actually says about your chances of running out of money, where the 4% rule comes from, and why many people end up being far too conservative with their spending. I’ll also share a more flexible way to approach withdrawals so ...

1 month ago

14 minutes

Ready For Retirement

This Is What Financial Planning Really Changes

What does it really mean to change someone’s life through financial advice? While we’re not saving lives like doctors, the impact we have on our clients’ futures can be just as meaningful. Often, it’s not about the numbers—it’s about helping someone move forward when fear is holding them back. We’ve seen it firsthand. Like the dentist who had every detail in place to open her own practice but couldn’t take the final step. What helped wasn’t another spreadsheet—it was a mindset shift. Or the c...

1 month ago

18 minutes

Ready For Retirement

How Much Do You Need to Retire on $10K a Month?

If your goal is to spend $10,000 a month in retirement, how much do you really need saved? The answer isn’t as simple—or as overwhelming—as it might seem. In this episode, I break down the key factors that influence your retirement number beyond the common 4% rule. We’ll explore how Social Security can significantly reduce what you need to save, why account types like Roth vs. traditional IRAs make a major difference, and how your withdrawal strategy and retirement age can shift the numbers ...

1 month ago

13 minutes

Ready For Retirement

I've Helped Hundreds of People Retire Comfortably. Here's the Exact 7-Step Framework I Used.

Retirement planning isn’t about chasing numbers, it’s about building a life with intention. The Sequoia System helps you get clear on what matters most, organize your finances around that vision, and create a plan that supports the freedom, peace of mind, and purpose you’re truly after. We start with your life vision, translate that into a monthly income goal, and map out your cash flow using a mix of reliable income sources and portfolio withdrawals. Then we align your investments with thos...

1 month ago

21 minutes

Ready For Retirement

Ready to Retire? Here's How to Tell Your Company │ Root Talks

In this episode, Ari and James explore the emotional and practical sides of retiring—specifically, how to have the conversation that officially ends your career. Whether you're months away or years out, this discussion tackles the fear, hesitation, and freedom that come with telling your boss you're done. You'll hear real stories from Root Collective members who’ve taken the leap, insights on counteroffers, and a powerful reframe: every “yes” to more work is a “no” to your time, your family,...

2 months ago

24 minutes

Ready For Retirement

How Much Can We Expect to Spend in Retirement with a $4M Portfolio?

In this episode, we walk through a retirement planning scenario involving a couple in their early 60s with a $4 million investment portfolio. Their financial plan reveals something surprising: they may not need to wait until 65 to retire. Instead, thoughtful planning opens the door to retiring earlier—without compromising the lifestyle they value. What we cover: • A breakdown of how a $4 million portfolio can support early retirement • Income sources, spending needs, and sustainable withdrawa...

2 months ago

18 minutes

Ready For Retirement

Social Security at 62 vs 67 vs 70: When should you start claiming your benefits?

Deciding when to start your Social Security benefits might be the single most consequential financial decision of your retirement journey. Should you claim early at 62, wait until full retirement age at 67, or delay until 70 to maximize your monthly check? The answer isn't as straightforward as many think. Your Social Security benefit is calculated using your 35 highest-earning years, adjusted for inflation. This forms your Primary Insurance Amount (PIA) – what you're entitled to at full ret...

2 months ago

19 minutes

Ready For Retirement

The Surprising Regrets of Wealthy Retirees | Root Talks

Retired with millions—but full of regret? In this episode of Root Talks, James and Ari share the real stories no one talks about: wealthy retirees who did everything “right” financially but still feel like they missed out. From sacrificing health and relationships for more savings, to realizing too late that they were planning for someone else’s version of success, these lessons are emotional, practical, and essential. What you’ll learn: Common regrets wealthy retirees confess after leaving...

2 months ago

16 minutes

Ready For Retirement

We have a $3M Retirement Portfolio. How Much Can We Spend Without Running Out of Money?

Jeffrey and Cindy came to me with $3 million saved and one big question: How much can we actually spend in retirement? In this video, we walk through a retirement planning scenario—looking at spending goals, taxes, travel, healthcare, and how Social Security might factor in. While the numbers vary, the framework we use applies whether you're working with $300,000 or $30 million. We explore how to think about sustainable withdrawal rates, portfolio flexibility, and trade-offs between spending ...

2 months ago

15 minutes

Ready For Retirement

Root Talks: Spend Your Way to a Happier Retirement: 5 Pillars of Better Spending

Many great savers hesitate to spend once they retire—unsure how to shift gears after years of discipline. In this episode, we talk through what it looks like to use money with intention, not just someday, but now. Prompted by a thoughtful note from a Root Collective member, we share stories—personal and client-based—about the small upgrades that matter: better experiences, more time, stronger health, and generosity that deepens relationships. We also walk through five areas where spending o...

2 months ago

19 minutes

Ready For Retirement

The Most Powerful Tax-Free Retirement Tool: Start Leveraging Your HSA Now

Health Savings Accounts (HSAs) don’t get much attention—but they should. With triple tax advantages (tax-free contributions, growth, and qualified withdrawals), HSAs offer a level of flexibility that’s hard to beat. I break down how to use an HSA not just for healthcare today, but as a long-term planning tool. That includes how to qualify, contribute, invest the funds, and take strategic withdrawals. I also explain why it’s worth tracking medical expenses—even if you don’t reimburse yoursel...

3 months ago

16 minutes

Ready For Retirement

When is the Best Time to Realize Gains in my Investment Account?

If you’re sitting on large investment gains in a brokerage account and wondering whether it’s worth taking the tax hit, this episode is for you. I walk through a clear framework I use with clients to help them decide when—and if—it makes sense to realize those gains. I also explain several strategies that can potentially reduce or even eliminate the taxes you might owe, including how to take advantage of the 0% long-term capital gains tax bracket, gifting appreciated assets, and tax-loss har...

3 months ago

17 minutes