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Ready For Retirement

James Conole, CFP®

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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 spe ...
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Your REAL personal finance questions answered by CERTIFIED FINANCIAL PLANNER™ professionals, Scott Frank and Nick Covyeau. With all of the misinformation and jargon in the financial industry, it's no wonder most people are confused about how to best manage their money. Scott and Nick are here to give clear answers to the important questions they hear most often. If you're ready to use your finances to create a more secure financial future, this show is for you.
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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 ma…
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When market volatility strikes, emotions often run high. Clients nearing retirement may feel especially vulnerable, and traditional conversations around long-term investing can sometimes miss the mark. In this episode, James Conole, CFP®, shares a powerful framework for navigating emotional client conversations during turbulent markets. Drawing ins…
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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, contribu…
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Is market volatility really all about tariffs? In the wake of the unexpectedly aggressive “Liberation Day,” headlines would have you believe so. But the bigger culprit isn’t trade policy—it’s uncertainty. While U.S. markets have taken a noticeable hit, international developed markets are down only about 1.3% as of this recording. So what’s really g…
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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 th…
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What actually goes into creating a world-class client experience at Root? We're walking through the structure behind Root's advisory team—and how we ensure every client gets consistent, thoughtful guidance no matter who they’re working with. We break down the different advisor roles, from Client Service Associate to Senior Financial Advisor, and ex…
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Struggling to get meaningful work done despite your technical expertise and people skills? You're not alone. Every financial advisor knows the frustration of ending a busy day feeling like nothing important was accomplished. The culprit? It's not your ability – it's how you're managing your time and attention in a world designed to fragment both. I…
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Wondering if you can retire at 60 with $2 million? In this episode, I walk you through a simple, 3-step process to figure out exactly how much you need in your portfolio to retire comfortably—and confidently. Whether you've already run the numbers or you're just starting to think about retirement, this is a great way to gut-check your plan. We'll t…
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Balancing today’s lifestyle with tomorrow’s goals isn’t easy, but it’s doable. In this episode, we answer a listener's question about 401(k) contribution limits and employer matching, which opens up a broader conversation about financial flexibility and smart savings strategies. We break down 2025 contribution limits, including catch-up provisions …
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Want to pay less in taxes during retirement? You actually have more control over your tax rate than you might think. James breaks down how different investment accounts—like brokerage accounts, 401(k)s, Roth IRAs, HSAs, and inherited accounts—are taxed and how smart withdrawal strategies can help you minimize taxes over time. He also explains key c…
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Many professionals find that retiring isn’t just about having enough money—it’s about feeling ready to leave behind the structure, identity, and comfort of a career. In this Root Financial podcast episode, James and Ari explore the emotional hurdles of retiring from a high-paying, high-stress job, even when financially prepared. They highlight the …
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We explore how advisors can effectively present portfolio performance to clients, especially during periods when their investments underperform relative to major market indices like the S&P 500. Through practical examples and a structured approach, we demonstrate how to transform potentially difficult conversations into relationship-strengthening o…
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Many retirees focus on achieving a high Monte Carlo “probability of success” in retirement—but is chasing a 99% success rate always the best move? In this episode, James highlights a real-life story of a man forced to delay retirement after a divorce dropped his probability of success from 99% to 70%. James explores why this single number shouldn't…
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Major financial transitions don't have to be binary choices – testing your assumptions before making big moves can prevent costly mistakes and regrets. In this episode, Nick and Scott talk about test-driving potential life transitions to help guide your decisions. • Looking at buying a home? Try setting aside the difference between rent and project…
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Relying too much on Social Security? You’re not alone—over 40% of retirees count on it for at least half their income. But that safety net has some major gaps. In this video, I break down four key reasons why Social Security isn’t enough—and what you can do to secure a more stable retirement. Questions answered: 1. Why is it a mistake to rely too h…
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How do you keep things fun when markets—or life—get tough? We're breaking down why “fun” isn’t just about ping pong tables and perks—it’s about being prepared, building trust, and maintaining strong relationships before challenges arise. James shares a personal story from the early Covid days, highlighting how mindset and self-care helped him show …
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A simple question from my dad years ago completely transformed my approach to financial advising: "What is your role as an advisor to your clients?" After several incorrect guesses, his answer stunned me with its clarity and wisdom - "Your role is to help organize your clients' thinking." This perspective shifted everything. While many of us excel …
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What separates truly exceptional financial advisors from the merely adequate ones? It's not credentials, years of experience, or even what firm they've worked for – it's something more fundamental. In this foundational episode of the Root Ready podcast, we define the six core standards that constitute excellence in financial advising. Drawing from …
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What does it truly mean to be an exceptional financial advisor in today's world? The answer goes far beyond technical designations or sales ability. The Root Ready podcast tackles a critical gap in advisor development. While the industry often laments talent shortages, the real issue lies in how we're preparing advisors to excel. James Conole, foun…
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If you're over 60, it's time to stop certain habits that may be holding you back from fully enjoying your retirement. In this video, I’ll share key lessons learned from working with retirees, including how small shifts can lead to a more meaningful and financially secure future. From when to stop saving, how to spend wisely, prioritizing health, an…
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In the face of the uncertainty of life, it’s difficult knowing that many things are out of your control. Focusing on your financial well-being can often feel daunting, especially with the unpredictability of markets. In this episode, we discuss aspects of your financial journey that you can control, like… - The importance of having a structured fin…
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Roth IRAs are a great way to build tax-free retirement income—but the withdrawal rules can be tricky. In this video, I’ll break down the five-year rules, how contributions, conversions, and growth are treated, and smart strategies to avoid unnecessary taxes. Understanding these rules can help you make the most of your Roth IRA and keep more of your…
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Root Collective member Gary asks how to fund a $40K home remodel before retiring—should he use a taxable brokerage account, tax-deferred 401(k), Roth IRA, or cash? Ari and I break down how to handle big one-off expenses into a three-part framework: Portfolio Sustainability – Can your investments handle both recurring and one-time expenses? Investme…
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Are You Spending Your Money on What Truly Matters? A few weeks ago, I challenged you to do the most important thing you can with your money this year—not Roth conversions, not optimizing Social Security, but something far more impactful: aligning your spending with what truly brings you joy. I asked you to write down one thing you've always wanted …
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This week, we welcome new co-host Nick Covyeau, a Certified Financial Planner and owner of Swell Financial Partners, to discuss safe retirement spending strategies. We talk about the different approaches to withdrawal rates and the factors that can impact these decisions including retirement timing, portfolio balance, navigating market changes and …
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One of the biggest ironies in retirement is that the people who save and invest the most often struggle the most with actually spending their money in retirement. In this video, I’ll walk you through a simple framework to make spending easier—without guilt or second-guessing. I’ll share a compelling client story, a personal experience, and actionab…
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You’ve worked hard, built wealth, and reached financial security… so why is it still so hard to spend? In this episode, we dive into the unexpected challenge of shifting from a saver’s mindset to actually enjoying your money. From a millionaire couple hesitating over a $5 bag of M&Ms to a husband upset about a bottle of Fiji water—this is more comm…
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Retirement isn’t just about the numbers—it’s about time, health, and the life you want to live. Too many people delay retirement, chasing "one more bonus" or "one more year" without considering the bigger picture. In this video, we’ll walk through five key questions that can help you decide. If you answered yes to any of these, retirement might be …
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The S&P 500 was up 25% in 2024, so is that all you need for a strong financial future? Not so fast. Putting all your money in one place—even a good one—is risky. Smart investors look beyond the U.S. to global markets, small-value stocks, and international giants like Toyota and Taiwan Semiconductor. More variety = less risk. Join us to see just how…
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In this episode, we're talking about the importance of a strategic withdrawal plan in retirement to keep taxes in check and set you up for long-term financial stability. Ari and I break down why a simple 50/50 split between traditional and Roth accounts isn't enough—you need to plan based on your tax situation and future needs. Using a listener's e…
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James challenges the idea that financial security comes from always having more—more savings, more income, more investments. Studies show that no matter how much people have, they often feel like they need twice as much to feel secure. That mindset can make fulfillment feel just out of reach. Instead, James asks: What’s one thing you could do or bu…
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Vanguard’s Advisor Alpha study shows that working with an advisor can boost net returns by around 3% annually through smart investing, tax planning, and behavioral coaching. But the real value? It’s not just about numbers. Ari and James break down how advisors help clients stay level-headed, avoid costly mistakes, and feel more confident about thei…
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For nearly 50 years after Social Security's inception in 1935, benefits were not subject to federal income taxes. That changed in 1983 when Congress introduced taxation on benefits for higher-income retirees, using a "provisional income" threshold of $25,000 for individuals and $32,000 for couples. However, these thresholds were never adjusted for …
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If you’re tired of checking on your portfolio every day, we’ve got good news! In this episode, we go back to Investing 101 to look at the basic principles of a healthy outlook on the markets. Join us for this quick overview of how to avoid the traps that others fall into and keep your financial plan on target! Ready to learn more? Scott Frank on Li…
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Join the new Root Collective HERE! Retirement isn’t just about having enough money—it’s about making the most of it. That’s why we’re launching a new retirement community designed to go beyond financial planning. Sure, we’ll cover investing, tax strategies, and estate planning, but we’re also creating a space to talk about the things that make reti…
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To maximize your Social Security benefits in retirement, it’s essential to understand five key limits and thresholds: ✅ Earnings Limit: If you start Social Security before full retirement age, benefits may be reduced if your wages exceed the annual or monthly earnings limit. Only income earned after starting benefits counts. ✅ Social Security Wage …
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Root Financial is redefining what it means to serve clients by putting team culture front and center. In this episode, James and Ari dive into the firm’s bold move to hire a Head of Culture—an uncommon role in financial advising—dedicated to supporting the growth and well-being of their advisors. Why? Because when advisors thrive, clients get the p…
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The Social Security Fairness Act, signed into law on January 5 by former President Joe Biden, repeals the Windfall Elimination Provision (WEP) and Government Pension Offset (GPO), which previously reduced Social Security benefits for individuals with non-covered pensions, such as teachers, firefighters, and postal workers. This change significantly…
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The new year is a great time to do an annual review. In this episode, we look at five things to look at regarding your investments to help you make the most of your money. Join us as we look at some of the simplest ways you can help keep your financial plan on track! Ready to learn more? Scott Frank on LinkedIn Stone Steps Financial Meg Bartelt on …
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In this behind-the-scenes episode, James and Ari explore what sets Root apart in the financial advising industry. Moving beyond traditional roles like stock pickers and planners, they emphasize Root’s mission as “protectors” of clients’ most cherished goals, helping them achieve a life of purpose and fulfillment. They discuss how Root’s culture pri…
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Direct indexing, an advanced investment strategy, allows investors to own individual stocks within an index instead of a mutual fund or ETF, offering greater control and flexibility. This approach is particularly valuable for tax-loss harvesting, where selling underperforming stocks and reinvesting can offset gains and reduce taxes without losing m…
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James and Ari provide a behind-the-scenes look at Root Financial, shifting from typical financial strategies to how their team operates. They discuss Root’s intentional approach to maintaining consistency in financial advising through rigorous hiring practices and its structured training program, "Root University." James emphasizes the importance o…
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Many individuals are hesitant to retire, even when financially prepared, due to uncertainty and a lack of clear planning. This episode provides a practical guide to making retirement a reality, focusing on three key steps: Assess Your Current Financial Health Envision Your Ideal Retirement Connect Financial Readiness to Goals By addressing these st…
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New year, new you, new episode! Failed New Year’s resolutions are so cliche. How can you achieve lasting results, whether you’re trying to get healthy, save more money, or something else? Tune in to hear how you can set yourself up for success – as well as our favorite financial habits for the new year! Ready to learn more? Scott Frank on LinkedIn …
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In this episode of Root Talks, James and Ari dive into the reality that retirement planning can be tricky, with the fear of running out of money and the regret of underspending often at odds. The key is finding balance—spending wisely while enjoying life. Tools like projections, guardrails, and trade-off scenarios help bring clarity. The “rule of 7…
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LJ and Kelly share their inspiring journey of embracing a retirement lifestyle before fully retiring. Motivated by Kelly’s experiences as a physical therapist, witnessing many patients unable to enjoy retirement due to health issues, the couple prioritized travel and adventure. In 2021, they embarked on a year-long U.S. road trip, staying in Airbnb…
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James and Ari discuss diversification and the nuances of managing investments. A client plans to split his funds across multiple institutions, like Schwab and Vanguard, believing it will improve diversification, but true diversification isn’t about holding accounts at different places but ensuring varied asset allocation. Using examples, James and …
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Retirement is an exciting milestone, but it often comes with common fears. With proper planning, these concerns can be addressed to ensure a fulfilling and secure new chapter. Here are five major retirement fears and strategies to overcome them: Fear of Outliving Savings Optimize your Social Security strategy (e.g., delay benefits for higher payout…
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What does your most fulfilled life look like? If you’re not sure, then this episode is for you. Join us as we discuss three questions to help you uncover what is most important to you! Resources mentioned in this episode: Goals for Life Worksheet Kinder’s 3 Questions Ready to learn more? Scott Frank on LinkedIn Stone Steps Financial Meg Bartelt on …
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Many middle-aged adults nearing retirement face anxiety over uncontrollable factors like Social Security cuts, lower investment returns, and increasing tax rates. Ari and James discuss how fear of these uncertainties can cause “analysis paralysis,” leading some to delay retirement unnecessarily. Instead of fixating on what cannot be controlled—like…
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