Ready For Retirement

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 money tax-free. Let’s dive in!Questions answered?1. When can you withdraw money from a Roth IRA without paying taxes or penalties?2. How do the two different five-year rules for Roth IRAs affect withdrawals?Questions answered?1. When can you withdraw money from a Roth IRA without paying taxes or penalties?2. How do the two different five-year rules for Roth IRAs affect withdrawals?Submit your request to join James:On the Ready For Retirement podcast: Apply HereOn a Retirement Makeover episode: Apply HereTimestamps:0:00 - The 5-year rule1:09 - Contributions3:39 - Conversions5:36 - Growth6:51 - An example8:55 - Conversions before 59.5 years10:23 - SummaryCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

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?Investment Allocation – Ensure your assets are positioned to avoid selling at a loss.Tax Optimization – Withdraw strategically to minimize lifetime taxes.The key? Plan ahead, align financial decisions with long-term goals, and make the most of your retirement funds.Submit your request to join James:On the Ready For Retirement podcast: Apply HereOn a Retirement Makeover episode: Apply Here  Timestamps:0:00 - Gary R's question2:52 - Can your retirement support it?4:43 - How should investments be allocated?6:28 - Have a tax strategy8:54 - A caution; a reminder about sleep12:03 - Intentionally set aside14:23 - Mental hang-ups and biases16:37 - The Collective CommunityCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

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 to do or buy but haven't, set a date to make it happen, and identify where the funds would come from.In today’s episode, I’m sharing some of the incredible responses I received—stories of travel, family experiences, and meaningful purchases that turned dreams into reality. These stories serve as a reminder: financial planning isn’t just about growing wealth; it’s about using it to create a life you love.If you haven’t already, take that step. Don’t wait for "someday." Let’s make sure we’re spending in a way that truly reflects what we value most.Questions answered:1. Why is it important to align your spending with what you truly value?2. How can you take action to ensure your money is being spent in a way that brings you joy?Submit your request to join James:On the Ready For Retirement podcast: Apply HereOn a Retirement Makeover episode: Apply HereTimestamps:0:00 - Reviewing the challenge1:42 - Ice fishing and family trips2:46 - Urgency4:19 - Diving the Red Sea, family cruise5:35 - Pets and optimizing travel plans7:28 - Uncertainty and urgency8:53 - Values, purpose, and happinessCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

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 actionable steps you can take to shift your mindset and enjoy the retirement you’ve worked so hard for. If you’ve ever hesitated to spend on things you value, even when you can afford to, this is for you.We’ll cover:Why our money habits from the past shape how we spend (or don’t spend) todayA five-step process to help you feel comfortable spending in retirementA practical tip that makes it easier to say “yes” to the things that truly matter🎯 Don't let a scarcity mindset hold you back—start living your best retirement!Questions answered:1. Why do some retirees struggle to spend money, even when they have more than enough saved?2. How can retirees overcome a lifetime of saving habits and confidently spend on things they truly value?Submit your request to join James:On the Ready For Retirement podcast: Apply HereOn a Retirement Makeover episode: Apply HereTimestamps:0:00 - A pertinent story3:24 - A personal story5:10 - Steps 1& 2—acknowledge and evaluate7:05 - Steps 4 & 5—Identify values and make it easy9:44 - Healthy tension12:30 - Step 5—Withdrawal and set aside14:49 - Wrap-upCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

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 common than you think! Behavioral finance reveals why past money habits stick with us, even when we don’t need them anymore.We’ll break down how to retrain your mindset, align spending with what truly matters, and ensure your wealth enhances your life instead of holding you back. Plus, a practical strategy to help you finally enjoy your money guilt-free!Submit your request to join James:On the Ready For Retirement podcast: Apply HereOn a Retirement Makeover episode: Apply Here  Timestamps:0:00 - A scarcity mindset story2:36 - Comment that sparked conversation4:12 - Identifying the problem7:00 - A personal story from James10:00 - Practical takeaways12:18 - Make small, aligned shifts16:14 - An example from Ben18:04 - Death is coming19:55 - The wrap-upCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

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 closer than you think! Watch now to gain clarity on your next steps.Questions answered?1. How do you know if it's the right time to retire?2. What are the risks of delaying retirement for financial reasons?Submit your request to join James:On the Ready For Retirement podcast: Apply HereOn a Retirement Makeover episode: Apply HereTimestamps:0:00 - Is time passing you by?2:30 - Is your health suffering?3:40 - Want more time for relationships?4:50 - What is your life and health span6:25 - Are you financially ready?7:59 - Wrap-upCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

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 example, we walk you through how to think about tax brackets, required minimum distributions (RMDs), and when it might make sense to convert funds to a Roth IRA.We also discuss the role of asset location—putting riskier investments in Roth accounts for tax-free growth and stable investments in traditional IRAs for withdrawals. It’s all about balancing tax strategies with your lifestyle goals. At Root, we prioritize your purpose first, and we encourage you to explore our resources, like our podcasts, YouTube channel, and community, to learn more about smart retirement planning.Submit your request to join James:On the Ready For Retirement podcast: Apply HereOn a Retirement Makeover episode: Apply Here  Timestamps:0:00 - The comment that prompted this chat2:39 - Run some projections5:14 - The benefit of Roth7:31 - Asset location and allocation10:07 - Root reserves13:50 - More often than not15:22 - Tax insurance17:17 - Cart before the horse?19:30 - It starts with purpose21:33 - Where to find James and AriCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

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 buy to make this year special? He shares stories like a couple who used an unexpected windfall to buy a boat—not as an investment, but to create years of unforgettable memories.The takeaway? Money isn’t the goal—it’s the tool that helps you build a life that feels rich in the ways that matter most.Questions answered:1. Why do people always feel like they need more money to feel wealthy?2. How can I use my money to create a more meaningful life?Submit your request to join James:On the Ready For Retirement podcast: Apply HereOn a Retirement Makeover episode: Apply HereTimestamps:0:00 - A question and some statistics3:07 - Steph's answer6:00 - Other answers8:01 - An exerciseCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

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 their future. Research even shows investors with $1.2M+ report greater financial happiness with an advisor by their side.Not everyone needs one, but knowing when professional support can make a real difference? That’s the key.Submit your request to join James:On the Ready For Retirement podcast: Apply HereOn a Retirement Makeover episode: Apply Here  Timestamps:0:00 - Vanguard Advisor Alpha study1:50 - The claim and a story3:56 - Asset allocation7:40 - Cost-effective implementation9:10 - Rebalancing13:38 - Behavioral coaching18:35 - Asset location21:49 - Spending strategy/withdrawal order26:17 - Total return vs income investing27:48 - An advisor can increase your happinessCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

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 inflation, leading to a significant increase in the number of retirees paying taxes on their benefits—now nearly 50%. President Trump has proposed eliminating federal taxation on Social Security, a move that could benefit retirees financially but would accelerate the depletion of the Social Security Trust Fund, currently projected to run out by 2034. Removing taxes could shift the depletion timeline up by about a year, raising questions about alternative funding solutions. Potential fixes include raising payroll taxes, increasing the wage base, or pushing back the full retirement age. While tax relief sounds appealing, long-term sustainability remains uncertain.Questions answered:1. Why are Social Security benefits taxed, and how did this change over time?2. What would happen if Social Security taxes were eliminated, and how could it impact the program’s future?Submit your request to join James:On the Ready For Retirement podcast: Apply HereOn a Retirement Makeover episode: Apply HereTimestamps:0:00 - SS payments are taxed?1:25 - Provisional income3:18 - Trump's plans for SS6:17 - The downsides8:06 - The SS Trust Fund9:19 - The challenge11:21 - In the meantimeCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!