Ready For Retirement

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 concepts like the 0% capital gains bracket, step-up in basis, and Social Security taxation. Learn how to make tax-smart moves with your retirement income so you can keep more of what you’ve saved.Questions answered:1. How can I reduce the amount of taxes I pay in retirement?2. How are different retirement accounts—like 401(k)s, Roth IRAs, brokerage accounts, and HSAs—taxed when I withdraw money?Submit your request to join James:On the Ready For Retirement podcast: Apply HereOn a Retirement Makeover episode: Apply HereTimestamps:0:00 - Brokerage accounts4:29 - Standard 401(k)6:27 - Health savings account9:54 - HSAs after age 6511:00 - Inheritance13:01 - Inherited IRA account15:33 - Social Security17:00 - Wrap-upCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

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 value of aligning retirement with your future self’s goals and priorities, not just your current fears. Submit your request to join James:On the Ready For Retirement podcast: Apply HereOn a Retirement Makeover episode: Apply Here  Timestamps:0:00 - A comment from the Collective3:03 - A first-day-of-school analogy4:25 - What would my future self do?6:47 - Helpful feedback8:32 - Make sure you're ready financially10:20 - A life you don't retire from13:18 - The opportunity cost16:39 - More words of wisdom18:44 - Making the decision is the scary partCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

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 drive such massive decisions. He explains how context—like income sources, spending flexibility, and home equity—matters more than a static success rate. You’ll learn why 100% isn’t always ideal, and how to build a retirement plan that supports a meaningful life, not just a perfect score.Questions answered?1. Should I delay retirement if my Monte Carlo probability of success drops?2. Is a 100% probability of success the best goal for my retirement plan?Submit your request to join James:On the Ready For Retirement podcast: Apply HereOn a Retirement Makeover episode: Apply HereTimestamps:0:00 - An encounter at the gym2:37 - What is Monte Carlo analysis?4:18 - Consider severity of failure6:19 - Consider other assets, like property7:35 - Is a 100% probability score really success?10:55 - Monitor and course correct14:13 - Margin15:07 - No universal number16:13 - Assumptions about spending18:27 - Retirement spending smile20:57 - Context mattersCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

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 heavily on Social Security for retirement income?2. What are some strategies to supplement Social Security income in retirement?Submit your request to join James:On the Ready For Retirement podcast: Apply HereOn a Retirement Makeover episode: Apply HereTimestamps:0:00 - One-off expenses1:34 - Inflation & CPIW4:21 - Tax on provisional income7:33 - Peace of mind8:33 - Maximize your benefit9:22 - Supplement SS10:24 - Leverage your homeCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

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 up for clients.The takeaway? A great advisor isn’t just there for the good times—they’re prepared to guide you through the tough ones, too.Submit your request to join James:On the Ready For Retirement podcast: Apply HereOn a Retirement Makeover episode: Apply Here  Timestamps:0:00 - About Root Collective0:56 - Making a serious topic fun2:07 - A lesson from Covid5:06 - "Fun" is being prepared8:04 - Emotional downtimes require a team11:27 - On building trust13:33 - Wrap-upCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

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, and letting go of worries that no longer serve you, these insights will help you make the most of your retirement years.📌 Watch now to discover how to live with more freedom, joy, and financial confidence!Questions answered:1. How can I make the most of my retirement years financially and emotionally?2. What habits should I stop after 60 to live a healthier, happier, and more fulfilling life?Submit your request to join James:On the Ready For Retirement podcast: Apply HereOn a Retirement Makeover episode: Apply HereTimestamps:0:00 - 1 - Saving2:24 - 2 - Spending when it's not fun3:38 - 3 - Trading time for money4:52 - 4 - Putting off experiences6:27 - 5 - Neglecting your health8:15 - 6 - Caring what others think9:17 - 7 - Watching dome-and-gloom news11:16 - 8 - Neglecting your financial plan13:00 - 9 - Making decisions as if you'll live foreverCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

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!