Ready For Retirement

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 today and planning for tomorrow.This isn’t just about getting by—it’s about using what you’ve saved to live intentionally. And just as important, it’s about avoiding the regret of leaving money (and meaningful experiences) unused.If you're thinking about how to align your spending with your values in retirement, this conversation is for you.Questions we explore:How can I estimate a sustainable spending level in retirement?How do I balance enjoying life now with preserving assets for the future? Submit your request to join James:On the Ready For Retirement podcast: Apply HereOn a Retirement Makeover episode: Apply HereTimestamps:0:00 - Jeffrey and Cindy's plan3:24 - Understand cash flows5:45 - Projected portfolio withdrawals7:22 - Probability of success9:26 - Monitor your withdrawal rate11:12 - Key takeaway13:26 - Wrap-upCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

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 often brings clarity and connection: experiences, time, giving, health, and environment.Submit your request to join James:On the Ready For Retirement podcast: Apply HereOn a Retirement Makeover episode: Apply Here  Advisory services are offered through Root Financial Partners, LLC, an SEC-registered investment adviser. This content is intended for general informational purposes only and should not be construed as personalized investment, tax, or legal advice. Advisory relationships are established only through a signed agreement. Any examples discussed are hypothetical and for illustrative purposes. If client experiences are referenced, no compensation was provided and their experience may not be representative of others. Root Financial does not provide tax or legal advice. Tax planning topics are discussed in the context of comprehensive financial planning and should not be relied upon as a substitute for professional advice. All investments involve risk, including possible loss of principal. Past performance is not indicative of future results. Watching or listening to this content does not create an advisory relationship. Comments shared publicly are unsolicited and do not reflect the views or experience of all clients. They are not verified and should not be construed as testimonials or endorsements.Create Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

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 yourself right away—to create future options for tax-free income.What you'll learn:1. How an HSA can help reduce your lifetime tax burden and fit into a broader retirement strategy2. Ways to maximize the tax benefits beyond just paying current medical billsSubmit your request to join James:On the Ready For Retirement podcast: Apply HereOn a Retirement Makeover episode: Apply HereTimestamps:0:00 - How HSAs work1:12 - Eligibility and contribution limits3:19 - HSA details and nuances4:36 - Timing flexibility8:11 - Case study -- John9:31 - Leveraging tax benefits10:50 - Qualified medical expense11:51 - Use HSA to the fullest extent14:19 - HSAs in the grand scheme of thingsCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

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 harvesting. Whether you're approaching retirement or just looking to be more intentional with your investments, these tools can help you make more informed decisions.Toward the end, I also point to a related video where I explain how a separately managed account may benefit high-income investors with significant brokerage assets.Questions answered:1. When does it make sense to realize investment gains in a taxable brokerage account—and when should you hold off?2. What strategies can help reduce or eliminate the taxes owed on long-term capital gains?Submit your request to join James:On the Ready For Retirement podcast: Apply HereOn a Retirement Makeover episode: Apply HereTimestamps:0:00 - When not to sell2:40 - Understand risks on both sides5:54 - Tax strategies8:55 - Gifting stocks to charities11:14 - Gifting to family12:44 - Understanding step-up in basis14:18 - Capital losses offset capital gains15:11 - Wrap-upCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

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 explain how our “farm system” approach helps us grow top-tier advisors from the ground up. It’s not just about years of experience—it’s about shared values, rigorous training, and a culture of mentorship.If you’re considering working with Root—or just curious about what makes us different—this behind-the-scenes conversation will give you a look at how we build a team designed to support you and your goals at every step.Submit your request to join James:On the Ready For Retirement podcast: Apply HereOn a Retirement Makeover episode: Apply Here  Timestamps:0:00 - Selling product vs service2:58 - Four roles supporting clients5:36 - Project management8:16 - Root's growth plan11:00 - A farm system12:33 - Requirements to be a Root advisor15:09 - Freedom within guardrails19:03 - Why this matters21:31 - Wrap-upCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

Curious if $2 million is enough to retire at 60? Discover a simple 3-step process to calculate your actual retirement needs. Learn how to accurately estimate retirement expenses beyond your current salary, and factor in potential income sources like Social Security. Delve into crucial factors such as uneven income, taxes, and the impact of losing a spouse on your financial plan. This insightful discussion offers practical tools to ensure you approach retirement with confidence.

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!