Ready For Retirement

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, your dreams.- Advisory services are offered through Root Financial Partners, LLC, an SEC-registered investment adviser. This content is intended for informational and educational purposes only and should not be considered personalized investment, tax, or legal advice. Viewing this content does not create an advisory relationship. We do not provide tax preparation or legal services. Always consult an investment, tax or legal professional regarding your specific situation.The strategies, case studies, and examples discussed may not be suitable for everyone. They are hypothetical and for illustrative and educational purposes only. They do not reflect actual client results and are not guarantees of future performance. All investments involve risk, including the potential loss of principal.Comments reflect the views of individual users and do not necessarily represent the views of Root Financial. They are not verified, may not be accurate, and should not be considered testimonials or endorsementsParticipation in the Retirement Planning Academy or Early Retirement Academy does not create an advisory relationship with Root Financial. These programs are educational in nature and are not a substitute for personalized financial advice. Advisory services are offered only under a written agreement with Root Financial.Create Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

Explore how a couple in their 60s can retire earlier with a $4 million portfolio through clever financial planning. Discover how different income sources and sustainable withdrawal strategies keep their lifestyle intact. The discussion highlights the impact of delaying Social Security for stronger future finances. The episode dives into how adjusting travel plans can extend financial longevity. Ultimately, it reveals that crafting a fulfilling retirement is more about tailoring a lifestyle than just hitting a financial target.

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 retirement age. But here's where strategy enters: claiming at 62 permanently reduces your benefit by about 30%, while each year you delay beyond full retirement age adds a valuable 8% to your monthly check (up to age 70).The early claiming strategy at 62 offers immediate cash flow and potentially preserves your investment portfolio longer. However, it comes with serious trade-offs: permanently reduced monthly benefits, earnings limits if you're still working ($23,400 before penalties kick in), and potentially smaller survivor benefits for your spouse. This decision isn't just about you – it affects your family's financial security after you're gone.Waiting until full retirement age gives you 100% of your calculated benefit and eliminates the earnings test if you're still working. It represents a balanced approach that neither maximizes nor minimizes your benefit. Meanwhile, delaying until 70 increases your monthly check by a substantial 24% over your full retirement age benefit – creating the strongest possible income floor for life and maximum protection against longevity risk. This delay strategy also opens tax planning opportunities in your 60s, particularly for Roth conversions.The optimal claiming age depends on your unique circumstances. Consider your health outlook, marital status, other income sources, tax situation, and overall retirement income needs. Remember that this isn't simply about break-even calculations – it's about creating security and maximizing quality of life throughout your retirement journey.Ready to get clarity on your optimal Social Security strategy? Visit our website to discover how personalized retirement planning can help you make the most of your benefits and create lasting financial security for you and your loved ones. Create Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

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 workWhy financial freedom means nothing without health, time, or joyHow to avoid estate planning mistakes that burden your spouse or familyWhy intentional living matters more than chasing a numberSimple, high-impact ways to prepare for retirement nowIf you're building wealth, nearing retirement, or want to live more meaningfully today—this conversation is for youCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

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.