Ready For Retirement

Here’s the thing: retirement isn’t just about hitting a magic number—it’s about understanding what you actually want out of your life once work is no longer in the picture. In their chat, Ari and James dive deep into this question, starting with a listener’s email: “I’ve got $7.8 million, no debt, and I’m 57—can I retire?” Sounds simple, right? Not quite. The duo walks through their Sequoia system, a framework designed to help people figure out whether they’re ready to retire and, more importantly, how to do it right. It starts with defining your purpose. Are you clear on how you’ll spend your time? Then it’s about crunching the numbers—your cash flow, investment strategy, and how your spending might change over time. They stress the importance of avoiding extremes. Sure, you want to make your money last, but don’t be so cautious that you miss out on enjoying life. Taxes, estate planning, and protecting your assets round out the process. It’s not just about financial security; it’s about confidence and living with purpose. As Ari puts it: “If you’re still worried, you’re not wealthy.” Retirement should be freeing, not nerve-wracking. Submit your request to join James: On the Ready For Retirement podcast: Apply Here On a Retirement Makeover episode: Apply Here Timestamps: 0:00 - The "simple" question 3:08 - Purpose 5:50 - Projecting cashflow 9:43 - Investments/creating income 13:50 - Taxes 18:50 - Strategies for reducing tax bills 20:37 - Insurance and estate planning 24:23 - The Sequoia System Create Your Custom Strategy ⬇️ Get Started Here.

James breaks down five common retirement mistakes and how to avoid them for a secure and fulfilling future: Plan wisely to balance financial security with an enjoyable, purposeful retirement. Questions answered: 1. How can retirees avoid common financial pitfalls to ensure a secure and enjoyable retirement? 2. What steps can retirees take to balance responsible spending with meaningful life experiences? Submit your request to join James: On the Ready For Retirement podcast: Apply Here On a Retirement Makeover episode: Apply Here Timestamps: 0:00 - Spending the wrong amount 4:13 - Retiring at the wrong time 7:08 - Focusing on only one risk 9:58 - Too much support for adult kids 12:43 - Not having a strategy Create Your Custom Strategy ⬇️ Get Started Here.

In their new podcast, Root Talks, James and Ari open up about the story behind Root—their financial advisory firm—and how it grew from humble beginnings into a nationwide company with hundreds of clients, a 30-member team, and nearly $1 billion in managed assets. James shares how the unexpected twist of being forced out of a stable financial advisor role led him to reevaluate everything. That introspection sparked the vision for Root, a firm built around purpose-driven financial planning. For him, it’s always been about using money as a tool to create meaningful lives—not just about building wealth for wealth’s sake. Ari talks about his journey to joining Root, which started with his persistence in convincing James to bring him on board. What drew him in? The firm’s deep integrity and mission. He reflects on how his own experiences with financial stress and lack of literacy growing up inspired him to make a difference in people’s lives. Together, they dive into what makes Root’s approach unique: blending financial management with holistic life planning. It’s all about helping clients align their money with their values and purpose. To cap it off, they share some exciting news: Root is expanding its reach with a new YouTube channel, more social media content, and increased team engagement. It’s all part of their commitment to growth, innovation, and leaving a lasting impact on their clients and the industry as a whole. Submit your request to join James: On the Ready For Retirement podcast: Apply Here On a Retirement Makeover episode: Apply Here Timestamps: 0:00 - Root Talks 2:09 - The roots of Root 5:38 - James and Ari meet 7:22 - The vision 11:08 - Focusing on integrity, not sales 13:46 - Business challenges 17:43 - More than financial planning 23:06 - Self-starters and systems 25:59 - Final thoughts from James 27:37 - Get connected Create Your Custom Strategy ⬇️ Get Started Here.

Chris was burned out. Despite enjoying aspects of his work, the relentless grind of long hours and aggressive saving left him exhausted and longing for retirement. His goal was to save as much as possible, retire in a few years, and finally spend time with his wife, travel, and enjoy life. However, James, founder of Root Financial, offered surprising advice: stop saving for retirement. After analyzing Chris’s portfolio, James discovered that the growth of Chris’s investments was outpacing his new contributions. Continuing to save aggressively was unnecessary and came at the cost of his health, relationships, and overall happiness. By redirecting funds toward enjoying life—such as taking trips, playing golf, and reducing work stress—Chris could create a more fulfilling life today without jeopardizing his financial future. James explains that compound growth allows established portfolios to do the heavy lifting, especially later in life. He outlines five scenarios where pausing retirement savings might make sense: when you already have enough, are on track to meet goals, feel sacrifices today are too great, lack legacy goals, or don’t need tax benefits. Questions answered: 1. When might it make sense to stop saving for retirement? 2. How can you balance enjoying life now while preparing for retirement? Submit your request to join James: On the Ready For Retirement podcast: Apply Here On a Retirement Makeover episode: Apply Here Timestamps: 0:00 - Chris's dilemma and James's advice 2:45 - An example of compound growth 4:46 - Unbalanced living 7:12 - Having enough and being on track 8:53 - Sacrificing important things today 10:25 - Legacy goals and tax benefits 12:25 - Summary Create Your Custom Strategy ⬇️ Get Started Here.

Roth conversions are almost a buzzword today, with many people jumping into them like they’re a guaranteed fix for tax worries—much like rushing into surgery hoping it will solve all your problems. But just like surgery, Roth conversions require careful consideration, and they’re not always the right solution. Before deciding to convert, it’s essential to understand why not to do it. Here are some key reasons to skip—or at least pause—on Roth conversions: - Lower Future Tax Bracket: If you anticipate being in a lower tax bracket during retirement, it might not make sense to pay taxes upfront. For example, retiring and moving to a no-income-tax state like Texas can naturally reduce your tax obligations. - No Significant RMD Issue: If your required minimum distributions (RMDs) won’t be large enough to push you into a higher tax bracket, the urgency to convert may not exist. - Charitable Giving Plans: Those planning to donate through qualified charitable distributions (QCDs) after 70½ can leave funds in tax-deferred accounts, making those donations tax-free without needing to convert. - Social Security Tax Torpedo: Conversions can increase your provisional income, causing more of your Social Security benefits to be taxed, effectively raising your tax rate. - Medicare Premium Surcharges (IRMAA): Conversions can push your income above IRMAA thresholds, leading to higher Medicare premiums. - Spending More or Retiring Earlier: Sometimes, simply increasing your spending or retiring sooner can reduce the need for conversions by naturally lowering tax-deferred account balances. While Roth conversions can be a valuable tool, they’re not a one-size-fits-all solution. Thoughtful planning and understanding your unique financial situation are key to making the right choice. Submit your request to join James: On the Ready For Retirement podcast: Apply Here On a Retirement Makeover episode: Apply Here Timestamps: 0:00 - Roth conversions are like surgery 3:07 - Questions that prompted this episode 5:28 - Why not to do a Roth conversion 8:38 - RMDs prompt Roth conversions 10:50 - Spend more money, and retire earlier 13:27 - Rethinking what Roth conversions mean 15:12 - A financial example 18:06 - IRMA considerations 22:31 - Knowing enough to be dangerous 24:04 - More reasons to be cautious Create Your Custom Strategy ⬇️ Get Started Here.

Meet Sarah—a retiree with a multi-million-dollar portfolio, no mortgage, and all her income needs covered by Social Security. Yet, she hesitates to furnish her newly expanded home, fearing it would “waste” money. In this episode, James unpacks Sarah’s story to explore why so many of us struggle to spend, even when we're financially secure. James explores concepts like: - The Purpose of Money: Money is a tool, not an end goal—it’s meant to be exchanged for experiences and joy. - Diminishing Marginal Utility of Wealth: More money doesn’t always bring more happiness, especially as wealth grows. - Time vs. Money: Time becomes more valuable as we age, making it critical to use wealth meaningfully. - Mindset Shifts: Frugality that builds wealth can hold you back from spending in alignment with your values. - Future Self Perspective: Align today’s decisions with the life you want in retirement to avoid future regrets. This episode challenges traditional views on retirement spending, encouraging listeners to shift their mindset, embrace their financial freedom, and focus on living a fulfilling life. Questions answered: Why do we sometimes struggle to spend our money, even when we have more than enough to meet our needs? How can you reframe your mindset to align your spending with the life you truly want to live? Submit your request to join James: On the Ready For Retirement podcast: Apply Here On a Retirement Makeover episode: Apply Here Timestamps: 0:00 - Wasting $ on furniture? 1:59 - What money is 3:26 - A different view of "waste" 5:30 - Diminishing marginal utility 8:49 - Consider what serves you 11:45 - An example from Charlie Munger 14:58 - Audit your decisions 17:04 - Consider your future self 18:55 - Conclusion Create Your Custom Strategy ⬇️ Get Started Here.

Are you delaying retirement, working for "just one more year" to feel ready? In this episode, Ari and James dive into goalpost planning—the tendency to postpone retirement over financial or emotional uncertainties. Learn how to prioritize life goals over arbitrary benchmarks, like saving $1M or following a generic 60/40 portfolio strategy. 🎙️ Highlights from the conversation: Submit your request to join James: On the Ready For Retirement podcast: Apply Here On a Retirement Makeover episode: Apply Here Timestamps: 0:00 - Goalpost planning 3:09 - Procrastinating finding meaning 4:42 - Tradeoffs 6:43 - An example 9:20 - Initial analysis 12:48 - Roleplaying 15:09 - Use your PTO 18:01 - Allocation 20:39 - No cookie-cutter formula Create Your Custom Strategy ⬇️ Get Started Here.

In today’s episode of Ready for Retirement episode James covers when to adjust your portfolio as retirement nears—a crucial step for balancing growth and security. If adjustments happen too late, market downturns could delay your plans; if too early, you might miss out on potential growth. The focus is on reallocating stocks to more stable investments like bonds as you approach the time you’ll need to start drawing from your portfolio. Historical data shows that while the stock market grows over the long term, short-term volatility can be risky close to retirement. Timing this transition, often starting about 10 years before needing funds, provides a smoother adjustment and reduces risk. Besides financial factors, psychological comfort with market swings also matters. Striking the right balance helps ensure your retirement funds last while maintaining your peace of mind. Questions answered: 1. When should I start adjusting my investment portfolio as I approach retirement? 2. How can I balance growth potential with stability in my retirement portfolio to minimize risks and ensure financial security? Submit your request to join James: On the Ready For Retirement podcast: Apply Here On a Retirement Makeover episode: Apply Here Timestamps: 0:00 - Protect against stock market decline 2:22 - Investment fundamentals and market trends 6:12 - When will you need the funds? 8:06 - Risk capacity 10:55 - Consider dividends and interest from bonds 14:20 - Use bonds for a specific purpose 17:07 - Risk tolerance 20:59 - 5-10 years before retirement 24:36 - Goal: minimize risk and regret Create Your Custom Strategy ⬇️ Get Started Here.

Meet Ari Taublieb 👋 If you didn’t already know, Ari and I work together at Root Financial, and we thought it was finally time to launch a podcast series together. In our very first episode, we dive into a topic that many people shy away from: talking to your parents about money. Whether it’s discussing their estate plans, long-term care, or the tough conversations around wealth, these talks can feel awkward—but they’re absolutely essential. In this episode, we break down: ▪️ Our personal stories and insights on how to approach these conversations ▪️ Tips for handling these talks with grace and understanding ▪️ Strategies to ensure peace of mind for everyone involved If you’ve ever felt uncertain about talking money or navigating estate planning with your parents, this episode is for you. Subscribe to Ari’s YouTube channel Submit your request to join James: On the Ready For Retirement podcast: Apply Here On a Retirement Makeover episode: Apply Here Timestamps: 0:00 - Ari and James 2:03 - A listener's question 5:54 - Approaching parents 9:26 - Focus on the parent's needs/desires 11:13 - Start with long-term care 14:33 - Initiating conversations 18:03 - Have questions? Ask! Create Your Custom Strategy ⬇️ Get Started Here.

Roth IRAs offer great tax-free income benefits, but to make the most of them in retirement, here are seven things you need to know: By understanding the points above, you can use a Roth IRA to manage taxes and increase flexibility in your retirement. Submit your request to join James: On the Ready For Retirement podcast: Apply Here On a Retirement Makeover episode: Apply Here Timestamps: 0:00 - What is a Roth IRA? 1:38 - Free withdrawals 3:15 - The 5-year rule 4:49 - Income thresholds 6:01 - Backdoor Roth contribution 8:18 - No RMDs 9:26 - Not provisional income 12:10 - Not part of IRMA calculations 13:06 - Income requirement nuances 14:49 - Wrap-up Create Your Custom Strategy ⬇️ Get Started Here.

Have you thought about what moving to a new state might mean for your retirement budget and lifestyle? In this Ready for Retirement episode, the focus is on preparing for an out-of-state retirement. James outlines three essential considerations for retirees planning a move: 1. Housing Costs and Expenses: From property values and local property taxes to potential capital gains from selling a current home. 2. Overall Cost of Living: Everything from groceries to utilities varies widely between regions. It’s also wise to consider personal lifestyle goals—like travel or access to nature—as these can impact ongoing expenses 3. A Solid Tax Strategy: Particularly if moving to a state with different tax laws. Retirees can benefit by adjusting their tax strategy based on the state they’ll be in, potentially saving thousands over time. These tips offer invaluable guidance for anyone considering a fresh start in a new state after retirement. Questions answered: How can moving to a different state impact my retirement expenses? What tax strategies should I consider if I plan to retire out of state? Submit your request to join James: On the Ready For Retirement podcast: Apply Here On a Retirement Makeover episode: Apply Here Timestamps: 0:00 - An overview 1:27 - Compare housing costs 4:04 - Moving to higher property tax state 6:32 - Moving to lower property tax state 7:12 - Compare cost of living 10:48 - Dial in your tax strategy 13:44 - Consider state tax rates 14:51 - Summary Create Your Custom Strategy ⬇️ Get Started Here.

Many dream of retiring early, but you would be surprised to learn that many people who retire early regret doing so. James reveals five things that lead people to regret early retirement and provides practical tips to avoid these pitfalls. He explains why many individuals who retire before 65 struggle due to a lack of planning, overly conservative investment strategies, and failure to envision life beyond work. He highlights the importance of aligning financial plans with personal goals, maintaining a balanced portfolio to outpace inflation, and considering part-time work as a transitional phase. He also encourages listeners to “practice” retirement before fully committing and cautions against adhering to common retirement “rules” without understanding their context. By addressing these critical aspects, listeners can make more informed decisions and transition into retirement, at any age, with confidence. Questions answered: Why is it important to have a life plan in addition to a financial plan when retiring early? What lifestyle adjustments should early retirees be prepared to make to sustain their retirement long-term? Submit your request to join James: On the Ready For Retirement podcast: Apply Here On a Retirement Makeover episode: Apply Here Timestamps: 0:00 - Defining early retirement 1:15 - Not knowing what you’re retiring to 4:14 - Being too conservative 7:51 - Not considering part-time work 12:25 - Not practicing retirement 14:05 - Relying on retirement “rules” 17:26 - Being too dependent on 401(k) Create Your Custom Strategy ⬇️ Get Started Here.

James sits down with someone who’s financially set to retire—mortgage paid off, kids through college, and investments in place—but he’s still grappling with one big question: what’s next? Instead of focusing solely on financial strategies or retirement planning, James gives him some unexpected advice: start journaling. This led to a deeper conversation about finding purpose beyond optimizing your portfolio. What would your life look like without constraints? What actually matters most to you? And how can you ensure your future is filled with meaning, not just money? It’s not just about retiring from something but retiring to a life you love. Questions answered: How can I avoid feeling unfulfilled in retirement, even if I have all the money I need? What are some practices I can do now to flush out what I really want out of life? Submit your request to join James: On the Ready For Retirement podcast: Apply Here On a Retirement Makeover episode: Apply Here Timestamps: 0:00 - A pertinent conversation 1:53 - Journaling prompts 3:00 - What matters 4:47 - Imagine no limitations 6:43 - Best, second-best, worst scenarios 10:00 - Addressing fears steps 1&2 13:22 - Addressing fears steps 3&4 16:43 - Take action 18:50 - Wrap-up Create Your Custom Strategy ⬇️ Get Started Here.

For many, Social Security makes up a large portion of their retirement income, so it’s important to know how to maximize your Social Security benefit. James explains how Social Security works, diving into some important foundational aspects. He then explains four key strategies for maximizing benefits: 1. Work for 35 years to avoid zero-income years in the calculation. 2. Delay benefits, if possible, until age 70, increasing payments by 8% annually after full retirement age. 3. Leverage spousal benefits, allowing a lower-earning spouse to claim up to 50% of the higher-earning spouse's benefit. 4. Plan for survivor benefits, where a surviving spouse can receive 100% of the deceased spouse’s benefits. By understanding how these factors work, retirees can make informed decisions to maximize their Social Security income, reducing pressure on their savings and ensuring a more stable retirement. Submit your request to join James: On the Ready For Retirement podcast: Apply Here On a Retirement Makeover episode: Apply Here Questions answered: How is Social Security funded, and how does it affect my retirement income? How are Social Security benefits calculated based on my earnings? Timestamps: 0:00 - How SS works 4:16 - Drilling deeper 6:27 - Full retirement age 8:08 - Work 35 years 10:08 - If possible, wait 12:17 - Spousal benefits 14:03 - Survivor benefits 17:39 - Summary Create Your Custom Strategy ⬇️ Get Started Here.

ames responds to a question from Chris regarding restricted stock units (RSUs) and how to avoid costly mistakes when managing them. He explores whether it’s wise to hold onto company stock or diversify for a safer financial future. He breaks down how RSUs work, from vesting schedules to the tax implications of receiving stock as part of your compensation package. He also explains the critical considerations you should make when deciding whether to hold or sell vested shares and how this decision fits into your broader investment strategy. Questions answered: Should I hold onto or sell my vested RSUs? What are the tax implications of RSUs, and how can I avoid mistakes? Submit your request to join James: On the Ready For Retirement podcast: Apply Here On a Retirement Makeover episode: Apply Here Timestamps: 0:00 - How RSUs work 4:24 - Like a cash bonus 7:17 - Question your performance assumptions 12:25 - How RSUs are taxed and paid 15:14 - Default withholding rate and wash sale rules Create Your Custom Strategy ⬇️ Get Started Here.

Patrick and Mary will soon both be retired. They are curious about what their withdrawal strategy should be as they balance various retirement accounts, including a pension, IRAs, and a brokerage account. They've been using tax gain harvesting to minimize taxes and plan to eliminate gains by 2024. A key question is whether to withdraw from their IRAs or brokerage account first, considering their state’s tax exclusion. James explains that by managing withdrawals and Roth conversions strategically, some retirees can reduce tax liability, optimize income streams, and preserve the tax-free growth of Roth accounts during retirement. Questions answered: Should retirees withdraw from their taxable brokerage accounts or IRAs first to minimize taxes? How can Roth conversions and state tax exclusions be used to optimize income and lower taxes during retirement? Submit your request to join James: On the Ready For Retirement podcast: Apply Here On a Retirement Makeover episode: Apply Here Timestamps: 0:00 - Meet Patrick and Mary 3:14 - Retirement taxes are different 6:37 - Consider combined tax rates 8:42 - Tax gain harvesting 12:35 - Strategizing income in retirement 16:48 - Realized gains 20:12 - A twist on traditional thinking 23:47 - The bottom line Create Your Custom Strategy ⬇️ Get Started Here.

Ben has been a saver his entire life, which helped position him for an early retirement at the age of 53. Yet, he faces a big challenge. Having maintained his modest lifestyle, Ben’s comfortable portfolio has continued to grow and has nearly doubled in value. James and Ben discuss the challenges of making mindset shifts and the proactive steps Ben has taken to encourage himself to spend more. Questions answered: How did Ben decide to retire when he was in his peak earning years? What are the steps Ben has taken to force himself to spend more? Submit your request to join James: On the Ready For Retirement podcast: Apply Here On a Retirement Makeover episode: Apply Here Timestamps: 0:00 - Meet Ben 2:36 - A lifetime saver 5:28 - Confidence to retire early 6:41 - Retirement reality vs expectations 9:12 - The appeal of retirement 11:46 - The biggest challenge - spending 14:13 - A growing portfolio 17:33 - The lure of subsidies Create Your Custom Strategy ⬇️ Get Started Here.

Monique aspired to retire early, and while she had faithfully saved throughout her working years, she wasn’t sure if she had enough to retire. After getting assurance from professionals, she took the plunge and quit working. Monique and James talk about the first two years of her retirement – how she’s been able to focus on her health and pursue some hobbies she didn’t have time for previously. Monique also shares some surprising challenges related to spending, travel, and family dynamics. Questions answered: What can retirees who are natural savers (and have more than enough) do to loosen the purse strings and spend more? What does Monique wish she had done differently during her working years in preparation for retirement? Submit your request to join James: On the Ready For Retirement podcast: Apply Here On a Retirement Makeover episode: Apply Here Timestamps: 0:00 - Meet Monique 3:58 - 5 years before retiring 8:03 - Money impressions from childhood 10:47 - Transition to retirement 15:06 - Spending and travel challenges. 20:50 - Family pressure and self-awareness 25:51 - A spending exercise 32:19 - Better physical and mental health 35:53 - Persons and social changes 39:01 - Advice for younger self Create Your Custom Strategy ⬇️ Get Started Here.

Elaine didn’t decide to retire at age 57, but changes in her company meant an early retirement for her. Being caught off guard, she didn’t feel emotionally prepared to make the shift, even though she knew that her family would be fine financially. One year into her retirement, she found her groove by focusing on her family, building new relationships, trying new things, and staying physically active. Today she says she’s never been happier. James and Elaine discuss how she found her footing in retirement, the advice she would give her younger self, and the plans she and her husband have for when they are both retired. Questions answered: How did Elaine find the activities and community she is now enjoying? What advice would Elaine give to others on the verge of retirement? Submit your request to join James: On the Ready For Retirement podcast: Apply Here On a Retirement Makeover episode: Apply Here Timestamps: 0:00 - Meet Elaine 2:55 - The “decision” to retire 4:44 - The loss of income 6:05 - New social outlets and new routine 8:15 - A year to make shifts 11:19 - Advice for younger self 13:58 - Search for activities; don’t say no 16:21 - Challenges and advice 18:37 - What’s next 19:58 - Try new things; build relationships Create Your Custom Strategy ⬇️ Get Started Here.

After his father lost healthcare coverage in retirement and had to pay for a major health event with savings, Derek was highly motivated to ensure sufficient coverage in retirement. He even considered leaving the job he loved for one with better healthcare and retirement benefits. Derek shares his retirement journey with James, including: ➡ Decisions he made pre-retirement ➡ How he addressed healthcare concerns ➡ How his perspective on life and giving back has shifted ➡ How he and his wife prepared for the changes retirement would bring to their marriage Questions answered: What are some questions my spouse and I could explore now in preparation for when we’re spending more time together in retirement? What is Derek’s advice for soon-to-be retirees? Submit your request to join James: On the Ready For Retirement podcast: Apply Here On a Retirement Makeover episode: Apply Here Timestamps: 0:00 - Meet Derek 3:23 - Importance of healthcare 6:48 - Health in retirement 10:07 - A new perspective and purpose 14:13 - Financial concerns and readiness 16:29 - The biggest challenge 19:30 - Adjustments in the marriage 23:13 - Derek’s advice 26:11 - Final thoughts Create Your Custom Strategy ⬇️ Get Started Here.