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Welcome to the Early Retirement Roadmap podcast, your audio guide to preparing for and thriving in early retirement! If you’re dreaming of retiring early but feeling overwhelmed about where to start, or if you’re already retired and looking to make the most of your freedom, you’re in the right place. I’m your host Mike Upland, and I successfully retired at 55. Through this podcast, I share my personal early retirement journey—the victories, the challenges, and all the essential lessons I’ve ...
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Ari Taublieb is a CERTIFIED FINANCIAL PLANNER™ and Vice President of Root Financial Partners. Ari Taublieb, CFP®, MBA specializes in helping people navigate an early retirement. I get it...retirement sounds overwhelming (an early retirement may sound particularly overwhelming)! Does it just feel like there's so much to consider and you just want to make sure you're doing everything you can to set yourself up right? If I may ask...why do YOU want to retire early? Do you want to travel? Have y ...
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Early Retirement

youngoldman

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Life after college graduation is never easy, especially when you're broke. As I go through my journey, I'm bringing some of the dopest creatives in the New York City with me. Join us as we drop knowledge on how to barely survive...and if this all goes according to plan, we'll all be set for Early Retirement.
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On Apartment Investing For Early Retirement, we sit down with accomplished investors, leaders, and industry experts in the world of multifamily real estate. We discuss how to capitalize on the vast opportunity that apartment investing presents to build wealth and help you achieve your financial goals.
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Wondering if you really have enough to retire? In this early retirement planning episode, I break down 6 levels of retirement wealth—from Survival to Fulfillment—so you can see which level you’re at and what it takes to move up. Too many people only ask, “Do I have enough to retire?” when the better question is, “Enough for what level of retirement…
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Deciding when to claim Social Security is one of the most important retirement choices you’ll make, but most people approach it the wrong way. They pick an age early, cling to it for years, and assume the “best” decision never changes. In reality, the right claiming strategy shifts as your life shifts: your spouse’s benefit, your health, your spend…
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Future-proof your retirement with habits of thriving retirees, early retirement planning tips, and simple retirement investing strategies to help you feel confident about the decades ahead. In this episode, I break down 9 practical habits I myself do and see over and over again in retirees who are not just “getting by,” but actually thriving—financ…
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Stop letting your birthday decide your bond mix. That “age in bonds” rule feels safe, but it can quietly rob you of growth, freedom, and spending power. In this episode, Ari challenges the traditional 60/40 rule and shows how to build a smarter allocation based on your actual life, not your birth year. Using a real client story—a couple with $2 mil…
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Everyone wants better returns. Almost no one talks about where those returns should live. You can own all the right investments and still lose thousands a year if they sit in the wrong place. Asset location is one of those quiet advantages that doesn’t make headlines but changes everything behind the scenes. It’s how you line up your accounts so th…
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Some retirees have more money than they ever imagined… and still feel guilty buying the $5 M&Ms. This episode is for the lifelong savers who nailed the retirement planning side—maxed out accounts, invested consistently, hit their “number”—but feel stuck when it’s time to actually spend. James and Ari share real client stories of multimillionaires w…
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Retiring by 55 sounds incredible, but it takes more than hitting a savings target. You need to understand how to bridge the gap between your last paycheck and the life you want to live. In this episode, Ari Taublieb, CFP®, shares the five things every early retiree should know before calling it quits. From the overlooked “Rule of 55” to navigating …
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Lazy retirement investing made simple: early retirement, index funds (VTI, VOO, VUG, VIG, VYM), withdrawal rate guardrails, 2–4 year cash liquidity runway, Roth conversions, MAGI/ACA & IRMAA tax strategy. Ready for a “do less, retire better” portfolio? In this episode, I walk through my lazy retirement investing plan—built for early retirees and an…
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Retirement doesn’t come down to a magic number, it comes down to your number. This episode gives you a simple, personalized framework to decide when you can truly retire based on the life you want, not generic benchmarks. First, get clear on monthly spending (baseline needs + lifestyle wants). Then reverse-engineer your target by layering in taxes,…
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What if the “smart” money choice isn’t the choice that builds your best life? This Root Talks episode starts with a bucket-list moment for James—throwing the first pitch at a Padres game—and turns into a bigger lesson: money is a tool to create meaning, not a score to keep. It’s a look at the Five Types of Wealth (financial, time, social, mental, a…
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Does retiring early reduce Social Security? The truth—how benefits are really calculated: the 35-year rule, Average Indexed Monthly Earnings (AIME), bend points, indexing only through age 59, and why “zeros” hurt. In this episode, I break down: Why Social Security is based on your highest 35 indexed years—not your last job. How indexing stops after…
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Most headlines shout that you need millions to retire comfortably. The truth? It depends on you. Ari breaks down what “enough” really means, and how to design a plan that fits your lifestyle, health, and peace of mind, not someone else’s spreadsheet. In this episode, you’ll hear real-life stories that prove one size doesn’t fit all. A saver with $3…
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Retirement planning, early retirement, 7 signs you’re ready to retire, retire earlier than you think, retire in your 50s, how to retire early—here’s how to know if the numbers and lifestyle say YES. If you’re wondering “Am I actually ready to retire sooner?”, this episode walks through 7 clear signs—financial, lifestyle, and mindset—that indicate y…
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2026 health insurance: If Affordable Care Act (ACA) subsidies end, Plan A vs Plan B. Open Enrollment Nov 1; enroll by Dec 15 for Jan 1. MAGI targets, 400% FPL, on-exchange vs off-exchange. In this video,“No Subsidies in 2026? Plan A vs Plan B (Do This)”— I provide two pathways so you’re ready to enroll by Dec 15 for a Jan 1 health insurance start, …
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Feeling like “flat” retirement spending plans don’t match real life? You’re not imagining it. Spending typically follows a retirement smile: higher in the early “go-go” years, lower in the “slow-go” years, then rising again later with healthcare needs. In this episode, Ari Taublieb, CFP®, shows how acknowledging that curve can unlock more life earl…
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What if the next 10 years bring just 3% returns from the S&P 500? In this episode, we turn that forecast into a real-world retirement plan—not panic. You’ll learn how to stress test your portfolio, build flexibility into your spending, and design a withdrawal strategy that can survive tough markets. Listen as Ari and James break down: Sequence-of-r…
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Retirement planning: 5 things to sell before you retire—downsize the house, cut support for adult children, ditch RV/boat “toys,” drop the second car, and release your work identity with my Keep-Sell-Swap test. If you want a calmer, freer retirement, subtraction beats addition. In this video I walk through five high-impact things to sell (or stop f…
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Feeling like healthcare makes early retirement impossible? It’s a common belief, but often fixable with thoughtful income planning. Premium tax credits under the ACA aren’t vanishing; the enhanced credits are scheduled to sunset after 2025, and the pre-2021 rules (including the ~400% FPL income cap) are slated to return in 2026 unless Congress acts…
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Retirement planning, early retirement, money traps: timeshares, vacation homes, high-fee annuities, whole life insurance, long-term care insurance, high-yield bonds, high-fee active funds, cash flow, withdrawal rate. In this episode, we break down 7 “assets” rich retirees avoid—and why skipping them protects your cash flow and flexibility before an…
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Feeling anxious about taking money from your retirement accounts? You’re not alone. That first withdrawal feels odd after decades of saving, but a clear process and tax plan turns uncertainty into confidence. In this episode, Ari Taublieb, CFP®, breaks down how withdrawals actually move from investment accounts to your checking—and what the tax bit…
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Are you overthinking your Roth conversion strategy? While Roth conversions can be powerful, not every retiree needs them. In this video, you’ll learn when a Roth conversion truly makes sense—and when it may just add unnecessary complexity. Using the “cauliflower analogy,” we break down how Required Minimum Distributions (RMDs) can push retirees int…
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We’ve all heard the clichés: focus on what you can control, embrace the pain not the suffering, fight for what you want. Easy to dismiss, right? But the truth is, those sayings stick around for a reason. They hold the kind of wisdom that can change how you approach life, work, and even setbacks. What often gets missed is that clichés aren’t about p…
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I retired early at 55. In this episode I show exactly how to retire early with 5 proven keys to early retirement: the mindset that powers compounding, how to raise your savings rate, the income multiplier, simple investing with low-cost index funds, and retirement planning that avoids sequence-of-returns risk. If you want to retire early—or just bu…
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Forget everything you thought you knew about retirement planning. While 401(k)s and IRAs get most of the spotlight, brokerage accounts can be a powerful tool for flexibility, tax savings, and early retirement. In this episode, you’ll learn the seven key advantages brokerage accounts offer, including how a married couple could generate over $126,000…
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ACA MAGI explained: how to calculate and manage Modified Adjusted Gross Income (MAGI) for Affordable Care Act (ACA) subsidies—step-by-step, with a free MAGI calculator to lower premiums and maximize premium tax credits/subsidies. In this episode, we calculate ACA MAGI step-by-step using a real early-retiree scenario and show you how to keep ACA pre…
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Retirement anxiety does not discriminate based on wealth. Even multi-million-dollar portfolios are not immune to the fear of running out of money. This creates one of retirement’s greatest paradoxes: having enough but feeling like you don’t. When clients hear they can safely spend $150,000 a year in retirement, many hesitate. They remember their fi…
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What makes you trust someone with your financial future? In this episode of Root Talks, James and Ari unpack the powerful role of intuition in building lasting relationships with financial advisors, business partners, and even loved ones. They explain how what we call a gut feeling is actually condensed pattern recognition, your brain quietly scann…
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Are you working longer than you need to because of a retirement planning mistake? One of the biggest misconceptions is assuming you will spend the same amount every year in retirement. The reality is different, and understanding it could change when you retire. Experts call it the retirement smile. In your “go-go years” (65–75), spending is highest…
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Roth conversions vs. ACA subsidies is the early retirement dilemma no one talks about. If you’re planning for early retirement, you need to know how Roth IRA conversions can raise your MAGI and cost you ACA health insurance subsidies before Medicare. In this episode, I’ll break down the trade-off, show you real examples, and share strategies to bal…
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Struggling to get your spouse involved in retirement planning? You are not alone. Many financially-minded partners lose their spouse’s attention by jumping straight into 401(k) allocations or tax strategies. The result is glazed eyes and little engagement. This approach works differently. Start with powerful, open-ended questions that spark curiosi…
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What happens when growth changes a company? We’ve all seen it—your favorite restaurant expands and suddenly the quality slips. The connection feels lost. But does growing always mean losing what made you special? At Root, we think about growth differently. We use “anti-goals” to define what we never want to become, with checks in place so expansion…
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Think you know how much people save for retirement? The median American over 65 has just $100,000 saved, yet the average household spends $57,000 a year in retirement, with $20,000 going to housing alone. The math doesn’t work. At Root Financial, most clients retire with $2–3M and plan to spend $100K–$200K annually. That’s not about bragging. It’s …
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Early retirement at 55 comes with financial and lifestyle challenges most people don’t expect. In this video, I share 5 things I wish I knew before retiring early, including lessons on retirement planning, healthcare costs, spending habits, and mindset shifts that can make or break your retirement years. Retiring early isn’t just about saving enoug…
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Early retirement is about more than money Science shows there are compelling reasons to retire sooner than most people think. The UK’s Whitehall 2 study found that retiring at 60 lowers the risk of chronic disease by 32 percent compared to working longer. Harvard research reveals that close relationships, not wealth or titles, are the strongest pre…
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What if the “financially optimal” choice doesn’t actually lead to your best life? This conversation explores the balance between optimizing money and optimizing happiness. We break down the Five Types of Wealth—financial, time, social, mental, and physical—and show why sometimes the decision that looks inefficient on paper may actually be the smart…
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Working past 60 might seem smart, but it could be the biggest retirement mistake you make. In this video, we reveal the hidden costs of working past 60 — from lost health years to missed financial opportunities — and how to find your perfect retirement timing. You’ll learn why the payoff for working longer can shrink after age 60, how taxes and Med…
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Some choose to grind a few more years in a high-paying job they dislike, aiming for an early, full stop at retirement. Others step into more fulfilling work that pays less, but adds purpose to their days—and often still results in more wealth than expected. Take John and Jennifer. Both start at age 50 with $1M saved and $150K salaries. John works f…
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Estate planning isn’t fun to think about, but skipping it can cost loved ones time, stress, and money. In this week's episode, Ari breaks down the essentials so you can take action with confidence. Learn the key differences between wills and trusts, which states make trusts especially valuable, and why even residents of “will-friendly” states might…
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Money conversations fall short when only one spouse is at the table. It’s easy to treat financial planning like another household task to divide and conquer, but unlike errands, your financial plan is the blueprint for your shared future. What we’ve seen time and again is that the person sleeping next to you often holds the key to your blind spots.…
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Estate planning doesn’t have to be complicated. This episode breaks down the essentials: wills, trusts, and what actually matters, so you can protect your assets and give your loved ones peace of mind. Wills determine where assets go after death. Trusts do that and more. They can manage assets during your lifetime and help avoid probate, offering m…
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Wondering how the 2025 tax law changes affect your retirement strategy? This video breaks down the One Big Beautiful Bill Act, a landmark tax bill signed into law by President Trump — and its HUGE implications for retirees, early retirees, and anyone planning for financial independence. 📌 Here’s what you’ll learn: 🏦 2025 retirement tax changes that…
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What does soccer have to do with retirement? A lot more than you'd think. As a 5'5" former college soccer player turned financial advisor, I’ve learned it’s not about brute strength. It’s about smart decisions. That mindset guides the way I approach financial planning today. At 29, people ask why I care so much about retirement. The answer is simpl…
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Want early access to your 401(k) or IRA before age 59½ without getting slammed by the IRS 10% penalty? In this episode, I’ll walk you through the IRS Rule 72(t)—a little-known but completely legal loophole that allows penalty-free early withdrawals through SEPP (Substantially Equal Periodic Payments). This strategy could unlock your early retiremen…
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The hardest part of retirement isn’t always financial, it’s psychological. For many, stepping away from work isn’t a light switch, but a dimmer that adjusts over time. This episode of Root Talks unpacks what makes the retirement decision so complex, especially for high-achieving professionals whose identity is tied to their careers. Through a real-…
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Ready to feel more motivated about retiring early? These five research-backed stats reveal how early retirement can positively impact everything from health to relationships—and might be the nudge you need to take your financial independence plan more seriously. The benefits go well beyond just having more free time. While many people delay retirem…
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Are you really ready for retirement? As your retirement countdown begins, I reveal the critical steps you must take to ensure you're fully prepared to retire confidently and securely. From defining your retirement vision to setting a realistic retirement age, I cover everything you need to know for effective retirement planning. In this retirement …
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Thinking about early retirement? Here are 6 powerful reasons to retire early—covering retirement planning, financial freedom, health, and why waiting longer could cost more than money. Whether you're close to retiring or just exploring the idea, these insights might change how you think about work, money, and time. Inspired by the popular topic “5 …
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Too many people delay retirement just to boost their Social Security benefits, often at the cost of time, energy, and joy. But at Root, we believe retirement planning should be about more than just maximizing one metric. It should be about maximizing your life. If you're working extra years simply to avoid gaps in your earnings history or to earn a…
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If you’ve ever found yourself wondering whether you really need a financial advisor, this episode is for you. James and Ari unpack the deeper reasons people seek financial guidance—and why the decision often goes far beyond dollars and cents. Much like seeing a doctor for preventative care, working with the right advisor is about protecting your fu…
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Think you need $1 million to retire? That Medicare covers everything? Or that your expenses will drop after you stop working? In this episode of the Early Retirement Roadmap Podcast, I bust the top 10 retirement myths—with real data and practical advice. These are the beliefs that could seriously derail your plans and cost you thousands if you fall…
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