Early Retirement Roadmap
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 in 2024. Through this podcast, I share my personal early retirement journey—the victories, the challenges, and all the essential lessons I’ve learned along the way. Each episode delivers practical strategies and real-world insights on crucial topics like financial planning, health insurance, tax strategies, developing the right mindset, and finding purpose in retirement. You’ll hear candid discussions about the realities of early retirement, actionable tips for building and managing wealth, and inspiring stories to help you navigate your own path to early retirement or thrive in it if you're already there! Whether you’re just starting to explore early retirement or fine-tuning your existing plans, this podcast provides the roadmap you need to build a financially secure and fulfilling post-career life. For visual guides and additional content, be sure to check out the Early Retirement Roadmap YouTube channel, where I share complementary videos and resources to support your early retirement journey. Your early retirement journey starts here—subscribe or follow now to ensure you never miss an episode!
Episodes
Gen X retirement won’t look like Boomer retirement. Here’s why retirement planning is changing for Generation X, from Social Security to health insurance, 401(k)s, and early retirement.
For many Baby Boomers, retirement followed a more familiar path: work until around 65, collect Social Security, go on Medicare, maybe have a pension, and settle into a more traditional retirement lifestyle.
But for Gen X, retirement may look very di...
Early retirement, retirement planning, retired at 55, and what to know before retirement—here are 10 lessons I’ve learned after 17 months of early retirement that could help you plan smarter.
When I retired at 55, I thought the hard part was getting the numbers to work. But after 17 months of actually living early retirement, I’ve learned that the money plan is only part of the story.
In this episode, I share 10 things I’ve learned...
Social Security is a much bigger part of early retirement planning than most people realize. In this episode, I share early retirement planning tips on claiming age, portfolio pressure, and how Social Security can change when you can retire.
Most people treat Social Security like a separate decision.
It’s not.
The age you claim can affect how much pressure your portfolio has to carry, how long the years between retirement and Socia...
Early retirement planning tips matter a lot when it comes to Roth conversions. In this episode, I explain why your Roth conversion window can close faster than you think — and how ACA subsidies, Social Security, IRMAA, taxes, and timing can all shrink the opportunity.
If you are planning Roth conversions in early retirement, this is one of the biggest mistakes to avoid.
A lot of retirees assume they will have a long stretch of low-...
Retiring soon? In this episode, I cover the biggest retirement planning mistake people make before retirement and the 7 things to figure out now, including spending, taxes, health insurance before Medicare, withdrawal strategy, and cash runway.
A lot of people do a good job saving for retirement, but they wait too long to plan the actual transition into retirement.
That’s the mistake.
In this episode, I walk through 7 key areas to ...
Early retirement planning is not just about net worth. In this episode, I break down the retirement number that matters more, plus ACA health insurance, taxes, spending, and sequence risk.
Most people ask, “How much net worth do I need to retire?” But that question can be misleading.
In this episode, I explain why the more important question is this: How much does your portfolio need to support each year?
Using simple examples, I s...
Early retirement planning tips from someone who actually did it: I retired at 55, and in this episode, I share 7 early retirement mistakes I missed so you can retire early with fewer surprises and avoid costly retirement planning mistakes.
If you’re searching for early retirement planning tips, retirement planning advice, and early retirement mistakes to avoid, this video walks through what caught me off guard after retiring at 55....
How much do I need to retire early? In this episode, I walk through the five numbers that really determine whether early retirement works — including spending, healthcare costs, taxes, your retirement bridge years, and how much your portfolio actually needs to support.
Most people searching “how much do I need to retire” are hoping for one simple number. But the reality is that early retirement is driven by several key numbers work...
Early retirement + retirement planning made simple: Can you retire now?
In this episode, I share 6 questions to test your financial independence and retirement readiness—before you make the leap. If you can honestly answer YES to all six, you may be closer to retirement than you think:
The 6-question retirement test:
1. Are you postponing the life you actually want?
2. Is your job taking a real toll on your health?
3. Have you outg...
Your first 5 retirement years decide everything—retirement planning, withdrawal strategy, taxes, health insurance, spending, purpose, relationships, and the mistakes that derail early retirees. Here are the lessons to get it right.
If you retire in your 50s or early 60s, the first five years aren’t a warm-up. The habits you set, the decisions you lock in, and the systems you build early will compound for decades.
In this episode, ...
Build a cash runway for retirement so you’re not forced to sell stocks in a down market. Learn how many years you need, how to build it, where to hold it (HYSA, CDs, T-bills), and simple refill rules.
If you’re retiring early (or already retired), sequence-of-returns risk can wreck an otherwise solid plan. A cash runway is your “seatbelt” — it buys you time during bear markets so your investments can recover without you selling at ...
ACA subsidy payback at tax time? Form 8962 + 1095-A reconciliation can trigger a surprise bill when your MAGI ends up higher than expected. In this episode, I’ll you'll learn why it happens, how to fix it, and how to prevent it next year.
If you had Marketplace coverage and your tax software suddenly says you owe thousands, you’re not alone. Here’s the real reason: the ACA premium tax credit you received during the year is an *adva...
Market volatility and choppy markets can wreck retirement plans—if you react the wrong way. In this episode, I share a simple framework to stay calm, avoid panic selling, and protect your long-term investing plan.
If you’re investing for retirement (or already retired), the goal isn’t to predict the market. It’s to have a repeatable plan for choppy years—so you don’t make permanent mistakes in temporary fear.
In this episode, you’l...
ACA premium shock for 2026? If your Marketplace/Obamacare health insurance premium jumped, this video shows 10 practical ways to pay less all year by controlling MAGI (modified adjusted gross income) and avoiding costly income mistakes.
Health insurance is the #1 “elephant in the room” for early retirement. With enhanced ACA subsidies ending after 2025, many early retirees are seeing big premium increases — but the ACA is still inc...
2026 401(k) and IRA contribution limits are rising from 2025—but maxing out can backfire if you’re planning early retirement. In this episode I break down 3 rules to fund the right accounts in the right order.
If you’re aiming to retire before 59½, the “max everything” advice can accidentally:
- lock up money when you need flexibility
- increase taxes later (required distributions and tax brackets)
- make health insurance more expen...
Monthly Dividend ETFs for retirement income can look like a paycheck—but it’s often an illusion. In this episode, I share 3 tests to avoid costly mistakes and keep Affordable Care Act (ACA) taxes in mind.
You’ll learn: • The 4 main types of monthly income ETFs (covered-call, high-dividend stock, preferred stock, bond funds) • Why yield can mislead if you ignore total return • Test #1: What the distribution is made of (dividends, in...
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?” In this episode, I walk through my framework of Survival, Stability, Comfort, Secu...
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—financially, emotionally, and health-wise.
We’ll talk about how to spend intentionally inst...
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 anyone who wants a low-maintenance, rules-based retirement approach that’s diversif...
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 age 59, so skipping some early-60s work years often matters less than headlines...
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