Retirement Roadmap

We tackle the often-overlooked issue of retirement tax liability and explore strategies to create tax-free income streams for a potentially more secure financial future.

• Understanding the "mortgage" on qualified plans (401(k)s, IRAs) where the IRS owns an unknown percentage of your savings
• The current "tax sale" has been extended but will eventually end with rates likely rising dramatically
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Are you playing retirement checkers when you should be mastering retirement chess? This episode unpacks a powerful analogy that demonstrates why traditional retirement planning often falls short.

When approaching retirement, most people arrive with what amounts to a checkerboard and a bag of identical checkers—assets that have served a single purpose during working years: growth. But retirement demands a more sophisticated...

The new federal budget bill makes the 2017 tax cuts permanent, creates a temporary senior deduction, and raises estate exemptions, but also adds $3.4 trillion to national debt while cutting social safety nets. We explore what these changes mean for retirement planning and identify strategies to maximize the limited window of opportunity created by today's low tax environment.

• Tax cuts from 2017 now permanent, but hi...

We explore how to maximize your 401(k) balance and integrate it effectively into your overall retirement strategy.

• 401(k) plans emerged in 1979, giving workers an automatic way to save for retirement without employer-provided pensions
• Most Americans lack proper education on 401(k) investing, contributing blindly without understanding rules or optimal strategies 
• We discuss how to start with your employer matc...

The Income-Related Monthly Adjustment Amount (IRMAA) is a Medicare surcharge that can significantly increase your healthcare costs in retirement based on income from two years prior.

• IRMAA affects both Medicare Part B and Part D premiums, potentially adding over $500 per month per person
• The surcharge is based on your Modified Adjusted Gross Income (MAGI) from two years prior
• Income thresholds begin at $106,0...

We examine essential mid-year financial steps that could help you finish the year strong and brighten your financial future. Time flies by quickly, making it crucial to check in on your financial goals periodically rather than putting them off indefinitely.

• Consider saving for retirement early, even if in small amounts, to harness the power of compound interest
• Check your workplace retirement plans - many now offer...

Longevity risk presents a significant challenge for retirees, with medical advancements potentially extending lifespans and creating decades-long retirements that require careful financial planning.

• Running out of money in retirement is often feared more than death itself
• Life expectancy now averages 79.5 years for men and 82 years for women
• Most retirees now believe they need about $1.5 million to retire com...

Social Security has reached a milestone with the average check surpassing $2,000 monthly for the first time in June 2025, but this achievement highlights serious concerns about retirement security in America.

• Maximum benefit for those claiming at age 70 will be $5,108 per month
• Social Security was designed to replace only about 40% of pre-retirement income
• Cost of living adjustments are designed to lag behind...

We explore eight common retirement planning myths that could potentially derail your financial future and explain why these outdated beliefs may no longer apply to today's retirement landscape.

• The 4% withdrawal rule from the 1990s has been updated to 2.8% by Morningstar research, meaning you need significantly more savings to generate the same income
• Social Security isn't going bankrupt, but its trust fu...

We explore the unexpected financial shocks that can derail even the most carefully constructed retirement plans and discuss strategies to help prepare for these challenges.

• Healthcare costs average $315,000 for couples throughout retirement, yet most Americans estimate only $75,000
• Medicare has significant gaps requiring additional coverage and costs that increase annually
• 70% of adults who reach age 65 will ...

Facing a layoff when retirement is on the horizon can feel devastating. That carefully planned timeline suddenly collapses, leaving you wondering if your retirement dreams are still possible. But what seems like a crisis might actually be an opportunity—if you know how to navigate it.

This episode dives deep into the strategies and considerations for those experiencing job loss within five years of retirement. Rather than ...

The traditional rules of retirement planning have changed dramatically in recent decades, calling for new strategies to generate plans for reliable income regardless of market conditions. Increased market volatility since 2000 has rendered the old "4% rule" obsolete, now reduced to 2.8%, while tax implications, sequence of returns risk, and the shift from pensions to 401(k)s create additional challenges.

• Market...

What if your dream retirement looked nothing like the standard Florida condo and golf course scenario? Evan and Mark dive into wildly unconventional retirement strategies—some absurd, some surprisingly practical—that could transform how you envision your golden years.

The conversation begins with AI-generated oddball ideas like starting hobby-based cults and living in haunted houses before evolving into legitimately viable...

Market volatility in 2025 doesn't have to derail retirement plans if you've properly structured your income sources and diversified your investments. Proper retirement planning involves creating stable income buckets that aren't totally dependent on market performance, allowing retirees to weather economic storms with confidence.

• Sequence of returns risk can pose a significant danger when withdrawing from ...

We examine the most common retirement fears that prevent people from planning effectively and offer practical solutions to address them.

• Running out of money tops the list of retirement concerns as people face longer lifespans without traditional pensions
• Healthcare costs average around $335,000 for a retired couple, with Medicare covering less than many expect
• Loss of identity and social isolation after leav...

We explore the financial and emotional benefits of part-time employment during retirement, discussing how it can both extend retirement savings and provide a sense of purpose during this major life transition.

• Part-time work provides social connections and purpose when transitioning from decades of career identity
• Working in retirement can help extend retirement funds by supplementing income and reducing the need t...

We explore strategies for optimizing your retirement plan with timely adjustments that can significantly impact your financial future. Spring cleaning your retirement plan involves reviewing multiple interconnected elements that work together to help secure your financial well-being.

• Roth conversion strategies while taxes are potentially at historic lows
• Evaluating tax brackets and timing conversions for maximum ef...

We explore several strategies for spring cleaning your retirement plan. Retirement planning deserves regular attention and adjustments as your life circumstances and the economic landscape evolve.

• Reviewing retirement accounts regularly to check balances, investment allocations, and risk levels based on your age
• Considering contribution limits and ensuring you're at least capturing employer matches
• Exami...

This episode dives deep into the current economic climate, focusing on how tariffs can affect the retirement landscape. We explore actionable steps to help secure your financial future amid rising costs and market volatility. 

- Understanding tariffs and their implications on consumer prices
- Historical context of tariffs versus the modern tax system
- How you can put your cash to work in during retirement
- C...