Your Retirement, Your Way

Is AI the future of retirement planning, or just a clever tool that misses the human touch? In this episode, Gary Garland dives into the real-life complexities of retirement, exploring why wisdom and personal advice matter more than algorithms. Discover the four essential questions every retiree must answer, from income strategies to legacy planning, and learn how to avoid common pitfalls that technology alone can’t solve. Tu...

What if your soaring 401k could suddenly become a “201k”? In this episode, Gary Garland unpacks the rollercoaster of today’s record-breaking markets and reveals why smart retirees need more than luck to secure their future. Discover the dangers of chasing returns, the importance of risk allocation, and how integrated planning—combining financial, tax, and estate strategies—can help you retire with conf...

Think you understand the new “One Big Beautiful Bill”? Think again—peel back the layers and discover how recent tax changes and Social Security updates could impact your retirement plans. Gary Garland breaks down the complexities, exposes hidden pitfalls, and shares practical strategies to help you navigate the shifting landscape of taxes, income streams, and long-term financial security—all in plain English...

Are you unknowingly leaving thousands on the table in retirement taxes? Certified financial planner and estate attorney Gary Garland reveals the hidden pitfalls most advisors miss, from overlooked tax strategies to Social Security myths that could derail your golden years. Discover why “do-it-yourself” retirement planning isn’t always enough, how to bridge the income gap, and what you must know before making criti...

What if one decision could haunt your retirement for decades? In this episode, Gary Garland exposes the “tricks” lurking in financial planning—from hidden fees and risky annuities to the dangers of lazy money and following the crowd. Learn how to avoid costly mistakes, optimize your investments, and build a retirement plan that truly fits your life. Real stories, practical advice, and a few Halloween laughs make t...

Are you risking your retirement by trusting “permanent” tax cuts and cookie-cutter advice? This episode unpacks the real impact of Roth conversions, explores new portfolio strategies beyond the classic 60-40 split, and reveals the warning signs that your financial advisor may not have your best interests at heart. Discover why retirement planning is never one-size-fits-all and how to protect your future from hidden fees...

Are you afraid of running out of money in retirement? Dive into the real anxieties retirees face, from “plutophobia” to the emotional shift of losing a steady paycheck. Gary Garland unpacks strategies to conquer retirement fears, balance spending, and avoid common pitfalls like overreacting to market headlines and hidden tax traps. Discover how to enjoy your golden years with confidence and financial clarity.

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Think retirement is one-size-fits-all? Think again. Discover how everyday products—and your financial future—can thrive when you think outside the box. Host Gary Garland shares surprising stories and practical strategies to help you avoid cookie-cutter retirement plans, sidestep risky gambles, and build a secure, personalized future. Learn why “boring” investments might be your best bet and how to answer the...

Are you ready to spend your retirement your way? In this episode, Gary Garland dives into the real-life choices retirees face—whether to splurge, save, or find a balance. From bucket lists and unexpected expenses to quirky side gigs and the importance of a solid income plan, discover how to make the most of your golden years without regret. Tune in for practical tips, laughs, and a fresh perspective on enjoying retirement on ...

Are you playing it too safe with your retirement—or risking more than you realize? On this episode of Your Retirement, Your Way Podcast, Gary Garland unpacks why knowing your true risk tolerance and understanding tax strategies can make or break your retirement. Hear real-life stories, practical advice, and learn how to build a plan that fits your unique needs—so your retirement truly is your way.

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Are you letting AI make decisions about your retirement? Discover why real wisdom—not just algorithms—matters when planning your future. In this episode, Gary Garland breaks down the four essential questions every retiree must answer: income longevity, asset allocation, tax efficiency, and legacy planning. Learn how personalized advice and real-life experience can protect your retirement dreams from costly mistakes and ...

What if everything you thought you knew about retirement planning was outdated—or even harmful? In this episode of Your Retirement Your Way, Gary Garland unpacks the myths around tax laws, mutual funds, the 4% rule, and retirement savings goals. From phantom income to bacon-based longevity strategies, Gary blends legal insight with humor to help listeners rethink how they plan for the next 30 years. Whether you're nearin...

What if your retirement plan is missing what you don’t even know you don’t know? On this episode, Gary Garland dives into the hidden risks of retirement planning—from market volatility and 401(k) fees to the underestimated impact of lifestyle choices. Learn how to avoid common pitfalls, explore smarter investment options, and rethink what “retirement your way” really means.

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Is your retirement plan built on certainty—or just hope? In this episode, Gary Garland breaks down the risks of chasing market highs and the value of boring, steady returns. From annuities and guaranteed income to avoiding financial fads and TikTok “thinfluencers,” Gary shares practical strategies for protecting your nest egg. Learn why “slow and steady” isn’t just a cliché—it’...

What if the biggest threat to your retirement isn’t running out of money—but not knowing how to manage what you have? In this episode, Gary Garland breaks down the psychology and strategy behind retirement spending, guaranteed income, and the hidden traps of financial planning. From the sandwich generation’s caregiving crunch to the dangers of overcomplicated portfolios, Gary offers insights to help you simplify, ...

What if your legacy could shape three generations—without waiting until you're gone? In this episode, Gary Garland explores the evolving mindset around giving while living, from skipping a generation in estate planning to the emotional and financial impact of gifting now versus later. He shares practical strategies like 529 plans, trusts, and tax-loss harvesting, while also reflecting on what retirement really means beyond th...

What does President Trump’s “One Big Beautiful Bill” mean for your retirement strategy? Gary Garland breaks down the tax law’s long-term impact, including Roth conversions, Social Security taxation, and market volatility. From the risks of tech-heavy portfolios to the potential of interest-sensitive annuities, this episode offers a candid look at how to protect your future in uncertain times. Whether you're ...

On this episode of Your Retirement, Your Way Podcast, Gary discusses the critical aspects of retirement planning, focusing on the psychological impact of market volatility, the importance of understanding sequence of returns risk, and the hidden costs associated with 401(k) plans. He emphasizes the need for personalized retirement strategies, the benefits of IRAs over 401(k)s, and the significance of proactive planning to ensure a ...

On this episode of the Your Retirement Your Way Podcast, Gary discusses the critical decisions facing baby boomers as they approach retirement, particularly regarding Social Security and income planning. He emphasizes the importance of creating a customized income plan based on individual circumstances and the need for guaranteed income in retirement. The conversation also touches on the concept of refinancing retirement strategies...