The Retirement Caddie

The retirement you’ve been saving for can get more expensive before you know it. Matt Eilers discusses how rising travel and lifestyle costs can influence retirement spending and why inflation deserves a place in the planning conversation. He also explores balancing today’s bucket-list goals with tomorrow’s expenses, creating retirement income, and determining where annuities may fit based on individual needs rather than a one-size-fits-all approach.

Ready to get out of the rough and get your retirement plan in place? Contact Matt today!

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The most misunderstood retirement tool may be getting judged by outdated opinions. Matt Eilers breaks down the emotional debate surrounding annuities and explains why they should be viewed as financial tools, not labels. He explores how annuities fit into retirement income planning, why today's interest-rate environment has changed the conversation, and the importance of evaluating options based on your goals rather than common misconceptions. Matt also discusses the role of independent advice, income predictability, and the process of determining whether an annuity belongs in a retirement strategy.

Ready to get out of the rough and get your retirement plan in place? Contact Matt today!

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How do you know when you're truly ready to retire, and not just hoping the numbers work out? In this episode, Matt Eilers explains why having a collection of accounts and investments is not the same as having a retirement plan. He discusses creating retirement income, evaluating Social Security timing, accounting for inflation, and stress-testing different retirement scenarios. Matt also explores why outdated retirement rules may not fit today's environment and how understanding the purpose of each asset can help bring greater understanding to retirement planning.

Ready to get out of the rough and get your retirement plan in place? Contact Matt today!

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What if the key to retirement isn't chasing happiness, but creating financial contentment? Inspired by a conversation from Jay Leno, Matt Eilers explores why covering essential expenses should be the foundation of every retirement income plan. He discusses the importance of coordinating income sources, the limitations of relying solely on the traditional 4% withdrawal rule, and how retirees can prepare for market volatility, inflation, taxes, and longevity. Learn why a structured income strategy may help reduce uncertainty and provide better strategies as you transition into retirement.

Ready to get out of the rough and get your retirement plan in place? Contact Matt today!

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That retirement balance may look impressive—but not all of it actually belongs to you. In this episode, Matt Eilers uses a surprising Oscar Awards rule to explain the often‑overlooked reality that Uncle Sam is a silent partner in many retirement accounts. The conversation explores why retirees shift from focusing on growth to focusing on what they keep, how taxes, RMDs, inflation, and healthcare intersect, and why retirement planning needs to go far beyond picking investments. It’s a candid discussion about rules, strategy, and building a plan that reflects this phase of life.

Ready to get out of the rough and get your retirement plan in place? Contact Matt today!

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The biggest threat to a retirement plan may be the costs you never expected to face. In this episode, Matt Eilers discusses how retirees can prepare for healthcare expenses, long-term care needs, and other financial surprises that can emerge later in life. He also explores the role of technology in modern financial planning and shares why legacy planning is about more than passing on assets. Inspired by the life and generosity of Dolly Parton, the conversation highlights how values, family traditions, and charitable passions can become part of the legacy you leave behind.

Ready to get out of the rough and get your retirement plan in place? Contact Matt today!

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Is your retirement plan designed for YOUR life—or just following outdated rules? This episode of The Retirement Caddie with Matt Eilers explores how creative strategies like deferment, intentional tax planning, and personalized income strategies can help you build a retirement that fits your unique needs. Learn why “one-size-fits-all” advice falls short, how to avoid ticking tax time bombs, and why a tailored plan matters more than ever in today’s changing landscape. Discover the power of making your money serve you, not the other way around.

Ready to get out of the rough and get your retirement plan in place? Contact Matt today!

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What if the biggest threat to your retirement isn’t a market crash, but the risks you never planned for? In this episode, Matt Eilers discusses why retirement planning should go far beyond investments and account balances. Using NFL quarterback Josh Allen's approach to preparing for the unexpected, Matt explains the importance of stress-testing your retirement plan against market downturns, healthcare expenses, inflation, taxes, and Social Security changes. The conversation highlights why flexibility matters, how to identify financial blind spots, and why a strong retirement plan is built to adapt when life throws a curveball.

Ready to get out of the rough and get your retirement plan in place? Contact Matt today!

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A surprise buyout, a health change, or even living longer than expected can reshape retirement faster than you think. In this episode, Matt Eilers discusses how major life events can impact your retirement strategy and why every financial decision should fit into a broader retirement plan. From evaluating buyout offers and unexpected lump sums to preparing for the different stages of retirement, Matt shares insights on building a plan that can adapt as your goals, lifestyle, and needs evolve over time.

Ready to get out of the rough and get your retirement plan in place? Contact Matt today!

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Retirement planning should feel less like a trip to the dentist and more like a conversation about what matters most to you. In this episode, Matt Eilers explains why financial planning goes far beyond investment returns and account balances. He shares how understanding your passions, family priorities, travel goals, and lifestyle dreams helps shape a retirement plan that reflects your unique vision. Matt also discusses why retirement planning should be an ongoing process, not a one-time event, and how a personalized approach can adapt as life changes over time.

Ready to get out of the rough and get your retirement plan in place? Contact Matt today!

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