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The Long Game in Retirement

The Long Game in Retirement is hosted by financial advisor Jaime Cowper, who brings clarity, calm, and straight-talk to the topics that matter most: income planning, tax strategy, Social Security, market risk, and building a retirement that actually supports your life.

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  • How To Stop The Government From Stealing Your Children's Inheritance
    6/9/26

    How To Stop The Government From Stealing Your Children's Inheritance

    You have spent decades building your retirement savings, but have you considered what happens to your IRA or 401K when your kids inherit it? Since the SECURE Act of 2019, non-spouse beneficiaries must withdraw the full balance within ten years, often during their peak earning years. That could push them into a higher tax bracket and send a significant portion of your legacy straight to the IRS. Jaime Cowper, a financial advisor with over 20 years of experience helping retirees plan with confidence, walks through exactly how the inherited IRA rules work now and explores a life insurance strategy that could help families pass wealth in a more tax efficient way. She shares a real client example where a couple used a survivorship policy to create $1 million in income tax free benefits for their four children. If you are thinking about retirement income planning, estate strategy, or how to protect your family's inheritance from unnecessary taxes, this episode was made for you.

  • How to Find a Financial Advisor Who Actually Understands You
    6/2/26

    How to Find a Financial Advisor Who Actually Understands You

    Retirement planning is personal, yet so many people work with advisors who talk over their heads, rush through meetings, or never ask what matters most to them. If you've ever left a financial conversation feeling more confused than when you walked in, this episode will resonate. Jaime Cowper, a financial advisor, shares why the advisor-client relationship is just as important as the retirement strategy itself. She explains what draws people to advisors who prioritize listening and patience, shares real stories from clients who found clarity after feeling overlooked, and discusses her work mentoring more women into the financial planning space. This episode is for anyone approaching retirement who wants to feel truly understood by the person helping guide their financial future.

  • What Sets a Great Financial Advisor Apart from an Average One?
    5/26/26

    What Sets a Great Financial Advisor Apart from an Average One?

    You might not be unhappy with your current financial situation, but there is a difference between "fine" and truly confident. Many people approaching retirement sense they could be getting more from their planning relationship but are not sure what that looks like. In this episode, Jaime Cowper, a financial advisor with over 20 years of experience, shares a story about a couple who switched advisors not because anything was wrong, but because they wanted the kind of retirement confidence they kept witnessing in others. Jaime explores what it means to build peace of mind on purpose through clear communication, consistent reviews, and a retirement plan that actually makes you feel secure. If you are a pre-retiree wondering whether your current plan is truly serving you, this one was made for you.

  • How To Achieve Peace of Mind in Retirement
    5/24/26

    How To Achieve Peace of Mind in Retirement

    Retirement planning involves more than simply saving money. It also requires a thoughtful approach to income, withdrawals, risk, and long-term decision-making. In this episode, Jaime Cowper discusses three important elements of retirement planning: a strategy, an income plan, and ongoing guidance. She explains the role of different financial buckets, the importance of distribution planning, and why many people benefit from greater clarity as they approach retirement. This episode is designed to help viewers better understand the planning considerations involved in retirement.

  • How to Maximize Social Security as a Married Couple (The Survivor Benefit Strategy)
    5/19/26

    How to Maximize Social Security as a Married Couple (The Survivor Benefit Strategy)

    If you and your spouse are approaching retirement, there is a good chance you are thinking about Social Security as two separate decisions. Most couples do. But that approach can quietly cost the surviving spouse for years, and most people never realize it until it is too late to fix. In this episode, Jaime Cowper covers the survivor benefit and why it should be the centerpiece of any couple's Social Security strategy. She walks through a real client example where one spouse nearly filed too early, explains why retirement and Social Security are not the same decision, and shares a simple framework for thinking about when each spouse should consider filing. If you are a couple trying to figure out Social Security timing, this episode was made for you.

  • The 3 Layers of Diversification Every Retiree Needs
    5/12/26

    The 3 Layers of Diversification Every Retiree Needs

    You might have a dozen funds spread across multiple accounts and still not be truly diversified. If your retirement portfolio is concentrated in one asset class, one risk level, or one tax category, you could be more exposed than you realize. In this episode, Jaime Cowper, a financial advisor who has spent over 11 years helping clients plan for retirement, explains the three layers of real diversification: asset class variety, risk category alignment across accounts, and tax qualification balance. Jaime walks through why so many pre-retirees unknowingly hold overlapping investments and how a thoughtful bucket strategy can help create more balance. If you are approaching retirement and want to understand whether your portfolio is actually working the way you think it is, this one is for you.

  • How to Talk to Your Aging Parents About Their Finances
    5/6/26

    How to Talk to Your Aging Parents About Their Finances

    There is a financial conversation most adults know they need to have with their aging parents, and almost no one has it early enough. Whether it is scattered accounts, unknown passwords, or outdated beneficiaries, the cost of waiting is measured in stress, lost time, and sometimes real money. In this episode, Jaime Cowper walks through a real client story where a son discovered his 90 year old father's accounts were far more aggressive than anyone realized. Jaime explains four practical steps to start this conversation with respect and clarity, covering everything from power of attorney to estate planning basics like gifting strategies and beneficiary designations. If you are an adult child wondering how to bring up money with aging parents, this episode was made for you.

  • Should You Retire Early or Keep Working? (How to Decide)
    4/28/26

    Should You Retire Early or Keep Working? (How to Decide)

    You have worked hard, saved well, and now the question is simple but heavy: can you actually retire when you want to? Most people approaching retirement have no clear answer, and that uncertainty can lead to either staying too long or leaving too soon. In this episode, Jaime Cowper, a financial advisor with over 20 years of experience, walks through how to evaluate whether early retirement is realistic for your situation. She breaks down the three options available when income doesn't yet cover expenses, shares a real client story about an ER nurse who reshaped her retirement timeline, and explains why the emotional side of retirement planning matters just as much as the math. If you are within a few years of retirement and wondering whether to stay or go, this episode brings the clarity you need to make that decision with confidence.

  • The Most Expensive Thing Retirees Don't Plan For (4 Reasons People Avoid It)
    4/19/26

    The Most Expensive Thing Retirees Don't Plan For (4 Reasons People Avoid It)

    You insure your car, your home, and maybe even your pet, but what about the care you might need when you can no longer take care of yourself? With nearly 70% of people turning 65 expected to need some form of long term care, this is one of the most important and most avoided conversations in retirement planning. In this episode, Jaime Cowper breaks down what long term care actually means, why health insurance and Medicaid likely won't cover it, and how newer hybrid policies have changed the landscape. She walks through real cost ranges, the Medicaid five year lookback rule, tax benefits, and the partnership programs most people have never heard of. If you're approaching retirement and wondering how to protect your savings and your family from one of retirement's biggest unknowns, this episode was made for you.

  • Will You Run Out of Money in Retirement? (The Four Variables That Determine It)
    4/14/26

    Will You Run Out of Money in Retirement? (The Four Variables That Determine It)

    Running out of money is the number one fear retirees report, even above health concerns. Many people who are in perfectly good financial shape still find themselves unable to enjoy what they have saved. Jaime Cowper, a financial advisor who specializes in retirement income planning, walks through the four key variables that drive this fear and explains how a simple one page income plan can bring clarity to where your money comes from each month. She covers longevity expectations, spending habits, sources of guaranteed income like Social Security and pensions. If you have done well financially but still feel uneasy about spending in retirement, this one was made for you.

  • Is Social Security Actually Running Out? (What the Data Shows)
    4/7/26

    Is Social Security Actually Running Out? (What the Data Shows)

    If you have heard that Social Security is running out and wondered whether you should claim your benefit early before it disappears, you are not alone. It is a common fear among pre-retirees, and the headlines only make it worse. In this episode, Jaime Cowper, walks through what the latest trustee report actually says about Social Security solvency, what a worst case scenario really looks like, and why fear driven decisions about when to claim can lock you into a lower benefit for life. She also shares a real client story that reveals how some advice about claiming early may not be in your best interest. If you are approaching retirement and trying to figure out your Social Security strategy, this episode brings the clarity you need.

  • The 6 Major Risks Every Retiree Needs to Know About
    3/31/26

    The 6 Major Risks Every Retiree Needs to Know About

    You have worked hard to build your savings, but do you actually know what could put your retirement at risk? In this episode, Jaime Cowper, a financial advisor and certified long term care specialist, breaks down the six major retirement risks: longevity, market volatility, inflation, taxes, health care costs, and personal circumstances like the loss of a spouse. Jaime explains why having different income buckets matters, how the widow tax surprises families, and why shifting everything to bonds may not solve the inflation problem. If you are close to retirement and want to understand what you are really planning for, this episode was made for you.