Jaime Cowper

The Long Game In Retirement

Education EN ↓ 16 episodes

Weekly episode to help you achieve peace of mind 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.

Author

Jaime Cowper

Category

Education

Latest episode

Jul 7, 2026

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Episodes

#16: Full Retirement Age Hit 67: Here's What That Actually Means For You 07.07.2026

If you have been wondering what the Social Security trust fund headlines actually mean for your retirement, or whether the benefit you have been counting on will really be there, you are not alone. With full retirement age now officially reaching 67 for everyone born in 1960 or later, the questions around timing, claiming, and long-term planning are more relevant than ever. In this episode, Jaime...

#15: The Savings Lesson I Wish Someone Taught Me at 22 (Pass It to Your Kids) 30.06.2026

In this episode, Jaime Cowper walks through a hypothetical side-by-side comparison showing how someone who saved $300 a month for just ten years starting at 22 ended up with more than someone who saved the same amount for 33 years starting at 32. She breaks down the Rule of 72, explains dollar cost averaging, shares age-based retirement savings benchmarks, and offers practical ways to bring up com...

#14: The Hidden Medicare Surcharge That Catches New Retirees Off Guard 23.06.2026

You finally retire, your income drops, and then Medicare charges you hundreds more per month based on what you earned two years ago. That is exactly how IRMAA works, and most people don't find out until the bill arrives. In this episode, Jaime Cowper breaks down how Medicare's income related monthly adjustment amount is calculated, why its cliff structure can be triggered by just $1 over a...

#13: How to Give Your Kids Their Inheritance While You're Still Around to Enjoy It 16.06.2026

You saved well, planned well, and now you're sitting on more than you're likely to spend in your own lifetime. But if you haven't thought carefully about how to share that wealth while you're still here to enjoy it, you could be missing one of the most rewarding opportunities in retirement planning. In this episode, Jaime Cowper walks through what she calls the Living Inheritance Playbook, explain...

#12: How the Wealthiest Families Pass Down More to Their Kids and Less to the IRS 09.06.2026

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. Ja...

#11: Why Female Advisors Are on the Rise and How to Find One Fluent in You 02.06.2026

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 st...

#10: What Separates a Great Financial Advisor from an Average One in Retirement Planning? 26.05.2026

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 switc...

#9: How to Maximize Social Security if You're Married 19.05.2026

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 Soc...

#8: Are You Really Diversified? Three Layers Most People Miss 12.05.2026

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 diversi...

#7: How to Talk to Your Aging Parents About Money 04.05.2026

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 fat...

#6: How to Plan for Early Retirement: Income, Expenses, and Alignment 28.04.2026

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 real...

#5: The Most Expensive Thing Retirees Don't Plan For: Long Term Care 21.04.2026

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 heal...

#4: How to Address the Top Fear Retirees Have: Running Out of Money 14.04.2026

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 c...

#3: The Truth About Social Security in Retirement 07.04.2026

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, an...

#2: The 6 Risks You Need to Know For Retirement Planning 31.03.2026

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 differen...

#1: How To Achieve Peace of Mind in Retirement 24.03.2026

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 wh...

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