E.A.S.E. Into Retirement Radio Show

Retirement is more complex than ever in today’s economy. What works for one person may not work for another—especially for small business owners. In this episode, we explore the evolving retirement landscape, highlight key challenges many business owners face, and take a deep dive into the unique financial and planning obstacles entrepreneurs encounter as they prepare for life after business. Whet...

A solid retirement plan isn’t complete without a well-crafted estate plan. In this episode, we break down why planning and protecting your legacy is just as important as building it. From living trusts and powers of attorney to tax-smart strategies and long-term care, discover the tools that ensure your wishes—and your wealth—are honored well into the future. Chapters00:00 Why an Estate Plan is so...

In this episode, we uncover the “investment crimes” you may be committing without realizing it—like chasing unrealistic returns, neglecting taxes, or relying on windfalls. Using infamous criminals like Al Capone, the Wolf of Wall Street, and D.B. Cooper as cautionary tales, we highlight what not to do with your money in retirement—and how to stay financially free. Chapters00:00 Investment Crimes Y...

In Part 2, Tom & Kristin reveal the biggest retirement mistakes retirees are making that they regret the most. Hindsight is 20/20, so take a listen so you can avoid the mistakes and take the steps you need to enjoy retirement regret free! You’ll learn details & strategies on:✅Social Security✅Taxes✅ROTH Conversions✅Long Term Care Chapters00:00 The Biggest Retirement Mistakes Retirees Re...

Tom & Kristin discuss the biggest retirement mistakes retirees are making that they regret the most. Since hindsight is 20/20, take a listen and learn what they are so you can avoid the mistakes, and take the steps you need to enjoy retirement regret free! Chapters00:00 The Biggest Retirement Mistakes Retirees Regret Making05:50 Mistake #1 15:50 Mistake #2 32:40 Mistake #3 41:05 Mistake #4 #Re...

Learn how to avoid a tax avalanche in retirement! We cover smart strategies to reduce taxes, the impact of income brackets, legislative risk, the rise of Roth accounts, and why tax planning beats tax prep. Plus, how RMDs and ROTHs fit in—and a look at EaseMyTaxBill.com. Tune in to learn how you can take control and ease the weight of taxes in retirement. Chapters00:00 – How to Save on TAXES in Ret...

𝗪𝗼𝗿𝗿𝗶𝗲𝗱 𝗮𝗯𝗼𝘂𝘁 𝗿𝗲𝘁𝗶𝗿𝗶𝗻𝗴 𝗱𝘂𝗿𝗶𝗻𝗴 𝗮 𝗱𝗼𝘄𝗻 𝗺𝗮𝗿𝗸𝗲𝘁? Market volatility can feel like a gut punch when you’re close to retirement. In this episode, we’re sharing 5 practical things you can do right now to protect your retirement savings and regain control of your plan—even when the market is tumbling. We cover how to adjust your retirement strategy, delay withdrawals, diversify income, and use powerful too...

Women face a very different retirement reality than men — and it’s not just about living longer. On average, women:•Have less saved for retirement due to caregiving roles and time out of the workforce•Receive smaller Social Security checks•Often feel less confident about financial decisionsIn this eye-opening episode, we explore the unique financial challenges women face in retirement — and the cr...

Taking money out of your retirement accounts before age 59 ½ usually triggers a 10% early withdrawal penalty – the good news is there are actually 20 (and soon to be 21) instances where you can AVOID the penalty! In part 2 of our 2-Part series, retirement experts Tom Mosley and Kristin Oakley walk you through more of the real-life situations where early withdrawals from your IRA, 401K, 403(b), and...

Taking money out of your retirement accounts before age 59 ½ usually triggers a 10% early withdrawal penalty – but what if life gives you no choice? In this episode retirement experts Tom Mosley and Kristin Oakley walk you through the real-life situations where early withdrawals from your IRA, 401K, 403(b), and other “4-plans” may be penalty-free. From medical emergencies to disaster relief, disco...

Knowing how and when to claim your Social Security is one of the most important retirement decisions you’ll make. In today’s video, retirement expert Tom Mosley breaks down the key things you need to consider before locking in your benefits. •The truth on Social Security “going broke” – what’s fact vs. fiction•How to determine the best age to claim Social Security for your situation•Why you won’t...

Rollercoasters can be fun - until they aren’t. 𝗧𝗵𝗮𝘁’𝘀 𝗲𝘀𝗽𝗲𝗰𝗶𝗮𝗹𝗹𝘆 𝘁𝗿𝘂𝗲 𝘄𝗵𝗲𝗻 𝗶𝘁 𝗰𝗼𝗺𝗲𝘀 𝘁𝗼 𝗿𝗲𝘁𝗶𝗿𝗲𝗺𝗲𝗻𝘁 𝗶𝗻𝘃𝗲𝘀𝘁𝗶𝗻𝗴 𝗱𝘂𝗿𝗶𝗻𝗴 𝗺𝗮𝗿𝗸𝗲𝘁 𝗱𝗼𝘄𝗻𝘁𝘂𝗿𝗻𝘀. While the ride up is exhilarating, the dips can leave you anxious & fearful. In this episode, retirement expert Tom Mosley shares practical tips and strategies to help you navigate market volatility in retirement without derailing your plans. ✅ Learn why going t...

In this follow-up to last week’s episode on Risks in Retirement, we dive even deeper into the challenges that can derail your retirement plans if you're not prepared. This week, we focus on housing and real estate risks, including:🏡 The rising costs of homeowners insurance and home repairs🔁 The pros and cons of owning vs. renting in retirement🚚 The risks that come with relocating out of state💸...

Retirement today presents more challenges than ever before. Without a strong plan, you could face unexpected obstacles that threaten your financial security and lifestyle. Last week we discussed risks associated with longevity, investments & the market, Taxes, and health. In today’s show, we add two more critical risks facing modern retirees:✅ Spending & Budget Risks – Are you overspendin...

Retirement should be a time of freedom and enjoyment, but without the right plan, unexpected risks can derail your financial future. In this video, we break down 4 key risks that modern retirees must navigate:✅ Longevity & Life Expectancy Risk – Will your money last as long as you do?✅ Investment & Market Risk – How do you protect your savings from volatility?✅ Tax Risk – Could rising t...

As you shift from building your nest egg to living off it, understanding and managing risk becomes critical. In this episode, we break down the biggest risks retirees face—and how they can derail your retirement if you're not prepared.👉 Topics we cover:✅ Why many stay in “accumulation mode” too long✅ The real danger of Sequence of Returns Risk✅ How working with a retirement-focused advisor dif...

💼 The Treasure of a Hidden or Forgotten 401K 💼Did you know the average person has 3 to 5 forgotten 401Ks? If you’ve ever changed jobs, there’s a good chance you’ve left behind valuable retirement savings without even realizing it! In this episode, we uncover the hidden treasure of old and forgotten 401K accounts—why they get left behind, the risks of managing multiple plans, and how to track the...

Retirement savings have changed dramatically over the decades. Gone are the days when most workers could count on a pension to fund their golden years. Today, the responsibility of saving for retirement largely falls on you—through 401(k)s, IRAs, and personal investments. But what led to this shift, and how does it impact your financial future? In this episode, we break down:✅ The rise and fall o...

Retirement is complicated—especially when it comes to Social Security. With changing rules and the looming threat of decreased benefits, when is the right time to take Social Security? Should you maximize or optimize your benefits? In this episode, we break it all down—helping you determine the best timing for your situation. Plus, we dive into why working with a financial advisor can make a real...

Retirement today looks nothing like it did for previous generations. Pensions are rare, Social Security faces uncertainty, and the responsibility of saving falls squarely on our shoulders. So how do you ensure you have enough to retire comfortably? In this episode, Tom & Kristin break down the biggest challenges facing retirees today—market volatility, increasing healthcare costs, longevity, a...

Retirement is about more than just saving money—it’s about creating a strategy that helps you keep more of what you’ve earned. In this episode, retirement experts Tom Mosley & Kristin Oakley tackle three critical topics that can make or break your retirement: Taxes, Risk, and Social Security.🔹 Taxes: Planning vs. Preparation – Are you an archeologist or an architect when it comes to your reti...

Are you ready to rethink retirement? For decades, the traditional path has been to work hard until your 60s, then retire completely. But with longer life expectancies and the desire for better work-life balance, this all-or-nothing approach may no longer make sense. In this episode Tom & Kristin dive into why semi-retirement could be your best financial and personal move. We’ll explore the ben...

Interest rates have shifted—so what does that mean for your retirement strategy? In this episode, we break down the concept of refinancing your retirement and how it differs when rates are low versus when they’re high. Whether you’re looking at annuities, bank investments, or Roth conversions, understanding the right move for your financial future is key. Here’s what we cover: ✅ How today’s inter...

Planning for retirement goes beyond saving money—it's about having a strategy to tackle the big challenges. In this episode, retirement experts Tom Mosley and Kristin Oakley cover: ✅ Taxes: Strategies to minimize your tax burden. ✅ Inflation: Tips to protect your purchasing power. ✅ Longevity: Solutions to avoid running out of money. ✅ The Power of a Plan: How a well-crafted retirement bluepri...

𝗔𝗿𝗲 𝘆𝗼𝘂 𝗮𝘀𝗸𝗶𝗻𝗴 𝘆𝗼𝘂𝗿𝘀𝗲𝗹𝗳, “𝗛𝗼𝘄 𝗗𝗼 𝗜 𝗞𝗻𝗼𝘄 𝗶𝗳 𝗜 𝗛𝗮𝘃𝗲 𝗘𝗻𝗼𝘂𝗴𝗵 𝘁𝗼 𝗥𝗲𝘁𝗶𝗿𝗲?” While studies show that a large majority of current retirees feel they have enough to live comfortably, other studies show that less than half of all pre-retirees feel they have enough. With so many viewpoints, Inflation, longer life spans, and unpredictable markets, determining if you have enough money to retire comfortably can...