Should you convert your entire traditional IRA or 401(k) to a Roth at once—or spread Roth conversions over several years?

In this episode, Dan Wendol of Dolphin Financial Group explains why a large one-time Roth conversion can create unintended tax consequences and why a strategic, multi-year Roth conversion plan may make more sense for many retirees and pre-retirees.

A Roth conversion can be a valuable retirement tax-planning strategy, but the amount you convert matters. A large conversion increases taxable income in the year of the conversion and could push some income into higher federal tax brackets. For retirees, it may also affect Medicare IRMAA surcharges, the taxation of Social Security benefits, and other income-based tax thresholds.

Dan walks through seven important factors to consider before converting a traditional IRA or 401(k) to a Roth.

The Social Security funding problem has been discussed for decades, but the projected trust fund depletion date is getting closer. In this episode, Dan Wendol examines the PROMISE Act of 2026 and what this proposed legislation could mean for Social Security, retirees, and Americans who are currently planning for retirement.

Thinking about claiming Social Security before your full retirement age while continuing to work?

Many retirees are surprised to learn about the Social Security earnings limit, also known as the Retirement Earnings Test. If you claim benefits early and continue earning wages, your monthly Social Security checks may be temporarily reduced—or even withheld.

Retirement planning isn't just about saving enough money—it's also about creating a life you'll truly enjoy living.

In this episode, Dan discusses one of the most overlooked aspects of retirement: the disenchantment phase. After the excitement of retirement fades, many retirees experience boredom, loneliness, loss of identity, or a lack of purpose. These emotional challenges are far more common than many people realize, yet they're rarely discussed during retirement planning.

You'll learn why these feelings occur, how they can affect your physical and emotional well-being, and five practical strategies to help build a more meaningful retirement. Whether you're already retired or planning for retirement in the coming years, this conversation will help you prepare for more than just the financial side of retirement.

The federal government has introduced Trump Accounts, a new retirement savings account designed specifically for children. But how do these new accounts work, who qualifies for the federal 1,000 contribution, and are they actually better than a Roth IRA, 529 plan, or UTMA account?

In this video, Dan explains the new Trump Accounts established under the 2026 legislation, including eligibility requirements, contribution limits, investment restrictions, tax treatment, and how they compare with other popular child savings strategies.

Whether you're a parent, grandparent, or simply planning ahead for your family's financial future, understanding these retirement savings options can help you make more informed decisions.

Could the United States eventually adopt a retirement system similar to Australia's?

In this video, Dan explores how Australia's Superannuation system works, how it differs from Social Security, why it's receiving attention, and what Americans can learn from one of the world's highest-rated retirement systems.

You'll discover how Australia's mandatory retirement savings compare with Social Security, the advantages and disadvantages of each approach, and why building your own retirement savings may become even more important regardless of future government changes.

In this inspiring episode of Real Retirement Stories, we sit down with Cheri, a Florida-based retiree who left her corporate job at age 62 to pursue a non-traditional retirement filled with slow travel, adventure, and intentional living. Now 64 and two years into retirement, Cheri shares her path from dreaming about international travel during COVID isolation to actually pulling the trigger after her mother's passing.

For years, investors accepted stock market volatility because the potential rewards significantly exceeded what safer investments could offer. But today's environment is different. With Treasury bonds, CDs, and fixed-income investments paying attractive yields, the traditional stock market risk premium has narrowed dramatically.

In this episode, Dan discusses what the shrinking risk premium means for retirees, why fixed income deserves another look, and how investors should evaluate their portfolio allocation in today's market environment.

If you're retired or approaching retirement, this conversation may help you determine whether your current mix of stocks and fixed-income investments still aligns with your goals and income needs.

Are you worried that Social Security won't be enough to support your retirement lifestyle?

In this video, Dan Wendol explains four practical ways retirees can create reliable income streams beyond Social Security. Learn how retirement savings, pensions and annuities, home equity, and even part-time work can help fill retirement income gaps and provide greater financial confidence.

If you've been wondering where your retirement paycheck will come from, this discussion walks through real-world strategies that can help create dependable income throughout retirement.

The Social Security Board of Trustees released its latest report, and the news isn't encouraging. The projected depletion date for the Social Security trust fund has moved closer, with the Old-Age and Survivors Insurance Trust Fund now projected to be depleted in 2032.

What does this mean for current retirees, future retirees, and anyone planning for retirement?

In this video, Dan breaks down the latest Social Security Trustees Report, explains why the projections have changed, discusses the demographic challenges facing the program, and outlines what retirees should be thinking about as they build a retirement income strategy.