Taxes, AI, and Artemis: A Surprisingly Hopeful Look at the Future

Retirement planning can feel like a roller coaster. One day the market is up, the next day a headline tells you the sky is falling. In this episode of The Own Your Retirement Show, Josh Bretl and Mark Elliott take on that emotional tug-of-war with something rare in today’s financial news: optimism.

Finding Optimism in an Uncertain World

Josh begins the show with a story about his daughter Maggie’s Greek mythology project. Watching her confidently present as Artemis reminded him that growth comes from new experiences, and the same can be true for investors facing today’s rapidly changing world. Despite headlines that make it sound like everything is falling apart, Josh argues that there’s plenty to be optimistic about.

Yes, the news can be depressing. But Josh points out that we often overlook the positive changes happening around us. Technology, especially artificial intelligence, is driving productivity and innovation across industries. Costs are coming down, efficiencies are going up, and that’s good news for companies, investors, and retirees who depend on healthy markets.

He compares today’s technological transformation to the invention of the printing press or the dawn of the internet: disruptive at first, but ultimately good for long-term growth. Add in some consistency in tax law and steady progress on inflation, and you have a foundation that supports optimism instead of panic.

The Importance of Long-Term Thinking

Josh and Mark emphasize a key theme: stop worrying about every headline and focus on the long game. While short-term events like elections, tariffs, or market swings can feel overwhelming, successful retirees plan for decades, not days. The “Own Your Retirement” planning process focuses on five core areas:

• Income: Knowing where your money will come from and how long it will last.
• Investments: Keeping your portfolio aligned with your goals and risk tolerance.
• Taxes: Managing taxes across your lifetime, not just year by year.
• Healthcare: Accounting for the true cost of care, including Medicare and IRMAA.
• Legacy: Ensuring your family is protected and your wealth is passed efficiently.

By keeping these areas connected, Josh helps retirees build plans that can adapt to change instead of reacting to fear.

Taxes: The Silent Partner in Retirement

A big part of this episode dives into taxes. Josh explains that for most retirees, taxes are their single largest expense, and one of the few they can actually control. He highlights common pitfalls like the “tax torpedo,” when higher income causes your Social Security benefits to become taxable, and IRMAA, the Medicare surcharge that surprises many retirees.

He also stresses the power of tax diversification, keeping money spread across taxable, tax-deferred, and tax-free accounts. That flexibility allows you to make smarter decisions each year about where to withdraw income. And for some, Roth conversions can turn future tax uncertainty into long-term peace of mind.