Most people don’t have a bad retirement plan; they just haven’t tested it yet. In this episode, Josh Leonard walks through what it really means to pressure-test your retirement plan before you step away from work. Using a real client story, he breaks down how a plan that looks solid on paper can still carry …
Markets move fast, headlines move faster, and emotions often follow. So how do you stay grounded when uncertainty feels constant and every decision seems urgent? In this episode, Josh Leonard speaks with Dominic Pappalardo, Chief Wealth Strategist at Morningstar Wealth, about maintaining discipline during volatile markets. They break down a bucket-based investment approach, the importance …
A tax return can reveal more than what happened last year; it can point to choices that may help reduce friction and improve retirement income over time. What hidden issues could be sitting in your paperwork, and what small moves today could help you avoid bigger tax headaches later? In this episode, Josh Leonard explains …
What if “just one more year” at work costs you more than it gives you? In this episode, Josh Leonard challenges one of the most common retirement assumptions, the idea that working one more year is always the safer choice. While extra income can feel reassuring, delaying retirement can quietly take time, health, energy, and …
If you have ever thought, “I make good money, so why does this still feel complicated?”, you are not alone. In this episode, Josh Leonard breaks down why higher income often brings more friction, not less, and why success can quietly add complexity to your financial life if it is not coordinated with intention. In …
Big goals often feel exciting at the start, but how many actually make it past February? What separates the intentions that fade from the habits that last? In this episode, Josh Leonard breaks down the SMART goal framework and shares his personal goals for the year, from conquering Pittsburgh’s Dirty Dozen bike race to building …
Big goals often look simple until you are in the middle of them, tired, uncertain, and second-guessing everything. How do you stay steady when the plan shifts? How do you prepare for the parts you cannot predict? In this episode, Josh Leonard shares how a grueling 60-mile mountain bike race deepened his view on preparation, …
Planning for retirement comes with many choices that can shape long-term comfort and confidence. Small shifts in timing, taxes, and income strategy can influence how well your resources support the life you want to enjoy. In this episode, Josh Leonard breaks down how Social Security fits into a broader retirement plan for high-net-worth individuals, explaining …
The end of the year can bring financial stress, but it’s also a valuable time to take control of your retirement strategy. In this episode of Relax, It’s Retirement, Josh Leonard walks through year-end tax planning steps that can make a real difference for retirees. From RMDs and charitable giving to Roth conversions and managing …
When you hit a milestone, you pause to reflect. In this special 100th episode, Josh Leonard is joined by his father, Bill Leonard, whose work laid the foundation of what is now the Leonard Advisory Group. Together, they revisit the firm’s humble beginnings, envelopes licked in a basement, meetings around kitchen tables, and the evolution …