Relax, It’s Retirement Podcast

Summer often brings vacations, family activities, and unexpected expenses, making it easy to lose sight of financial goals.  Taking a few proactive steps before spending ramps up can help you avoid unnecessary taxes, overlooked opportunities, and preventable financial headaches. In this episode, Josh Leonard and Pete Belcastro explore five financial questions to ask before summer gets into full sw...

Owning multiple mutual funds doesn’t mean you have a diversified retirement plan, and for many retirees, it can create surprises they never saw coming. In this episode, Josh Leonard sits down with Leonard Advisory Group CFP® Peter Belcastro to unpack the five common problems they see with mutual funds, especially for people nearing or living in retirement. While mutual funds can be a great startin...

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 hidden risks if it hasn’t been coordinated across income, taxes, investments, healthcare, a...

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 of long-...

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 how a closer look at your tax return can uncover planning opportunities befo...

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 meaningful experiences you may never get back. Josh walks through real cli...

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 this episode, Josh walks through what he commonly sees with high earners who are cap...

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 non-negotiable daily habits. He explains how this same intention...

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, mindset, and the importance of thinking ahead. He talks about the parallel...

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 how timing, tax brackets, portfolio d...

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 Medicare costs, Josh highlights how intentional planning today can l...

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 into a practice that now helps hundreds of families retire w...

Earning a high income doesn’t automatically translate to lasting wealth. The real challenge is how to transform those peak earning years into a retirement filled with stability and freedom. In this episode, Josh Leonard shares three practical strategies to reduce taxes now and build wealth for the long term. From maxing out tax-advantaged accounts to using charitable giving vehicles and understand...

Tax law changes are here, some good, some complicated.  But one thing’s for sure: now is the time to adjust your plan. In this episode, Josh Leonard breaks down the One Big Beautiful Bill Act and what it means for those nearing or entering retirement. From enhanced deductions to planning around RMDs and Social Security, he outlines six crucial areas that deserve your attention now. Josh covers: Ho...

What if your child said “I love you” for the first time thanks to an iPad? That’s just one of the many moments families experience with Variety’s life-changing programs. In this episode, Josh Leonard sits down with Tom Baker, CEO of Variety the Children’s Charity of Pittsburgh, to share powerful stories about helping children with disabilities participate in everyday joys like riding a bike, going...

Retirement isn’t just an end, it’s the beginning of everything you’ve always wanted to do.  What if you could approach this next chapter with purpose and confidence, not just hope?  In this episode, Josh Leonard breaks down the True Intent Planning System and its five pillars for a purposeful retirement. He emphasizes the importance of planning for income, investments, taxes, healthcare, and estat...

New laws have reshaped retirement planning, and staying informed could mean the difference between saving money and paying avoidable taxes. In this episode, Josh Leonard explains the impact of Secure Act 1.0 and 2.0 on retirement planning and why constant plan updates are necessary. He highlights how changes to RMD ages, IRA rules, and Medicare surcharges can affect retirees, especially those who...

Retirement can be a time of reflection and purpose, where intentionality meets impact. What if your golden years were not just for relaxation but a journey to uplift others while enriching your own life? This episode reveals how retirement and service can harmoniously coexist. In this episode, Josh Leonard speaks with Matthew Reichart, Executive Director of Pine Valley Camp, and Julie Saenz about...

Market swings, inflation, and shifting headlines can make retiring this year feel uncertain. But with the right plan, you don’t need to delay your goals — even in a tough market. Are you prepared financially and mentally for what comes next? In this episode, Josh Leonard shares how to build a flexible retirement strategy that can weather short-term challenges while aligning with your values and li...

Buying a car can be exciting, but it can also be financially confusing, especially as you enter retirement. How do you decide between leasing, buying new, or buying used? What financial factors should retirees consider before making a vehicle purchase? In this episode, Josh Leonard guides listeners through the key financial and personal considerations when choosing a new vehicle in retirement. He...

Worried about market volatility and what it means for your retirement?  You’re not alone. Many people get anxious when their retirement accounts seem to shrink after years of growth. In this episode, Josh Leonard discusses market volatility and strategies to remain patient. Josh explains what market corrections are, why they happen, and how to prepare for them. He also details the bucket str...

Are your finances due for a little spring cleaning? Just like airing out your home after winter, it’s time to dust off your financial strategy! Join Josh Leonard as he dives into five key tips for a fresh start this spring. He explores ways to tidy up old retirement accounts, refresh your financial planning outlook, and manage risk in a market full of surprises. Josh covers: Consolidating ou...

Could saving smart lead to a tax nightmare?  Join Josh Leonard as he unravels the unexpected “Good Saver Tax Problem” that even the most prepared might face. Josh explores strategies to sidestep surprise tax burdens during retirement. Dive into proactive approaches like phase-based tax stacking and unravel the complexities of Roth conversions, Required Minimum Distributions (RMDs), and...

Social Security remains a critical foundation for retirement, but recent changes bring new opportunities and challenges for retirees. What strategies can maximize your Social Security benefits? How do recent legislative changes impact your retirement income plan? In this episode, Josh Leonard explains the updates to Social Security regulations, including the removal of provisions like WEP and GPO,...

Retirement should be a time of fulfillment, not financial stress, yet many retirees face unexpected challenges. How can you make decisions today that your future self will thank you for? What steps can you take to avoid common retirement regrets and financial pitfalls? In this episode, Josh Leonard and Pete Belcastro discuss essential retirement planning strategies, from managing healthcare costs...