Relax, It’s Retirement Podcast

Helping your children and grandchildren can become one of the most meaningful parts of retirement, but how much time, money, and energy can you comfortably give?

In this episode, Josh Leonard and Yana Leonard, Chief Risk and Operations Officer at Leonard Advisory Group, explore how grandparents are becoming a bigger part of childcare, family finances, and everyd...

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 B...

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....

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 coordi...

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. ...

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 h...

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...

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.

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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....

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 h...

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...

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 th...

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...

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 Se...

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 powerfu...

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 ret...

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 af...

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 Matth...