Relax, It’s Retirement Podcast

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 epis...

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 highlights ...

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...

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 chari...

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 ...

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 childr...

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

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...

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 th...

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...

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, w...

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 surp...

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 c...

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 ...

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 discus...