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 client stories and practical planning scenarios that show why one more year is often an emotional decision, not a financial one. He introduces a simple trade-off filter to help listeners evaluate whether delaying retirement truly improves their plan or simply postpones living the life they’ve already earned.
Josh discusses:
Why being financially ready does not always make retiring emotionally easy
How taxes, required distributions, and healthcare can change the math
The hidden cost of delaying retirement when time and health are limited
A three-question framework to evaluate if one more year actually helps
How intentional income planning creates confidence to retire sooner
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 with clarity and confidence.
Key takeaways:
How Bill transitioned from architecture to financial advising
Family lessons that shaped Leonard Advisory Group’s mission
Stories of clients whose planning ensured lasting comfort
The importance of foresight over hindsight in retirement
William Leonard laid the foundation for the Leonard Advisory Group to fill in the gaps he saw when helping his mother plan for retirement. Bill focused much of his career on the insurance and annuity industry. As an independent advisor, he helped thousands of retirees and pre-retirees face the financial challenges that lie ahead with confidence. Since 1996, Bill has worked in a variety of capacities, gaining valuable experience with insurance. In 2007, he became an independent consultant, focusing on income protection and retirement planning. Bill was an honorary host of the “Protecting Your Profits” radio show on 94.5 3WS Pittsburgh and a weekly guest on the national broadcast “Financial Safari” radio show heard locally on NewsTalk 104.7 FM. He has also been featured on WISR 680 AM and WORD FM. In his free time, Bill enjoys traveling, boating, skiing, hiking, biking, restoring antique vehicles, and spending quality time with family, friends, and clients. He has been married to his wife, Cindy, for almost 40 years. They have three children: Zach, Josh, and Zoey, as well as a crazy border collie named Sweep. After over 25 years assisting families transition into retirement Bill transitioned himself into retirement at the end of 2022.
With the large number of clients under our belt, we pride ourselves in adapting and catering to any of our client’s needs, in any circumstances. This is why we work with trusted professionals, as well as other partnered firms such as AE Wealth Management and Morningstar Investment Management.
In this episode, Josh Leonard is joined by some of the key players from his team: Angela Ferrante, Desiree Hoosac and the founder of Leonard Advisory Group, Bill Leonard. They explain what you can expect while working with them as you plan your retirement. Additionally, they talk about some fun events you can look forward to participating in when you join the clientele.
The Leonard Advisory Group team discusses:
Everyone’s individual role within the business and how it all works together
How the Leonard Advisory Group started out
The importance of a close-knit environment among the staff
How we have helped clients no matter what step in their planning process they are at
William Leonard founded Leonard Advisory Group to fill in the gaps he saw when helping his mother plan for retirement. Bill focused much of his career on the insurance and annuity industry. As an independent advisor, he helped thousands of retirees and pre-retirees face the financial challenges that lie ahead with confidence. Since 1996, Bill has worked in a variety of capacities, gaining valuable experience with insurance. In 2007, he became an independent consultant, focusing on income protection and retirement planning. In his free time, Bill enjoys traveling, boating, skiing, hiking, biking, restoring antique vehicles, and spending quality time with family, friends, and clients. He has been married to his wife, Cindy, for almost 40 years. They have three children: Zach, Josh, and Zoey, as well as a crazy border collie named Sweep. After over 25 years assisting families transition into retirement Bill is excited to transition himself into retirement at the end of 2022.
Angela Ferrante is a 1987 graduate of Allegheny College with a degree in Economics and Finance. She started with Equitable Life as an insurance representative 2 weeks after graduation selling life and disability insurance to the medical community. By 2005 she was supervising 165 representatives in 4 states and running the brokerage side of the office which included the opening of accounts, research, trade placement, cashiering of upwards of $2 million per month, as well as her own client base. Angela became an Accredited Investment Fiduciary in 2015. Angela and Mark live in Somerset County where she enjoys skiing, hiking, biking and gardening.
Desiree Hoosac has worked for over 20 years in client service and administrative roles in the financial and medical industries. Her top priority is to provide exceptional service to clients. This includes assisting the team in preparing for client reviews, updating plans and various service items. Desiree resides in New Eagle, Pennsylvania, with her two rescues: Maggie, a Lab mix, and Mittens, her cat. She has a daughter, Deanne, and granddaughter, Eliza. Desiree stays active trying to keep up with her many great nieces and nephews and enjoys golfing with her dad, playing pinochle, reading, spending time with family, history and being outdoors.
