About
Transition Into Retirement
Transition Into Retirement is a comprehensive financial services firm that helps Florida’s soon to be retired and retired residents effectively plan for and prepare for life’s greatest journey.
We understand that retirees face many important decisions that can affect their long-term financial success. Some of these decisions revolve around making investments that will help create a hedge against outliving their income, the impact of inflation, taxation, and rising healthcare costs. As the majority of our clients are retirees with similar concerns, we’ve had the opportunity to gain the skills and experience necessary to provide the help and insight you need when planning for your future.
Our focus is on empowering pre-retirees and retirees towards a safe, secure, and stress-free retirement. We are committed to guiding our clients through the intricate landscape of retirement income planning, protection, and wealth preservation by minimizing unnecessary risks. With a dedicated emphasis on financial literacy and strategic holistic planning, we strive to assist you in making informed and smart decisions that resonate with your goals.
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Our Educational Events
UPCOMING EVENTS
Events in September 2026
- There are no events scheduled during these dates.
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Stress Free Retirement
This book has done for the annuity marketplace what Tax-Free Retirement did for life insurance. The response has been overwhelming. Nearly every person who reads this book wants to schedule a follow up with the person who gave it to them to discuss how this product can enhance their retirement. Don’t miss out! This is the book you have been waiting for. A book that could revolutionize your retirement years.
Browse Our Blog
How Home Sales Are Taxed: What Every Homeowner Should Know
Selling a home is a significant financial event, and understanding the tax implications can help homeowners protect their profit and [...]
Income Tax vs. Capital Gains Tax: What’s the Difference?
Understanding the difference between income tax and capital gains tax is a key part of smart financial planning. While both [...]
Retirement Readiness for Generation X: Overcoming the “Sandwich Generation” Squeeze
As a financial advisor, I've had the privilege of working with many clients from Generation X—the often-overlooked cohort born between [...]
Contact Us
Our experience and expertise can help you customize a plan for retirement, make sure you have enough income to last you for the rest of your life, minimize unnecessary risks, and leave behind a legacy for your loved ones. If you would like to schedule a complimentary, no-obligation consultation or second opinion review, please contact us today.
Office Location:
700 South Rosemary Avenue,
West Palm Beach,
Florida 33401
Our Email:
• mattsherman@insurancemyway.com
• meagan@insurancemyway.com
Our Phone:









