Prosperous Living™ | The Roger Fishel Financial Blog
Prosperous Living: A Florida Retirement Blog
Free, plain-English guides on retirement income, taxes, Social Security, Medicare and legacy planning, written for pre-retirees and retirees in Orlando, Central Florida and beyond.
✓ 50+ in-depth articles and growing
✓ Written by Orlando retirement advisor Roger Fishel
✓ Updated for 2026 tax, Medicare and Social Security rules
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Find Answers on the Retirement Topics That Matter Most
Every article is organized by topic, so you can go straight to the questions on your mind.
Retirement Income and Planning
Turning savings into a paycheck, withdrawal strategies, pensions, market risk and staying on track.
Browse retirement planning articles →Related service: Retirement Planning
Taxes in Retirement
Roth conversions, RMDs, IRMAA, tax-friendly states and year-end moves to keep more of your savings.
Browse tax planning articles →Related service: Tax-Efficient Strategies
Social Security
When to claim, calculating your benefit, spousal and survivor rules and the most common claiming mistakes.
Browse Social Security articles →Related service: Social Security Optimization
Medicare and Healthcare
Enrollment deadlines, Supplement vs Advantage, bridging coverage before 65 and long-term care.
Browse Medicare and healthcare articles →Related service: Medicare Insurance
Insurance and Risk
Life insurance, annuities, critical illness coverage and protecting your income from the unexpected.
Browse insurance articles →Related service: Insurance & Risk Management
Estate and Legacy
Wills, trusts, beneficiaries and Florida homestead rules so your wealth goes where you intend.
Browse estate planning articles →Related service: Estate Planning
Start Here
Our Most Popular Retirement Guides
New to Prosperous Living? These in-depth guides answer the biggest questions Florida retirees ask, and they are a great place to begin.
Retirement Planning
50 Retirement Planning Questions Orlando Retirees Ask Most
Straight answers to the most common questions about income, taxes, Social Security and Medicare.
Read the guide →
Retirement Income
How to Turn Your Retirement Savings Into Monthly Income
A step-by-step look at building a reliable paycheck from your 401(k), IRA and other savings.
Read the guide →
Taxes
Roth Conversions: The Complete 2026 Guide
When converting makes sense, how much to convert and how to avoid IRMAA and bracket surprises.
Read the guide →
Social Security
10 Social Security Mistakes Florida Retirees Make
The claiming errors we see most often, and how to avoid locking in a smaller check for life.
Read the guide →
Medicare
Medicare Supplement vs Medicare Advantage in Florida
How the two paths really compare on cost, doctor choice and protection as you age.
Read the guide →
Estate & Legacy
Estate and Legacy Planning in Florida: The Complete Guide
Protecting your family, your home and your legacy, including Florida homestead rules.
Read the guide →Latest Articles
New on Prosperous Living
Our newest retirement, tax, Social Security and Medicare articles. New guides are added every month.
The Most Affordable Places to Retire in Florida on $3,000 a Month (2026 City-by-City Guide)
Can you retire in Florida on $3,000 a month? Yes, in the right city. Here are 9 affordable places to retire in Florida in 2026, with home values, a sample budget, healthcare costs, and the hidden expenses to plan for.
Year-End Retirement Tax Moves for 2026: A Central Florida Retiree’s Checklist Before December 31
Some of the most valuable tax decisions of your entire year have a hard deadline, and it is
Estate and Legacy Planning in Florida: The Complete Guide to Protecting Your Family, Your Home, and Your Legacy
Most people think estate planning is a task for the very wealthy, something to worry about only if
The Fall 2026 Open Enrollment Guide for Retirees: Medicare AEP and ACA Marketplace Deadlines
Every fall, two of the most important health coverage windows of the year open within weeks of each
Retiring Before 65 in Central Florida: How to Bridge the Health Insurance Gap to Medicare
You have run the numbers, watched your retirement accounts grow, and started to imagine a life that begins
How to Retire Early in Florida at 50, 55, or 60: What Changes at Each Age
The question sounds simple. Can I afford to stop working early? The real answer is that “early” means
Roth Conversions for Orlando and Central Florida Retirees: The Complete 2026 Guide to Paying Taxes Once and Never Again
Most retirees in Central Florida are sitting on a tax bill they do not know they have. If
Long-Term Care Planning in Orlando and Central Florida: Protecting Your Assets Before Care Starts and After It Begins
There are two kinds of phone calls I get about long-term care. The first comes from a healthy
Mega Backdoor Roth in Florida: How Orlando High Earners Can Add Up to $47,500 a Year in Tax-Free Retirement Savings (2026 Guide)
If you are a high earner in Orlando, Winter Park, Lake Mary, Lake Nona, Oviedo, Clermont, Winter Garden,
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Retirement Tips in Short, Easy-to-Follow Videos
Many of our most popular topics are also on video. Roger breaks down Social Security, taxes and retirement income mistakes in just a few minutes each.
✓ Social Security claiming mistakes
✓ Retirement income gaps and how to close them
✓ New videos added regularly
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Frequently Asked Questions
About Prosperous Living
Who writes the Prosperous Living articles?
Every article is written and reviewed by Roger Fishel, an Orlando-based retirement advisor, based on the real questions clients ask every day. Learn more about Roger.
Where should I start if I am new?
Begin with our most popular guides, or browse by topic above. The 50 Retirement Planning Questions guide is a great overview of everything you should be thinking about.
How often are new articles published?
New articles are added throughout the year, with timely guides around Medicare open enrollment, year-end tax deadlines and rule changes. Subscribe to the newsletter to get them by email.
Is this financial advice?
No. Our articles are for education only. Everyone's situation is different, so talk with a qualified professional before acting on any strategy. For personal guidance, book a free Clarity Session.
Do you have videos too?
Yes. Our video blog and YouTube channel cover many of the same topics in short, easy-to-follow videos.
Can I suggest a topic?
Absolutely. If there is a retirement question you would like answered, send us a message and we may cover it in a future article.
Plan. Protect. Prosper.
Ready to Apply This to Your Own Retirement?
Articles give you the ideas. A free Retirement Clarity Session shows how they fit your situation, in person in Orlando or virtually from anywhere in the U.S.
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