Retired at 57. Still Learning. Sharing What Matters.
Practical guidance on income, Medicare, taxes, Social Security, healthcare, and building a next chapter that fits real life.
Retirement isn’t one decision. It’s a series of them.
After decades in real estate and human resources — and retiring at 57 — I found myself navigating the same trade-offs most people face.
I’m not writing from theory. I’m writing from the middle of it.
Income strategy.
Medicare timing.
Tax exposure.
Social Security coordination.
Healthcare costs.
Lifestyle shifts.
Not abstract concepts. Real decisions. Real consequences.
This site organizes those decisions into six essential pillars and breaks them down in plain English — the way I wish someone had done for me.
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The Essentials of Retirement
The Six Pillars of Retirement
A practical framework for the financial and life decisions that shape your next chapter.
INCOME
Withdrawal strategy, tax coordination, portfolio drawdown, and keeping income steady without unnecessary risk.
MEDICARE
Get the timing right. Parts A–D, supplements vs. Advantage, IRMAA, and real-world coverage decisions after 65.
TAXES
Roth conversions, brackets, IRMAA triggers, capital gains coordination, and long-range tax planning.
SOCIAL SECURITY
Claiming strategies, spousal coordination, delayed credits, and how SS interacts with taxes and Medicare.
HEALTHCARE
Plan for costs before they plan for you. Premiums, out-of-pocket exposure, long-term care decisions, and practical coverage strategy.
LIFESTYLE
Build a next chapter that fits real life. Purpose, structure, health, relationships, and avoiding the “Now what?” phase.
Latest Retirement Insights
Real-world decisions. Real tradeoffs. No theory — just lived experience.
Lessons from someone living it
— not selling it —
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ABOUT RETIRED.LIVING
Retired.Living was created, designed, and is written by me, Jay Thompson.
I retired at age 57, woefully unprepared for what was ahead.
All my life, I’ve been a writer, reader, and researcher. As a freshly minted retiree, I dove into everything I could get my hands and brain on.
Swiftly noticing that there is very little research and writing by someone actually retired, I set out to create this site.
My goal is to share knowledge and insight with anyone considering retirement or already living the life.
Welcome, I’m glad you stopped by!
THE MAN THE MYTH THE LEGEND
Me, sitting on the beach in Port Aransas. Not pondering retirement, but wondering what if I tried surfing — and how long it would take before I wound up in the ER…