Copyright
NOT AN OFFICIAL FRS PUBLICATION
This book is not an official FRS publication or FRS material. It is not published, reviewed, approved, or endorsed by the Florida Retirement System, the Florida Division of Retirement, the State Board of Administration of Florida, MyFRS, the State of Florida, any municipal firefighter or police officer pension plan or board of trustees, or any government agency. It is an independent educational book written by Derrick Johnson and published by Benowitz Wealth Management.
After the Last Shift
Income, Taxes, Health Care, and Legacy for Florida's Special Risk Retirees
The Special Risk Retirement Blueprint Series, Book Three
Copyright © 2026 Joy Financial Group LLC. All rights reserved. No part of this book may be reproduced, stored, or transmitted in any form or by any means without written permission from the publisher, except for brief quotations in reviews.
Published by Benowitz Wealth Management, a brand of Joy Financial Group LLC, 605 Northlake Blvd #10, Altamonte Springs, FL 32701. benowitzwealth.com
First Edition. Information in this book is current as of September 2026.
This book is provided for educational and informational purposes only. Nothing in it is individualized financial, investment, tax, legal, Social Security, Medicare, pension, benefits, insurance, or estate advice. Readers should consult qualified professionals, and should confirm current benefit information directly with MyFRS, the Florida Division of Retirement, their employer or human resources office, their plan providers, and the Social Security Administration or Medicare, before acting on their personal circumstances.
FRS rules, tax laws, Social Security and Medicare rules, contribution limits, and employer policies change. Investing involves risk, including possible loss of principal. Past performance does not guarantee future results. No strategy can guarantee profit, protect against loss, eliminate taxes, or ensure retirement success. Examples in this book are hypothetical, clearly labeled, and for educational purposes only. The people in its stories are fictional. They do not describe actual clients or actual results.
Benowitz Wealth Management is not affiliated with, endorsed by, approved by, or sponsored by the Florida Retirement System, the Florida Division of Retirement, the State Board of Administration of Florida, MyFRS, the State of Florida, or any county, city, municipality, school district, sheriff's office, police department, fire department, public employer, municipal pension board, local retirement plan, board of trustees, the Social Security Administration, Medicare, or any government agency. FRS members may obtain free guidance from the MyFRS Financial Guidance Line at 1-866-446-9377.
Benowitz Wealth Management is the public-facing brand of Joy Financial Group LLC, a Florida-registered investment adviser providing fee-only investment advisory services. Advisory services are offered only in jurisdictions where the firm is properly registered, notice filed, excluded, or exempt from registration requirements. Registration as an investment adviser does not imply a certain level of skill, training, approval, or endorsement by any regulatory authority. Additional information, including services, fees, conflicts of interest, and disciplinary history, is available in the firm's Form ADV Part 2A at adviserinfo.sec.gov, CRD #331545. Benowitz Wealth Management does not provide tax or legal advice, does not sell insurance, and does not enroll anyone in Medicare or Social Security.
A Note from the Author
Book One got you to the date. Book Two got you through the corridor. This book is about the part that comes after, and it is the longest part by a wide margin.
Look at the arithmetic no other retirement book has to face. A deputy who leaves at fifty-one, married to someone forty-nine, is planning for a span that can run forty years. That is longer than the career that paid for it. It is longer than most marriages last. The money has to outlast market cycles nobody has lived through yet. And the person reading this page will become more than one person before it is over.
Most retirement writing is built for twenty-five years, because most people stop working in their sixties. Your class does not. You finish one demanding career while you are still young enough to start another, and that single fact reshapes almost every page that follows.
There is a second thing I want to say plainly, at the front, rather than leave it for a chapter deep in the book.
You will probably work again. Most of this class does. That is not a failure of planning, and it is not a sign the numbers came out wrong. It is what capable people do when they finish at fifty-one or fifty-six with decades of energy still in the tank. This book treats going back to work as ordinary, prices it honestly, and lays out the rules that govern it. There are rules, and they have teeth. The first six calendar months after you leave are the sharpest of them. The moment you most want to go back is the moment going back is most costly.1 For most who return, the work adds no second pension, and that is worth knowing before you take it, not after.2
So this book has a shape, and it comes from one idea. The plan you built has two halves. The first half is money: the paycheck you assemble from a pension, savings, and later Social Security, the taxes on it over decades, the markets it has to survive, the care it may have to pay for. That half is arithmetic. It is the half this book spends most of its pages on, because it can be worked, checked, and written down.
The second half is a life. Forty years is not one long retirement. It is two or three lives lived back to back, and each one asks a different question of you. The money half is the easier half. Most people are surprised by that, because for twenty-five years the money was the part that felt hard. I will not pretend the second half is a formula. But I will not leave it out either. Leaving it out is how a well-funded retirement can still feel like a bad one.
I should tell you what this book will not do, because it is as important as what it will.
It will not tell you what to spend. It will not tell you when to claim Social Security, which account to draw first, or what to buy. Those answers are real, but they are not general. They live in your service record, your marriage, your health, your other savings, and your timeline, and no book can see those. What a book can do is hand you the frameworks, the arithmetic, and the questions. Then it points each decision toward the person who can see your file. The Division of Retirement for a rule about your pension. A tax professional for a number on your return. A Florida attorney for a document. And an adviser for the part where it all has to fit together.
A word about who is at the table. In the first two books I asked you to bring the person who would live with your decisions into the room. That does not stop at the last shift. A forty-year plan is a household’s plan, and it changes hands. The spouse who never ran the money may run it alone one day, on the worst week of their life. This book is written so it can be picked up cold and still make sense. Chapter 9 is written for exactly that reader. Read it while it is still theoretical. That is the point, and the chapter says so itself.
You spent a career doing hard things on a schedule other people set. The work was measurable. A shift ran a set number of hours, a call had an outcome, a rotation ended. Retirement hands you forty years and no schedule at all. That sounds like a gift and lands, for a while, like a question. This book answers the money side of that question in full. It also tells the truth about the side it cannot put in a table. Both halves earned the same care you gave the job.
One more thing, because it shapes how to read what follows. A forty-year plan is never finished in one sitting. The version you build the year you leave will be wrong by the time you are sixty-five, not because you made a mistake but because the facts moved: a market you lived through, a tax rule that changed, a spouse’s diagnosis, a grandchild. The households that do well are not the ones who guess right once. They are the ones who put the plan on paper, keep the paper, and sit back down with it on the same Saturday every year. Several chapters here end with a page you can fill in and file. That is not busywork. It is how a plan built at fifty-one is still yours at ninety.
That is the book. The chapters take the decisions one at a time, in the order they tend to arrive, and each one ends where every good decision should: with the questions to ask before anything is signed.

Derrick Johnson
Chief Executive Officer, Benowitz Wealth Management
How to Use This Book
This book is for members of the Florida Retirement System’s Special Risk Class who have retired, or are about to, and for the spouses, partners, and survivors who share the plan with them. That means deputies and police officers, correctional and correctional probation officers, firefighters, and EMTs and paramedics, now on the far side of the last shift. Most of you left in your late forties or fifties. The plan in these pages has to run forty years.
It is the last book of a series
This is Book Three of The Special Risk Retirement Blueprint Series. Book One, The Special Risk Retirement Foundation, covered the years before retirement: your class, the benefit formula, the two plans, DROP, and the accounts beside the pension. Book Two, The Special Risk Transition Playbook, covered the transition itself: the pension option, the DROP payout, Social Security timing, and the coverage bridge to Medicare. This book covers everything after: the retirement paycheck, taxes over decades, markets, long-term care, the survivor’s side, estate basics, and staying retired.
Where a point rests on the earlier books, you will find a short pointer rather than a repeat, using those books’ chapter numbers. This is the last book of the series.
Four ways to read it
- The bridge years, from your date to sixty-five. Read Chapters 1 through 5 first, then come back for Chapters 6 and 8 as you near sixty. Your bridge has no Social Security yet, no Medicare yet, a pension-first floor, and the heaviest demand your savings will ever carry. Chapters 2, 3, and 5 are built for that stretch on purpose.
- Recently landed, years zero to three. Read Chapters 1, 2, 3, and 6, then the rest as they become relevant.
- Established, three years out and beyond. Read front to back once, then let Chapter 13 become your annual instrument.
- The survivor, or the couple preparing. Read Chapter 9 together, out loud, while it is still theoretical, then Chapter 10. Reading it early is the entire point, and Chapter 9 says so itself.
If you open to Chapter 6 and find yourself reading about required distributions twenty years before they touch you, that is not the book misjudging you. It is the book being written for a forty-year span. Skip ahead. The chapter will still be there.
Two appendices
Two appendices follow the chapters. Appendix A is for Special Risk members who retired on disability, whose benefits, reexamination rules, and reemployment limits differ from a service retirement. Appendix B is for members of local police and fire pension plans under Chapter 175 or 185, whose own plan document controls. If one of those describes you, read it alongside the chapters, not instead of them.
What the boxes mean
A few kinds of boxes repeat throughout the book.
- Fictional examples. Every story about a person is fiction, and it is labeled that way. None describes a real person or an actual client.
- Hypotheticals. Worked numbers carry the label “Hypothetical,” with their assumptions stated. They show how a rule works. They are not projections or promises.
- Ask your team. The desk that can answer a question about your own record: the Division of Retirement, MyFRS, Social Security, Medicare, a tax professional, a Florida attorney, or an adviser.
- What can go wrong, what to check, and questions to ask. The ways a decision tends to break, the facts to confirm first, and the questions to bring with you.
- Checklists and Reflect. Tasks to tick off, and a few questions to think over.
- For you and your spouse. A short conversation to have at home.
- Benowitz Wealth Principles. A handful of short ideas, placed only where a chapter earns one.
- Worksheets. Chapters 2, 3, 4, 5, 9, 10, and 13 each carry a worksheet for your own numbers.
How the figures are dated
The rules and figures in this book are current as of the date on the copyright page. Amounts that change every year carry the year they apply to, such as “for 2026.” Florida’s retirement law changes often, and many changes take effect on a July 1. Federal tax and Medicare figures move every year too. Before you act, confirm the point with the desk that owns it. The sources sit in the Notes at the back, keyed by page.
The one rule
One sentence governs a forty-year plan: it is a living document, not a monument. You will write it once and revise it many times, because your health, the tax law, the markets, and your own life all keep moving. Chapter 13 turns that revision into a yearly habit.
There is an honest exception, and it is why the chapters name every deadline they can find. A handful of clocks are real, and they do not wait for you to feel ready. The six calendar months you must stay clear of every FRS employer are real, and month one is when they bite.1 Medicare’s enrollment windows at sixty-five are real, and a missed one can carry a penalty that never expires.2 Required minimum distributions arrive in your seventies whether or not you need the money.3 When a real deadline is in front of you, this book will say so plainly. Everything else can wait for the understanding to catch up.
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Six calendar months of separation from all FRS employers after a service retirement effective date or a DROP termination date: s. 121.021(39), Florida Statutes (2026); FRS-TAR (July 2024). See Chapter 1 and Book Two, Chapter 12.
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Medicare enrollment periods and late-enrollment penalties, which for Part B generally last as long as you have Part B: Medicare.gov, “Avoid late enrollment penalties.” See Book Two, Chapter 9.
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Required minimum distributions from most retirement accounts begin by April 1 of the year after the account owner reaches the applicable age (73 or 75 depending on birth year): 26 U.S.C. 401(a)(9). Roth IRAs have no lifetime required distribution. The exact ages are in Chapter 6.
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Introduction: The Longest Part
Fictional example. Not a real person or an actual client.
The retirement party is the same in every county. A room off the main hall, a sheet cake with the wrong shade of icing, a plaque, and a speech from someone one rank up. People who ran toward the worst moments of strangers’ lives stand around holding paper plates, unsure what to do with their hands now that the radio is off.
The retiree gets asked the same question all afternoon. So what are you going to do now? And the answer is always some version of the same thing. Fish. Fix up the house. Finally sleep. Everyone laughs, because it is the right answer, and because the real answer is that nobody at the party knows.
Then the party ends. The plaque goes on a shelf. The first Monday feels like a day off, and so does the second. Somewhere in the first month or two, on an ordinary afternoon, a quiet arrives that nobody mentioned at the party, because at the party everyone assumed retirement was going great.
That quiet is not a crisis. It is the sound of a very large change arriving on schedule. And it is the first thing this book is about, because the plan you spent two books building does not end at the party. That is where it starts.
This is the third and last book of a series that has walked one decision at a time. Book One got you to the date you could leave. Book Two got you through the corridor of the leaving itself: the pension option, the payout, Social Security timing, the coverage bridge. Both of those books were about a passage with a clear end. You crossed it. The last shift is behind you.
What is in front of you has no clear end, and that is the whole difference. A retirement is not an event you complete. It is a stretch of years you live, and for your class the stretch is longer than almost anyone else’s.
Three things make your retirement different
Retirement writing is written for a general reader who stops working at sixty-five and plans for twenty good years. Almost none of it fits you, for three plain reasons.
The length. You did not stop at sixty-five. You finished a demanding career while you were still young, often in your late forties or fifties, and the plan now has to run as long as forty years. That is not one long retirement. It is two or three separate lives, lived back to back. The person who leaves at fifty-one is not the person they will be at seventy, or the one they will be again at ninety. A plan that speaks only to the first of them will fail the other two. Length changes the math on every page. Money that has to last forty years is invested differently, drawn on differently, and taxed across more changes in the law than a twenty-year plan will ever see. It also has to survive you being wrong once or twice, because over forty years everyone is, and the plan has to hold anyway.
The bridge. A sixty-five-year-old walks out of work and into Social Security and Medicare almost at once. You do not. You may have a decade or more before Social Security makes sense to claim, and years before Medicare turns sixty-five and lets you in.1 In that stretch your pension is doing most of the work alone. Your health coverage has to be bought and paid for. Your savings carry their heaviest load of the entire retirement, because they are covering the gap that Social Security will later help close. Nobody who retires at sixty-five ever faces the bridge. For you it can be the hardest decade of the forty, and it comes first, when you are least practiced at any of this.
The COLA your service earned. Here is one thing that runs the other way, in your favor, and most retirees will never have it. Your pension carries a cost-of-living adjustment tied to the years you worked, and for many in this class a 2026 law puts a floor under it.2 A private retiree with a fixed pension watches inflation quietly shrink the check for forty years. Part of yours is built to keep pace. That single feature changes how much the rest of your plan has to do. It is also widely misunderstood, including by people who sell things to retirees. So it deserves to be understood exactly, not assumed. Chapter 4 does the arithmetic.
Length, the bridge, and the COLA. Hold those three, and the shape of everything ahead makes sense. The rest of the book is detail, and the detail is where a good forty years is either protected or slowly given away.
What the book covers
The chapters come in three parts, sequenced the way the decisions tend to arrive.
Part One, The Paycheck You Build (Chapters 1 to 5), starts with the quiet you just read about, then builds the retirement paycheck itself. How much you can safely draw, which account it comes from and in what order, how to keep it ahead of inflation, and how it survives markets that will fall more than once across forty years.
Part Two, Keeping It (Chapters 6 to 8), is about the forces that take money back. Taxes over decades, including a long low-income valley that is a genuine opportunity for this class. The sales pitches aimed squarely at newly retired public safety households, and how to tell an honest tool from an expensive one. And long-term care, sized honestly, before a hallway conversation sizes it for you.
Part Three, The People It Is For (Chapters 9 to 13), turns to the household. The survivor’s chapter, written to be read on the worst week of a life. Estate basics for Florida retirees. Helping grown children and aging parents without sinking your own plan. The life half of the plan, the purpose and routine that a badge used to supply. And the annual review that keeps the plan current.
Two appendices follow, one for members who retired on disability and one for members of local police and fire plans.
What the book will not do
It will not tell you what to spend, when to claim, which account to draw first, or what to buy. Those answers are real, but they are not general. They live in your service record, your marriage, your health, your savings, and your timeline, and no book can see those. What this book hands you is the frameworks, the arithmetic, and the questions, and it points each decision toward the person who can see your file.
One thing the book does ask of you. Read it with your own paperwork nearby, not in the abstract. The pension option letter from the Division, your most recent MyFRS benefit estimate, the statements for whatever savings you have, a rough figure for what your household actually spends in a month. The frameworks in these chapters are built to be filled in with your numbers, and they do almost nothing until they are. A chapter read as a story is interesting. The same chapter read with your own figures in the margin is a plan.
You spent a career being the person other people could count on when everything went wrong. You were good at it because you prepared, and because you stayed calm while you did the hard thing in front of you. The next forty years ask for the same two habits, turned toward your own household. Prepare in calm weather. Then, when the weather turns, and across forty years it will, you follow a plan you already understand instead of guessing in the storm.
The first chapter goes back to that quiet, and to a jail lieutenant who found herself, four months in, driving to a parking lot she no longer had any reason to visit.
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Social Security retirement benefits may begin as early as age 62, with full retirement age of 67 for anyone born in 1960 or later, so early claiming permanently reduces the benefit: Social Security Administration, “Retirement benefits” and “Starting your retirement benefits early.” Medicare eligibility generally begins at age 65: Medicare.gov, “When does Medicare coverage start.”
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FRS retirement benefits carry a cost-of-living adjustment based on the share of service earned before July 1, 2011; for retirements effective on or after July 1, 2011, ch. 2026-235 sets a minimum annual adjustment (the greater of the member’s calculated rate or 1.5%) for Special Risk retirees and annuitants with at least 72 months (enrolled before July 1, 2011) or 96 months (on or after) of Special Risk service, beginning with the July adjustment after the fifth anniversary of retirement: s. 121.101(4)-(5), Florida Statutes (2026). Explained in full in Chapter 4.
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The Paycheck You Build
Chapter One
The Last Paycheck
The reemployment rules in this chapter carry real consequences and are current as of the date on the copyright page. Before you take any work, or provide any service to a former or new employer, confirm your status with the Division of Retirement, in writing.
Fictional example. Not a real person or an actual client.
Lieutenant Monique Delacroix ran a housing unit at a county jail for thirty-three years, the last eight of them in DROP, and she walked out for the last time on the final day of December.
By April she still woke at 4:40. The body does not read a calendar. Twice that month she had driven most of the way to the jail before she noticed where the truck was pointed, and both times she turned around in a gas station lot and drove home with the radio off. She told her niece Renelle it was nothing. Renelle, who is a nurse and reads her aunt’s statements with her, did not think it was nothing.
The money was fine. Delacroix had made sure of it. Her pension landed on the last business day of every month, the amount she expected, in the account she expected. There was nothing left to verify, nobody’s schedule to run, no unit to count, no radio. For thirty-three years the worst thing that could happen was her responsibility. Now the worst thing that happened most days was the sprinklers coming on at the wrong hour.
Then the jail chaplain called. His name was Ellison, and he ran a Tuesday re-entry class for men about to be released, and he was short a pair of hands. You know these guys, he said. You know what actually helps them. Come do the Tuesday class with me.
Everything in her wanted to say yes on the spot. Not for the money, which was nothing. For the fact that on Tuesday, twenty men would need her to show up ready.
She almost said yes. Then she remembered a sentence from the corridor she had just crossed, the one about the six calendar months, and she told Ellison she had to make a call first.
She was right to. The call is what this chapter, in the end, is about.
The quiet, named properly
Book Two closed by promising this conversation, so here it is, before any dollars.
The money is the measurable half of retirement. It is the half you can check, and by the time you read this you have probably checked it. The other half does not show up on any statement, and for a career like yours it is frequently the harder half. It has a name, and naming it is most of the work, because unnamed it feels like something is wrong with you, and named it is just weather.
Here is why it lands where it does. Most jobs provide a paycheck. Public safety work provides a paycheck and a load-bearing identity underneath it: a mission, a crew, a schedule someone else set, a uniform, and the daily, verifiable fact of being needed at a specific time and place. Retirement removes all of that in a single afternoon. The removal does not announce itself at the party. It arrives in the second or third month, as a flatness nobody warned you about, in the exact season when everyone has stopped asking how retirement is going because they assume it is going great.
Name its two parts, because they have different fixes.
Structure loss. Thirty years of time imposed from outside, gone at once. The fix is building time on purpose, which is the routine work of Chapter 12. It is real, and it is not enough by itself, which is why reorganizing a garage that is already organized does not touch it.
Mission loss. This is the deeper one. Who needs me now is not a figure of speech. It is the actual wound, and hobbies do not close it. Its fix is service redirected rather than retired, and it is also Chapter 12’s work. Delacroix’s pull toward Ellison’s Tuesday class was mission loss looking for somewhere to go. That instinct was healthy. The only problem was the timing, and the timing was a legal one.
One usually shows up before the other. Structure loss arrives in the first week, when the alarm still goes off out of habit and there is nothing on the far side of it. Mission loss takes longer. It surfaces once the postponed chores are finished and the quiet has nothing left to hide behind.
Why it lands harder at fifty-one than at sixty-five
Everything above is true for any retiree. Three things make it sharper for you.
Your peers are still working. A sixty-five-year-old joins a crowd. Everyone they know is doing the same thing at the same time, there are clubs for it, and the neighbors have a word for it. You walked out into a world where everyone your age is at work, including your spouse, including your friends from outside the department. Delacroix left at fifty-six. The isolation is not in her head. It is in the calendar, and the calendar belongs to people who are all still on shift.
Nobody has a word for what you are. Retired means something to people, and to most of them it does not mean fifty-six, and it certainly does not mean fifty-one. You will spend a decade explaining yourself at cookouts, and the explaining wears a particular groove. People assume you were hurt, or fired, or rich. None of those is the answer, and the true answer takes longer than a cookout allows.
The span is enormous. A sixty-five-year-old asking what am I for is asking about maybe twenty years. You are asking about forty. That is not a season to get through. It is a second adult life, and it deserves to be built rather than endured. A plan that treats it as a long wait for the end will produce exactly that.
None of this is a sign the retirement was a mistake. It is the predictable cost of finishing something big while you still have most of your energy left. The cost is worth paying. It is just easier to pay when you saw the bill coming.
The trap in month four is a legal one
Now the part that belongs in this chapter.
The pull that arrives around month four is the pull to go back. Not always to the same job. Sometimes to any job, to anything with a schedule, a purpose, and people who need something from you at a set time. It is the healthiest instinct in the whole difficult season. And it arrives during the single window when acting on it can cost you everything.
For the six full calendar months after your retirement effective date, or after your DROP termination date, you may not be employed by, or provide services to, any FRS employer, in any capacity.1 That reaches part-time and contract work, and even a private company that holds a contract with an FRS employer. There are no exceptions to the six-calendar-month rule, and the Division says so in those words. There is also a step before the clock even starts: to retire, you must first terminate every FRS employment relationship you hold, even a second, part-time one the pension never counted. Keep any of them open and you have not terminated, which means the retirement, and the clock, never began. Book Two’s Chapter 12 lays the rest out in full, and this book’s Chapter 12 returns to working again; if you are near your exit, both are worth rereading.
Break it, and the consequences are not a slap. Your retirement is treated as never having happened. You and the employer can be held jointly and severally liable to repay every benefit you received, which for a DROP retiree includes the entire payout, and each of you can be pursued for the whole amount. Few mistakes in the first year cost more, and this one is available precisely when you least want to be careful.
So look at the timing honestly. The month you most want to go back is the month going back is most dangerous. That is not bad luck. It is a genuine cruelty built into the calendar, and knowing it is coming is most of the defense.
Two facts cut the other way, and Delacroix’s phone call turns on both. Since July 1, 2023, unpaid volunteering inside an employer program that meets seven conditions in the statute is not employment, so it does not break the clock.2 The conditions are specific. No arrangement made before you retired. No pay, or anything worth pay. No employee benefits. Hours capped at a fraction of what you used to work, a clear line between the volunteer role and the paid one, your control of the schedule, and records kept by both sides. Ellison’s Tuesday class might fit that program, or it might not, and the difference is not something a chaplain who means well can confirm across a phone. That is why the answer comes from the Division, in writing, before the first Tuesday, not after it.
And for most of you, going back to an FRS job buys nothing extra from the system. A Pension Plan retiree first reemployed after July 1, 2010, earns no renewed membership and no new FRS benefit.3 The work can be welcome, but it is worth knowing you build no second pension before you take a job for the wrong reason, in the wrong month.
Two things help with the trap itself.
Put the end of month six on a calendar the day your termination date is set. Then the season has a known end instead of feeling like an indefinite condition. For Delacroix, whose DROP ended on the last day of December, the six restricted months run January through June, and the seventh month, when the restriction lifts, is July.
Separate two questions that month four blurs together. Do I want to work again is a real question, worth answering slowly and well. Do I need something to do on Tuesday is a different question, and most of its good answers do not involve employment at all. Month four hears them as the same question and demands you solve both today. They are not the same, and neither is due today.
What actually helps, briefly
The full catalog is Chapter 12, because building a good retired life is the work of years, not of a first quarter. Three things belong in month one.
Tell the people close to you that the quiet is coming, out loud, before it does. Households and friends who have heard it named in advance handle it as weather. The ones who meet it cold sometimes handle it as a crisis about the marriage, or the money, when it is neither. If you live alone, as Delacroix does, tell the person who reads your statements with you, or the friend two years ahead of you who already went through it.
Keep one standing commitment where other people depend on you showing up. A class, a shift somewhere, a regular volunteer slot once the rules allow it. Mission loss answers to being needed on a schedule far better than it answers to hobbies. The instinct that pulled Delacroix toward Ellison was the right instinct pointed at the right kind of thing, held one season too early.
Do not turn it into a money decision. The two reflexive escapes are unretiring in a panic, which is the legal trap above, and spending your way past the quiet, which Chapter 7 will show you has an entire industry waiting for it. Neither fixes anything, and both are expensive. A garage of new equipment and a boat in the driveway can look like a plan for the quiet. Most of the time they are just the quiet, with a payment book attached.
The month you most want to go back is the month going back is most dangerous.
Hypothetical · Here's what this means in real life
Delacroix’s month four, laid out on a calendar. The figures illustrate the rules and are not estimates of anyone’s real numbers.
Her DROP ended on the last day of December. That sets the clock. The six restricted calendar months run January through June. The seventh month, when the reemployment restriction lifts entirely, is July.
Her pension, about $5,158 a month, arrives on the last business day of every one of those months, whether she works or not. It does not pause during the restricted window, and a job would not raise it. Reemployed after 2010, she would earn no new FRS benefit for any work she takes, so any decision to go back is about purpose and cash flow, never about building a second pension.
Ellison’s Tuesday class is the live question. If the jail runs it as a qualifying volunteer program, and the seven conditions are met, she can help even inside the six months, because protected volunteering is not employment. If it does not qualify, then helping at the jail, an FRS employer, is providing services during the restricted window, and that would void a retirement she spent thirty-three years earning. She cannot tell which it is from Ellison’s description. So she calls the Division, gets the answer in writing, and puts the end of June on the calendar either way. If the answer is no, she tells Ellison she will be there the first Tuesday in July.
What can go wrong
- Meeting the quiet cold, having been told retirement is a reward rather than a large change to manage.
- Mistaking structure loss for mission loss, and spending a year fixing the wrong one.
- Taking work in month four, the one month it can cost you the whole retirement.
- Assuming unpaid help for a former employer is automatically safe. Only a program meeting all seven conditions is.
- Asking a well-meaning former coworker whether the work is allowed, instead of asking the Division in writing.
- Treating a second career as proof the plan failed. In this class it is the norm.
- Spending your way through the quiet, on exactly the schedule the pitch economy counts on.
- Assuming a forty-year span is a wait to endure rather than a life to build.
What to check before deciding
Put the end of your six-calendar-month window on a calendar today, with the year on it. Write down, somewhere you will find it, the difference between wanting to work again and needing something on Tuesday. Before you accept any work at all, confirm in writing, from the Division of Retirement, whether the employer touches the FRS, including through a contract. And name the quiet to someone before it arrives.
Ask your team
The Division of Retirement, 1-844-377-1888, for any question about working again, in writing, before you accept anything. Not a former coworker, not the hiring employer’s HR. Other retirees from your agency who are a year or two ahead of you will tell you the truth about the quiet. And a professional if it does not lift, because there is a difference between an adjustment and something that needs treatment, and the second one responds well to help.
Questions to ask before deciding
- What did the job give me besides money, listed honestly?
- Which of those things is structure, and which is mission?
- What year does the end of my six-calendar-month window fall in, and is it on a calendar?
- Who, other than my family, will need me to show up on a schedule next month?
- Does any work I am considering touch an FRS employer, including through a contract, and have I confirmed it in writing?
- What is one thing I could commit to this month that would give next week a point?
- If this span runs forty years, what is it for?
Benowitz Wealth Principle
The plan has two halves, and the money is the easier one.
Chapter checklist
- The end of my six-calendar-month window on the calendar, with the year.
- The quiet named out loud to someone before it arrives.
- Structure loss and mission loss written down as two separate problems.
- One standing commitment where other people depend on me, cleared against the rules first.
- The two reflexive escapes identified and named as escapes.
- Any post-retirement work confirmed with the Division, in writing, before I accept it.
- Chapter 12 flagged to read in month five.
Reflect
- What will you miss that is not the paycheck?
- Who needed you last week, and who will need you next year?
- When someone asks what you do now, what do you want to be able to say?
For you and your spouse
Have the quiet conversation now, while it is still theoretical. Say the words out loud: this is coming, it is normal, and it is not about us. Households that name it in advance handle it as weather. Households that meet it cold sometimes handle it as a crisis about the marriage, and it is not one. If one of you retired years before the other, the one still working is the one most likely to miss the arrival, so agree now on how the quiet will get mentioned when it comes.
If you take one action from this chapter, make it this. On the day your termination date is set, put two dates on the same kitchen calendar. The first is the last day of your sixth restricted month, so the season has a known end instead of an open one. The second is a day the following week, blocked out for whatever comes next, whether that is a class, a regular shift somewhere, or an afternoon that is finally yours to spend. The first date protects the pension you spent a career earning. The second one starts the half of the plan that no statute, and no amount of money, can hand you on its own.
Delacroix made her call. The answer, whatever it turned out to be, cost her four minutes and the price of asking. That is the whole lesson of month four: the pull is real, the timing is a trap, and one phone call is the entire defense. She kept the end of June circled on the kitchen calendar. Under it, in the block for the first Tuesday of July, she wrote a single word, which was class. The money was already handled. What she was building now was the other half, the harder half. The next chapter starts where that half meets the arithmetic again: turning a pension and a pile of savings into a paycheck you can live on for forty years.
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For the six full calendar months after a service retirement effective date or a DROP termination date on or after July 1, 2010, a retiree may not be employed by, or provide services to, any FRS employer, in any capacity, including part-time, temporary, substitute, adjunct, contract, poll work, and work through a third-party company that serves an FRS employer; a violation means termination did not occur, the retirement and any DROP election are void, and the retiree and employer are jointly and severally liable to repay all benefits received, including the DROP payout: s. 121.021(39) and (56), s. 121.091(9)(c)3. and (13)(c)5.d., Florida Statutes (2026); FRS-TAR (July 2024); DROP Guide, 2026 Edition, p. 20. Covered in full in Book Two, Chapter 12.
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Since July 1, 2023, volunteer service in an FRS employer’s program is not employment or provision of services if it meets seven conditions: no pre-retirement arrangement to serve; no compensation or cash equivalent; no employee benefits (task items such as a uniform allowed); weekly hours, including training, no more than 20% of pre-retirement expected weekly hours; a clear distinction from employee duties; the volunteer controls the schedule; and both keep records: s. 121.021(39), s. 121.091(15), Florida Statutes (2026); ch. 2023-316, Laws of Florida; Form DP-TERM (08/26).
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A Pension Plan retiree, including a former DROP participant, first reemployed in a regularly established position on or after July 1, 2010, earns no renewed membership and no new FRS benefit; such a retiree cannot rejoin the Pension Plan or the Investment Plan: s. 121.122, Florida Statutes (2026); s. 121.091(9)(c)1., s. 121.4501(2)(e).
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Disclosures
This book is not an official FRS publication or FRS material. It is not published, reviewed, approved, or endorsed by the Florida Retirement System, the Florida Division of Retirement, the State Board of Administration of Florida, MyFRS, the State of Florida, any municipal firefighter or police officer pension plan or board of trustees, or any government agency. It is an independent educational book written by Derrick Johnson and published by Benowitz Wealth Management.
This book is provided for educational and informational purposes only. Nothing in it is individualized financial, investment, tax, legal, Social Security, Medicare, pension, benefits, insurance, or estate advice. Readers should consult qualified professionals, and should confirm current benefit information directly with MyFRS, the Florida Division of Retirement, their employer or human resources office, their plan providers, and the Social Security Administration or Medicare, before acting on their personal circumstances.
FRS rules, tax laws, Social Security and Medicare rules, contribution limits, and employer policies change. Investing involves risk, including possible loss of principal. Past performance does not guarantee future results. No strategy can guarantee profit, protect against loss, eliminate taxes, or ensure retirement success. Examples in this book are hypothetical, clearly labeled, and for educational purposes only. The people in its stories are fictional. They do not describe actual clients or actual results.
Benowitz Wealth Management is not affiliated with, endorsed by, approved by, or sponsored by the Florida Retirement System, the Florida Division of Retirement, the State Board of Administration of Florida, MyFRS, the State of Florida, or any county, city, municipality, school district, sheriff’s office, police department, fire department, public employer, municipal pension board, local retirement plan, board of trustees, the Social Security Administration, Medicare, or any government agency. FRS members may obtain free guidance from the MyFRS Financial Guidance Line at 1-866-446-9377.
Benowitz Wealth Management is the public-facing brand of Joy Financial Group LLC, a Florida-registered investment adviser providing fee-only investment advisory services. Advisory services are offered only in jurisdictions where the firm is properly registered, notice filed, excluded, or exempt from registration requirements. Registration as an investment adviser does not imply a certain level of skill, training, approval, or endorsement by any regulatory authority. Additional information, including services, fees, conflicts of interest, and disciplinary history, is available in the firm’s Form ADV Part 2A at adviserinfo.sec.gov, CRD #331545. Benowitz Wealth Management does not provide tax or legal advice, does not sell insurance, and does not enroll anyone in Medicare or Social Security.