A successful retirement in The Villages is not just about how much you saved, it is about how you use it, and which avoidable mistakes you sidestep on the way down “Retirement Mountain.” Greg Parady likes to remind clients that getting to the top is only half the mission. The descent, turning a nest egg into predictable income while taxes, markets, and health all change, is where most surprises happen.
After nearly three decades working with Modern Retirees, Greg has seen the same “gotchas” repeat themselves: portfolios with no downside protection, decisions made in the heat of the moment, plans that assume too short a timeline, and people trying to do everything alone without a coordinated team. His 7 Rules for UnStressing™ and UnTaxing™ Your Retirement are designed to help you avoid exactly these traps so you can live Your Life, Your Way℠ with fewer regrets.
Think of this post as a simple stress test for your plan. If you recognize yourself in any of these retirement planning pitfalls, now is the perfect time to make adjustments while you still have plenty of choices.
Pitfall #1: Skipping Your “Retirement Seatbelt”
Greg devotes his very first chapter to the “Retirement Seatbelt Act” for a reason. For most of us, seatbelts used to feel optional; now we buckle up automatically because we know cars are not the only things that crash, markets do too.
In 2008–2009 and again in 2020, retirees watched account values fall sharply while the government scrambled to temporarily suspend Required Minimum Distributions. Helpful, but late. Greg’s point is simple: you do not want your entire lifestyle riding in the front seat without a seatbelt when the next “once in a lifetime” drop shows up again.
How to avoid it
In UnStress & UnTax Your Retirement™, Greg makes the case for using Fixed Index Annuities, what he calls Modern Annuities®, as a kind of retirement seatbelt. When they are properly designed, your principal is protected from market loss while you still participate in index-based growth, and you can add riders that create guaranteed lifetime income for one or two lives.
Practical ways to “buckle up”:
- Use Modern Annuities® to cover your essential monthly income, housing, food, healthcare, golf cart, and Villages fun, so those checks keep coming no matter what the market does.
- Keep a healthy “Yellow” bucket, after-tax money in bank or brokerage accounts, for liquidity instead of forcing withdrawals from risk assets during downturns.
- Coordinate your Red (tax-deferred), Yellow (after-tax), and Green (tax-free) “trees” so you are not forced to harvest from the wrong place at the wrong time.
Retirees in The Villages who combine Social Security with pension-like income from Modern Annuities® are often Greg’s most relaxed clients. They tend to drive nicer cars, take more trips, and say “yes” to grandkid adventures because they know their next paycheck will still arrive next month.
Pitfall #2: Making Big Decisions When You Are Stressed or Emotional
In the “Retirement Golf” chapter, Greg tells a story about a frustrated golfer in a slump who is greeted after the round by a salesperson eager to swap out every club in the bag. The lesson: decisions made when you are angry, scared, or exhausted almost never turn out to be smart in the long run.
The same thing happens with retirement plans. A bad headline, a rough quarter in the market, or a personal health scare can trigger emotional moves, bailing out of investments at the worst time, stopping income strategies that were working, or buying products that are not really a fit.
How to avoid it
Greg’s remedy is process, not panic:
- Rebuild a “paycheck system” in retirement. Instead of staring at a big account balance, translate your strategy into predictable monthly income that feels like the paychecks you lived on for decades.
- Use Modern Annuities® and coordinated withdrawals from your Red, Yellow, and Green trees to create a clear income plan, so day-to-day market moves feel less urgent.
- Lean on your “swing coach”, a team that knows your tendencies, your family, and your goals, before you change clubs. Greg stresses the value of having professionals who coach you through tough conditions instead of reacting to every bump in the fairway.
When markets get choppy, your best first move is often to do nothing drastic and schedule a review. That keeps your plan grounded in numbers and strategy, not in today’s news cycle.
Pitfall #3: Underestimating Longevity, And Outliving Your Money
Greg devotes an entire section of UnStress & UnTax Your Retirement™ to what he calls Emotional Economics. One of the biggest fears he sees is not dying, but “living with no money”, outliving the savings you worked 30 or 40 years to build.
Because today’s Modern Retirees are more active and live longer than previous generations, many will spend 25–30 years or more in retirement. Greg notes that baby boomers in particular are rewriting the actuarial tables, often enjoying more healthy retirement years than any generation before them.
How to avoid it
Instead of planning to “age 85 and out,” Greg encourages clients to think in three phases:
- First Half, roughly your next 10 years, when you are healthiest and can “Make Your Next 10, Your Best 10!®” with travel, family experiences, and memories.
- Second Half, slower pace, more focus on stability and healthcare.
- Overtime, funding independence as long as possible, including home health care and long-term care.
To support a longer life:
- Build a solid income floor with Social Security, any pension, and Modern Annuities® so essential lifestyle costs in The Villages are covered every month for as long as you live.
- Gradually reposition some Red Trees into Green Trees using tools like Roth conversions and properly structured Modern Life Insurance™ for tax-free income and survivor protection.
- Review how the “widow’s penalty” might affect a surviving spouse so you can plan ahead while both of you are still alive and healthy.
Planning for a 30-year retirement may feel conservative, but for many Modern Retirees it is simply realistic.
Pitfall #4: Going It Alone Without a Coordinated Team
Retirement today is not just about picking investments. It is about Social Security timing, tax strategy, widow and widower planning, Required Minimum Distributions, Modern Life Insurance™, Modern Annuities®, and long-term care. Greg is candid: this is a lot for one person, or one advisor, to juggle.
That is why he built Parady Financial around a team model: CPAs, CFP® professionals, Certified Annuity Specialists, and licensed insurance professionals collaborating under one roof, much like a “Mayo Clinic” for retirement planning.
How to avoid it
Greg suggests asking a few questions about your current team:
- Are they proactively educating you about the SECURE Act, RMD rules, tax planning, and strategies like Roth conversions, not just reacting at tax time?
- Do they talk about income replacement for a surviving spouse and ways to soften the widow’s tax penalty?
- Are they present in both good times and crises, or only when it is convenient? Greg calls this the “relationship test”, real partners show up when life gets hard.
His 7 Rules for UnStressing™ and UnTaxing™ Your Retirement tie all of this together: understand income vs assets, get help with Social Security, plan ahead for taxes, have an income replacement strategy, protect your assets, “insure” your lifestyle and invest the rest, and know who is watching the store.
Bringing It All Together: Stress-Test Your Plan Now
The biggest retirement planning pitfalls usually are not exotic. They are simple: no seatbelt against market crashes, reacting emotionally, underestimating how long retirement might last, and trying to navigate it all without help.
The good news is that each pitfall has a clear antidote rooted in Greg Parady’s experience and the strategies in UnStress & UnTax Your Retirement™: build predictable income, protect your downside, diversify your tax buckets, and work with a coordinated team that treats you like family.
If you are ready to “take the plastic off” your retirement and Make Your Next 10, Your Best 10!® while still protecting the later years, a stress test of your existing plan at the Parady Learning Lounge® can be a powerful next step.
FAQ: Retirement Planning Pitfalls for Modern Retirees in The Villages
What are the biggest retirement planning pitfalls for retirees in The Villages, FL?
The most common pitfalls Greg sees are going into retirement without a “seatbelt” against market crashes, making emotional decisions when markets get rough, underestimating how long retirement will last, and trying to navigate everything without a coordinated tax and income team. All four can quietly erode your lifestyle and your confidence over time.
How can I protect my retirement from market crashes?
A practical way to protect your retirement from crashes is to use Modern Annuities®, especially Fixed Index Annuities, as a “Retirement Seatbelt.” They are designed to protect principal from loss while still offering index-linked growth and optional lifetime income riders, so your essential monthly income does not depend on stock market performance. Pairing them with liquid Yellow assets for emergencies makes it easier to stay calm in volatile years.
Why are emotional decisions so dangerous for my retirement plan?
Emotional decisions are dangerous because they often lead you to “change clubs in the middle of the round,” selling low or abandoning a solid strategy after a rough patch. Greg explains that decisions made from frustration, fear, or anger almost never turn out to be smart in the long run. Having a written income plan and a trusted “swing coach” to talk to before making big moves can keep you from locking in losses.
How do I avoid outliving my money?
To avoid outliving your money, plan for a long retirement that includes a vibrant First Half, a steadier Second Half, and an Overtime phase that may involve more healthcare expenses. Build a strong income floor with Social Security, pensions, and Modern Annuities®, then use tax-smart strategies like Roth conversions and Modern Life Insurance™ to create Green Trees that can provide tax-free income later in life. This combination helps address both longevity risk and future tax risk.
Do I really need a financial advisor, or can I handle retirement planning myself?
You can certainly gather information on your own, but Greg argues that today’s Modern Retirement™ is best handled by a coordinated team, not a single do-it-yourselfer. Taxes, RMDs, Social Security rules, Modern Annuities®, Modern Life Insurance™, and estate considerations all interact. A team that includes CPAs, CFP® professionals, and insurance specialists under one roof can help you stress-test your plan, spot hidden risks like the widow’s penalty, and keep everything aligned with Your Life, Your Way℠.
Disclaimer
This is Paid Advertising for Annuities and Life Insurance. The content above is for educational purposes only, and should not be relied on for tax, legal, investment or accounting advice. Annuity guarantees are backed by the financial strength and claims paying ability of the issuing carrier. You may inquire about a future appointment to continue discussing whether or not annuities or life insurance are suitable for your individual needs. The Parady Learning Lounge® is not an accredited education center. Parady Financial Group, Inc. is a licensed insurance agency and works closely with Parady Tax Solutions, LLC. ©2020 Parady Financial Group, Inc, All Rights Reserved.
Make Your Next 10, Your Best 10! ®
