Will my savings really last?
We line up your expected spending against Social Security, any pension and your savings, year by year, so you can see whether there is a gap and how big it is.
Try the Income Gap Calculator
Pre-retirees · 5 to 10 years out
Free toolWill your savings cover your spending?Try the Income Gap Calculator →
Retiring in the Next 5 to 10 Years? This Is Your Window to Get It Right.
The choices you make before your last paycheck shape the next 30 years: when to claim Social Security, how your income will be taxed and how you will pay for healthcare before 65. Make them with a clear, written plan while there is still time to adjust.
- Know your monthly income gap before it surprises you
- Pick your Social Security age with your real numbers
- Plan for taxes and healthcare years ahead, not months
Every session is free. No pressure, no obligation. In Orlando or by video.
Plan Ahead,
Not After
Not After
Social Security
Timing
Timing
Tax-Smart
Income Plan
Income Plan
Healthcare
Before 65
Before 65
Why the next few years matter most
Most retirement mistakes happen before retirement starts
You have spent decades saving. Now the questions change. It is no longer “How much can I put away?” but “How do I turn this into a paycheck that lasts as long as I do?”
Ten years out, you have time to adjust: work a little longer, change how much you save, line up your taxes, plan your healthcare. One year out, most of those doors are closing. The earlier you see the full picture, the more choices you keep.
Common surprises we help people avoid
- Claiming Social Security early and locking in a smaller check for life
- Retiring at 62 with no plan for health insurance until Medicare at 65
- A bigger tax bill than expected once withdrawals and required distributions start
- Monthly spending that runs higher than the budget on paper
- A spouse who would lose a large share of income after a death
Dates and numbers that shape your plan
The retirement rules worth knowing now
These are a few of the rules we build every pre-retirement plan around. Each one is easier to plan for five years early than five months early.
Up to 30%smaller monthly Social Security check if you claim at 62 instead of your full retirement age of 67
8% a yearadded to your Social Security benefit for each year you wait past full retirement age, up to age 70
Age 65when Medicare starts for most people. Retire earlier and you need another way to cover healthcare
73 or 75the age required minimum distributions begin from most pre-tax retirement accounts, depending on your birth year
Full retirement age is 67 for anyone born in 1960 or later. RMDs begin at 73 if you were born 1951 to 1959 and at 75 if born in 1960 or later. Sources: SSA.gov, Medicare.gov, IRS.gov. Your own numbers depend on your situation.
Your retirement countdown
What to do 10, 5 and 1 year before you retire
A simple, year-by-year checklist. Find where you are today and start there.
- 10 years out
Get the picture
- Sketch the retirement you want: where, how and with whom
- Estimate what you spend each month today
- Download your Social Security statement at ssa.gov
- List every account, pension and insurance policy
- 7 years out
Find the gap
- Compare future spending with expected income
- Note which savings are pre-tax, Roth or after-tax
- Set a plan to be debt-free, or close to it
- Talk with your spouse about timing
- 5 years out
Test the big decisions
- Compare Social Security ages for both spouses
- Plan health insurance if retiring before 65
- Review life, disability and long-term care coverage
- Check any pension payout and survivor options
- 2 to 3 years out
Write the income plan
- Decide which money pays for what, and in what order
- Map your taxes year by year, including RMDs
- Update your will, powers of attorney and beneficiaries
- Practice living on your retirement budget
- The final year
Make it official
- Mark your Medicare enrollment window around 65
- Make pension and employer plan elections
- Choose your Social Security start date
- Set up your first retirement paycheck
60-second self check
Are you on track for retirement?
Answer eight quick questions. You will see where your plan is strong and where it may need work. Nothing is saved or sent.
1. I know about how much I will spend each month in retirement.
2. I know how much of that Social Security and any pension will cover.
3. I have compared Social Security claiming ages using my own numbers.
4. I have a plan for health insurance if I stop working before 65.
5. I know which accounts I will draw from first, and how each one is taxed.
6. I have estimated my taxes in retirement, including required minimum distributions.
7. My will, powers of attorney and beneficiary forms are up to date.
8. I have a plan if my spouse or I ever need long-term care.
Answer all eight to see your result. 0 of 8 answered.
What a pre-retirement plan answers
Five questions to settle before you retire
Every question below touches the others. That is why we look at them together, in one plan, instead of one at a time.
When should I claim?
Claiming at 62, 67 or 70 can mean a very different lifetime benefit, especially for married couples and the surviving spouse. We compare the ages side by side.
Social Security planningHow much will I keep after taxes?
The order you draw from your accounts can change your lifetime tax bill. The years between retiring and RMDs are often a chance to plan ahead. Roth conversions are taxable in the year of conversion and may not be appropriate for everyone.
Tax-efficient strategiesHow do I cover healthcare before 65?
Retiring early means planning a bridge to Medicare, then choosing the right Medicare coverage on time to avoid lifelong late penalties.
Healthcare planningWhat happens to my spouse?
When one spouse dies, one Social Security check usually stops and taxes can go up. We plan now so the person left behind keeps a steady income.
Estate planningNot sure where you stand?
Bring your questions and your latest statements. You will leave with clear next steps, whether or not we work together.
Book a Free Consultation
Same savings, two different retirements
Retiring with a plan feels different
Winging it
- Claim Social Security when the paychecks stop
- Pull from whichever account is easiest
- Find out about the tax bill in April
- Hope the money lasts and check the balance often
With a written plan
- Claim at the age that fits your whole household
- Know which account pays for what, and when
- See your tax picture years in advance
- Know your monthly paycheck and what to do if things change
How it works
Three simple steps to a clear plan
Book a free session
Pick a time that suits you, in Orlando or by video. Bring your questions and whatever statements you have.
See your full picture
We look at income, Social Security, taxes, healthcare and your family together, and show you where the gaps are.
Leave with next steps
You get a clear list of what to do and when. If you want help putting it in place, we can talk about that too.
Your guide
Hi, I’m Roger Fishel.
I help people in the last stretch before retirement turn decades of saving into a plan they understand. I work independently, so my job is to look at your whole picture and explain your choices in plain English.
- 20+ years guiding retirement decisions
- Independent since 2021, not tied to any one company
- One person who coordinates with your CPA and attorney
Free tools to get started
Not ready to talk yet? Start here.
CalculatorRetirement Income Gap CalculatorSee whether your savings, Social Security and pensions may cover your monthly spending.
CalculatorSocial Security Break-Even CalculatorCompare claiming at 62, 67 and 70 and find your break-even age.
QuizRetirement Readiness QuizGet your readiness score and a free personal PDF report in about a minute.
Free guide9 Retirement Blunders to AvoidThe common mistakes people make in the years right before retirement.
Questions
Retiring in 5 to 10 years: common questions
What should I do 5 years before retirement?
Five years out is the time to test the big decisions. Compare Social Security claiming ages for you and your spouse, plan how you will cover health insurance if you retire before 65, estimate your taxes in retirement, review your life and long-term care coverage and update your will and beneficiaries. It is also a good time to practice living on your expected retirement budget.
How do I know if I can retire in 10 years?
Start by estimating what you will spend each month in retirement, then compare it with your expected income from Social Security and any pension. The difference is your income gap, the amount your savings will need to cover. Our free Income Gap Calculator gives a quick hypothetical estimate, and a free session can look at your full picture.
What is the best age to claim Social Security?
There is no single best age. Claiming at 62 can cut your monthly benefit by up to 30% compared with a full retirement age of 67, and each year you wait past full retirement age adds 8% until age 70. Your health, other income, marriage and the benefit your spouse would keep as a survivor all matter, so it helps to compare the ages with your own numbers.
How do I get health insurance if I retire before 65?
Options can include retiree coverage from your employer, COBRA for a limited time, a spouse’s plan or a plan from the Health Insurance Marketplace. Marketplace costs often depend on your income, so your income plan and your healthcare plan work best when built together. Medicare generally starts at 65, with a seven-month window to enroll around your birthday month.
How will my retirement income be taxed?
Part of your Social Security can be taxable, withdrawals from pre-tax accounts such as a traditional 401(k) or IRA are taxed as ordinary income, and qualified Roth withdrawals generally are not taxed. Florida has no state income tax. The order you draw from your accounts can change your lifetime tax bill. Neither the firm nor its agents or representatives may give tax or legal advice, so we coordinate with your tax professional.
When do required minimum distributions start?
Required minimum distributions from most pre-tax retirement accounts begin at 73 if you were born from 1951 to 1959 and at 75 if you were born in 1960 or later. They can push your income into a higher bracket and raise Medicare premiums, so the years before RMDs begin can be a useful planning window. Roth conversions are taxable in the year of conversion and may not be appropriate for everyone.
Should I pay off my mortgage before I retire?
It depends on your situation. Retiring without a mortgage lowers your monthly spending, but pulling a large sum from pre-tax savings to pay it off can raise your taxes and reduce the cash you can reach in an emergency. We look at your income, taxes and comfort with debt together before you decide.
How much does a retirement planning session cost?
Nothing. Every session is free, with no pressure and no obligation. You can meet in Orlando or by video from anywhere in the country, and you will leave with clear next steps whether or not we work together.
Your next step
Your retirement date is coming either way. Walk into it with a plan.
In one free conversation you will see where you stand, what could get in the way and what to do next. No pressure and no obligation.
Book My Free Retirement Clarity SessionPrefer to talk now? Call (407) 974-7100
