When should I start pre-retirement planning?

The most useful window is somewhere between age 50 and 60. That gives you 5 to 15 years before retirement, with time to adjust savings rate, run Roth conversions through the low-tax years, and model Social Security claiming. If you're inside 5 years, the work is still worth doing but tighter.

How do I know if I have enough to retire?

There's no single number. The honest version: you need enough that the withdrawals you take after tax and inflation cover your spending for as long as you live. For most clients we model three or four scenarios with different spending and longevity assumptions. Use the calculator for a starting number, but a real plan goes deeper.

What's the healthcare bridge?

The healthcare bridge is the gap between when employer coverage ends at retirement and when Medicare starts at age 65. Options include COBRA (usually 18 months), the ACA exchange with potential subsidies based on income, retiree health plans where available, or spousal coverage if applicable. Planning involves both the cost and the income management that affects subsidy eligibility.

Should I delay Social Security?

For most clients in good health with other income to bridge the gap, delaying produces the largest expected lifetime payout. The benefit grows about 8 percent per year for each year you delay past full retirement age, up to age 70. However, health, marital status, and other income sources should all be considered before deciding.

What's the order I should withdraw from my accounts in retirement?

It depends on your tax situation, but a common strategy is to withdraw from taxable accounts first, then tax-deferred accounts while managing your tax bracket, and finally Roth accounts because qualified withdrawals are tax-free. Many retirement income plans draw from multiple account types each year to optimize taxes, and the best sequence depends on your specific financial situation.

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Financial Planning For Pre-Retirees. In The Years That Matter Most.

Financial planning for pre-retirees in their 50s and early 60s, when most of the levers still work. Roth conversions, Social Security timing, healthcare bridge planning, and withdrawal sequencing all get decided here.

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Fiduciary CFP® Multi-Year Models Roth Conversion Window Healthcare Bridge

HOW WE WORK WITH PRE-RETIREES

The 5 to 10 years before retirement is the biggest planning window of your life.

Multi-year tax modeling

Roth conversion strategy, charitable timing, capital gains realization, withdrawal sequencing. Modeled over the years where the brackets are flexible.

Healthcare bridge

From end of employer coverage to Medicare. ACA exchange subsidies, COBRA, retiree health plan timing. One of the bigger out-of-pocket questions in early retirement.

Social security timing

When to claim, how spousal benefits factor in, and how the claim sequence fits with the withdrawal sequence.

Income strategy, written down

By the time work income stops, the withdrawal plan should be written and rehearsed. The order of operations matters.

Long-term, not transactional

We meet twice a year on a set schedule, and when life calls for it in between. The plan flexes as your life and the tax code change. Most relationships span decades.

South Florida-rooted, nationally licensed

Offices in Boca Raton and Plantation, plus licensed in all 50 states. Existing clients keep us when they move.

What we cover.

Cash flow modeling at age 60, 65, 70. Replacement-income targets, spending assumptions, and the savings rate needed to bridge the gap.

Roth conversion strategy. The window between when work income stops and when RMDs begin is often the highest-value tax planning window of a client's life. See Roth conversion.

Withdrawal sequencing. The order you draw from taxable, tax-deferred, and Roth accounts has more impact than most clients realize. We model it explicitly.

Social Security claim timing. When to claim, how spousal and survivor benefits factor in, and how Social Security fits the broader income sequence. See Social Security.

Healthcare bridge. COBRA, the ACA exchange, retiree health plans, and Medicare timing. Coordinated with the broader retirement income plan.

IRA and 401(k) rollovers. Consolidating old employer accounts into a single managed structure. See rollovers.

Estate plan refresh. Often the existing estate plan was built in a different decade. Pre-retirement is the right moment to update.

WHAT THIS LOOKS LIKE IN PRACTICE

Common situations we work through.

Composite scenarios drawn from real client work, anonymized.

01 The first 90 days

Cash flow stabilized, beneficiaries audited, a draft plan in hand. Most clients feel oriented by month three.

02 The first year

Tax positioning implemented, investment policy in place, the first semiannual reviews done. Decisions start compounding.

03 Three years in

The plan has flexed to handle real-life shifts (a new job, a sale, a loss). The pattern is steady decisions, not reactive ones.

How we work together.

Most pre-retirement planning relationships are intensive in year one (when the planning gets built) and then settle into a semiannual review cadence. The first year typically involves 4 to 6 meetings to build the full picture. After that, the rhythm is set by the calendar of the planning itself: Roth conversion deadlines, year-end tax work, Social Security filing milestones.

If you're within 10 years of when you want to retire, this is the window. The Roth conversion years, the Social Security claim decision, the healthcare bridge, the rollover timing. All of it benefits from real-time modeling and a written plan.

RELATED SERVICES

What pre-retirement planning typically covers.

Common entry points:

Retirement Planning

The complete hub. Income strategy, withdrawal sequencing, RMDs, healthcare.

See retirement planning

Roth Conversion Strategy

Multi-year tax modeling for the low-income window before RMDs start.

See roth conversion strategy

Social Security Optimization

When to claim, how spousal and survivor benefits factor in.

See social security optimization

Who This Is For

Related specialty pages.

Many pre-retirees also fit one of these:

Executives Business Owners Widows Divorced Women Inheritors

What we don't do.

Contact Us Today

We don't lead with proprietary products, structured notes, or non-traded REITs as a portfolio building block. We don't take custody of your assets. We don't promise market-beating returns. The honest answer is that nobody who has to tell the truth to a regulator can.

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No obligation. We respond the same business day.

QUESTIONS, ANSWERED
Common questions about Financial Planning for Pre-retirees

The most useful window is somewhere between age 50 and 60. That gives you 5 to 15 years before retirement, with time to adjust savings rate, run Roth conversions through the low-tax years, and model Social Security claiming. If you're inside 5 years, the work is still worth doing but tighter.
There's no single number. The honest version: you need enough that the withdrawals you take (after tax, after inflation) cover your spending for as long as you live. For most clients we model three or four scenarios with different spending and longevity assumptions. Use the calculator for a starting number, but a real plan goes deeper.
The healthcare bridge is the gap between when employer coverage ends (retirement) and when Medicare starts (age 65). Options include COBRA (usually 18 months), the ACA exchange (with potential subsidies based on income), retiree health plans where available, or spousal coverage if applicable. The planning involves both the cost and the income management that affects subsidy eligibility.
For most clients in good health with other income to bridge the gap, delaying produces the largest lifetime expected payout. The benefit grows about 8 percent per year for each year you delay past full retirement age, up to age 70. But the default math isn't the right answer for everyone. Health, spouse situation, and other income all matter.
Depends on the tax situation, but the general principle: taxable accounts first (to use up cash, basis is high), then tax-deferred (manage the bracket), then Roth (last, since growth is tax-free). The actual sequence usually involves drawing partially from multiple buckets each year to manage the tax bracket. We model it for your specific situation.

Find Us

Two offices, one team.

Boca Raton (Home Office)

1200 North Federal Highway, Suite 300

Boca Raton, FL 33432

(561) 210-7339

Monday to Friday, 8:30 AM to 4:30 PM ET

Plantation

7901 SW 6th Court, Suite 320

Plantation, FL 33324

(954) 809-3553