What pre-retirement planning actually is
Pre-retirement planning is the work of making the last decade of work do its job. Some of that job is technical — fitting the accounts together, modeling the income, mapping the brackets. Some of it is quieter — getting honest about what the next thirty years are supposed to feel like and finding the gap between the household's picture of retirement and the math of the household's actual balance sheet.
Most people we sit down with at this stage are not asking whether they can retire. They are asking how, and when, and what to do about the items they have been postponing for the last twenty years. Social Security claiming. Long-term care. The bridge from a job that provides health insurance to a Medicare year that does not start until sixty-five. The decision about whether to keep working part-time, or consult, or stop entirely.
These are the conversations the brochures skip and the ones that matter most.
Pre-retirees are one of several audiences we treat as their own planning category — see the broader list of the people we sit down with most often.
The questions pre-retirees actually bring us
The questions in this window are the ones that produce the largest single dollar impact of any planning conversation we have. None of them get a good answer in twenty minutes at a brokerage office.
- When do we actually have enough — not in a brochure number, but in our specific situation?
- Should I claim Social Security at sixty-two, sixty-six, or seventy, and what does my spouse claim?
- If I retire before sixty-five, how do I handle health insurance for the years before Medicare without going broke?
- Which account do I spend from first, and what does that do to my tax bill?
- What do I do about long-term care — buy a policy, self-fund, or do something in between?
Where most advice gets pre-retirees wrong
The standard playbook for pre-retirees is to run a Monte Carlo simulation, hand the household a binder, and call the work done. The simulation produces a percentage and the percentage produces a feeling of certainty. Neither one tells the household what to do in the year a market drops twenty percent in the first six months of retirement.
The other failure mode is the firm that shifts the household into a heavy annuity allocation in the name of safety. Annuities have their place. They are also commission-heavy products that get sold to pre-retirees more aggressively than to any other group, and the policies that get sold are rarely the policies the household actually needed.
We do something quieter. We build a written income plan that maps the next ten years account by account, bracket by bracket, year by year. We stress test it against a 1970s-style bad decade, not an average one. We tell the household what to do in the bad year before the bad year arrives.
The Social Security claiming decision is one of the largest single-dollar financial decisions a household will ever make, and it deserves more than a twenty-minute conversation at a federal office. Our notes on claiming strategies for couples and surviving spouses walk through how we run the math.
The work we do for pre-retirees
We start with the picture on one page — every account, the income, the expected expenses, and the household's honest picture of what retirement is supposed to look like. From there, the work splits into three tracks.
The first track is the income plan. We map the next ten to fifteen years of withdrawals against tax brackets, identify the years where Roth conversions earn their keep, and lay out a sequence that does not force the household to sell stocks during a down market.
The second track is Social Security and pensions. The claiming math for a couple is not the same as the claiming math for an individual, and the right answer often involves one spouse claiming early and the other delaying. We run the actual numbers and we show our work.
The third track is healthcare. The years between an early retirement and the start of Medicare can cost more than a small mortgage. We build the bridge into the plan instead of finding it in the mail.
When old employer plans need to be moved into a single account before withdrawals begin, the mechanics matter — see our notes on handling a rollover from an old plan without the paperwork migraine.
The shift from accumulation to decumulation changes the goal of the portfolio. Our piece on what changes when the job of the portfolio shifts from growing to lasting walks through how we redesign allocations for the income years.
Disability is an underrated risk in the last working decade — losing the ability to finish the years you were counting on can change the entire plan. Our notes on why disability coverage is the policy late-career professionals most often get wrong are a good companion read.
The tax treatment of where the dollars sit is the lever we lean on most heavily during the gap years between retirement and required distributions. Our piece on why the tax wrapper around an account matters as much as the account itself explains how we use the gap years for Roth conversions and bracket management.
For households where the planning question is more about what comes after a partner is gone than about retirement itself, the parallel page on planning as a surviving spouse covers the longevity questions from a different angle.
What working with us looks like
First meeting — sixty minutes, in person
We meet at our Paramus office, at your home, or at your workplace. Bring whatever you can find — recent statements, the most recent Social Security earnings report, any pension paperwork. We ask what retirement actually looks like in your head and where the gaps are. By the end of the hour we have enough to know whether we can help.
Second meeting — your written income plan
We come back with a written retirement income plan: withdrawal sequence, Social Security claiming strategy, healthcare bridge, and a stress test against a bad decade. The plan is yours to keep whether or not we work together. If we are not the right fit, you still leave with the work.
A note on fit
When this might not be right for you
Pre-retirement planning is not for every household. Some of the people we are not the right fit for:
- Anyone looking for a firm that will sell them an annuity as a finished retirement plan. We do not sell annuities, and we have opinions about most of the policies sold to households at this stage.
- Anyone who wants someone to actively trade their portfolio. We do not market-time, and we will not pretend to.
- Anyone whose plan is to figure out the income side after they retire. By then most of the planning runway is already gone.
- Anyone who would rather receive a quarterly PDF than meet in a room. We do the opposite of that on purpose.
If any of that describes the seat you're in, we'd rather say so on the first call.
Frequently asked questions
When should I start planning for retirement?
The five to ten years before your intended retirement date are the most consequential planning years of your financial life. There is still time to size Roth conversions, restructure savings, plan the healthcare bridge, and run real Social Security claiming math. Households that wait until the year they retire usually leave money behind.
How do I know if I have enough to retire?
Not by a single number on a brochure. The honest answer comes from mapping your actual expected expenses, your reliable income sources, and your portfolio against a stress-tested withdrawal plan that survives a bad decade — not just an average one. We build that plan in writing.
What is the best age to claim Social Security?
It depends on your other income, your spouse's earnings record, your expected tax brackets, and your honest read on your own health. For most healthy married couples, delaying the higher earner's benefit to seventy produces more lifetime income. We model the full claiming math for both spouses before any election.
How do I handle health insurance if I retire before sixty-five?
The years between an early retirement and Medicare can cost more than a small mortgage in private health coverage. The planning has two parts: lining up the retirement date with a coverage transition that actually works, and using the right tax-advantaged account where possible. We build the bridge into the income plan.
Which retirement account should I spend from first?
The standard rule is to drain taxable first, then tax-deferred, then Roth. That rule is wrong more often than right. The better answer is to map your tax brackets across the next ten years and pull from whichever account fills the bracket without overflowing it. The right answer changes every year.
Do I need long-term care insurance?
Maybe. For some households, a properly priced policy makes sense. For others, the right answer is to self-fund the risk. We model the household's specific situation and we have honest opinions about the policies actually being sold today. We do not earn commissions on any of them.
How much does fee-only retirement planning cost?
It depends on the engagement. A standalone written income plan is usually a flat fee. An ongoing advisory relationship is typically charged as a percentage of investable assets in the 0.6 to 1.0 percent range. We publish fees in writing before you agree to anything and we accept no commissions.