The retirement planning conversation people imagine, “do I have enough?”, is the wrong opening question for most of my clients. By the time someone is sitting in my office actually asking it, they usually already have a reasonable sense of the answer. The harder, more interesting questions are about structure: which accounts to draw from in which order, how to handle the years between retirement and Required Minimum Distributions, when to claim Social Security, what to do about the tax cliff that often hits in the year a business is sold or a large position is unwound. Those questions don’t have generic answers. They have right-for-you answers, and getting them right meaningfully changes how much money is left at the end.
I’m Lawrence Israeloff. I’m a Certified Financial Planner™, a CPA, and an attorney based in Melville, NY. I’ve been helping clients across Long Island and the New York City metro plan their retirements for over two decades, with a focus on the tax and coordination work that often falls between specialists.
The questions that actually matter
A few areas where the work I do tends to materially change the outcome:
Withdrawal sequencing
Most retirees end up with three account types: taxable, tax-deferred (traditional IRA, 401(k)), and tax-free (Roth). The default rule of thumb (taxable first, tax-deferred second, Roth last) is roughly right but often suboptimal. The actual best sequence depends on current tax brackets, projected RMDs, IRMAA thresholds for Medicare premiums, state tax considerations, and what the estate plan calls for. Small adjustments to the sequence, pulling some tax-deferred income each year to fill the lower brackets rather than letting RMDs spike taxable income later, can move six figures over a long retirement.
The Roth conversion window
The years between when earned income stops and when Social Security or RMDs begin are often the lowest-tax-bracket years a high-earner will ever have. That’s the window for Roth conversions, and it closes quietly. Converting traditional IRA balances to Roth in years when taxable income is artificially low (early retirement, a sabbatical, a business loss year) can substantially reduce the lifetime tax bill on retirement assets. The math gets more compelling for clients who don’t actually need the IRA money for living expenses and want to leave it to children, since inherited Roths come out tax-free under the post-SECURE-Act ten-year rule.
Required Minimum Distributions and SECURE 2.0
SECURE 2.0 raised the RMD age to 73 (and to 75 starting in 2033), reduced the missed-RMD penalty from 50 percent to 25 percent (or 10 percent if corrected promptly), and added several new provisions worth knowing about – the 529-to-Roth rollover, expanded Roth contributions for SEP and SIMPLE plans, mandatory Roth catch-up contributions for high earners starting in 2026, and surviving-spouse election rules that affect how inherited retirement accounts are treated. The rules have changed enough in the last few years that retirement plans drafted before 2023 often need updating.
Social Security claiming
The choice between claiming at 62, at full retirement age, or at 70 is almost never a pure breakeven calculation. Marital status matters (spousal benefits, survivor benefits, the rules around dependents). Health and family longevity history matter. Earned income in early retirement matters because of the earnings test before full retirement age. For married couples, the optimal strategy often involves coordinated claiming (one spouse files earlier, the other delays) and the right combination depends on relative ages, earnings histories, and projected longevity. The decision is mostly irreversible, so getting it right the first time has real consequences.
Medicare and IRMAA
Once enrolled in Medicare, your premium is determined by your income from two years prior. A high-income year (selling a business, exercising options, taking a large IRA distribution) can push you into IRMAA surcharges that add several thousand dollars per year to Medicare premiums for both spouses. Coordinating retirement-account distributions, capital gains realization, and Roth conversions with the IRMAA brackets is part of the planning, not an afterthought.
The state-tax move
A meaningful share of my retiring clients consider relocating from New York to Florida or another lower-tax state. The tax savings can be substantial, but the planning is more involved than people expect. New York audits residency changes aggressively and looks at factors like primary home, location of family and business interests, the “183-day rule” with detailed day-counting, and where personal items and pets are kept. Clients who handle the move carelessly often find themselves dual-state for years longer than they planned. If a relocation is on the table, it’s worth planning before the move, not after.
Working with your existing advisors
The same positioning that applies to my investment and insurance work applies here: I don’t manage retirement assets, I don’t sell annuities or rollover products, and I don’t earn commissions on anything I recommend. What I do is provide written analysis of your retirement picture, run the projections that show how different scenarios play out over time, and coordinate with your investment advisor, your CPA (if separate), and your estate planning attorney to make sure the strategy works as a whole.
The clients who get the most value from this kind of engagement are usually within five to ten years of retirement, recently retired, or in the middle of a complex transition – a business sale, a relocation, an inheritance, a divorce. If retirement is decades away and the situation is straightforward (steady earned income, regular 401(k) contributions, no business interests) the work I do is probably more than you need yet.
Who I work with
The retirement planning conversations I have most often are with: business owners thinking about how to wind down or transition out of a company they own; high-income professionals (physicians, attorneys, executives) with concentrated equity compensation and complex deferred comp; couples in the five-to-ten-year run-up to retirement who want to stress-test their plan; recent retirees figuring out the actual mechanics of drawing income from a portfolio for the first time; and clients planning a state-tax relocation. Each group has its own set of recurring issues and its own set of high-leverage decisions.
Long Island, NYC, and the surrounding metro
I work out of Melville, NY and serve clients across Long Island, the five boroughs, and Westchester. Where the planning involves federal tax law and Social Security, the rules are the same everywhere; where it involves state income tax, residency, or estate tax, New York’s specific rules shape what’s possible. Useful starting points if you want to read on your own: the CFP Board, the IRS retirement plans portal, and the Social Security Administration. None of those replace advice tied to your specific situation.
Let’s talk
If you’re within a decade of retirement, recently retired, or working through a transition that’s going to reshape your financial picture, that’s typically the right window for this kind of planning. Schedule a consultation and we’ll work through where you are and what the next decisions look like.
