Rich LoPresti, CFP®

Most people arrive at retirement having done everything they were told to do. They saved. They stayed invested. They avoided the big mistakes. And then they discover that nobody ever told them how much of what they saved they actually get to keep.

That gap is the work.

By the time someone is three to seven years out, the number of things they still control has narrowed — but the ones that remain are the ones that matter. When you claim Social Security. Which account you draw from first, and in what order. Which kind of asset sits in which kind of account. And the one almost nobody has modeled: how and when you pay the taxes on money you have already earned.

Most of those decisions get made by default, one at a time, without anyone looking at how they interact. Made deliberately, and early enough, they change the arithmetic.

I start with what you already have. Not a questionnaire — the actual documents. The tax return, the account statements, the Social Security estimates, the pension election. Then I model what happens on the path you are currently on, and what happens on two or three alternatives, so you can see the difference rather than take my word for it. People often arrive with a spreadsheet of their own, or a plan from a previous advisor. That is a good starting point, and going through it carefully is usually where the useful conversation begins.

I have been doing this since 1999 — five years at E*TRADE helping open their first Manhattan offices, five at Fidelity Investments, and five at a boutique wealth management firm in Manhattan — before opening Milestone's Milford office. I earned the CERTIFIED FINANCIAL PLANNER™ certification in 2014 and hold the Certified Wealth Strategist® designation. Milestone is fee-only and independent: we don't sell products, we don't earn commissions, and we sit on the same side of the table as you.

Outside the practice, I write and teach at Retirement Approaching, a project aimed at the people who will never hire an advisor but still deserve to know which levers they control. I'm president of the board of the Milford Arts Council, which runs out of the old Milford train station. I live about two minutes from the office, which after years of commuting into the city I still appreciate more than I probably should.

The first conversation is an hour and there is no cost and no obligation. If it turns out I'm not the right fit, I'll tell you.

You saved successfully. Let’s look at what that success could mean after tax.

Traditional planning. A sharper tax lens.

Investment decisions still matter. So do income, healthcare, family and the freedom to make choices. Tax efficiency belongs inside that full picture—not as a standalone pitch for one strategy.

The goal is to make tradeoffs understandable and coordinate the decisions you can control.

Not ready to talk yet? Start with where you stand →

Clear advice starts with clear roles.

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