Skinner Wealth Strategies

Fairfield County · Connecticut

Financial Advisor in Newtown, CT

Fee-based fiduciary tax-sensitive retirement planning for Newtown pre-retirees and retirees age 50+.

We work with households who have $1 million or more in investable assets.

Retirement Planning for Newtown

Skinner Wealth Strategies is a fee-based fiduciary financial advisor serving Newtown and the surrounding Fairfield County communities. We work with people who have spent a career building savings and now need a plan for turning it into income. Our focus is tax-efficient retirement planning for pre-retirees and retirees — coordinating your investments, your taxes, and your retirement income as one plan instead of three separate problems.

Newtown is one of Connecticut's largest towns by land area, with the Sandy Hook and Hawleyville villages and quick I-84 access.

We serve Newtown as part of a broader Fairfield County practice that also covers Monroe, Bethel and Brookfield. Milford is close enough that clients who want to meet in person easily can, and far enough that plenty choose video instead.

Newtown is about 38 minutes from our Milford office. Many clients at this distance do the first meeting in person and the rest by video. We meet clients in person at either our Milford or West Hartford office, or virtually — whichever fits your schedule.

Who we work with in Newtown

We specialize in people over 50 who have more than $1 million in savings and who need help turning a life's work into a steady income stream for retirement, in a tax-sensitive way. When you have spent your career in saving mode, reorganizing those habits for a new phase of life is a genuine shift, and it is the shift we are built to help with.

The common thread is almost never a lack of savings. It is that the investments, the taxes, and the income have never been planned together — an investment manager here, a CPA there, and nobody owning the whole picture.

Where we start with Newtown clients

The same three steps for everyone, and the first two cost nothing:

  1. DiscoveryA no-cost call to understand your situation and see whether we are a fit.
  2. AssessmentA deeper review of where you stand, and the strategies actually available to you. Also no cost.
  3. OpportunityThe plan itself — projections, personalized strategies, and a decision that is yours to take your time over.
See the full process

What we do for Newtown retirees and pre-retirees

  • Retirement Planning — retirement readiness analysis, scenario planning, and bringing a lifetime of separate pieces — an old 401(k), a pension, a brokerage account, an insurance policy — together into one coordinated plan.
  • Retirement Income — an academically grounded approach built on income guardrails and investment buckets, taking every income source into account so the portfolio is not doing work that Social Security or a pension already does.
  • Tax Planning — reviewing your annual return, planning Roth conversions each year, coordinating the timing of different income streams, and watching the thresholds that would otherwise spike your Medicare premiums later.
  • Social Security Strategy — analyzing your filing age against your actual plan, understanding how your other income affects the benefit, and protecting a spouse's survivor benefit.
  • Investment Management — keeping investment cost low, focusing on quality, and building the mix around the income you actually need rather than an abstract risk score — with tax efficiency decided at the holding level.
  • Coordinated coverage review — we review existing policies as part of the plan and introduce you to qualified outside resources when something should be shopped. We do not sell insurance.

Building the portfolio around the income

A portfolio built to accumulate and a portfolio built to distribute are not the same portfolio, even when they hold similar things. While you are saving, a decline is an inconvenience and arguably an opportunity. Once you are drawing an income from it, the same decline is a forced sale. So the allocation stops being a question of abstract risk tolerance and becomes a question of funding dated, sequenced withdrawals: what has to be spendable in the next few years is held in short-duration assets, and only what is genuinely long-dated carries market risk. Mapping known income — Social Security, a pension — against required distributions and voluntary withdrawals also shows which years land in a lower bracket than the ones around them, and those are the years worth using for a conversion or a change in asset location.

Retirement income here starts with a chosen withdrawal rate and a dollar amount. Each year that amount adjusts for inflation, unless the portfolio has had a negative return over the prior twelve months. If strong performance pushes your withdrawal rate well below where it started, spending can increase; if a downturn pushes it well above, spending is trimmed. The point of setting the boundaries in advance is that you know before it happens what would cause your income to move and by how much — which is a very different experience from deciding what to do in the middle of a bad market.

Planning in Fairfield County

Fairfield County households often arrive at retirement with the most moving parts: a workplace plan, a taxable brokerage account built over decades, and a house that represents a large share of net worth. The planning question is rarely whether there is enough. It is how to draw an income from all of it without handing an avoidable share to taxes, and how to step down from a high-bracket working life into a retirement income plan deliberately rather than by default.

A question we get a lot here

Should I be converting to a Roth, and how much? The window between your last paycheck and your first required minimum distribution is usually the lowest-bracket stretch you will ever have, which makes it the most valuable planning years most people never use. We model income across those years and convert up to the top of a target bracket rather than guessing at a round number — while watching the income thresholds that raise Medicare premiums two years later, and modelling the Connecticut tax alongside the federal.

Other things that come up often around Newtown

Consolidating a career's worth of accounts. An old 401(k) from two employers ago, a rollover IRA, a pension election letter, a brokerage account someone opened in the nineties, and a life insurance policy nobody has looked at since. Almost every plan starts by finding all of it and deciding what still has a job to do. Consolidation is not the goal in itself — clarity about what each piece is for is.

Required minimum distributions. At some point the IRS stops letting a tax-deferred balance sit. Required minimum distributions arrive whether you need the income or not, and for households who saved diligently into a 401(k) for thirty years they can push you into a higher bracket in retirement than you were in while working. The planning happens in the years before they start, not in the year they do.

What the plan does in a bad market. The question worth answering before you retire is not what the portfolio returns in a good decade — it is what you do in a bad one. A guardrails approach defines in advance what triggers an adjustment and how large that adjustment is, so a market drop produces a known response rather than an improvised one.

Medicare premium surcharges. Medicare Part B and Part D premiums are income-tested, and the test looks back two years. That means a decision at 63 — a large conversion, a property sale, a lumpy distribution — can raise your premiums at 65 without anyone having flagged it at the time. Watching those thresholds is routine work, and it is one of the most commonly missed costs of an otherwise sensible move.

Working alongside your CPA and attorney. We do tax planning, not tax preparation. Your CPA files what already happened; our job is what happens next — which account funds this year, how much to convert, which thresholds to stay under. The same applies on the estate side: we handle the financial and tax work and coordinate with your attorney on the documents rather than replacing either of them.

How We Plan

The Parts That Move the Number Most

Three areas where the decisions made in the years before retirement tend to matter more than anything that happens inside the portfolio.

Required minimum distributions and the bracket spike

Required distributions start at 73 or 75 depending on when you were born, and they arrive whether you need the income or not. The damage is rarely the distribution itself — it is that it stacks on Social Security and pension income, increases how much of your Social Security is taxed, and can trip a Medicare surcharge that behaves as a genuine cliff rather than a bracket.

What Connecticut does differently

Connecticut exempts retirement income only below an AGI line, taxes Roth conversions in full at 2%–6.99% with no carve-out, and offers no preferential rate on long-term gains the way the federal system does. Its estate tax is also widely misdescribed: since 2023 it applies only to the excess over the exemption, not the whole estate.

Three of the biggest risks to a retirement plan

The order returns arrive in matters more than the average — research puts the correlation with a sustainable withdrawal rate at roughly 0.80 against the first decade's real return, versus only 0.21 against the first year alone. Add unmanaged tax risk on a large deferred balance and two or three decades of inflation, and you have most of the structural damage we are asked to repair.

By the Numbers

What This Looks Like in Practice

A hypothetical illustration of the planning we do for Newtown households — with the arithmetic shown.

Worked example

The eleven-year conversion window

$48,000modeled federal rate arbitrage

A Westport couple retiring at 64 has eleven years before required distributions begin. Converting $600,000 across four of them, sized to stop at the top of the 24% bracket, models out $48,000 ahead of drawing the same dollars later at an assumed 32% — before counting growth on the converted balance.

Hypothetical example — not an actual client.

See the full Roth conversion example

Watch

Retirement Planning, Explained

Brian covers the questions we hear most from Connecticut households approaching retirement.

Financial Planning in Newtown — Common Questions

Do you work with clients in Newtown, CT?
Yes. Skinner Wealth Strategies serves clients throughout Fairfield County and the rest of Connecticut. Newtown is about 38 minutes from our Milford office. We meet clients in person at either office or virtually, whichever you prefer.
What is IRMAA and why does it affect my Roth conversion timing?
IRMAA is the income-related surcharge on Medicare Part B and Part D premiums, and it is assessed on the return you filed two years earlier — so a large conversion at 63 sets your premium at 65. The detail that catches people is that it behaves as a genuine cliff rather than a bracket: ordinary tax brackets only charge the higher rate on income above the line, but crossing an IRMAA threshold by a single dollar applies the whole surcharge for that tier. It is one of the most commonly missed costs of an otherwise sensible conversion.
Can I convert after I've already started required minimum distributions?
Yes, though the arithmetic changes. Once RMDs begin you must take the distribution first, and it can't be converted — so the room available for conversion in a given bracket shrinks. This is a large part of why the pre-RMD window matters.
What kind of Newtown households do you typically work with?
Our clients are generally age 50 or older with $1 million or more in investable assets who are approaching or already in retirement and need their investments, taxes, and income planned together rather than separately. Within that, a recurring topic here is multi-year Roth conversion strategy, bracket management, and IRMAA-aware income sequencing.
Are you a fiduciary?
Yes. As fiduciaries and CERTIFIED FINANCIAL PLANNER™ (CFP®) professionals, we're committed to putting your needs first whenever we provide financial advice, with transparent pricing and personalized guidance.
Do you work alongside my CPA and attorney?
Yes, and we prefer to. We do tax planning rather than tax preparation — your CPA files what already happened, and our job is what happens next: which account funds this year, how much to convert, which thresholds to stay under. The same applies on the estate side, where we handle the financial and tax work and coordinate with your attorney on the documents. We are not looking to replace either relationship, and if you don't have one we can point you to qualified people locally.
How do I get started?
Schedule a no-cost discovery call. We'll learn about your situation, answer your questions, and tell you honestly whether we're the right fit.
What's the biggest tax mistake people make in retirement?
Leaving a large tax-deferred balance unmanaged through the low-bracket years. The stretch between your last paycheck and your first required distribution is usually the lowest-bracket period you will ever have, and it is the one most commonly left unused. Ed Slott's framing is that an unmanaged deferred balance is a tax bill waiting to happen, and it grows the longer it is ignored — because the balance compounds and the eventual required distributions compound with it.
Should I take my required distribution or convert to a Roth first — does the order matter?
It matters, and the order is not actually optional. Once required distributions begin at 73 or 75 depending on your birth year, the required amount has to come out first and it cannot itself be converted. That distribution occupies room in your bracket, so the space left for a conversion in any given year shrinks accordingly. It is a large part of why the pre-distribution window is worth planning deliberately rather than arriving at.

Nearby

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Get Started

Talk to a Newtown Financial Advisor

A first conversation costs nothing and carries no obligation. We’ll learn about your situation and tell you honestly whether we can help.

Our planning work is built for households age 50+ with $1 million or more in investable assets. If that isn’t you yet, we’d rather say so now than on the call.

Skinner Wealth Strategies serves clients throughout Connecticut from offices in Milford and West Hartford. Meetings are available in person or virtually. This page is informational and is not a solicitation in any state where the representative is not registered.