New Haven County · Connecticut
Fee-based fiduciary tax-sensitive retirement planning for Seymour pre-retirees and retirees age 50+.
We work with households who have $1 million or more in investable assets.
Skinner Wealth Strategies is a fee-based fiduciary financial advisor serving Seymour and the surrounding New Haven 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.
Seymour anchors the middle of the Naugatuck Valley, with easy Route 8 access to both the shoreline and Waterbury.
Seymour is part of the Lower Naugatuck Valley, and we work with households here alongside neighbours in Ansonia, Beacon Falls and Derby. Meeting at our Milford office is straightforward for the two or three in-person meetings a plan actually requires.
Our Milford office is roughly 25 minutes from Seymour, an easy trip for the two or three in-person meetings most plans involve. We meet clients in person at either our Milford or West Hartford office, or virtually — whichever fits your schedule.
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.
The same three steps for everyone, and the first two cost nothing:
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.
New Haven County spans the shoreline from Milford east to Madison and runs north through the Naugatuck Valley. It is a mix of long-tenured healthcare, academic, and manufacturing households — which in practice means a lot of 403(b) and 457 balances, legacy pensions, and people who intend to stay in the same house through retirement rather than relocate. Deciding which of those accounts funds which year, and what that does to the tax bill, tends to matter more here than relocation planning.
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.
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.
The first five years of withdrawals. Sequence-of-returns risk is the reason two retirees with the same average return can end up in very different places: it matters enormously whether the bad years land early, while you are drawing income. We hold near-term spending in short-duration assets specifically so a downturn is funded from the reserve rather than by selling depressed holdings at the worst possible moment.
Spending it once you have permission to. A surprising amount of the work is not about whether the money lasts — it is about giving people a defensible reason to spend it. Decades of saving builds a habit that does not switch off, and plenty of retirees underspend their way through the healthiest years they will have. A plan with guardrails is as much about permission as it is about restraint.
How We Plan
Three areas where the decisions made in the years before retirement tend to matter more than anything that happens inside the portfolio.
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.
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.
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
A hypothetical illustration of the planning we do for Seymour households — with the arithmetic shown.
Worked example
A Milford couple two years from required distributions converts $180,000 at a modeled 22% instead of drawing it later at an assumed 28% — $10,800 ahead on rate alone, and about $6,792 off the first year's required distribution, because it is calculated on a balance that is now smaller.
Hypothetical example — not an actual client.
See the full RMD planning exampleWatch
Brian covers the questions we hear most from Connecticut households approaching retirement.
Nearby
Read
Yes — once you become eligible for Medicare at 65, you generally lose eligibility for the ACA premium tax credit. But the years leading up to 65 are when income planning matters most.
Health insurance is one of the biggest financial challenges of retiring early — but with the right income strategy, Connecticut pre-retirees may be able to dramatically reduce what they pay for coverage through Age 65.
Get Started
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.
