New Haven County · Connecticut
Fee-based fiduciary tax-sensitive retirement planning for Ansonia 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 Ansonia 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.
Ansonia's manufacturing history means many retirees here are coordinating a legacy pension with Social Security and a smaller 401(k) balance.
Much of our New Haven County work happens across one cluster of towns — Ansonia and neighbours like Derby, Seymour and Beacon Falls. The drive to Milford is short enough that in-person meetings stay easy to schedule around a workday.
Our Milford office is roughly 22 minutes from Ansonia, 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.
When should I claim Social Security? We model your actual benefit at 62, at full retirement age, and at 70 against your real spending and other income, rather than applying a rule of thumb. For married couples the higher earner's decision permanently sets the survivor benefit, and that consequence usually outweighs the break-even math people focus on. If delaying is right, the next question is which assets fund the years in between.
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.
The order you spend from. Most households arrive with three kinds of money — taxable, tax-deferred, and Roth — and no plan for which one funds which year. There is no universal answer, because the right order changes with your bracket, whether you are converting, whether you are on marketplace coverage before Medicare, and what your future required distributions look like. It is a decision that gets made annually, with the return in front of us.
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.
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.
What happens to the 401(k) when you actually retire. Leaving it, rolling it, or taking it in stages are all defensible depending on the plan's costs, what it holds, and what you need the money to do. What is rarely defensible is deciding by default because a form arrived in the mail. It is worth a deliberate look in the months before your last day, while you still have options the plan may close afterward.
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 Ansonia households — with the arithmetic shown.
Worked example
An Avon couple on Medicare planned a $15,000 Roth conversion that would have crossed the first surcharge threshold. Resizing it to $5,000 keeps income $3,000 under the line and avoids about $2,296 a year in premiums — a cost that would not have shown up until 2 years later.
Hypothetical example — not an actual client.
See the full Medicare surcharge exampleWatch
Brian covers the questions we hear most from Connecticut households approaching retirement.
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Connecticut taxes retirement income differently than most states — and the rules changed significantly in recent years. This guide breaks down exactly how Social Security, pensions, 401(k) withdrawals, and capital gains are taxed for CT residents in 2026, so you can plan with clarity.
Make informed decisions about when to claim Social Security benefits, with timing that accounts for Connecticut's unique tax landscape.
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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.
