Skinner Wealth Strategies

New Haven County · Connecticut

Financial Advisor in Derby, CT

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

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

Retirement Planning for Derby

Skinner Wealth Strategies is a fee-based fiduciary financial advisor serving Derby 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.

Connecticut's smallest city by area, Derby sits at the confluence of the Housatonic and Naugatuck rivers at the center of the Valley.

We serve Derby as part of a broader New Haven County practice that also covers Ansonia, Seymour and Orange. Milford is close enough that clients who want to meet in person easily can, and far enough that plenty choose video instead.

Our Milford office is roughly 18 minutes from Derby, 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.

Who we work with in Derby

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 Derby 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 Derby 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 New Haven County

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.

A question we get a lot here

I already have an advisor — is it worth a second look? Often, yes, particularly right as the job changes from growing the money to spending it. We review what you own and what it costs you, your tax posture, whether there is a defined plan for which accounts fund which years, and the gaps nobody has looked at in a few years. If the plan is in good shape we will say so. There is no cost and no obligation to move anything.

Other things that come up often around Derby

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.

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.

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.

How much of Social Security gets taxed. How much of your Social Security benefit becomes taxable depends on the rest of your income, which means the withdrawal decision and the claiming decision are really one decision. Planning them separately is how households end up paying tax on a benefit they could have partly sheltered by sequencing the year differently.

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.

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 Derby households — with the arithmetic shown.

Worked example

Two and a half years of spending, held in reserve

$0growth assets sold in a 20% decline

A Mystic couple keeps $350,000 — two and a half years of spending — in cash and short-duration bonds, separate from $2,750,000 of growth assets. When markets fall 20%, the year's $140,000 comes from the reserve and nothing is sold at a loss. The decision that does the damage was removed in advance.

Hypothetical example — not an actual client.

See the full spending reserve example

Watch

Retirement Planning, Explained

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

Financial Planning in Derby — Common Questions

Do you work with clients in Derby, CT?
Yes. Skinner Wealth Strategies serves clients throughout New Haven County and the rest of Connecticut. Derby is about 18 minutes from our Milford office. We meet clients in person at either office or virtually, whichever you prefer.
What does a second opinion actually involve?
We review your current portfolio, your tax posture, and your withdrawal plan, and tell you plainly what we'd do differently and why. Sometimes the answer is that your existing plan is sound. There's no cost and no obligation to change anything.
I already have an advisor. Is it worth having someone else look?
It's reasonable to want a periodic outside check, particularly as you approach the transition from saving to spending, since that's where tax and income coordination starts to matter much more than investment selection alone.
What kind of Derby 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 an independent review of your portfolio, tax posture, and withdrawal plan — with no obligation.
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.
How do I plan for 20 to 30 years of inflation in retirement?
By treating inflation as a planning input rather than a background assumption. A retirement that has to fund two or three decades is exposed to it for the whole stretch, and the erosion is deceptive early because the first few years look manageable. In practice that means keeping a long-duration growth allocation intended to keep pace with it, adjusting income annually rather than fixing it at a nominal dollar amount, and modelling what the same standard of living costs in year twenty-five rather than year one.
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.

Nearby

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Talk to a Derby 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.