Skinner Wealth Strategies

Fairfield County · Connecticut

Financial Advisor in New Fairfield, CT

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

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

Retirement Planning for New Fairfield

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

New Fairfield wraps around the western shore of Candlewood Lake, Connecticut's largest lake, right on the New York border.

Much of our Fairfield County work happens across one cluster of towns — New Fairfield and neighbours like Sherman, Brookfield and Bethel. The drive to Milford is short enough that in-person meetings stay easy to schedule around a workday.

New Fairfield is about 52 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 New Fairfield

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 New Fairfield 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 New Fairfield 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

What happens to this when we're gone? Connecticut has its own estate tax on top of the federal one, and the thresholds move, so exposure is worth reviewing periodically rather than assuming a number you read years ago still applies. Beneficiary designations pass outside your will and quietly override an otherwise sound estate plan when they go stale — so they get audited as part of the plan, and we coordinate with your attorney rather than replacing them.

Other things that come up often around New Fairfield

Retiring before Medicare. For households leaving work before 65, health insurance is usually the deciding variable, and the rules moved this year. With the enhanced subsidies expired, the marketplace premium tax credit is once again an all-or-nothing threshold at 400% of the federal poverty level — approximately $62,600 single or $128,600 for a family of four. A dollar over and the credit is gone entirely, and the cap that used to limit how much excess advance credit you had to repay is gone too. Because the test is on realized income rather than net worth, the years between retiring and turning 65 are years where how you fund your spending sets what your coverage costs.

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.

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.

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.

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 New Fairfield households — with the arithmetic shown.

Worked example

$4.5 million of assets, under $100,000 of income

$3,575modeled annual Connecticut tax difference

A Fairfield couple with $4,500,000 funds $145,000 of spending on about $90,420 of reported income, because most of it comes from Roth distributions and return of basis. A household spending the same from a traditional IRA reports roughly $197,700 — past the point where Connecticut's retirement-income exemption has phased out entirely.

Hypothetical example — not an actual client.

See the full Connecticut tax example

Watch

Retirement Planning, Explained

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

Financial Planning in New Fairfield — Common Questions

Do you work with clients in New Fairfield, CT?
Yes. Skinner Wealth Strategies serves clients throughout Fairfield County and the rest of Connecticut. New Fairfield is about 52 minutes from our Milford office. We meet clients in person at either office or virtually, whichever you prefer.
How often should beneficiary designations be reviewed?
At least annually, and immediately after any major life event — a marriage, divorce, death, or birth. Beneficiary designations on retirement accounts and insurance policies pass outside your will, so an outdated form can override an otherwise well-drafted estate plan.
What does the 10-year rule mean for what my children inherit?
Most non-spouse beneficiaries must now empty an inherited retirement account within ten years. That can land the distributions in your children's highest-earning years, at their rates. It's a significant argument for doing some of the tax work during your lifetime rather than passing it forward.
What kind of New Fairfield 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 Connecticut estate tax exposure, beneficiary review, and tax-aware wealth transfer.
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.
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.
Do we have to meet in person?
No. Many clients do the first meeting in person and everything after that by video. For this kind of planning, meeting virtually loses nothing.

Nearby

We Also Serve These Fairfield County Communities

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Talk to a New Fairfield 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.