Skinner Wealth Strategies is a fee-based fiduciary financial advisor serving Southbury 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.
Southbury's Heritage Village is one of the largest active-adult communities in the Northeast, so retirement income and healthcare-bridge planning are everyday conversations here.
Much of our New Haven County work happens across one cluster of towns — Southbury and neighbours like Oxford, Middlebury and Woodbury. The drive to Milford is short enough that in-person meetings stay easy to schedule around a workday.
Southbury 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 Southbury
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 Southbury clients
The same three steps for everyone, and the first two cost nothing:
What we do for Southbury 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
Can I stop working before 65, and what happens to health insurance? This answer changed this year, and not in a small way. The enhanced subsidies that softened the marketplace premium tax credit expired at the end of 2025, so for 2026 coverage the old cliff is back: cross 400% of the federal poverty level — roughly $62,600 for a single filer or $128,600 for a family of four — and the entire credit disappears. Not a reduced credit. All of it. Since the credit is driven by the income you realize rather than by your assets, that makes the size of a Roth conversion or an IRA withdrawal between 60 and 65 a materially bigger decision than it was two years ago.
Other things that come up often around Southbury
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.
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.