Skinner Wealth Strategies is a fee-based fiduciary financial advisor serving Trumbull 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.
Trumbull's Pequonnock River Valley and established neighborhoods make it a town people tend to retire in rather than leave.
Households we work with in Trumbull — part of central Fairfield County — often have friends and neighbours in Shelton, Monroe and Stratford weighing the same set of retirement decisions. Our Milford office is a comfortable trip for the handful of in-person meetings involved.
Our Milford office is roughly 20 minutes from Trumbull, 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 Trumbull
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 Trumbull clients
The same three steps for everyone, and the first two cost nothing:
What we do for Trumbull 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
How much can I actually spend, and from which account? Instead of a fixed withdrawal percentage you hope holds, we set a starting rate with defined upper and lower guardrails that trigger an adjustment, and hold near-term spending in short-duration assets so a bad market is funded from the reserve rather than by selling depressed holdings. Which account funds which year is then a tax decision, and it changes as your bracket and your required distributions change.
Other things that come up often around Trumbull
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.
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.
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.
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.
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.