Proactive tax planning & preparation
Tax Strategy & Preparation
A tax return records the decisions of a year that has closed. Planning is the work we do while those decisions are still open to us.
Monument Group Tax Advisors provides both year-round tax planning and in-house tax return preparation. Because the same team manages your investments and coordinates your estate plan, tax strategy is built into decisions before they are made — targeting lower lifetime tax, not just a lower bill this April.
Planning and preparation under one roof
Monument Group Tax Advisors is our in-house tax firm, which means the people who prepare your return and the people who manage your investments work from the same office and the same set of facts.
When both sit in the same Concord office, the conversation changes. A Roth conversion gets modeled against this year’s bracket before December. A charitable gift gets structured with appreciated shares rather than cash. A capital gain gets timed against a low-income year instead of landing by accident.
Where the leverage usually is
- Roth conversion timing
- The years between retiring and the start of required distributions are frequently the lowest-bracket years of a lifetime, and the room they create is available only while they last. Using it deliberately is one of the most valuable things we do.
- Withdrawal sequencing
- The account a year’s spending comes from changes lifetime tax materially, and the effect compounds across a thirty-year retirement.
- Required minimum distributions
- Planned for a decade ahead rather than absorbed as a surprise at 73.
- Charitable strategy
- Appreciated securities, donor-advised funds and bunching, matched to the years where the deduction is worth most.
- Asset location
- Holding the right assets in the right account type, which lowers tax on the same portfolio.
- Estate coordination
- Massachusetts has its own estate tax with a threshold well below the federal one. Planning around it is a local specialty.
A note on the Massachusetts estate tax
Massachusetts levies its own estate tax at a threshold well below the federal exemption. A family with no federal estate tax exposure at all can still face a substantial Massachusetts liability, and it is a common surprise in a first review.
Because our tax advisors and the estate attorneys at Woodman & Eaton work in the same building, this is a question we are able to answer properly rather than flag and refer elsewhere.
Who this is for
The people who get the most from this are the ones whose tax picture is about to change: retiring in the next few years, holding equity compensation that will vest or expire, or supporting a parent whose estate will pass through them.
It also suits people who simply have too many moving parts for a filing-season relationship to handle — several account types, income that varies, charitable intent, property in more than one state.
If your return is a W-2 and a standard deduction, you do not need us for tax work, and we will tell you that in the first conversation.
Families supporting a parent in long-term care are a common case, because the deductible medical expense and the withdrawal that funds it need to fall in the same year to be worth anything. So are households where one partner retires a year or two before the other, which opens a window that is straightforward to use and easy to let pass.
What planning ahead is worth
A return prepared in isolation is accurate, and it arrives after the decisions that shaped it. Planning moves the work forward into the part of the year when the conversion window is still open, when a gain can still be timed, and when a withdrawal can still be taken from the account that makes it least expensive. That is where the value is.
The years around retirement are where this is worth the most, because they are usually the most flexible years a household will have. Income is lower, required distributions have not begun, and the bracket capacity that creates is available only while both remain true. Planning in that window, deliberately and year by year, is some of the most valuable work we do.
What a year with us looks like
Planning happens before the year is over, not after. We look at projected income in the fall, while there is still time to act on what we find — conversions, harvesting, charitable timing, deciding which account a withdrawal should come from.
Preparation then happens in the spring, in the same office, from the same set of facts. Nothing has to be explained twice, and the return reflects decisions that were made deliberately rather than discovered afterwards.
The pattern matters more than any single maneuver. A conversion done in the right year, a gain deferred to a lower-bracket one, a charitable gift bunched rather than spread — individually each is modest. Repeated deliberately across a decade of retirement, they compound into the difference between a plan that funds what you wanted and one that nearly does.
From the Enjoying Retirement & Beyond case study“How do we make the most of the low-tax years between retiring and required distributions — and agree on what we actually want?”
Tax Strategy & Preparation
Questions about tax strategy & preparation
Do you provide tax preparation or only tax planning?
Both. Monument integrates year-round tax planning with in-house tax return preparation through Monument Group Tax Advisors. That coordination means your investment decisions, retirement strategy and tax outcomes are handled by one team, which reduces surprises.How do financial advisors help reduce taxes in retirement?
By optimizing Social Security timing, structuring tax-efficient withdrawals, managing required distributions, implementing Roth conversions, coordinating asset location, and using charitable strategies. The goal is minimizing tax across decades of retirement rather than in any single year.When is a Roth conversion worth doing?
Usually when your current marginal rate is meaningfully lower than the rate you expect later — often in the years between retiring and starting required distributions. It depends on bracket space, Medicare premium thresholds, state tax and legacy goals, so it is modeled rather than assumed.Does Massachusetts have its own estate tax?
Yes, with a threshold considerably below the federal exemption. Many Massachusetts families face a state estate tax liability while having no federal exposure at all. It is one of the most common planning gaps we find in new client situations.Can you work with my existing CPA?
Yes. Some people keep a long-standing accountant, and we coordinate directly with them. Others move preparation in-house so that planning and filing sit with one team, and either arrangement works well.Do I have to move my investment accounts to work with your tax team?
No. The tax work stands on its own, and plenty of people use it alongside an investment relationship elsewhere. The advantage of having both here is that a decision about a withdrawal or a conversion does not need to be explained twice or coordinated across two firms, but it is not a condition of the engagement.When in the year should tax planning happen?
Before the year ends, which in practice means fall for anything involving conversions, harvesting or charitable timing. Once the calendar turns, most of the useful levers have already moved and preparation becomes a matter of reporting decisions rather than shaping them.
Talk through tax strategy & preparation
Every plan starts with a conversation about what’s actually on your mind.
Schedule a time to discuss whether our approach is the right fit for you.