FAQs

• Filing at the wrong time can cost clients tens of thousands of dollars over their lifetime, some of which may never be recovered.

• Many elections are one-time only. The wrong decision can trap retirees for the rest of their lives with no do-overs.

• People often lose guaranteed income by ignoring the earnings test, costing themselves and their family needed income later.

• Most Social Security recipients do not understand how taxes on their benefits are calculated.

• Benefits may be smaller because Medicare shrinks their Social Security check.

• Bad decisions can cost surviving spouses and dependents needed income at a time when they are most vulnerable.

• Divorcees don’t understand how a previous marriage may boost their benefit.

Retirement is not a one-time event—it is an evolving process. Life changes, markets shift, and laws change. Regular plan reviews ensure your financial strategy remains aligned with your goals.

If your plan has not been reviewed recently, schedule a planning review to ensure your strategy remains current and aligned with where you are today.

Asset allocation, retirement planning, and money management are core services that most financial advisors provide. For many advisors, this is both the starting point and the endpoint of their work.

Over the years, however, we have observed that clients often experience fragmented planning. They may work with multiple professionals—such as attorneys, CPAs, and other specialists.  Those advisors are frequently operating in a vacuum, with little or no coordination or communication. The result is inefficient, disjointed advice, impacting clients’ financial planning, including duplicated efforts and, more concerning, critical gaps that can negatively impact the clients overall financial plan.

We believe it is essential to coordinate planning across all relevant parties. By aligning advisors, resources, and family members involved in recommendations or decision-making, we reduce redundancy and costs, improve efficiency, and minimize the risk of critical issues being overlooked—ultimately protecting our clients’ financial outcomes.

A key area of emphasis in our process is risk management. We place significant importance on identifying and addressing underlying risks because unmanaged risk can undermine even the most well-designed lifestyle or retirement plan. Our process is designed to systematically identify, evaluate, and prioritize strategies to reduce or eliminate these risks, helping to safeguard your financial life and improve long-term plan durability.

The ability to retire comfortably depends largely on how well your major retirement expenses and income sources are understood and planned for. For most retirees, the three largest expense categories are housing, healthcare, and taxes.

Housing

• Are you mortgage-free, or will payments continue into retirement?

• Do you plan to downsize or relocate, and how would that affect your cost of living?

• What are your ongoing property taxes, insurance, and maintenance costs?

Healthcare

• What will you pay for Medicare premiums, including Part B, IRMAA surcharges, supplemental coverage, and prescription plans?

• Medicare Part B premiums have historically increased by 5–10% over time.

• What level of out-of-pocket healthcare costs should be expected?

• Have you considered long-term care risks and how they may be funded?

Taxes

• Tax-deferred retirement accounts create future tax liabilities.

• Proper withdrawal sequencing can significantly affect how long your assets last.

• How will Required Minimum Distributions (RMDs) impact your tax bracket?

• Social Security taxation and IRMAA thresholds require proactive planning.

Beyond these core areas, it is also important to account for other anticipated expenses, lifestyle goals, and discretionary spending, as well as all sources of retirement income.

By stress-testing your retirement plan against real-world risks—market volatility, longevity, and rising healthcare costs—we help you determine whether retirement is financially sustainable and identify specific actions that can strengthen your plan. A professional review can turn uncertainty into a clear path forward.

We recently met with a new client whose spouse had a medical emergency. Because there was no Health Care Proxy, the spouse was required to go to court for guardianship before he could make medical decisions.

Many people are surprised to learn that Massachusetts does not recognize automatic spousal authority for health care decisions. Without a valid Health Care Proxy, hospitals may delay decisions, rely on ethics committees, or require court involvement.

A Massachusetts Health Care Proxy allows your spouse to make medical decisions only if you are incapacitated and helps eliminate uncertainty during a crisis.

Common Misconception:
“We’re married, so I can decide.”
That is not reliable in Massachusetts.
A key role of a financial advisor is helping ensure all essential planning documents are in place and coordinated—not just investments. If you or your spouse have not reviewed your Health Care Proxy and related documents, now is the time to do.

A recent paper from the Center for Retirement Research at Boston College highlights a major retirement risk: long-term care (LTC) costs are largely uninsured, creating financial strain for many aging households.

Key findings from the research:

• Long-term care expenses pose a serious financial risk because most costs are not covered by insurance.

• Researchers compared what people think they will do if care costs exceed their resources with what retirees in similar situations actually do.

• Results show a significant disconnect between expectations and reality:

  • Many retirees plan to rely on Medicaid, but only a small percentage will meet the program’s strict financial eligibility rules.

  • People generally do not expect to use home equity, yet this becomes one of the most common real-life funding sources.

  • Those who need care rarely end up moving in with their children, but they often leave their children smaller inheritances than planned.

Source: Chen, Munnell, & Wettstein (2025), “How Do Retirees Cope with Uninsured Healthcare Costs?” Center for Retirement Research at Boston College.

What Is Long-Term Care?

The National Institute on Aging defines long-term care as a range of services that help individuals meet health or personal care needs when they can no longer perform everyday activities independently and safely.

These everyday tasks are known as Activities of Daily Living (ADLs):

• Bathing

• Dressing

• Eating

• Transferring (moving in and out of bed or chairs)

• Toileting

• Continence

Common Misunderstandings About Coverage

Myth: Medicare covers long-term care.
Reality: Medicare covers only short-term, rehabilitative care, typically following a hospitalization. Coverage is limited (often under 90 days) and only applies if medical professionals believe recovery is likely.

Medicare may pay for:

• Skilled nursing care (short term)

• Physical, occupational, or speech therapy

Medicare does not pay for:

• Custodial care (help with ADLs)

• Ongoing long-term care

• Assisted living

• Independent senior housing

What About Medicaid?

Medicaid can cover long-term care, but only after strict financial qualification.

Key rules include:

• Applicants must spend down most assets before qualifying.

• A single applicant typically may keep only about $2,000 in countable assets (rules vary by state).

• A healthy spouse at home may keep limited assets under spousal protection rules.

• Medicaid has a five-year “look-back” period. Asset transfers during this period can result in penalties or temporary disqualification.

Even for those who qualify, access is limited:

• Not all facility beds accept Medicaid

• Long waiting lists are common

Why This Matters Now

By 2030, all Baby Boomers will be age 65 or older, dramatically increasing demand for long-term care services. This growing need, combined with limited public coverage, means planning ahead is essential.

Long-term care is not just a health issue — it is a retirement income, asset protection, and family legacy issue.

What should I do next?

Do not wait until a health event forces rushed decisions. Proactive planning creates more options, more control, and better financial outcomes.

Schedule a long-term care planning review with a financial advisor to:

• Estimate your potential care costs

• Stress-test your retirement plan

• Evaluate insurance and funding strategies

• Protect your assets and your family’s future

The earlier this is addressed, the more choices you keep.

A Roth conversion may be worth considering if you expect to be in the same or a higher

tax bracket in the future, want to reduce future required minimum distributions (RMDs),

or are looking to create tax-free income later in retirement. By converting a portion of a

traditional IRA or pre-tax retirement account to a Roth IRA, you pay income taxes today

in exchange for tax-free growth and withdrawals in the future.

Roth conversions are often most effective during lower-income years—such as early

retirement before Social Security and RMDs begin, after a job change, or in years with

unusually low taxable income. They can also be a valuable estate-planning tool, as

Roth IRAs are not subject to RMDs during your lifetime and can provide tax-free

benefits to heirs.

However, conversions are not appropriate for everyone. Paying the tax upfront can

increase current-year tax liability, potentially trigger higher Medicare premiums (IRMAA),

or affect other tax-based benefits. The decision should be evaluated in the context of

your cash flow, tax brackets, long-term retirement income plan, and overall financial

picture.

Because the cost of getting this wrong can be significant, Roth conversions

should never be done without a strong plan addressing the multiple issues that

you may face. The window to act is often limited, and once missed, it cannot be

recovered. Before making assumptions or taking action, schedule a personalized

Roth conversion analysis to quantify the tax savings, identify the optimal

conversion amount, and determine the right timing. A personalized tax analysis

can identify whether a conversion strategy adds value—or creates unnecessary

tax exposure. Roth conversions can permanently reduce lifetime taxes—but only

if executed correctly.

Traditional IRA vs. Roth IRA as part of your estate:

A traditional IRA can be left to a spouse subject only to a RMD Required Minimum

Distribution. However, when your heirs inherit the IRA, the account must be liquidated

within a 10-year period and RMD’s may need to be taken. The taxes can be significant

and potentially add additional taxes to other earnings. An inherited ROTH IRA has no

RMD’s, does not need to be liquidated until the end of the 10 years following death. The

fund continues to grow and accumulate tax free.

A single coordinated strategy today can add tens—or even hundreds—of

thousands of dollars, to your after-tax retirement income.

Schedule a consultation to review your current tax bracket, future income

projections, and determine whether a Roth conversion strategy fits your

retirement plan.

When are you going to retire?

How did you make that decision?

Many of us look at finances and health when we’re deciding when to retire.

Whether or not we realize it, we’re also considering our emotions and what we imagine for the future — we compare how we feel in our current circumstances to how we expect to feel in our anticipated retirement.1

With that, we tend to overestimate our future emotions, thinking we’ll be a lot happier as retirees.1

And that can motivate short-sighted decisions that lead to more regrets than satisfaction in retirement.1

To avoid that and make better decisions about retiring, let’s look at some of the leading retiree regrets, what’s behind them, and what you can do now to set yourself up for a dream retirement later.

Retirement Regret #1. Retiring Too Early

Retiring as soon as possible can be a priority, but retiring too early can be a big mistake. For one, premature retirement can mean gambling with your financial security in the future. If you leave work too early, you could be forfeiting some key, higher-earning years to build up your savings.

Beyond that, retiring too early can turn the page on your social life or drain a sense of purpose if you’re not prepared for the next stage.

Pro Tip: If retiring early is a goal, consider a phased retirement that lets you work part-time while you transition into retired life. A phased approach could let you continue to earn income, stay connected to your social life, and wade into retirement (instead of taking an instant plunge).

Retirement Regret #2. Sidelining Retirement Plans for Too Long

Retirement planning can stall when we think we have years or even decades to put plans in place. Unfortunately, the longer you wait to start retirement planning, the more challenging it can be to build the nest egg you may need.

That, in turn, could leave you with less retirement savings and far less flexibility later. It may also mean that you have to make more tradeoffs and more difficult decisions later, like foregoing certain luxuries or bucket-list adventures.

Pro Tip: No matter how old you are now, start planning for retirement. Your strategies and objectives can evolve over time, but the sooner you take a hands-on approach to mapping out your retirement, the better. Time can be an invaluable resource in retirement planning that you can’t get back. So, give yourself as much time as possible.

Retirement Regret #3. Underestimating the Length of Retirement

How long will you need to live off of your retirement savings? If you don’t know the answer to that question, how can you save enough for retirement? That’s another major issue today’s retirees face because many lack “longevity literacy.”2

In other words, we tend to have a poor sense of how long we’ll live. Failing to consider that in retirement planning can really short-change us in the long run.2

Pro Tip: Don’t look to your parents or ballpark estimates when it comes to life spans and the duration of retirement. Crunch the numbers and look at the latest life expectancy data (it does change from generation to generation). Also, work with a professional who can help you double-check your estimates, assumptions, and calculations.

Retirement Regret #4. Overlooking Inflation

Inflation is an inevitable part of the market cycle, and it’s almost impossible to ignore these days.3 Still, inflation can take more of a back seat in retirement planning, with many people making the mistake of relying on today’s costs when estimating tomorrow’s expenses.

Just like underestimating the length of retirement, underestimating inflation can put a real drag on retirement savings, creating unnecessary financial stress in the future.

Pro Tip: Don’t forget to account for rising costs when you’re planning for retirement. Use current projections to estimate future inflation. Then, create a budget for yourself in retirement, estimating your costs so that you have a more realistic idea of how much you need to cover your monthly expense as a retiree. Also, revisit these estimates regularly, updating them as needed. Keeping an eye on inflation can keep you mindful of savings goals and the expenses you need to be prepared for in retirement.

Retirement Regret #5. Not Having a Sound Investment Strategy

What’s your current strategy for building your retirement savings? When will it be time to adjust that strategy?

Believe it or not, many people have a set-it-and-forget-it view of retirement planning. They know they need to save and that they want to retire, but they’re not necessarily thinking about risk tolerance or how aggressive to be at various phases of retirement planning.

That can result in lost opportunities to amplify retirement savings, like missing out on employer contributions and options to make catch-up contributions.

Pro Tip: Automating savings is a good start, but it shouldn’t be the only part of your retirement planning strategy. Bolster that with diversified investments and routine reviews of both your strategies to ensure they continue to work for you.

A Better Path to a More Fulfilling Retirement

Retirement is a complex financial decision that’s also deeply personal. As exciting as it can be to cross the “finish line” of work life and retire, timing it right matters. So does sensible planning that takes a realistic approach to your needs and goals for the future.

So, if you’re serious about setting the stage for a comfortable retirement unburdened by regrets, don’t cheat yourself by cutting corners or assuming you know it all now.

Instead, look at retirement planning as a work in progress and equip yourself with the resources you need to make more solid plans for the future. That can include deeper knowledge about retirement and finances. It can also involve the support and guidance of an experienced financial professional.

Sources

1. https://www.ssa.gov/policy/docs/ssb/v71n4/v71n4p15.html

2. https://ceal.sdsu.edu/2023/08/18/how-long-will-you-live-how-financial-and-longevity-literacy-can-predict-retirement-readiness/

3. https://www.nasdaq.com/articles/whats-the-ideal-inflation-rate-and-how-does-the-fed-plan-to-get-us-there

This content is developed from sources believed to be providing accurate information. The information provided is not written or intended as tax or legal advice and may not be relied on for purposes of avoiding any Federal tax penalties. Individuals are encouraged to seek advice from their own tax or legal counsel. Individuals involved in the estate planning process should work with an estate planning team, including their own personal legal or tax counsel. Neither the information presented nor any opinion expressed constitutes a representation by us of a specific investment or the purchase or sale of any securities. Asset allocation and diversification do not ensure a profit or protect against loss in declining markets. This material was developed and produced by Advisor Websites to provide information on a topic that may be of interest. Copyright 

There is no universal “right age” to claim benefits. The optimal strategy depends on

several personal and financial factors, including your cash flow needs, health and family

longevity, marital status (married, divorced, or widowed), and the availability of other

income sources. The performance of your investments and your plans for continued

work also play a critical role.

Understanding the rules is essential. Once you reach full retirement age, you may work

and earn unlimited income without any reduction to your Social Security benefit.

However, claiming benefits before full retirement age while continuing to work can result

in a temporary reduction due to the earnings test.

Because Social Security provides lifetime, inflation-adjusted income, the decision of

when and how to claim should be approached strategically. For most retirees, it is one

of the most consequential financial decisions they will make, and careful analysis can

materially improve long-term retirement security.

We can help calculate your benefit at different claiming ages, identify your break-even

points, and model multiple scenarios to evaluate the trade-offs. A personalized Social

Security analysis can help you make a confident, informed decision that supports your

broader retirement plan. If you are approaching retirement or already receiving benefits,

now is the time to review your strategy and ensure it is aligned with your long-term

financial goals.