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Hypothetical client example

I’m Worried About My Retirement Security

This hypothetical example is for illustrative purposes only. The names, circumstances, and outcomes are fictional and do not represent an actual client or actual results. Actual recommendations and results will vary, and no outcome is guaranteed.

The decision to retire, even for successful people, is fraught with worry. Retirement is often described as a “finish line,” but in truth it’s really a starting line, a phase of life with tremendous potential, but also with serious threats that must be identified and managed.

If you’ve spent thirty years doing all the responsible things, maxing out every retirement account, paying off the mortgage, funding your kids through college without a dollar of debt, and you still can’t quite bring yourself to set a retirement date, you’ll probably recognize something in Sandra and Tomas’s story. A Family Office Director uses a holistic approach to solve exactly this kind of problem: not a shortfall of savings, but the absence of a plan that turns those savings into confidence. Sandra and Tomas’s specific numbers are their own, but the underlying uncertainty is common to almost anyone who’s saved responsibly for decades: no one has done the real math on how long the money needs to last, no one has weighed the cost of a health crisis against the cost of retiring too early, and no one has shown them what, if anything, will be left for their children.

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The Retirement Math Says Yes. The Worry Says Not So Fast.

Sandra and Tomas have been married more than thirty years, and both have built long, successful careers, Sandra as a creative director at a regional advertising firm, Tomas as an engineer in oil field services. Both have earned six-figure incomes for years, maxed out their retirement plans at work, and paid their children’s way through college without either of them carrying a dollar of student loan debt.

Tomas is 61 and Sandra is 58. Their daughter is a practicing lawyer and their son is on a management track at a logistics firm. The kids are launched, the mortgage is a few years from paid off, and both are in good health. Between them, they hold $2.6 million in retirement and investment accounts, and both are on track for near-maximum Social Security retirement benefits that will total more than $8,000 a month in today’s dollars.

On paper, they will be ready to retire on time, but in reality they are not so sure. Years of high inflation have them questioning what their cost of living will actually look like in retirement, and they wonder what AI might do to the economy, the market, and their children’s careers. Sandra’s mother died of complications from Alzheimer’s at 75. Tomas’s father died of coronary disease at 81. Health care and assisted living costs are not an abstraction for either of them.

Sandra and Tomas know they need real financial planning help. What they don’t have is a plan that tells them, with any real confidence, that they won’t outlive their money, and that there will be something meaningful left for their children when they’re gone. Until they have that confidence, they’ve decided not to set a firm retirement date at all.

Sandra and Tomas Need a Plan That Turns Savings Into Confidence

Sandra and Tomas have done the hard part: they’ve saved consistently, invested wisely enough to build up a $2.6 million nest egg, and raised two children without debt. What they haven’t done is convert that discipline into a plan that tells them exactly how much they can spend, for how long, and what happens if the cost of living, the market, their health, or all three, don’t cooperate.

Income taxes will not stop when Sandra and Tomas retire

When Sandra and Tomas retire, they will need to roll over their 401(k) plans into IRAs, and by their early 70s, both will be required to begin annual minimum withdrawals of over $80,000 whether they need the income or not. That number will only grow as they age, and will be taxed as ordinary income.

Up to 85 percent of Social Security retirement benefits are taxable. For Sandra and Tomas, this will push their taxable income to over $160,000 per year, a number that will grow as they age. Income taxes will take a serious bite out of their retirement income.

A Family Office Director reviews Sandra and Tomas’s accounts in the context of their time horizon, spending needs and risk tolerance. The goal is to manage income, market risk and required withdrawals together so the timing of every rollover and distribution works in their favor, not against it.

Tax planning

HALO™ reviews which assets belong in which accounts and how income is generated, to keep the combined portfolio as tax-efficient as possible.

Sandra and Tomas must not underestimate their longevity

Even if the couple waits until Sandra is 68 to retire, it’s prudent to expect at least one of them will live another 25 years. Over that much time, more than one bear market and one inflationary stretch isn’t a risk, it’s close to a certainty.

The instinct to retreat to cash after a downturn, or chase the market on the way back up, is one of the most damaging patterns in retirement investing. The safer path is finding the exact point where growth potential and the ability to tolerate volatility meet.

A Family Office Director builds a plan that keeps Sandra and Tomas appropriately invested in stocks for growth, while managing the sequence of returns so a bad market year early in retirement doesn’t permanently damage the plan.

Asset management

Real Risk Meter™ finds the optimal intersection of portfolio risk and return, so their market exposure captures enough upside potential but not so much they succumb to market timing.

Common withdrawal strategies can fail

A multi-decade retirement demands a plan with built-in flexibility. Social Security benefits will be cut when one partner dies, while Required Minimum Distributions will eventually drain IRAs. Sandra and Tomas will need exposure to riskier assets, and would benefit from an active, rebalancing retirement income strategy.

Taxable Social Security benefits, Required Minimum Distributions and withdrawals from non-qualified accounts will meaningfully affect how much of their money the government takes and how much Sandra and Tomas get to spend.

A strategy that blends liquid, short-term accounts, annuities and equities will offer maximum flexibility for Sandra and Tomas, creating a cushion for market volatility while ensuring several years of income are available from less volatile assets.

A Family Office Director builds a dynamic income plan that draws from the right accounts in the right years, reacting to real market conditions instead of a fixed withdrawal schedule that ignores market behavior.

Retirement planning

Incomize™ draws income from stocks in strong market years and from annuity or liquid accounts in down years, ensuring the portfolio outlives the couple by avoiding the need to sell into a correction.

Inheritance needn’t wait until death

Sandra and Tomas want to leave their children a meaningful inheritance and would like that to start long before they pass away. However, gifting and transfer decisions made without regard to market conditions can create tax consequences that threaten the plan’s longevity.

Every year that passes without a gifting strategy is a year of tax-free giving that can’t be recovered. In 2026, a married couple can give up to $38,000 to each child or grandchild without touching a dollar of their lifetime exemption, gift after gift, year after year. Left unused, that allowance doesn’t roll over, it simply expires.

A Family Office Director coordinates gifting and transfer decisions with market conditions and tax timing, so what Sandra and Tomas hope to leave their children is coordinated with actual events in their personal lives and the market as they move through retirement.

Legacy planning

Control the Controllables® focuses on what retirees can actually manage, tax consequences, costs, and diversification, as well as gifting, to protect both their lifestyle and what they pass on.

Four Steps to Guide Sandra and Tomas’s Retirement Journey

A Family Office Director starts with all the plan inputs: assets, liabilities, risks, expenses, legacy desires and desired retirement schedule. Working with specialists, a plan for security over multiple decades is created, implemented and periodically revisited with one goal in mind: Sandra and Tomas’s best interests.

01
Start with the whole picture

The assets are only one part of the plan. Sandra and Tomas’s hopes for lifestyle and legacy are equally important inputs.

02
Build a coordinated plan

A 25-year retirement demands a plan flexible enough to rebalance as market realities change, not a static one set once and left to fate.

03
Coordinate the work

Investment management, withdrawal strategy, and gifting plans have to work together in a future that holds real uncertainty.

04
Keep the plan current

An annual review updates every variable and every account, so the plan reflects how life actually unfolds, not how it was expected to.

Your first conversation covers the same ground for your situation: what you have, what you want it to do for you, and where disconnects and risks exist. There is no charge and no obligation.

Schedule a Call

If you would rather talk first, please schedule a call. Family Office Directors are located across the country, and also meet remotely. A discovery conversation is complimentary.

Sandra and Tomas’s Family Office Advantage™

Sandra and Tomas’s story is one of decades of discipline rewarded, and real uncertainties over a multi-decade retirement. It’s also a common situation for many successful people who think they’ll be okay, but who should plan for the unexpected.

Now that Sandra and Tomas have a Family Office Director, they understand all of the questions, even if the answers won’t be known for many years. When to retire, when to begin Social Security benefits, how to allocate across asset classes, how a dynamic income strategy can help manage the risk that they may outlive their assets.

Their tax strategy, their investment risk, their income timing, and their legacy plans are all part of one holistic plan, a plan that also contemplates health and longevity risks, and accepts that market volatility and inflation are likely events over a 25-year span.

Retirement is not a finish line for Sandra and Tomas, it’s the start of a new phase of life, one they’ve worked hard to prepare for, and one filled with endless possibilities.

Retirement Requires More Planning, Not Less

Every client’s situation will differ from Sandra and Tomas’s in its particulars, but the underlying worry rarely does. Inflation, market risk, and the cost of long-term health care turn retirement from a reward into a threat assessment, and no single account or single decision can answer all three at once. That’s exactly the kind of problem holistic planning is built to solve.

Even successful families face real threats in retirement, and not all of them are financial. Health care, assisted living, and memory care costs have risen sharply and can dramatically change what a retirement plan actually needs to fund. A retirement that could last 25 or even 30 years has to be built to handle more than one kind of threat at once.

What would it take for you to feel as ready as your account balance suggests you should? Have you actually run the numbers on how long your money needs to last, or are you estimating? Do you know what, if anything, will be left for the people you hope to leave something to?

Inflation, market downturns, and health and longevity are all real risks but the right plan, and the right ongoing management in retirement, can help manage these risks. The sooner you begin planning, the more control and confidence you can build into your plan.

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Other client profiles
You Own a Business
When a business outgrows its original structure, favorable tax strategies can be missed, and the quality of life in retirement can hinge on a successful exit.
You Hold Assets in More Than One Place
Accounts opened over the years, at different institutions and for different reasons, rarely add up to a coordinated plan.
You Want What You Have Built to Last, Intact, Beyond You
What you have built becomes a legacy when it passes, intact, to the people and causes that matter most to you.

Request a Taxes First, Then Math™ Analysis

Taxes can materially reduce investment gains over time, but often don’t get the attention they should. The right investment program starts with tax considerations. Wise investors also carefully consider all the costs of managing their money, and they use diversification to solve for a wide range of risks that go far outside the ones in their portfolio.

On top of all that, many investors simply do not know what their maximum downside loss exposure is. Do you? Can you say just how risky your portfolio really is?

It costs nothing to find out if your portfolio is right for you. Get your Taxes First, Then Math™ Analysis with no obligation. After all, a quality second opinion never hurt anyone.

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