Chances are, you already have enough to retire.
At least, if we view “enough” through a financial lens.
You may have flush retirement accounts, taxable investments, home equity, business interests, deferred compensation, or other assets that suggest you’re in formidable financial standing. But life is not measured by account balances, and retirement is not a math equation you solve once and move on from.
It’s a transition. One that asks bigger questions than, “Do we have enough?”
Questions like: What is this next chapter actually for? How do we want to spend our time? What kind of life are we trying to build or reclaim?
In this guide, we’ll walk through the pillars of high-net-worth retirement planning, from building tax-efficient retirement income and managing required minimum distributions to planning for healthcare, legacy, and the deeper question of how to step into retirement with both financial readiness and life readiness.
Start With the Life You Want Your Wealth to Support
A lot of retirement planning starts with a number.
How much do we have? How much do we need? What can we safely withdraw?
Those are important questions. But it’s much easier to answer them once you know what you’re trying to fund.
“Comfortable” retirement looks different for every family. For one household, it means a paid-off home, time with grandkids, and the freedom to travel luxuriously a few times a year. For another, it means maintaining multiple properties, underwriting a family philanthropy effort, helping adult children with home purchases, or pursuing a different form of work.
That is why high-net-worth financial planning should begin with lifestyle clarity before wealth management. Otherwise, you risk building a technically sound plan around a life you haven’t quite defined.
- When you imagine a Tuesday six months into retirement, what does it look like — and does that appeal to you?
- Do your retirement expectations and your partner’s align? Have you had that conversation explicitly?
- Which relationships in your life have been running on the fumes of “we’ll catch up when things slow down?” Who do you want to invest in?
- Is there work you’d do even if you didn’t need the income?
- Are your children financially prepared for what they’ll eventually inherit?
- If you knew your health would diminish ten years from now, how would that impact what you’d do today?
In other words, retirement planning should outline the kind of life you’re trying to build and then what it takes to support it.
Planning for the Non-Financial Transition
I’ve sat across from executives, founders, and career professionals who retired with everything in order. Income sequenced, taxes managed, estate plan updated. By every financial measure, they were ready.
And many of them still struggled.
Not financially. Personally.
The structure that had organized their lives for decades was gone. The identity they’d built around their career — the title, the team, the daily sense of forward motion — suddenly had nowhere to go. They’d reached financial freedom and felt, at least initially, more disoriented than relieved.
This is quite common. And it’s worth planning for as deliberately as the financial side.
The identity gap. For high achievers, a career is a framework for how they understand themselves and how others understand them. Retirement removes that framework without automatically replacing it.
The structure problem. Work provides a reason to get up, a schedule to organize the day, a set of problems worth solving. Without it, even people with abundant resources and good intentions can find themselves unmoored.
The partnership dimension. For couples, retirement can expose misaligned expectations that never needed to be resolved while both people were busy. One partner may be eager to travel extensively; the other may want to stay close to home and grandchildren. One may want to pursue a second act professionally; the other may be ready for a full stop. These are worth discussing before retirement begins rather than after.
The “what am I retiring to?” question. The people I’ve seen struggle most post-retirement share a common thread: they knew exactly what they were leaving but had never seriously considered what they were moving toward. Six months of travel sounds appealing in the abstract. Living it, without a longer-term answer to that question, tends to feel hollow.
At Five Oceans, we think about this through the lens of the Personal Five Oceans — the five domains that constitute a fully realized life: Money, Career, Health, Relationships, and Fun. A retirement strategy that addresses only the financial domain is an incomplete plan. The goal isn’t just to fund the next chapter. It’s to design it.
Sequencing Income: Developing a Withdrawal Strategy
Once you have a more tangible vision of the life you’re building, the next question is how to fund it as efficiently as possible. To do so, consider which accounts you draw from, in what order, and when — because the sequencing of withdrawals is vital to tax efficiency and wealth preservation.
The general framework:
- Taxable accounts first. Drawing from taxable brokerage accounts early allows tax-advantaged accounts to continue growing. It also creates opportunities to manage capital gains recognition deliberately — harvesting losses, timing gains in lower-income years, and gradually reducing the embedded tax liability in the portfolio over time.
- Tax-deferred accounts next. Traditional IRAs and 401(k)s generate ordinary income at withdrawal. Drawing from these before Roth accounts preserves the tax-free growth of Roth assets for as long as possible — and positions them for eventual transfer to heirs, who benefit from tax-free inherited distributions.
- Tax-free accounts last. Roth IRAs carry no required minimum distributions during the owner’s lifetime and pass to heirs income-tax-free. For high-net-worth families, Roth assets are among the most valuable to preserve and transfer.
A few considerations that complicate the sequencing picture for HNW retirees specifically:
Required Minimum Distributions (RMDs). Beginning at age 73 (or 75 if you were born in 1960 or later), the IRS mandates withdrawals from traditional IRAs and most employer-sponsored retirement plans, calculated annually based on account balances. If you have well-funded tax-deferred accounts, RMDs can push income into higher tax brackets, potentially triggering Medicare surcharges and accelerating the depletion of tax-deferred assets faster than intended.
The Roth conversion window. The years between retirement and RMDs is often a period of lower taxable income. This is a popular window for Roth conversions: moving assets from traditional IRAs into Roth accounts, paying tax at today’s rate, and reducing future RMD obligations while building a larger pool of tax-free assets.
Social Security timing. Delaying Social Security past full retirement age increases the benefit by 8% per year up to age 70. If you have other income sources to draw from in the early retirement years, the case for delay is quite compelling — particularly for the higher-earning spouse, whose benefit establishes the survivor benefit for the household.
IRMAA. Medicare Part B and D premiums are income-tested. High-income retirees pay significantly more through a surcharge known as IRMAA, calculated based on income from two years prior. A large Roth conversion, significant RMD, or other income event can trigger a premium increase worth thousands of dollars.
Managing Taxes Across a 30-Year Retirement
Tax planning is an ongoing responsibility during retirement. The decisions you make about when and how to recognize income compound over a horizon that can span three to four decades. Beyond the sequencing framework above, consider these three tools.
Qualified charitable distributions (QCDs)
Once you reach age 70½, you can direct up to $105,000 per year from an IRA directly to a qualified charity. The distribution counts toward your RMD for the year, but is excluded from taxable income — it never appears on your return as income in the first place.
That’s more tax-efficient than the alternative route of taking an IRA distribution, paying ordinary income tax on it, and then donating cash to charity. This produces a deduction, but only if you itemize and only up to applicable limits. With a QCD, the tax benefit is automatic and complete, regardless of whether you itemize.
Donor-advised funds (DAFs)
For larger or more structured charitable giving, a donor-advised fund allows you to make a significant contribution in a high-income year, take the full deduction immediately, and distribute grants to charities over time, on your own schedule. The fund can be invested and grow tax-free in the interim.
The most powerful version of this strategy involves funding a DAF with appreciated securities rather than cash. Doing so avoids recognizing the capital gain entirely while still generating a deduction at full fair market value. If you have significantly appreciated positions in taxable accounts, this combination (deduction plus capital gains avoidance) makes a DAF one of the most tax-efficient charitable vehicles available.
Tax-Loss harvesting
Market volatility in taxable accounts creates ongoing opportunities to sell positions that have declined in value, capture the realized loss, and immediately reinvest in similar (but not identical) securities to maintain market exposure. Those losses can offset capital gains elsewhere, with any excess carrying forward indefinitely.
Employing a systematic harvesting strategy in substantial taxable accounts can materially reduce the tax drag on the portfolio over a 30-year retirement horizon.
Note: the wash sale rule prohibits claiming a loss if you repurchase the same or substantially identical security within 30 days before or after the sale.
Healthcare, Long-Term Care, and the Costs Most Families Underestimate
Healthcare tends to surprise retirees. According to Fidelity’s 2025 Retiree Health Care Cost Estimate, a 65-year-old couple retiring today may need approximately $345,000 in after-tax savings to cover healthcare expenses in retirement — and that figure doesn’t include long-term care. That’s why planning for it ahead of time is imperative.
The pre-Medicare gap
If you and your spouse retire before 65, you’ll need private coverage during the window between retirement and Medicare eligibility. Depending on the plan, location, and health, costs for a couple can run $25,000–$40,000 per year or more.
Two options are COBRA continuation coverage from a former employer or individual marketplace plans. Neither is a perfect solution — the right choice depends on your health, your timeline, and what coverage you need in the interim.
Long-term care
About 70% of people turning 65 today will need some form of long-term care during their lifetime, according to Jackson National Life Insurance Company.
The cost of a private room in a nursing facility now exceeds $135,000 per year, and home care costs continue to rise as well. For a couple, the probability that at least one spouse will need care at some point is high enough that leaving this unplanned isn’t a reasonable option.
For families with sufficient assets, self-insuring is often the most appropriate path — setting aside a dedicated pool of assets specifically designated to cover potential care costs. The key is maintaining a realistic picture of what care could cost and how it would be funded, rather than assuming it will sort itself out. Assets earmarked for long-term care are unavailable for other purposes, which is a tradeoff worth acknowledging.
Social Security can serve as a meaningful floor in this context. If you delay claiming in order to maximize your monthly benefits, the guaranteed income stream provides a baseline of coverage that doesn’t depend on portfolio performance or asset depletion. It likely won’t cover the full cost of care, but it reduces the draw on assets and provides a degree of stability.
What Is Your Wealth Actually For?
The financial questions in this guide have relatively concrete answers. The personal ones, like what this next chapter is actually for, what a fully realized life looks like for your family, what you want this wealth to do beyond funding your lifestyle, are nebulous and subjective.
Those are Life Strategy questions. Answering these calls for a deeper conversation.
If you’re approaching retirement and want to think through both sides of that conversation, I’d welcome it.
