Retirement is a major transition for high-net-worth individuals and families. There’s a lot to look forward to, but also much to consider. More resources mean more choices and sometimes more questions. That’s why having a plan made just for you is so important. A generic approach won’t do. Whether you’re thinking about diversification, tax strategies, estate planning, or risk management, you need information that helps you handle your unique situation. Our goal is to help you use what you’ve built to create a future that feels secure and rewarding so that you can enter this new chapter with real peace of mind.
Wealth Creates Different Concerns
If you’re reading this, you already know that wealth changes the way you approach retirement. You’re past the basics, like wondering if you’ll have enough or what Social Security will provide. But having more brings its own set of concerns:
- Will my standard of living be secure, even if the markets crash or tax policy changes?
- Can I actually relax, or am I just trading one set of worries for another, such as income or estate taxes, family legacy issues, business exits, and charitable aspirations?
- Am I maximizing the advantages of my position, or leaving opportunities on the table?
If you’re a high-net-worth individual, you could be categorized as:
- High Net Worth (HNWI): $1 million+ in liquid assets
- Very High Net Worth (VHNWI): $5 million–$30 million
- Ultra High Net Worth (UHNWI): $30 million+ (with more complexity: business interests, assets, large trusts, and charitable giving)
The higher the net worth, the more rules and decisions, along with a greater chance for mistakes. Protect what you’ve built and stay flexible as tax laws and family needs change.
The Biggest High-Net-Worth Retirement Planning Pitfalls We See
If you don’t balance growth, preservation, and flexibility, you might miss opportunities or create challenges for your family. Develop a plan that can adapt to life’s changes. The right approach protects your wealth and your relationships.
Once you reach retirement, financial planning does not just magically end! Whether it’s tax laws, economic and monetary policies, or family dynamics, change still occurs. Failing to address these items could lead to problems and increased stress. Here are the patterns I see most often, and why planning is so important:
- Underestimating true lifestyle costs. It’s easy to assume that your current assets will carry you through. But inflation, family events, unexpected health issues, and market turns can erode your confidence and security. Unfortunately, lifestyle expectations are higher, and small missteps can have multi-million-dollar impacts.
- Neglecting Investments: You can’t set and forget, since laws, markets, and family needs are always in flux. It leads to missed opportunities for growth, allows inflation to erode purchasing power, increases financial risk due to a lack of diversification, and forfeits valuable tax benefits. Additionally, it limits the ability to achieve long-term goals, such as maintaining financial security, planning for a legacy, and charitable giving, all of which are best supported by an investment management strategy.
- Poor Tax Planning. A lack of a proactive tax strategy can drain your annual returns and reduce how much you leave behind. Whether it’s missing Roth conversion windows, neglecting to set up advanced charitable giving vehicles, or simply underutilizing advantageous account structures, this is often where HNWIs lose ground.
- Insufficient Estate Planning. A basic will might seem comforting, but it rarely matches the complexity of your needs. For HNWIs, it’s about more than just asset transfer; think trusts, family governance, and protecting heirs from future mismanagement or disputes.
- Healthcare complacency. Most people don’t realize just how limited Medicare is, or how quickly skilled nursing care can deplete even significant funds. We always assume you will need two years of long-term care at the end of your life and design a tax-efficient plan to cover that possibility.
- Inflexibility. Life changes, tax laws change, families grow, and surprise us. Sticking too rigidly to an old plan often proves just as risky as making no plan at all. See your wealth as a tool. The more you have, the more important it is to use it wisely and adapt to changes.
What a Smart High-Net-worth Retirement planning Strategy Looks Like
What does it take to retire on your own terms, not just comfortably, but with the impact and security your assets can offer? We’ve found that every high-net-worth retirement plan should cover four key areas.
1. Strategic Diversification Beyond the Textbook
“Don’t put all your eggs in one basket” is a starting point, not a strategy. True diversification means thinking ahead and spreading risk across various asset types, timelines, tax treatments, and return sources.
- Asset Classes: It’s not just stocks and bonds. Your money should work across diversified real estate and alternatives (private equity, venture capital, hedge funds, art, collectibles). This adds growth and stability, so no single asset class can derail your plan.
- Geographies: A truly robust portfolio spans more than the U.S. market. International investments protect you from single-country risks, including political, economic, or sector-driven risks.
- Liquidity Planning: We encourage clients to keep some “powder dry.” You want enough in short-term and liquid vehicles to seize opportunities or weather storms without selling long-term assets at the wrong time.
- Rebalancing Discipline: Portfolios naturally drift with market swings. Don’t “set and forget.” Schedule annual or semi-annual rebalancing conversations with your advisor.
Client Stories: Several years ago, we worked with a family that held a significant stake in their business. It fueled their wealth until an industry downturn reduced its value overnight. What preserved their lifestyle and legacy? We had shifted enough assets into uncorrelated investments, so their income plan remained stable.
We’ve also seen portfolios built on legacy business holdings or a few “winning” tech stocks deliver decades of growth, only to be impacted by sudden shifts in the market. Layered diversification could have softened those blows.
2. Tax Optimization: Turning Strategy into Savings
If you only look at pre-tax returns, you might miss out on valuable opportunities. Smart tax planning can help you grow your wealth and protect your legacy.
- Capital Gains Timing: Harvest losses in tough years, lock in gains strategically in strong years, and always weigh short vs. long-term impacts.
- Municipal Bonds: For those in higher brackets, the tax-free income from munis often beats riskier after-tax alternatives, and when managed across states, you can shield yourself from shifting state tax rules.
- Giving Vehicles: Charitable remainder trusts, donor-advised funds, and direct gifts of appreciated assets enable you to amplify your giving while reducing this year’s and future years’ taxes.
- Own With a Plan: If you own businesses or real estate, ask yourself if it’s time to shift assets to a trust or family entity for long-term savings and creditor protection.
- Retirement Account Sequencing: Strategically convert to Roths, leverage HSAs if eligible, and sequence withdrawals to minimize required minimum distributions and manage your taxable income, especially as you approach age milestones.
Practical Tip: Clients who meet with their advisor, who also provides tax planning services, inevitably discover more opportunities for growth. As the rules change, the right advisor ensures you don’t leave cash on the table.
3. Estate Planning: Crafting a Legacy, Not Just a Windfall
For wealthy families, a will by itself usually isn’t enough. Estate planning should help you transfer wealth smoothly, support your values, prevent disputes, prepare your heirs, and carry out your vision.
- Revocable & Irrevocable Trusts: Go beyond the basics; revocable trusts dodge probate and protect privacy, while irrevocable trusts shield assets and lock in wealth transfer strategies.
- Family Partnerships/LLCs: These offer control, discounts for estate tax, structured inheritance, and powerful asset protection.
- Dynasty Trusts & GST Planning: For those thinking generations ahead, these tools prevent taxes from gutting your estate with each transfer.
- Healthcare Directives & POAs: Protect yourself in the event of incapacity, make sure your wishes are clear and your chosen advocates are empowered.
- Family Transparency: Don’t keep heirs in the dark and leave everything a surprise after you pass away. Hold a family meeting and keep them updated on your wishes and plans for assets after you pass.
Practical Tip: It’s not just about crossing the t’s and dotting the i’s in your estate documents. The most successful legacies, with the least amount of stress for heirs, are communicated beforehand. Invite your heirs into the estate planning discussion.
4. Healthcare and Long-Term Care: A Plan for Life’s Wild Cards
Wealthy families are often prepared for a long life, but living longer can bring new risks, such as higher healthcare costs, unexpected medical needs, and long-term care expenses.
- Healthcare Inflation: Top-tier coverage becomes increasingly expensive every year. Build that escalation into your projections.
- Long-term Care: Medicare does not cover long-term care. Consider hybrid policies or self-funding with segregated investments, and decide in advance how you’d prefer to receive care.
- Family Impact: We’ve seen wealthy families struggle emotionally when a loved one needs care. The right plan addresses both finances and the personal side, so your spouse, children, or friends aren’t forced to scramble.
Practical Tip: We recommend having a written formal plan for long-term care needs, whether it be long-term care insurance or self-funding. Don’t forget to include in-home care versus facility decisions to reduce anxiety and family burden.
A Five-Step Action Plan for High-Net-Worth Retirement Planning Success
It’s one thing to know the rules, but it’s another to turn them into a plan that works. Here’s how we help clients, and ourselves, create and stick to a retirement roadmap.
Step 1: Define Your Vision. In Writing
Start with a blank page. What does a stress-free, meaningful retirement look like for you? Is it a second home, travelling, a foundation, or mentoring the next generation?
- Write down your “must-haves” and “nice-to-haves.”
- Don’t hold back on your ambitions or feelings. This isn’t just about numbers. It’s your real life.
- Quantify specific targets (e.g., “$50,000 per year for travel”; “$100,000 seed fund for grandkids’ education”).
Practical Tip: The best plans begin when you can answer: “What will I regret not having done, given the resources I’ve built?”
Step 2: Audit Spending, Income, and Risks. Brutal Honesty Required
High-net-worth families are often surprised by how hidden expenses can add up during retirement.
- Map every lifestyle expense, expected or not, including gifts, home remodels, weddings, and support for adult children.
- List all sources of income, from business holdings to real estate, pensions, and investment portfolios.
- Factor in inflation and lifestyle changes.
- Stress-test your plan. What if you live to 100, require seven figures of healthcare, or face major market shocks? Does your withdrawal plan still stand up?
Client Stories: One client, a longtime executive, nearly underestimated their post-retirement tax bill by over $50,000 a year until we mapped out the actual distributions and taxes. Our approach caught the oversight and preserved their financial plan.
Step 3: Build Your Personalized high-net-worth Retirement planning Blueprint
Work only with advisors who have a deep understanding of high-net-worth complexity. “Off-the-shelf” won’t work here.
- Coordinate your investments, tax strategies, estate plans, and insurance to ensure alignment.
- Detailed timelines: When will you access different accounts? When do charitable gifts kick in? How will business transitions unfold?
- Stress-test with scenario analysis, not just projections, but “what-ifs” for both your life and the world around you.
Practical Tip: Ensure that every advisor you work with acts as a fiduciary, and that your CPA and estate attorney are all aligned on the same page each year. We believe a unified advisory team is key to your success.
Step 4: Manage Investments Passively and Emotions Actively
A static portfolio is a risky one, but so is trying to outguess every headline.
- Hold regular, objective reviews. Adjust allocations as your priorities or tax picture change.
- Look at private opportunities carefully. Alternatives can add value, but they need close review. Don’t chase returns where it’s hard to see what’s happening or get your money out.
- Recognize when your own behavior presents the biggest risk. Often, the wisest move is confidently choosing to “do nothing” during market panic.
Client Stories: We’ve seen clients lose more to knee-jerk reactions during corrections than from any actual bear market. Have an investment process that defends you from yourself and an investment Policy Statement that spells out your allocation, expected return, and potential loss. It’s investing. Not every year will be great. You have to accept the down times as part of the long-term growth process.
Step 5: Schedule Reviews: Life Changes, So Should Your Plan
Revisit the entire plan each year and after any significant change: marriage, divorce, move, sale, illness, or economic surprise.
- Revisit risk tolerance, update beneficiaries, review insurance needs, and refresh your letters of instruction.
- Review tax laws and opportunities. Is a Roth conversion now even wiser? What is the impact of your RMDs?
- Most importantly, check in on your vision. Sometimes your goals, or those of your family, shift in a way that no spreadsheet can predict.
Practical Tip: Regular, scheduled reviews keep your plan current and aligned as your life and goals change.
Retirement Redefined: A Last Word on Confidence, Impact, and Living Your Legacy
High-net-worth retirement planning is about shaping your next chapter with flexibility, control, and a sense of purpose. You want your family to be protected, your options to be open, and your impact on people and causes you care about to continue growing. High-net-worth planning works best when you:
- Regularly revisit your goals as your life evolves.
- Make your vision and values clear to both your family and advisors.
- See legacy as a set of actions and priorities you embody now, not just a future transfer of wealth.
Ask yourself: Does my current plan reflect what matters most to me and my loved ones? Where can my financial choices have the most lasting and positive impact?
Here’s Our Invitation for high-net-worth retirement planning
Set aside time to revisit your plan and ask the hard questions. Please share this with the people who matter: family, advisors, and use it to start an honest dialogue. You’ve earned more than just reaching the finish line. You’ve earned a thoughtful next chapter.
Take the next step and contact us to refine your plan or explore new possibilities. Let’s start building your future today.
