Retirement has always been one of the biggest financial milestones in life — but in 2025, it comes with new challenges and opportunities, especially for high-net-worth families.

With shifting tax laws, rising healthcare costs, and market volatility, creating a secure retirement plan isn’t just about growing your wealth anymore — it’s about keeping more of it. Over the years, I’ve sat across the table from hundreds of families, and one thing has become crystal clear: the number one retirement killer isn’t poor investments, it’s inefficient tax planning.

If you’ve worked hard to build significant wealth, the way you structure your retirement income, investments, and estate plan can make the difference between living comfortably and leaving unnecessary dollars on the table. Let’s break down some of the key strategies we use at Stanley Wealth & Retirement to help clients maximize income, reduce risk, and protect their legacy.

Step 1: Understand the 2025 Tax Landscape

The starting point for any tax-efficient retirement plan is understanding how the current tax laws impact you. And in 2025, there’s a lot to pay attention to.

With provisions of the Tax Cuts and Jobs Act (TCJA) set to expire in 2026, we’re looking at a potential increase in federal income tax rates. High-net-worth families, in particular, may see significant shifts in:

• Capital gains taxes
  
• Estate and gift tax exemptions
  
• Required minimum distributions (RMDs)
  
• Social Security taxation thresholds
  

These changes could dramatically affect how much you pay in retirement. Planning ahead now gives you the opportunity to lock in today’s lower tax rates, especially when considering strategies like Roth conversions or gifting assets to heirs before exemption limits potentially drop.

Step 2: Diversify Your Tax Buckets

When most people think about diversification, they think about spreading money across stocks, bonds, and real estate. But one of the most overlooked strategies in retirement planning is tax diversification — making sure your assets are allocated across different types of accounts so you can control when and how you pay taxes.

I like to think of retirement savings in three buckets:

1. Taxable Accounts (e.g., brokerage accounts)
   
   • Taxes apply annually on dividends, interest, and realized gains.
     
2. Tax-Deferred Accounts (e.g., 401(k)s, traditional IRAs)
   
   • Contributions lower taxable income today, but withdrawals are fully taxed later.
     
3. Tax-Free Accounts (e.g., Roth IRAs, Roth 401(k)s)
   
   • Funded with after-tax dollars, but future withdrawals are 100% tax-free.
     

The mistake I see many high-net-worth families make is having too much in tax-deferred accounts. If tax rates rise — and all signs point to that — those future withdrawals could cost you more than expected.

We often help clients execute strategic Roth conversions, shifting money from tax-deferred to tax-free accounts while rates are lower, creating long-term flexibility and more control over taxable income.

Step 3: Sequence Withdrawals to Reduce Lifetime Taxes

Retirement income planning isn’t just about how much you withdraw — it’s about when and from where. One of the most effective strategies we use is called withdrawal sequencing.

Here’s an example:

• In your early retirement years, you may pull from taxable accounts first, giving your tax-deferred accounts more time to grow.
  
• As you approach required minimum distributions (RMDs), we might shift withdrawals to balance your overall tax exposure.
  
• If you’ve built up a Roth account, we save that for later years, when tax-free income becomes even more valuable.
  

This level of planning isn’t about avoiding taxes; it’s about managing them strategically so you can stretch your retirement dollars further.

Step 4: Use Tax-Efficient Investments

Not all investments are created equal when it comes to taxes. High-net-worth families need to pay close attention to where they hold their assets:

• Taxable accounts benefit from tax-managed funds, ETFs, and municipal bonds for more efficient returns.
  
• Tax-deferred accounts are ideal for investments that generate ordinary income, like bonds or REITs.
  
• Roth accounts are perfect for growth-oriented assets since future withdrawals are tax-free.
  

By aligning the right investments with the right accounts, we help clients reduce unnecessary tax drag and improve net after-tax returns — the number that actually matters.

Step 5: Leverage Charitable Giving for Tax Advantages

For many of my clients, giving back is a priority — and philanthropy can also be a powerful tax strategy. Two of the most effective tools are:

• Donor-Advised Funds (DAFs): Contribute today, take the deduction immediately, and distribute funds to charities over time.
  
• Qualified Charitable Distributions (QCDs): If you’re 70½ or older, you can direct up to $105,000 per year from an IRA to a charity tax-free, while satisfying RMD requirements.
  

These strategies not only reduce taxable income but also allow families to leave a lasting impact on the causes they care about.

Step 6: Protect Your Legacy Through Estate Planning

For high-net-worth families, retirement planning isn’t just about you — it’s about what you leave behind. With the federal estate tax exemption expected to be cut in half after 2025, now is the time to act.

Strategies we often discuss include:

• Irrevocable trusts to remove assets from taxable estates
  
• Spousal Lifetime Access Trusts (SLATs) for couples looking to maximize exemptions
  
• Gifting strategies to pass wealth to heirs tax-efficiently
  
• Life insurance planning to cover potential estate tax liabilities
  

Acting today ensures your family keeps more of what you’ve worked so hard to build.

Step 7: Make Retirement Planning a Living, Breathing Process

Here’s the truth: retirement planning isn’t a one-time event. The tax code changes. Markets shift. Your goals evolve. That’s why the most successful plans are dynamic — built to adapt, not collect dust in a drawer.

At Stanley Wealth & Retirement, we create living retirement plans designed to be reviewed regularly. Our goal isn’t just to make smart decisions today — it’s to make better decisions year after year as life changes.

Bringing It All Together

The bottom line? Tax-efficient retirement planning isn’t just about saving money — it’s about creating control. By understanding the tax landscape, diversifying your income streams, optimizing your investments, and protecting your legacy, you can reduce risk and keep more of your wealth working for you.

For high-net-worth families, the earlier you plan, the more options you have — and the better positioned you are to live the retirement you’ve always envisioned.