5 Things Affluent Investors Should Do Before Year-End

After more than 25 years in the wealth management business, I’ve seen that many of the most successful investors share one key habit: they pause at the end of each year to make intentional adjustments.

It’s not about chasing performance or predicting markets: it’s about controlling what you can control.

A year-end wealth review is one of the most valuable exercises you can do to protect, grow, and align your wealth with your long-term goals. Here are five things every affluent investor should do before December 31.

1. Revisit Your Tax Strategy

Taxes are often your single largest ongoing expense, which means small, proactive steps can have a big impact. Reviewing your gains and losses before year-end can reveal opportunities to offset taxable income.

For example, you might identify investments that have underperformed and use tax-loss harvesting to offset gains from a property sale or business wind-down.

Or if you’re planning charitable gifts, consider donating appreciated stock through a donor-advised fund rather than writing a check. This allows you to give more and potentially reduce capital gains taxes at the same time.

The key is timing. Transactions executed before December 31 count toward this year’s taxes. Waiting until January means missing the window entirely.

2. Maximize Retirement Contributions

Even high earners miss opportunities here. The IRS adjusts contribution limits almost every year, and those extra few thousand dollars can compound significantly over time.

If you’re still working, confirm you’ve maxed out your 401(k) ($23,000 for 2025, plus a $7,500 catch-up if you’re over 50). High-income earners who aren’t eligible for a Roth IRA might consider a backdoor Roth conversion—a move that shifts after-tax dollars into a tax-free growth vehicle.

If you’re retired, double-check your Required Minimum Distributions (RMDs) have been taken. Missing one can trigger a 25% penalty—an entirely avoidable mistake. A quick review with your advisor can prevent that.

3. Rebalance Your Portfolio for the Year Ahead

Over time, portfolios drift. A year of strong market performance can shift your allocation from 60/40 to 70/30, quietly increasing your risk exposure without you realizing it.

Rebalancing now helps lock in gains, trim overexposed positions, and align your investments with your actual comfort level and time horizon. It’s also an opportunity to take a hard look at any concentrated holdings – such as company stock or private investments – and decide whether to diversify.

Doing this review before year-end allows you to manage realized gains and losses strategically within the current tax year, rather than reacting in January when your options are limited.

4. Reassess Your Estate and Legacy Plans

Your estate plan isn’t something to “set and forget.” Life changes like new grandchildren, marriages, moves, or evolving charitable priorities can all affect how your wealth is distributed.

Before the year ends, review your will, trusts, and beneficiary designations to make sure they reflect your current wishes. It’s surprisingly common for old retirement accounts or insurance policies to list outdated beneficiaries, leading to unintended outcomes later.

A coordinated review with your advisor, attorney, and CPA ensures your plan is both tax-efficient and true to your intent. And with potential estate tax law changes on the horizon, staying proactive can make a significant difference.

5. Review Cash Flow and Liquidity

Affluent investors often face a different kind of challenge: being “asset rich” but “cash poor.” Real estate, private equity, and other illiquid holdings can tie up capital and limit flexibility.

An annual liquidity review helps you identify upcoming expenses—like tuition, tax payments, or capital calls—and confirm you have the right amount of accessible cash to cover them without disrupting your portfolio. It’s also a smart time to evaluate borrowing capacity, especially if you’re considering a major purchase or investment opportunity early next year.

Liquidity planning isn’t about hoarding cash: it’s about positioning yourself to act decisively when opportunities arise.

A Final Thought

An annual wealth review is more than a financial checkup: it’s an opportunity to make sure your wealth is working in sync with your life. By addressing these five areas before year-end, you give yourself the chance to minimize surprises, strengthen your plan, and start the new year from a position of confidence and control.

If you haven’t yet scheduled your review, now’s the time. Preparation today is what allows for flexibility tomorrow. And that’s the hallmark of a well-managed financial life.

Let’s schedule a conversation: https://calendly.com/winstone-wealth-partners/financial-consultation-with-jeff-green