Julie is a high-earning executive in her early 50s. Like many in her position, her income picture is layered and complex: salary, annual bonuses, stock options, restricted stock units (RSUs), rental income, and a sizable taxable portfolio. On paper, this looks like success—and it is. But without proactive tax planning, the result could easily be painful checks each April, unpredictable quarterly estimates, and ongoing anxiety about whether she’s paying enough or too much.

At Members’ Wealth, we take a different approach. By working directly with Julie’s CPA, we turn what could be a year-end scramble into a steady, year-round strategy. The coordination doesn’t just save her money—it gives her clarity and confidence.

Avoiding Surprises With Estimated Payments

For Julie, the turning point was realizing that “tax season” never really ends. Each quarter brings changes: RSUs vest, capital gains are realized from rebalancing, or stock options are exercised. Any of these could throw off her tax picture if left unmonitored.

That’s why we check in with her and her CPA every quarter to update projections. When RSUs vest, we adjust estimates in real time. When she considers exercising stock options, we model both the immediate cash needs and any potential Alternative Minimum Tax (AMT) exposure. The result is precision: Julie never overpays out of fear, and she never gets caught off guard with a shortfall.

The value isn’t just in the numbers. It’s in knowing that her advisory team and CPA are on the same page, eliminating the guesswork and giving her confidence that every move has been fully evaluated.

Tax-Loss Harvesting in Real Time

Markets don’t follow a calendar. Volatility happens when it happens—and that can create planning opportunities.

Last fall, several of Julie’s taxable holdings dipped temporarily into the red. Instead of waiting until December, we harvested those losses immediately and reinvested the proceeds into similar—not identical—positions, keeping her allocation intact while creating a bank of capital losses. Her CPA documented everything, ensuring those losses could be applied to offset future gains or even up to $3,000 of ordinary income each year.

Today, strategies like direct indexing can make this process even more powerful. By holding the individual stocks of an index rather than just a fund, losses can be harvested automatically across hundreds of positions throughout the year. That way, no opportunity slips through the cracks, and the portfolio stays aligned with her overall allocation.

Tax-loss harvesting may sound straightforward, but without integration it can backfire—triggering wash sales, distorting an allocation, or missing opportunities altogether. When done with precision, it transforms volatility into long-term tax assets.

Looking Ahead: Roth Conversions and Asset Location

Julie’s story isn’t just about today’s tax bill. She’s already looking at her next phase of wealth management—what retirement will look like in 10–15 years. This is where collaboration with her CPA allows us to move from reactive to proactive.

We’ve modeled scenarios for partial Roth conversions during lower-income years, showing how moving money from traditional retirement accounts to Roth IRAs can reduce required minimum distributions (RMDs) later in life. We’ve also structured her portfolio across accounts—placing income-heavy assets inside retirement accounts and long-term growth equities in taxable accounts—to improve after-tax returns.

Each of these strategies requires coordination. Her CPA ensures the reporting is airtight; we make the planning deliberate and forward-looking. Together, we give Julie a plan that doesn’t just minimize taxes now but also prepares her for decades to come.

The Next Phase: From Reactive to Proactive

At Members’ Wealth, we believe tax planning should never feel like a one-time event. Yet for many, that’s still the reality: scramble in March, file in April, and move on. For families with significant assets, business interests, or complex income streams, this approach leaves too much uncertainty—and often too much money on the table.

The truth is, taxes touch nearly every financial decision: how much you save, when you withdraw, where you invest, and even how you structure gifts to the next generation. That’s why we don’t just coordinate with CPAs at year-end; we collaborate throughout the year, aligning strategies so clients don’t just file returns—they shape outcomes.

Julie’s experience is proof of what’s possible when tax planning is treated as a process, not an afterthought. With her CPA and wealth team working side by side, she’s not only saving money—she’s eliminating uncertainty and building confidence that her strategy is working as hard as she is.

You don’t have to navigate taxes alone. With Members’ Wealth and your CPA working side by side, you can move from reactive to proactive.

Schedule a call to get started.

The information provided is for educational and informational purposes only and does not constitute investment advice and it should not be relied on as such. It should not be considered a solicitation to buy or an offer to sell a security. It does not take into account any investor's particular investment objectives, strategies, tax status or investment horizon.

These examples are for illustrative purposes only and do not represent actual client experiences. Individual results will vary based on personal financial circumstances and tax laws.

About the Author – Stu Caplan, CFP®

Stu Caplan is Senior Wealth Strategist at Members’ Wealth, a boutique wealth management firm that offers a comprehensive approach to serving individuals, families, business owners, and institutions.

The firm’s goal is to preserve and grow its clients’ wealth to endure over time, while thoughtfully evolving its strategy to suit an ever-changing world. With over 20 years of industry experience, Stu and the Members' Wealth team thrive on bringing clarity and confidence to clients' unique situations.

Stu received his MBA from The Robert H. Smith School of Business at the University of Maryland and his bachelor’s degree from the Eller College of Management at the University of Arizona. Stu resides in Bucks County, PA with his wife and two sons. He’s an avid golfer and is thrilled that his boys have embraced the game. He also volunteers his time as a board member of the PKD Foundation and Abrams Hebrew Academy.

To get in touch with the Members’ Wealth team today, I invite you to email info@memberswealthllc.com or call (267) 367-5453. 

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Investment strategies, including rebalancing, do not guarantee improved performance and involve risk, including potential loss of principal. Past performance does not guarantee future results.

The information provided is for educational and informational purposes only and does not constitute investment advice and it should not be relied on as such. It should not be considered a solicitation to buy or an offer to sell a security. It does not take into account any investor's particular investment objectives, strategies, tax status or investment horizon. 

All information has been obtained from sources believed to be reliable, but its accuracy is not guaranteed. There is no representation or warranty as to the current accuracy, reliability or completeness of, nor liability for, decisions based on such information and it should not be relied on as such.

Investment advisory services are offered through Members’ Wealth, LLC., a Registered Investment Advisory Firm.

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Members’ Wealth does not provide legal, accounting or tax advice. Please consult your tax or legal advisors before taking any action that may have tax consequences.

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