Tax Planning

We do not wait until April. Tax planning decisions are part of our Fall Planning Meetings and every major financial decision you make. Moving jobs? Exercising stock options? Selling a rental property? Retiring early? Tax planning is a part of almost every aspect of the overall financial planning process.

During market declines, we can identify opportunities to sell positions at a loss (intentionally). Those realized losses can offset gains in your portfolio or other outside gains you may have. If you don’t have any gains that need offsetting that year, we can use this loss as a carry forward indefinitely. This is not something a typical CPA handles, as it requires real-time investment management.

For clients who give to charity, there are smarter ways to do it than writing a check. Donating appreciated stock avoids capital gains entirely. Bunching donations into a Donor-Advised Fund in a high-income year can exceed the standard deduction threshold and produce larger tax savings.

RSUs, ISOs, NSOs, and deferred compensation each come with distinct tax consequences. We work with clients who receive equity comp to model exercise timing, holding periods, and diversification strategies that minimize tax drag. This is one of the most common planning needs we see in San Diego, given the concentration of tech and biotech professionals here.

Now. The most impactful tax strategies require time. Roth conversions are best done over multiple years. Tax-loss harvesting requires catching market dips as they happen. Charitable giving strategies work best when planned before December, not in a rush. If you wait until tax season, you have already missed most of the opportunities.

If you earn over $500,000, own investments outside retirement accounts, receive equity compensation, or are within 10 years of retirement, your taxes are more complicated than you think. Even a single well-timed Roth conversion or a disciplined tax-loss harvesting strategy can save tens of thousands of dollars over time.

Tax preparation deals with the year that just ended. Your preparer takes your income and deductions and files the return. Planning happens before that. We look at the years ahead and find ways to lower what you owe over time, so by the time the return is filed, the decisions that matter are already made.

Perhaps, though we plan around your lifetime tax bill, not a single return. In some years it makes sense to pay a little more now to avoid paying a lot more later, like when we run a Roth conversion. The goal is the smallest total tax across your retirement.

Quite a bit. When you claim Social Security, whether you convert part of your IRA to a Roth before required distributions begin, which accounts you draw down first. These choices add up over a long retirement. The point is to lower what you pay across all of those years, not just the next one.

Tax law shifts often, and so does your life. We review your plan every year and adjust for new rules, new income, and anything that changed since we last met. A plan you set once and never revisit is not much of a plan.