Tax Planning and Advisory

Tax preparation is looking backward — recording what already happened. Tax planning is looking forward — deciding what to do before December 31 so the return in April looks different. Planning is where the actual dollar savings come from. A well-planned year with a competent preparer is always cheaper than a scrambled year with a brilliant one.

The highest-leverage window is October through mid-December — after the year's income picture is reasonably clear but before December 31 closes most opportunities. That's when decisions like Roth conversions, charitable bunching, capital gains harvesting, retirement contributions, and year-end bonuses become actionable. Earlier planning (summer or earlier) is valuable for longer-horizon decisions like equity comp exercises or entity restructures.

It depends on your marginal tax bracket this year compared to what you expect in retirement, your time horizon, whether you have non-retirement assets to pay the tax, and whether a conversion pushes you into IRMAA surcharges on Medicare. The right answer is almost always "do some, not all" and "do them in low-income years before RMDs start." Running the actual multi-year projection is what turns this from a guess into a decision.

If you expect to owe more than $1,000 in federal tax beyond withholding, you're required to pay estimates quarterly — April 15, June 15, September 15, and January 15 of the following year. Safe harbor rules let you pay either 100% of last year's liability (110% if AGI exceeds $150k) or 90% of the current year, whichever is lower. Underpaying triggers an interest-like penalty that many clients are surprised to see. Planning means getting the right amount paid at the right time.

Absolutely yes — and ideally several months in advance, not weeks. Big liquidity events create tax bills that can often be reduced meaningfully with advance planning: installment sales, 1031 exchanges, qualified opportunity zone investments, charitable remainder trusts, or simply timing the transaction across tax years. Once the sale closes the planning window is mostly closed.

Equity comp is one of the areas where planning delivers the most value per dollar spent. RSU withholding is usually under-collected, leaving a big April bill. ISO exercise timing affects AMT exposure. ESPP sales have qualifying vs. disqualifying treatment worth thousands. 83(b) elections on founder stock can save ordinary-income tax rates on future appreciation. Every one of these is a decision you can actually influence if you're paying attention.

No — I am not a financial advisor and do not recommend specific investments, securities, or allocation strategies. Tax planning works alongside your financial advisor: you decide what to invest in, and I help you decide when and how to do it in the most tax-efficient way. If you don't have a financial advisor, I can refer you to trusted ones I coordinate with.

It varies enormously. For straightforward W-2 situations, planning might save a few hundred to a couple thousand in a typical year. For business owners, equity-comp holders, or people with big transactions, planning can save five or six figures. The honest answer during a free consultation is that I'll tell you whether there's real planning leverage in your situation before taking the engagement — if there isn't, I'll say so.