Attorneys sit on a rare combination: high self-employment income, lumpy contingency fees, and — by career’s end — concentrated appreciated positions. This page maps the whole structure: how the practice is held (and California’s special rule for lawyers), the retirement stack that turns fee income into six-figure deductions, what “paying yourself through a foundation” actually requires, and the four honest exits from highly appreciated stock. Educational only — entity and charitable moves are made with your CPA and counsel at the table.
Most professionals reach for an LLC by reflex. In California, attorneys can’t — the law practice may not be conducted through an LLC. The menu is: stay a sole proprietor (simple, fully exposed to self-employment tax), form an LLP with partners, or form a professional corporation registered with the State Bar — and it’s the professional corporation with an S election that does the heavy lifting.[1]
The S election splits your income into reasonable salary (payroll-taxed) and distributions (not subject to self-employment/Medicare tax). On a high six-figure practice, the Medicare-tax savings alone routinely run five figures a year — if the salary is genuinely defensible. The IRS’s single biggest S-corp audit issue is salary set too low; the fix is a comp study, not a guess.[2] And the salary number matters twice, because it also sets your retirement-plan limits below.
Schedule C. Full SE tax on every dollar. Fine at the start; expensive at scale.
The multi-partner default. Flow-through; partners still face SE tax on their shares.
State Bar–registered corporation, taxed as an S-corp: reasonable salary + distributions. The Medicare-tax saver, and the base for the plan stack.
Available to lawyers in some states — not California. Attorneys here use the professional corporation instead.
The order of operations for a profitable practice: max the 401(k) employee deferral, add profit sharing to reach the annual additions limit, then — and this is where attorneys beat almost every other profession — bolt a cash balance plan on top. A defined-benefit plan’s limits are set by age and income, not by a flat cap, so a 55-year-old partner can often deduct $200,000–$300,000+ per year across the combined stack. Steady high income, an S-corp salary to anchor it, and few (or well-covered) employees is exactly the fact pattern DB plans were built for. We built a full page on the mechanics: Cash Balance & DB Plans →.[3]
Owner income comfortably above the 401(k) limits, expected to stay high 3–5+ years, age 40s–60s (older = bigger DB room), and a payroll you’re willing to cover — employee costs are real and we model them before anyone signs.
Contingency fees arrive in spikes, which fights a DB plan’s love of steady funding. The PI-specific tool is the structured attorney fee: elect, before the case resolves, to take the fee as a fixed schedule of future payments — taxed as received, smoothing a $2M year into ten deductible-plan-friendly ones. Timing is everything: after the fee is earned and payable, the door closes.[4]
Every plan limit keys off W-2 compensation from your professional corporation. Set salary too low to chase Medicare savings and you’ve capped your own DB deduction; the right number balances both. This is the calculation, not a vibe.
In multi-party settlements, a QSF can hold the recovery while allocations, liens, and fee structures are decided — buying the time to do the planning above correctly instead of in a wire-deadline panic.
You’ve heard the story — a colleague runs a private foundation and draws a salary from it. Here’s the version that survives an audit: a foundation may pay a disqualified person (including its founder) for personal services that are reasonable and necessary to its charitable purpose, at reasonable compensation. Everything else — using foundation assets, below-market loans, padded salaries, paying family beyond fair value — is self-dealing, and the excise-tax regime taxes the person, not just the foundation, until it’s unwound.[5] It’s a real strategy with a narrow lane: contemporaneous comp documentation, real duties, real charitable output.
The honest comparison for most attorneys: a donor-advised fund delivers the deduction (up to 30% of AGI for appreciated stock, 60% for cash), the timing control, and the family-giving ritual — with no excise rules, no 990-PF on the public record, and no payroll. The foundation earns its complexity when you want governance — a board, successors, staff, a permanent family institution — not when you want a deduction.[6]
Decades of fees invested well — or one client’s stock that ran — leaves the classic problem: a position you shouldn’t hold at that size and can’t sell without a six-figure tax bill. The four exits, in rising order of commitment:
Donate appreciated shares held over a year (to a DAF or charity): deduct fair market value, and the embedded gain is never taxed — to anyone. Every charitable dollar you were going to give anyway should be an appreciated share first.
Move the position into a CRT: the trust sells tax-free, reinvests diversified, pays you (or you and a spouse) an income stream for life, and the remainder goes to charity — with a partial deduction up front. The classic answer when you want income from the position, not just escape. Drafted by counsel; we model the payout math.[7]
Contribute the stock to a pooled exchange fund alongside other concentrated holders; after the seven-year seasoning, redeem a diversified basket at your original basis. No deduction, no income — just diversification with the tax deferred. Illiquid by design; read the fund terms twice.
For a position you may never need to spend: hedge the downside (collars and prepaid forwards exist, with sharp tax edges — counsel first), harvest losses around it, and let the basis step-up at death erase the gain for heirs. Sometimes the best sale is the one your estate never has to make.