The business decisions
1. Entity and election. LLC, S corporation, C corporation — the choice drives self-employment tax, the QBI deduction, exit options, and state costs. It deserves a review whenever profits, payroll, or plans change materially, not a one-time decision at formation.
2. Owner compensation. Salary versus distributions versus rent is simultaneously a tax question (reasonable compensation), a retirement question (plan contributions key off W-2 wages), and a lending question (banks read the number). Set it deliberately, with the CPA and the plan design in the same conversation.
3. Business cash reserves. How many months of operating expenses the company holds determines how it survives a bad quarter — and how much the household can safely take out. The reserve target belongs in writing.
4. Value the business honestly. An annual back-of-envelope valuation — even a rough multiple on normalized earnings — keeps the retirement math tethered to reality and flags the gap between what you assume and what a buyer would pay.
The household decisions
5. Personal liquidity policy. Cash outside the company, sized to the household's real fixed costs; distributions deployed on schedule. The single highest-leverage habit an owner can build — it makes every other decision calmer.
6. Retirement plan design. Solo 401(k), safe-harbor 401(k) with profit sharing, or a cash balance layer — the owner's biggest legal tax shelter, matched to payroll and cash flow. We compare them on the business-owner page.
7. The outside portfolio. Built to be strong when the business is weak: liquid, diversified away from the company's industry, and located tax-efficiently across account types — the discipline described in our approach to investment management.
8. Education and family goals. 529 funding, help for parents, the vacation home — real goals with real numbers and owners, funded on schedule instead of promised vaguely.
The protection decisions
9. Insurance that matches the plan. Life and disability sized to what the household would actually need if the owner's income stopped; key-person coverage sized to what the business would need. Umbrella coverage for the liability that success attracts. Reviewed against the plan, not sold by the pound.
10. The buy-sell agreement. If there are partners, the buy-sell decides what happens to your family's largest asset on the worst day. It needs a funding mechanism (usually insurance), a current valuation formula, and a re-read every few years — most were signed long ago and quietly no longer work.
The legacy decisions
11. Estate documents and titling. Wills, trusts, beneficiary designations, and how the business interest itself is titled — coordinated with your attorney and the estate planning team, and checked whenever the company's value moves. Several of the most valuable estate techniques for owners only work before a sale is on the table.
12. The exit itself. Sale to a third party, to management, to family, or a wind-down — each has a different tax shape, timeline, and preparation list. Deciding the intended path early, even loosely, tells every other decision on this page what it's aiming at.
How often each decision gets revisited
Not everything needs annual surgery. A workable cadence: every year — compensation, plan contributions and design, cash reserves (both), the valuation sketch, and the portfolio's location and rebalancing. Every two to three years — entity election, insurance amounts, the buy-sell's valuation formula, and the estate documents. On every trigger event — a partner change, a big contract won or lost, a move between states, a health event, or the first serious inbound from a buyer: re-run the whole page. The point of the cadence is that nothing waits for a crisis to be looked at.
Where owners usually start
If the twelve feel overwhelming, the sequence that unlocks the rest is short: write the liquidity policy (decision 5), set compensation deliberately (decision 2), and get the retirement plan design current (decision 6). Those three create the cash, the structure, and the tax shelter that fund everything else — and they surface every coordination problem worth solving in year one. The rest of the page follows in the annual rhythm.
Run it as a system
Twelve decisions, one page, reviewed once a year with the advisor, the CPA, and — when the estate or the exit is moving — the attorney at the same table. That cadence is the whole method behind our financial planning engagement: not a binder produced once, but a system that keeps the answers current while you run the company. The U.S. Small Business Administration's owner resources are a useful public complement on the business side.
Before you act: model the expected benefit, the deadline, the documentation required, and the effect on cash. Tax and retirement rules are fact-specific and change every year — confirm any strategy for the current year with your advisor and CPA before implementing it.