Year-round tax planning

Saving tax is not one trick. It is finding the moves that fit the whole picture.

Business structure, payroll, retirement plans, Roth strategies, education accounts, family employment and property decisions interact. Start by identifying which questions deserve an actual calculation.

No strategy is recommended from this page. Suitability, cost, timing and documentation require the client’s facts and an accepted scope.

Randall Stone, Enrolled Agent, in a warm office setting
Business ownersEntity, payroll, retirement and owner compensation
Professionals & contractorsIncome timing, benefits and deductible structure
FamiliesRoth, education, dependents and multigenerational planning
Property clientsBasis, gain, depreciation and reinvestment choices

Questions worth calculating

The opportunity is often in the interaction—not the headline strategy.

These are screening questions, not recommendations. The useful answer depends on income, entity, payroll, existing accounts, deadlines, state rules and the cost of implementation.

S corporation election or conversion

Would an S election reduce total cost after reasonable compensation, payroll, state taxes and fees, bookkeeping, benefits and compliance? Is the business eligible, profitable and operationally ready?

401(k) and business retirement plans

Which plan design fits the owner, employees, cash flow and contribution goals? How do employee deferrals, employer contributions, testing, deadlines and administration interact?

IRA and Roth conversion planning

Should income be accelerated into a Roth conversion now or preserved for another year? What do brackets, Medicare premiums, credits, withholding, charitable plans and future distributions change?

Backdoor Roth process

Are there traditional, SEP or SIMPLE IRA balances? Is nondeductible basis documented? What must Form 8606, timing and account movement show before treating the transaction as simple?

529-to-Roth rollover review

Does the account history, beneficiary, contribution age, earned compensation, annual limit and lifetime rollover limit support the contemplated transfer—and what records will the custodian require?

Hiring a dependent child

Is the work real, age-appropriate and documented? Is pay reasonable? Which entity employs the child, and what payroll, withholding, employment-tax and retirement-account rules follow?

Property-sale and basis planning

Can purchase records, improvements, occupancy, rental history, depreciation and selling costs be reconstructed before the closing date fixes the transaction?

Charitable and nonprofit coordination

Would the timing and form of a gift better serve the donor and organization? What valuation, substantiation, governance or related-party issues require another professional?

Year-end income and deduction timing

Which items can still change before their controlling deadlines—and which apparent savings merely move tax, create another cost or conflict with the larger financial plan?

Who this is built for

Clients whose tax choices cross business, family, property and retirement lines.

Owner-operated businesses

Real-estate and insurance professionals, attorneys, consultants, general contractors, specialized contractors and other service businesses balancing compensation, cash flow, benefits and growth.

Families with changing income

Households approaching retirement, selling property, funding education, supporting dependents or deciding when pre-tax and Roth strategies fit.

Advisers and organizations

Attorneys, agents, nonprofits and charitable entities that need a defined tax or financial analysis coordinated beside their existing legal, accounting or governance work.

Why the facts come first

Every attractive strategy carries conditions, records and tradeoffs.

Official material reviewed October 30, 2026. Current-year limits and guidance should be checked when work begins.

Defined-scope opportunity review

Tell me which decisions are in play—not which strategy you already decided to buy.

The first inquiry identifies fit, timing and the areas that may deserve calculations. Do not send returns, statements, account balances or taxpayer identifiers.

  • Engage only for the analysis you need
  • No investment-management requirement
  • Federal tax planning available remotely nationwide
What should the review screen?

This submits a business inquiry, not tax documents. See the privacy policy.

Avoid the shortcut

Common questions before choosing a strategy.

Will an S corporation always reduce taxes?

No. Eligibility, reasonable compensation, payroll, California costs, bookkeeping, benefits, income level and administrative burden can change the result. The election should be modeled before it is filed.

Is a backdoor Roth automatically tax free?

No. Existing traditional, SEP and SIMPLE IRA balances, nondeductible basis, conversion timing and Form 8606 reporting can affect the taxable result.

Should every business owner open a 401(k)?

Not automatically. Plan design depends on employees, owner goals, cash flow, contribution capacity, testing, administration and the alternatives available.

Can unused 529 money simply become Roth money?

Only if the statutory and account-history requirements are satisfied. The beneficiary, account age, contribution timing, earned compensation and annual and lifetime limits all matter.

Can a business owner hire a dependent child?

Potentially, for bona fide work at reasonable compensation with proper payroll and records. Employment-tax treatment differs by entity, age and services.

Do I need a comprehensive financial plan?

No. The review can be scoped to one transaction, election, retirement-plan comparison or coordinated set of tax questions.