Tax Planning Services for Business Owners & Retirees

The cost of a tax advisor varies according to the scope and complexity of the work. A focused review may be priced differently from ongoing planning that coordinates retirement withdrawals, investments, business income, estate considerations, and annual tax projections. Before engaging an advisor, ask what services are included, how compensation is structured, what deliverables you receive, and whether tax preparation is part of the engagement.

The “5 D’s” is not a single IRS-defined tax planning standard, and firms may use the phrase differently. It commonly refers to major life events that can require planning, such as death, disability, divorce, departure from work, and disaster. Each event can affect income, deductions, beneficiaries, ownership, insurance, and estate documents, making coordinated financial and tax review important.

Business owners can use tax planning to assess how compensation, retirement plan contributions, investment activity, charitable giving, business sales, and cash-flow needs interact. A coordinated strategy helps identify decisions that may affect taxable income now and later. Planning should also account for entity structure, records, estimated taxes, and the role of a CPA or tax attorney when specialized tax or legal advice is needed.

Retirees benefit from tax planning before retirement and throughout retirement. The years between leaving work and required distributions can create opportunities to evaluate Roth conversions, capital gains, charitable giving, and withdrawals from different account types. Reviewing the plan annually, and before significant income or legislative changes, helps keep distribution decisions aligned with current cash-flow needs and longer-term legacy objectives.

A tax-efficient withdrawal strategy coordinates distributions from taxable, tax-deferred, and tax-free accounts rather than treating each account separately. It considers projected income, tax brackets, required distributions, investment gains, Medicare-related income thresholds, and future estate goals. The appropriate sequence differs by household and should be reviewed regularly because market performance, spending needs, tax rules, and account balances can change over time.

Yes. A Roth conversion moves assets from a tax-deferred account to a Roth account, generally creating taxable income in the year of conversion. It may be considered when projected current tax rates are favorable relative to future rates, but it requires careful analysis. The converted amount can affect tax brackets, Medicare premiums, estimated taxes, and other planning decisions, so timing and size matter.

Tax planning can be coordinated with estate and charitable goals by reviewing beneficiaries, account titling, gifting strategies, trusts, and the tax character of assets. For eligible retirees, qualified charitable distributions may be one option to evaluate. Sentinel coordinates financial planning considerations with estate attorneys and tax professionals where appropriate, helping ensure legal documents, financial accounts, and intended distributions remain aligned.

Review a tax plan at least annually and whenever a major change occurs, such as a business sale, retirement, inheritance, divorce, large investment gain, relocation, or change in charitable objectives. An annual review can assess realized income, projected withdrawals, capital gains, required distributions, and possible planning opportunities before year-end. Ongoing coordination helps keep decisions consistent with changing goals and tax rules.