Tax Planning

A Proactive, Audit-Ready Approach to Lower Taxes

Lower lifetime taxes using simple, scheduled moves — not a scramble every April.

Plan My Tax Moves 2-Minute Tax Readiness Check
What Is It

What Is Tax Planning?

  • How to pay less tax over your lifetime, not just this year.
  • What to do each quarter so April isn't a surprise.
  • Which accounts to add to or pull from so taxes stay lower.
  • How to time big moves — charitable gifts, stock sales, equipment purchases — so they help at tax time.
  • What records to keep so everything is simple and audit-ready.
Tax planning strategy
For Retirees / Nearing Retirement
  • When to move pre-tax money to Roth to reduce future taxes — especially in the lower-tax years before RMDs begin.
  • When to start Social Security so income and taxes line up, integrated with portfolio withdrawals and survivor benefits.
  • How to handle required withdrawals (RMDs), paired with QCDs (70½+) for tax-efficient giving.
  • Managing capital gains using harvest bands, using the 0%/15% brackets when available.
  • Ways to avoid Medicare surcharges (IRMAA) and plan healthcare costs around MAGI (ACA and Medicare tiers).
For Business Owners
  • Quarterly estimated payments sized to what the business actually made that quarter — not last year's total divided by four.
  • Balancing reasonable compensation vs. distributions for payroll tax efficiency and the QBI deduction.
  • Reviewing entity structure and S-Corp election timing as the business grows.
  • Retirement plan contributions (Safe Harbor 401(k), profit-sharing, cash balance) as tax-deferred savings.
  • Timing equipment purchases and bonus depreciation around income spikes, not just year-end.
How It Works

The Framework, in Plain English

01

Projections First

See the year before it happens, not after.

02

Choose the Levers

Compensation, plans, gifts, harvesting, conversions — picked for your bracket and cash flow.

03

Put It on a Calendar

Q1–Q4 tasks replace last-minute guesses.

04

Execute & Document

A small binder or folder so April takes minutes, not days.

05

Adjust As Needed

Mid-year and Q4 check-ins capture life and business changes.

Deliverables

Real Deliverables, Not Just Advice

Annual Tax Moves Calendar

Owner and retiree versions, mapped to Q1–Q4 tasks.

Quarterly Projections

Bracket, credit, and IRMAA guardrails, before choices are made.

Entity & Compensation Review

For business owners — reasonable comp, entity structure, and timing.

Roth / Withdrawal Game Plan

For owners post-exit and retirees — sequencing that fits your bracket.

Charitable Giving Playbook

DAF and QCD timing to make generosity tax-smart.

Audit-Ready Documentation Checklist

Everything organized so April takes minutes, not days.

See a Sample Tax Moves Calendar
Where Do You Stand?

2-Minute Tax Readiness Check

Three quick questions. We'll tell you exactly where the biggest opportunity is.

What's your biggest tax frustration right now?

Real Scenarios

Mini Case Studies

Business Owner

Electrical Contractor, Age 45

Reasonable compensation, a Safe Harbor 401(k), and a quarterly projection calendar that ended the annual tax-season scramble.

 Retiree Couple

Retiree Couple, Ages 67 & 64

Roth conversions in a low-income window, IRMAA-aware withdrawal sequencing, and a plan before RMDs begin.
Common Questions

FAQs

Smart timing matters. Coordinating withdrawals between taxable, tax-deferred, and tax-free accounts can reduce your lifetime tax bill. A good plan balances income so you stay in lower brackets, while keeping Medicare premiums and Social Security taxes in check.
Once you reach age 73, the IRS requires annual withdrawals called Required Minimum Distributions (RMDs). Taking too little means a hefty penalty. Taking too much can bump you into a higher tax bracket. Planning withdrawals before 73 can smooth out taxes over time.
A Roth conversion moves money from a traditional IRA into a Roth IRA — paying taxes now to enjoy tax-free growth later. It's not for everyone, but for many retirees in lower tax years (like before RMDs begin), it's a strategic move that can save thousands long term.
They can be. Up to 85% of benefits may be taxable depending on your total income. Smart coordination of withdrawals, Roth conversions, and other income sources can help keep more of your benefit in your pocket — not the IRS's.
It depends on your tax bracket, RMD timing, and income needs. Many retirees benefit from a tax-efficient withdrawal strategy that blends different accounts each year to minimize overall taxes.

Ready to Lower Lifetime Taxes With a Clear, Audit-Ready Plan?

Plan My Tax Moves
Book a Call

Who would you like to meet with?

Both offer a free, no-pressure first conversation — no charge, no obligation.

Sean Williams
Sean Williams
Principal & Lead Advisor
Business owners, retirement income, and exit planning.
Schedule with Sean →
 Nick O'Kelly
Nick O'Kelly
Director of Financial Planning
Financial planning and veteran & military families.
Schedule with Nick →
Not sure who's the right fit? Either one can point you in the right direction.