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Chapter 06 · Planning

Tax Strategy

Tax planning is legal. Tax evasion is not. Strategy, timing and knowledge can save hundreds of thousands of dollars over a lifetime.

Legal Optimisation

Tax Strategy: Legal, Powerful, Essential

Tax planning is legal. Tax evasion is not. The difference between them is strategy and knowledge.

The US tax system is progressive. Higher tax brackets apply only to the income within that bracket.

Tax Hack

Capital gains on assets held over 12 months are taxed at lower long-term rates (0%, 15%, or 20%). Holding investments longer can dramatically reduce taxes.

Maximise 401(k) — reduce taxable income by up to $23,000 in 2026

Contribute to an HSA — the only triple tax-advantaged account

Hold investments 12+ months to qualify for long-term capital gains

Tax-loss harvesting — offset gains before December 31

Roth conversion ladder in low-income years

Bunch deductions to alternate between itemizing and standard deduction

Accounts First

The Tax-Advantaged Account Hierarchy

01
401(k) to Employer Match

Always capture the full employer match first. It is a guaranteed return.

02
Max Your HSA

Triple tax advantage: deductible contributions, tax-free growth, tax-free medical withdrawals.

03
Max Your Roth IRA

$7,000 annual limit. Tax-free growth and withdrawals in retirement.

04
Back to 401(k)

After IRA is maxed, contribute up to the $23,000 annual limit.

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