The IRS isn’t going to call you and remind you about deductions you’re missing.

Tax strategy is something you have to go looking for. And most people don’t — not because they don’t care, but because they assume it’s complicated, or only for rich people, or something their accountant is already handling.

Most accountants file what you give them. They’re not proactively hunting for every dollar you could save. That job is yours.

Here are five moves that most W-2 employees and side hustlers can use, starting now.

Move 1: Max Out Your Tax-Advantaged Accounts

This is the single highest-leverage tax move available to most people, and most people aren’t doing it.

Every dollar you contribute to a traditional 401(k) or traditional IRA reduces your taxable income by that amount. If you’re in the 22% federal tax bracket and you contribute $10,000 to a traditional 401(k), you save $2,200 in federal taxes this year.

The 2025 limits:

  • 401(k): $23,500 (plus $7,500 catch-up if you’re 50+)
  • Traditional or Roth IRA: $7,000 (plus $1,000 catch-up if you’re 50+)
  • HSA (if you have a high-deductible health plan): $4,300 individual / $8,550 family

The HSA is especially underrated. Contributions are pre-tax, growth is tax-free, and withdrawals for qualified medical expenses are tax-free. It’s the only triple-tax-advantaged account available to most people.

Move 2: Use an HSA as a Stealth Retirement Account

If you’re eligible for an HSA, most people use it wrong.

They contribute to it, then immediately spend it on medical expenses. That’s fine — but you’re leaving the best part of the HSA on the table.

The real power: invest your HSA funds and let them grow. Pay your medical expenses out of pocket now (if you can afford to), save the receipts, and reimburse yourself years later — with no deadline.

After age 65, you can withdraw HSA funds for any purpose without penalty (you’ll owe ordinary income tax, just like a traditional 401(k)). Before 65, withdrawals for non-medical expenses get hit with a 20% penalty plus income tax.

Result: max your HSA, invest it, and treat it as a bonus retirement account that also happens to cover future healthcare costs tax-free.

Move 3: Deduct Side Hustle Expenses

If you have any self-employment income — freelance work, a side business, content creation, consulting, anything — you can deduct legitimate business expenses against that income.

This includes:

  • A portion of your home internet bill
  • Equipment (computer, camera, microphone)
  • Software and subscriptions used for work