Fund it.

Your benefits package is stuffed with free money and tax wins most people leave on the table. Take the full match, let time compound, stop overpaying for a PPO. Four dead-simple calculators that make the case viscerally.

01 · The employer match

It's free money. Take all of it.

Your employer's match is the highest guaranteed return you will ever get. A 100% match isn't a "good return" — it's doubling your money the instant it lands. Anything below the cap is a raise you're declining.

Annual salary

Your contribution (% of salary)

Employer match rate (e.g. 100% or 50%)

…up to this % of salary

Free money you're leaving on the table

Match you get now

Match if you hit the cap

Instant return on cap money

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02 · Compounding

Time is the whole game.

Your contributions are the small part. The growth on top of them is the prize — and it only shows up if you give it years. Waiting is the single most expensive thing you can do.

Monthly contribution

Assumed annual return

Years until retirement 35 yrs

If you started 5 yrs later…

Future value at retirement

Total you contributed

Growth (FV − contributions)

The cost of waiting

03 · PPO vs. HSA-eligible HDHP

The PPO almost always costs you more.

The PPO's fat premium is a cost you pay every paycheck no matter what — sick or healthy. The HDHP trades that for a higher deductible you only pay if you get sick, plus an HSA with a triple tax advantage and often free employer dollars. Plug in your real numbers.

PPO annual premium (your share)

HDHP annual premium (your share)

PPO deductible

HDHP deductible

PPO out-of-pocket max

HDHP out-of-pocket max

Expected annual medical spend $2,000

Employer HSA contribution

Your own HSA contribution

Marginal tax rate (fed + state)

PPO

High premium, low deductible

Expected total cost / yr

Premium$0
Out-of-pocket$0

HDHP + HSA

Low premium, triple-tax HSA

Expected net cost / yr

Premium$0
Out-of-pocket$0
− Employer HSA $$0
− Tax saved on HSA$0

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The model, plainly: Each plan's cost = premium + expected out-of-pocket, where out-of-pocket = your medical spend capped first by the deductible-to-OOP-max band (we treat spend up to the deductible as 100% yours, then cap at the out-of-pocket max — a simplified, no-coinsurance model). For the HDHP we then subtract the free employer HSA dollars and the income tax you avoid on your own pre-tax HSA contribution (contribution × tax rate). Not modeled: coinsurance between deductible and OOP-max, HSA investment growth (which only widens the HDHP's lead), or premium tax treatment. Keep it directional, not exact.

04 · The order of operations

Once the calculators have convinced you, here's the order to actually fund things in. Top to bottom.

401(k) to the full match

Always, before anything else. An employer match is an instant 50–100% return. There is no investment on earth that beats free money. If you do one thing, do this.

Max the HSA

On an HDHP? The HSA is the only triple-tax-advantaged account that exists: pre-tax in, tax-free growth, tax-free out for medical. Don't spend it — invest it and treat it as a stealth retirement account. Save receipts; reimburse yourself decades later, tax-free.

Max the 401(k)

After the match and HSA, fill the rest of your 401(k) up to the annual limit. Pre-tax (or Roth) dollars compounding for decades — this is the workhorse.

Backdoor Roth

Earn too much to contribute to a Roth IRA directly? Contribute to a traditional IRA and convert it to Roth. Legal, common, and worth it. Watch the pro-rata rule if you hold other pre-tax IRA balances.

Mega backdoor Roth

If your plan allows after-tax 401(k) contributions plus in-plan Roth conversion, you can funnel tens of thousands of extra dollars per year into Roth, far beyond the normal limits. Not every plan supports it — ask HR for "after-tax contributions" and "in-plan conversion." If yours does, it's the biggest tax-free-growth lever most people have never heard of.

One honest disclaimer: This is educational, not financial or tax advice. The math here is deliberately simplified to make a point. Contribution limits, income thresholds, and rules change every year — check the current IRS limits and your own plan documents (or a fee-only advisor / CPA) before you act.