Zero
No. 10Retirement

Squeezing more juice from your 401(k)

The 401(k) setting most people never consider

Most people think maxing out a 401(k) is the whole game. It isn't.

The amount matters, but so does the calendar. By default, payroll providers and 401(k) plans spread your contributions evenly across the year. That setting is worth questioning.

The 401(k) Mechanics

Under the hood, 401(k)s have two limits and multiple buckets.

Whenever you contribute paycheck funds into a 401(k), the funds fill a specific bucket and count towards one or both of the limits.

Contribution TypeCounts towards $24,500Counts towards $72,000
Pre-tax 401(k) contributionsYesYes
Roth 401(k) contributionsYesYes
Employer MatchNoYes
After-tax 401(k) contributionsNoYes

The first limit is purely for Pre-tax & Roth 401(k) contributions — $24,500 in 2026. Pre-tax contributions lower your taxable income today, which can save you thousands on this year's tax bill. The tradeoff is withdrawals are taxed later as ordinary income. Roth contributions work in the opposite direction: you pay tax today, then qualified withdrawals can come out tax-free later.

The second is the total amount that can land in the account from every source combined: your contributions, your employer match, and any after-tax contributions. In 2026, the all-in limit is $72,000. (After-tax contributions are simply additional funds you can set up to be pulled from you paycheck).

The Timing

By default, payroll providers and 401(k) plans spread contributions across every paycheck. So if the limit is $24,500, about $2,050 could be contributed each paycheck across 24 pay periods. There is nothing wrong with doing this.

Because most 401(k) plans let you adjust your contribution rate each paycheck, you can frontload it and push more of the money into the earliest months of the year.

Your take-home pay drops at first because the 401(k) gets funded before your checking account does. But once you hit the limit, contributions stop and your paycheck jumps back up.

Frontloaded

Fully funded by May

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

Even monthly

Fully funded by December

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Frontloading does not change the annual limit. It changes how long each dollar has to work.

In this backtest, front-loading beat equal paycheck contributions in every year since 2010 except 2022. Using the base limits for every year and a conservative investing strategy, front-loading would have added roughly $25K. Using the full $72,000 total limit, it would have added roughly $76K.

In theory, the yield could be even greater based on the investing strategy in the 401(k).

S&P 500 monthly closesJanuary 2000 - May 2026
Hover the line to see the index level at each monthly close.

Over long periods, the aggressive version tends to win for one simple reason: more time invested.

The Matching Trap

If your employer offers a 401(k) match, be careful with front-loading. Some plans match paycheck by paycheck, and some plans add a year-end true-up if you max out early.

That detail matters. Without a true-up, you could hit the annual limit early and miss employer match dollars in the later months.

The Lifestyle Trap

The other trap is cash flow. You still need funds for rent, groceries, travel, and everything else that happens before the 401(k) is fully funded.

ESPPs can create the same problem. At some employers, 401(k) contributions come out of payroll before ESPP purchases. If you aggressively front-load the 401(k), you may leave too little paycheck behind to fund the ESPP.

What's your next move

Most people optimize the contribution amount.

You should also look at the contribution calendar.

Front-loading is not free money. You still have to protect the employer match, your ESPP, and your monthly cash flow. But once those are covered, the default may be leaving your best dollars waiting until December.

Sree TripuramalluFounder & CEO

P.S. These letters reflect personal opinion and are not investment advice.

By invitation only