Free Flights Won’t Show Up on a 65-Year-Old’s Pay Stub. That’s Why She’ll Take the Part-Time Job at the Southwest Ticket Counter Over One That Pays $4 More an Hour

A 65-year-old retiree has two part-time job offers. The first pays $21 an hour, while the other is a ticket counter job at Southwest Airlines (NYSE:LUV | LUV Price Prediction) that pays about $17 to $19 an hour and includes free standby flights. She has $400,000 saved, collects $2,600 a month from Social Security, is on Medicare, and spends about $9,000 a year flying to see her kids in Seattle and Austin.

In her real budget, the $21 job loses by thousands of dollars a year. Retirees often make this trade. The New York Times profiled retirees who took part-time travel-industry jobs for the perks, including a couple whose flights cost $462 total because they paid only the taxes.

Why Flights Beat a Bigger Paycheck

Her benefit already sits above the $2,071 average for retired workers in 2026, so she works to fund extras, and airfare is her biggest one. The deciding factor is which job leaves more money in her pocket after she pays for the travel she plans to take regardless.

Southwest gives employees free, unlimited travel privileges for themselves and eligible dependents. The tax code treats this kind of perk as a “no-additional-cost service”: something the employer already sells to customers and can provide to staff at little added cost. That’s why it never shows up on a pay stub, and why it’s worth more than its sticker price.

Running the Pre-Tax Math

Every dollar she stops spending on flights is an after-tax dollar. Say she’s in the 12% federal bracket and also pays the 7.65% employee payroll tax. To keep $9,000, she’d have to earn about $11,200 in wages. Twenty hours a week at Southwest comes to about $18,000 a year. The flight perk is worth roughly 60% of that paycheck.

Earnings Test Room at Both Jobs

Because she took Social Security at 65, before full retirement age, the earnings test applies. In 2026, wages above $24,480 trigger withholding of $1 of every $2 over the limit. At about $18,000, Southwest keeps her well under. The $21 job at the same hours pays $21,840, so a handful of extra holiday shifts could push her over the line.

Health insurance also drops out of the comparison, as she already pays the standard $202.90 monthly Part B premium, so employer coverage adds little. For a reader under 65, part-time health benefits can outweigh both the pay gap and the flights, so check that first.

Where Standby Travel Falls Short

One potential issue is that standby travel doesn’t guarantee a seat. Thanksgiving and Christmas flights fill up, and she may get bumped repeatedly. International trips on partner airlines carry taxes and fees. Her adult kids won’t qualify either because eligible children must be under 19 (or up to age 24 if they’re full-time students). When they come to visit her, they pay full fare, which may or may not be a big deal.

Southwest offers a partial fix: an unlimited 20% discount on all Southwest flights employees and eligible travelers purchase. Buying confirmed holiday seats at a discount still costs less than paying full fare on every trip. Keep in mind that the perk disappears when the job does, unless she reaches the service years required for retiree privileges.

Two Moves That Settle This Decision

1. Price your actual travel before comparing wages. The break-even is about $3,340 of after-tax flight spending a year. If you fly to family less than that, take the $21 job. If you fly more, the airline job wins, and the gap grows with every trip.
2. Plan your hours around the earnings test until full retirement age. Keep wages under $24,480 unless you decide the extra pay is worth having benefits withheld for now. To earn the fee, a fee-only planner models two things: whether to keep working past full retirement age (when the test goes away) and how extra wages push more of your Social Security into taxable income.

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