Five vacation days, for someone earning $68,000 a year, are worth $1,307.69. That is just division: $68,000 across 2,080 working hours is $32.69 an hour, and five days is 40 hours. If your employer runs a buy/sell program, you can sell unused PTO for close to that number, and the only window to say yes is the open enrollment period your HR team has been emailing you about since Labor Day. Miss it and the days go back to being days, which is fine if you take them and expensive if you don’t.
Plenty of us don’t. A Pew Research Center survey of 5,188 U.S. workers conducted in February 2023 found that 46% of workers who get paid time off take less of it than they are offered. Among upper-income workers the figure was 51%. Those days do not sit in an account somewhere waiting for you. Depending on where you live and what your handbook says, they either expire on a date or they stop accruing at a ceiling, and either way the meter is running against you right now.
Open enrollment is the only week you can sell unused PTO
Buy/sell programs almost always live inside a cafeteria plan, which is the same piece of tax plumbing that runs your health FSA. That matters because cafeteria plan elections are prospective. You choose before the plan year starts, the choice locks, and you generally cannot revisit it in March because your summer trip fell through. The elective days you buy also have to be used, cashed out, or given up by the end of that plan year, since a cafeteria plan cannot be used to push compensation from one year into the next.
Capital One’s published benefits page shows what this looks like in practice. Associates working at least 20 standard hours a week can purchase up to 40 hours of additional vacation, only during open enrollment, and they have to re-enroll every year because purchased time does not carry over. Five days is a common ceiling. Kris Battistoni of Ayco, the financial planning arm of Goldman Sachs, told HR Brew that many companies cap what employees can cash in at five days, partly so nobody strands themselves without sick time and partly so finance doesn’t face a run on the bank in December.
Ayco reported that just over a quarter of its corporate partners now offer a PTO purchase program, up from 21% in 2021, which puts it well ahead of unlimited PTO at 15%. A few employers have gone further and let workers route the cash into a 401(k), an HSA, a 529, or a student loan payment instead of taking it as pay. Almost none of them advertise it well. It shows up as one checkbox on screen four of the enrollment portal, somewhere below dental, which is roughly where most people stop reading. That is one of the workplace benefits going unused every year for no better reason than bad interface design.
Selling gets taxed like a bonus, and that still beats letting the days expire
Run it with a real balance. Take the $68,000 earner above with 15 vacation days, which sits near the middle of the distribution: the Bureau of Labor Statistics found in March 2025 that 32% of private industry workers get 15 to 19 days after five years of service, while 31% get 10 to 14 days after just one year. Say she uses 10 days and has 5 left in November.
Sell those 5 days and she is paid $1,307.69 in gross wages. Cash-outs are frequently run through payroll as supplemental wages, withheld at the flat 22% federal rate, plus 7.65% for Social Security and Medicare. That is $387.73 off the top, leaving about $920 in her account before state tax. Forfeit the same 5 days and she gets $0, with no deduction, no credit, and no note in her file. The comparison is not $1,307 against $920. It is $920 against nothing, for a decision that takes about as long as picking a dental plan.
Buying days runs the same math backward. Purchasing 5 days costs $1,307.69 spread across 24 pay periods, or $54.49 a check, which is less than most people spend on streaming and takeout in the same two weeks. Whether that deduction comes out pre-tax depends entirely on how your employer structured the plan, so ask instead of assuming you are getting a tax break. Framed as a price rather than a benefits election, it is an easy call: an extra week off, at $54 a paycheck, is either worth it to you or it isn’t. Your enrollment portal will never put it that plainly.
Your carryover cap date decides this, not your travel plans
The deadline that actually governs your balance is buried in the handbook, and it is not always December 31. Some employers run the clock on your hire anniversary. Some allow a partial carryover, say 40 hours, and wipe everything above it. Some cut you off at zero.
State law changes the shape of the problem in a handful of places. California treats earned vacation as wages that vest as you work, so a use-it-or-lose-it policy is flatly illegal there and unused vacation has to be paid out when you leave. The state’s Labor Commissioner says so directly, calling forfeiture of unused vacation “an illegal policy under California law” in its vacation FAQ. What California does allow is a cap: once you hit the ceiling, you stop accruing until you spend some down. People read that as protection and relax. It isn’t, quite. If you sit at the cap from August onward, every week you work after that earns you no vacation at all, and the lost accrual costs exactly what a forfeiture would have. You just never see the subtraction.
In most states, a clearly written forfeiture policy is enforceable. So the first move is not a transaction at all. Open the handbook, find the accrual cap and the reset date, and put both in your calendar with a two-week warning.
What to ask HR before the enrollment window closes
Three questions, and an email will do. What is my current balance and what is the cap? Does the company offer a buy/sell or cash-out option, and what is the election deadline? If I sell days, are they paid at my current rate, and in which paycheck? That last one matters more than it sounds. A December cash-out lands in a month when many people are already stretched, which is a decent argument for lining it up against the holiday bills rather than treating it as a surprise.
If the answers come back bad, meaning no program and a hard December 31 reset, you still have about fifteen weeks. Booking a Friday off every other week through year end clears eight days without touching a single project deadline, and the people who do this in October get their picks approved while the people who wait until December are fighting over the same week between Christmas and New Year’s.
While you are in the portal, the same logic applies one row down. Your health FSA election is a use-it-or-lose-it decision too, though the uniform coverage rule tilts that one in your favor in a way the PTO rules do not.
Most employers do not offer a way to sell unused PTO, and the ones that do bury it. Either way, the days on your balance are compensation you already earned, priced at your own hourly rate, and the next few weeks are the only stretch of the year when you get to decide whether they become money, time off, or nothing. Go look up the number. Five days is $1,058 at a $55,000 salary and $1,635 at $85,000, and nobody at work is going to run that math for you.
