Most Americans don’t live life to the fullest. This is a bold statement, but I can back it up with data: the majority (52%) of U.S. workers don’t use up all their annual paid time off (PTO).

If you’re among the few who are already making the most of your PTO by using every one of your vacation days, these tips are for you. This is your guide to finding more time in your life for the fun things you’d like to be doing.

1. Get a new career.

Most jobs have 10 or so days of PTO. There are plenty of notable exceptions for career paths that will help you advance your vacation and travel goals.

  • Work at a school: Take summers off, forever, by becoming a teacher or school administrator at an educational institution where summers are still sacred. The trade-off: low pay and burnout.
  • Work for yourself: Set your own hours and decide when the can’t-miss meetings will take place by starting your own business. Ideally, your business won’t be brick-and-mortar, so wherever you travel can become your office (see: digital nomad). The trade-off: Never having a day off from being the responsible one.
  • Work seasonally: Vacation destinations and farms often have jobs where it’s perfectly acceptable to stay for just the summer (or fall, or winter, or spring). By stringing along enough seasonal gigs, you can afford to take time off in between. The tradeoff: You may lack stability and you’re unlikely to make a fortune.
  • Work in a travel profession: Traveling nurse, flight attendant, event planner, flight attendant, study abroad coordinator, au pair, English teacher. These entry-level careers can get you someplace new. The trade-off: You may be underpaid and you won’t necessarily be able to travel on your own terms.

2. Find a workplace culture that isn’t vacation-shaming.

Office life can be competitive in any number of ways. Who can brew the best pot of coffee? Who has the funniest meme in their presentation? It’s problematic when sizing up “Who is most dedicated to their work?” This takes the form of working long hours, being on email at all hours, or perhaps most tragically, rarely taking a vacation.

If you’re job searching but not ready to fully switch careers, look for a place of employment where you’ll feel comfortable actually using the vacation time that is part of your benefits package. This means avoiding workplaces where you receive “unlimited vacation,” which is often code for “vacation at your own risk.” A good way to judge is to ask a current employee or the hiring manager, “How much vacation do you typically take, and what are your expectations around vacation?”

3. Negotiate more time off.

Perhaps your company has long-standing policies around vacation, corporate holidays, personal days, and sick days. Maybe a PTO balance is something you earn with seniority. But people are creative (if there’s anything people excel at, it’s finding ways to not do their work) and you can take a lesson from the brilliant minds who have come before you.

  • Delayed start date: The easiest and hardest time to take a vacation is before starting a new job. Your life may be in flux, but on the plus side, you have free time. Negotiate a few extra days, weeks, or months before you begin working.
  • Comp time: If your work has a busy season, or you travel for extensive periods, push for “comp time” or compensatory time — days off to balance out the value of your overtime.
  • Floating federal holidays: Most workers receive a handful of days off, scattered throughout the year. Some of these may have more meaning to you than others – Labor Day, Veteran’s Day, and Presidents’ Day are a few that, for me, hold no special meaning. Negotiate to take off the equivalent of some of these solo days together to form a full vacation week.
  • Vacation seniority: Push for more vacation days in recognition of your years of dedication to your current employer.

4. Buy yourself time, literally.

Some employers will let you pay them (or deduct money from your paycheck) in order to get extra vacation time. Known as a “vacation buy” or “PTO purchase,” this is a trade-off between making money and having free time (you might guess my bias!).

There may also be the option to take unpaid time off, just check with your company policies first. Ask yourself how much you value your free time and how much money you need to meet your financial goals, then make a judgment call.


I’m continuing to share out about topics at the intersection of travel and self-care, with a forthcoming post all about “staycations.”

Do you have advice or ideas for folks who want more paid time off? Share them in the comments.

Feel free to leave a comment, question, or suggestion!