What To Do When You Really Want More Paid Time Off

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.

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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.

Take the Time You Deserve: How to Make the Most of Your Paid Time Off

I haven’t written in a while. In part, it’s because I’ve been on vacation! I was lucky enough to be able to take a break from my regular life to travel around with my family, get my life in order, and explore the city where I live.

A few weeks later, real life is settling in, and I want to plan my paid time off (PTO) — all 25+ days of it. Okay, so this is not real life for the typical American worker, who receives about 10 days of PTO on average. I see myself as incredibly fortunate to have five weeks of vacation, but I’m looking to make the most of my PTO by maximizing every minute!

Here are some strategies if you are looking to schedule the maximum fun in your calendar, whether that’s spent visiting with family, taking an intentional staycation, or splurging on a jetsetting jaunt:

1. Work while in transit.

A place where I used to work provided a super sweet free shuttle to and from work in Boston’s suburbs. Sometimes I’d catch the early bus home and take advantage of the free WiFi to skip the traffic and make it to after-work obligations. This has stuck with me: why not take advantage of Amtrak, commuter rail, or in-flight WiFi, to get a head start on your journey while wrapping up your work before vacation begins?

Let your manager know your plans, set an out-of-office message if you are worried that you’ll reach a dead zone, and prep as though you’ll be offline, just in case, by downloading copies of all the PDFs and lengthy emails you’ve been meaning to review.

2. Plan your vacation around work trips.

In 2017, U.S. travelers took 462 million domestic business trips. Whether for a conference, sales meeting, or other obligatory trip, if you already have to travel for your job, plan a vacation around it! Not interested in spending more time at your work trip’s destination? Consider booking a flight with a long layover on your way home or take a day trip to a nearby location before heading home.

3. Don’t forget about… Presidents’ Day? 

Nothing against our nation’s presidential history (recent history aside), but some holidays are too easily skipped over. Don’t miss out on long weekends, even the ones that sneak up on you in the middle of February. Take a short trip during all those built-in three-day weekends — or turn them into four-day weekends.

While your colleagues might be itching to take off the Friday before a long weekend, you might be able to get better flight deals by taking off the Tuesday that follows a Monday holiday like Labor Day or Martin Luther King Jr. Day. And when it comes time to book the longer vacation you’ve been plotting, you only need to use four vacation days to turn a long weekend into a nine-day dream trip.

4. Spend a chunk of time working from somewhere new. Remote work is looking a lot more postcard-worthy than ever before. That’s because office jobs are increasingly enabling employees to work from anywhere, so long as the tasks get done. Services like Remote Year, Outsite, Roam, and behere built business models around the idea that people want to keep their jobs while enjoying new experiences and challenges abroad. Browse your options and find a new temporary office location for yourself, then show your manager how you can make it work. Practical considerations include:

• Time zone – Can you easily collaborate with colleagues by working in the same time zone? If not, can you cover business needs that take place during hours when everyone else is done for the day?
• Expenses – What will it take for you to be accessible and safe? Make a budget that includes internet, phone, and travel insurance, in addition to living expenses.
• Business reason – Can you represent the company at events or meet with business partners in the area?
• Professional development – Can you study a new language, bring back knowledge of a culture, or develop leadership skills?
• Cost of living – If you have pulled every other card, consider whether you will have fewer costs to maintain current your lifestyle in a new place. If so, consider accepting a temporary cut in pay if it will seal the deal. If you are currently based in the U.S., there are likely many places where you can live much more cheaply than in your current city.
• Regulations and company rules – While I was working at Amazon, for complicated tax reasons, it was against corporate policy to work remotely, even to send one work email, from my home state. Most employers aren’t set up to legally support your living abroad for long periods. And of course, most countries won’t let you live and work indefinitely without the proper visa.

5. Limit your time-zapping obligations by staying healthy, practicing self-care, and taking advantage of flexible hours. 

You can lose a lot of PTO or personal days here and there when you catch a cold or need apartment maintenance. Eat healthy, sleep, and exercise regularly to avoid unplanned doctor’s visits. Be proactive about the “adulting” things you need to do like getting your home’s water damage repaired (before the ceiling caves in) or getting your regular teeth cleaning (before you need a filling). An annual flu shot fits into a regular workday; getting the flu will cost you days of work.

This is written from the perspective of a relatively healthy young adult. If you live with a chronic health condition or disability or if you have children or other dependents, unfortunately you may be unable to avoid using your paid time on things that are less than fun, even with the Family and Medical Leave Act providing benefits in some cases. But if you aren’t burdened or obligated in these sorts of ways, you should be able to budget just a few days of “incidentals” each year to provide you flexibility when you need a mental health day.

6. Remind yourself that you deserve a vacation.

While you might feel you don’t have enough time off, the truth is, 52 percent of Americans don’t use all their limited PTO. The portion of American women using all their PTO is even lower at 56 percent (let’s close this gap, women travelers!). You know this, but it is worth reiterating: taking breaks with the chance to unplug and refresh makes you a better employee. You’ve worked hard, now go play hard!

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As someone who loves lives to travel, I am looking to carve out space in my own work schedule in order to visit my dream destinations. I’m continuing to share out about this topic in my next post on steps to take if you’re already making the most of your PTO, but you still crave more of it.

Do you have advice or ideas for folks looking to make the most of their vacation time? Share them in the comments.