How Can You Get More Vacation Time From Work?

Chris asked,

Can you tell me how I can convince my boss to give me more time off so I can travel more?

For most people this question may not be meaningful, since on average Americans take only half the vacation time they’re already ‘given’.

But if you use yours and what more, the simple answer is to tell you to become your own boss. But many entrepreneurs find that they’re able to take even less time off, rather than more — there’s huge responsibilities, and there are consequences if things go wrong. They don’t have, and maybe can’t pay for, someone they can trust to manage things in their absence.

A knowledge economy business may be able to work better from the road, but if you need to be on the phone with clients or responsive quickly by email then time zones may prove challenging.

So you’re back to being grateful for a job that gives you time off, especially if expectations are that you don’t have to work while you’re going.

It’s probably hard in most companies to negotiate for more time off with a boss — company policies may be firm, and there may be a stigma against negotiating for time off because it can signal that you aren’t serious about contributing to the company, you’d rather not work than work hard, advance, and earn more.

I was fortunate to drive a re-write of my company’s employee manual, and benefits policies, about 7 or 8 years ago. One of the things we did at the time was eliminate tracking of vacation entirely. That meant that we paid out accrued leave. instead of paying attention to attendance, we began focusing only on performance.

Attendance can be important for performance — especially when working as part of a team, team members need to be able to reach you, and your responsiveness and work is something that others rely on.

But how you manage to get your work done is less important that the fact that you do, and the consequences for the business that follow from it.

For me it means that I travel more, but that I vacation less – in the sense that I don’t really unplug when I’m on trips. I check my email every day, I respond to questions, and I work on documents. There’s more days out of the office, but those are at least partial work days.

Whether that’s a benefit to you, or to your company, will likely vary by individual, corporate culture, and industry. But it’s the sort of responsible environment that I wouldn’t want to trade for any other.

About Gary Leff

Gary Leff is one of the foremost experts in the field of miles, points, and frequent business travel - a topic he has covered since 2002. Co-founder of frequent flyer community, emcee of the Freddie Awards, and named one of the "World's Top Travel Experts" by Conde' Nast Traveler (2010-Present) Gary has been a guest on most major news media, profiled in several top print publications, and published broadly on the topic of consumer loyalty. More About Gary »

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  1. Or become a teacher! Work 10 hours a day, but get summers and Christmas off and a monthly (or so) 3 day weekend!

  2. I wouldn’t mind getting a job in the travel industry… some say then traveling won’t be fun because it’s work.. but I think you can have fun during work travel.. plus earning all those miles/points would be bonus.

  3. Vacation/PTO days is something I negotiate as part of any job offer, just as I would salary and other benefits.

  4. Gary, may be it’s a change of times and mindset but I find it annoying when people complain that they have to work (read/answer emails) when they are on vacation or weekends. I suppose they would prefer employers track every minute of their time (you know all the time spent reading travel blogs and forum, twitter, facebook…). But enough of the rant.

    Like you, I love the flexibility of having work email at my fingertips whenever I need that allows me to be out of the office but within reach if something needs to be resolved quickly. No longer being tethered to the desk is awesome!

  5. Except that for lots of people, vacation is part of a larger HR infrastructure with very clear policies. Personally, I liked the PTO approach. Even though I still check some e-mail, it’s nice to set a boundary.

  6. As a RN, I work 3, 12 hour shifts a week, we have self schedule which allows me the freedom to get 8 days off in a row if I like, so I can basically take a vacation without using any PTO time, not many professions allow you to do this… So to get this 8 days off, I work the first 3 days of a pay period, then work the last 3 days.

  7. People often don’t realize this, but you can sometimes negotiate more PTO when accepting a job offer. This is company specific, but it’s not unheard of to say, “the salary looks great, but the one area I’m a little concerned about is time off. My previous role gave me X days and it’s going to be tough to adjust to this role’s Y days. Is there any wiggle room here?” The best part about negotiating for PTO rather than salary is that you’re very likely to get a routine raise/bonus given enough time at the company, but getting increased vacation is usually much more difficult.

  8. I’m fortunate to have a job I can do from anywhere in the world where there’s a Wi-Fi signal. I’ve worked half time the last several years, which has given me enormous flexibility. I’d much rather keep up with things while I’m on the road than face major crises and backlogs when I return home (though I find a lot of “traditional” people don’t understand or like my approach).

  9. agree with andrew. negotiate, negotiate. i have found the key to my travel ability has been working my hardest since college and then leveraging my hard work and accomplishments into negotiating flexibility at new jobs. i usually just mention during salary negotiations that “i have a serious love for travel and will need the flexibility to do 1-2 week-long trips per year in addition to accrued PTO”. now, these 1-2 week-long trips are not paid vacation but i budget accordingly. most HR and management appreciate travel and this isn’t an issue as long as i deliver when i need to. it never hurts to ask.

    of course, the industry i work in (advertising) is generally more flexible than others. i understand that some large corporations and other industries might not give you such wiggle room.

  10. Go work for the American Embassy in any country in Latin America. You get ALL US holidays plus all local holidays and LA is known for having many holidays (they celebrate every saint you can imagine).

  11. Meh to not tracking vacation.

    Like Gary, I can (and like to) check email when on vacation, if only because I like what I do and it reduces stress on return. But there are times that I am truly out of reach (by choice or not) and I like that when I’m on vacation I can set the Out Of Office message and reply if and when I want, with no expectation of a response.

    I suspect that for senior employees, a policy like Gary’s works well, but it seems like it might come with an expectation that you’re kind of in touch most of the time. While I like to be in touch, I don’t like to be expected to be in touch and greatly prefer formal vacation time, no expectation that I am getting any work done and the ability to disconnect without any concerns. As you move down the chain too, junior folks might feel pressure to compete and I’m not sure it’s good thing overall.

    While this might be a bit of a generalization, fixed vacation time provides a good separation between work and personal time. While I don’t usually disconnect, I value the option very highly and removing vacation accruals seems to be a easy way for companies to demand more and actually encourage people to take less vacation.

  12. Self employed in the entertainment industry. I actually get paid (very well sometimes) to travel to destinations and events to do my job – all on someone else dime (but earn all the points for travel and lodging). It frees up a ton of time each year I can do with as I like. Renovate my old house. Build furniture. Travel as I see fit. Downside is sometimes I am busy as a one armed paperhanger. Once I learned how to budget from busy to lean times it’s the best job I could ever have hoped to do.

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