How to Use Your Vacation and Paid Time Off

I once went at least 8 years without taking a sick day. It’s not that I wasn’t sick. I just went to work sick whole bunch of times. I came to work sick one day, and my coworker was like, “What are you doing here?” I told him about my streak, and how I had to preserve it like I was Cal Ripken or something. “No one cares,” He said. “Go home.”

What an idiot I was. Not only did no one care about my streak, but no one even knew about it, including the person I guess I was trying to impress, my boss. It’s amazing I was so stupid, because I am a boss, and I’m not aware of nor would I ever be in favor people who work for me subjecting themselves to such frivolous torture.

I’ve since changed my ways, learning the hard way the value of balancing work ethic with family time, relationships, and hobbies.

Fast forward to this past July. I sat my direct reports down to talk about paid time off and vacation use. This was my first full year leading this particular team. I told them about my old silly self-imposed limit on using my PTO, and that I never wanted anyone who worked for me to make the same mistake. I told them my expectation was that each of them use all of their earned paid time off by the end of the year. They all looked at me like I had three heads, because no boss before me had ever asked them to use their PTO, and they felt like prior bosses implicitly did not want them to use their time.

This post is for anyone thinking they shouldn’t use their PTO because it might upset their boss or cause their boss to look unfavorably upon their work ethic. Because that’s just not the case.

I’m also thinking there might be an even bigger problem for folks like my direct reports, who have earned a lot of PTO by staying with our company for a long time (more than half of my team earn 4 weeks of vacation plus another week and a day of holidays, plus sick and personal time every year).

I’ve heard coworkers say, “I’ll never use all that time,” or, “I can’t afford to miss that much work.” Non-sense.

If any of this is hitting home for you, then maybe these tips on using vacation and PTO will set you straight:

1. It’s your time. You earned it. Use it. All of it*. Even if you have a lot of PTO and even if you think you’re a big fancy-pants executive like I think I am. Your boss will not “penalize” you for taking your time, and if she’s the type of boss that is going to give you a hard time about using your time, maybe you should look for a new boss.
2. Plan ahead. Each year, in January, I sit down and plan out most of my time off for the entire year. I plug my days off into my Outlook calendar, so I can see them coming all year long. I always leave a few days unplanned for those “break glass in case you must get away from work,” moments.
3. Planning your time off in advance lets you have something to look forward to. This is important and fun. If you’re having a bad day or a bad stretch of days, you can think, “If I can just make it till…” It’s also nice to find a planned day off sitting in your Outlook calendar that you may have forgotten about.
4. Advance planning also gives you the best chance at getting your time off requests approved, if you have to submit your requests to an approver. This is especially important if you’re on a team that services customers, and a minimum employee coverage level is important. Bosses might only be allowed to approve a certain number of vacations around busy holiday times, and you can be the first one in line by asking early.
5. Space it out. I try to have some time off every quarter, so I’m never more than a few months away from some time off. You don’t have to be sitting on 5 weeks like me and my tenured coworkers. You can still space out your time by putting weekend adventures on your calendar that use 0–2 PTO days.
6. I may have a lot to learn about travel, but I do know how to take time off without spending a lot of money. Staycations are cool, but going someplace special is cooler. And special does not have to be expensive or far away. Almost all of our vacations in the past 10 years have been local day trips or short trips to regional destinations that don’t require expensive flights or long hotel stays. It amazes me how people ignore regional attractions that other people travel to their area for. We’ll travel internationally when we have the money to burn, but for now the two-hour drive to Virginia Beach is perfect for us. (tip 6a, the topic of a future blog post will be “How to get over your fear of flying like I kind of did”)

I was raised valuing hard work and toughness. Working hard is still valuable, but burning out is not. Remember, managers are chasing effectiveness, not efficiency, and I find using all of my PTO each year makes me a more effective leader.

*The one exception to my “use all of it” tip might be your sick time, if its separated from your other PTO. Just use that when you’re actually sick. In other words, sick time shouldn’t be used like vacation time — scheduled in advance to go to the beach. It’s there for when you’re ill and you have to call out. And don’t be afraid of calling out. If you’re sick, you’re sick.

Afterword: A brief reminder that this post, just like all posts on this blog, are just my opinions. This stuff has not been reviewed or endorsed by my employer or any other organizations I’m affiliated with.