How to Talk to Your Boss About Time Off

woman watching the sunset on mountain
woman watching the sunset on mountain

Whether your planning for the 221 mile John Muir Trail, just need a few days to go car camping in the Sequoia National Park, or you want 2 weeks to trek to Everest Base Camp, here’s how you talk to your boss about taking time off.


1. Make sure you’re kicking butt at work! This will help build your case for time off. Your employer might not be so happy about you taking 2 weeks off if you’re already slacking off.


2. Check your employee handbook for policies on time off. It will walk you through how much time you’re accruing based on how long you’ve been with the company and how much notice you need to give.


3. After you’re all caught up on your company’s rules, check how much time you have accumulated. It should be written on your paystub. If you still are unsure, ask your payroll department. If you don’t have enough paid time off for your trip, consider taking time off without pay. You’ll need to check your company’s rules about this.


4. Don’t ask for time off during a bad time at work. Like right before a major trade show.


5. Plan the best time to ask your boss. You can either send them an email asking or send them an email letting them know what you want to talk to them about and then schedule a time. Avoid stressful times of the day, week or month.


6. Give your boss as much notice as possible! Most employee handbooks will say 2 weeks in advance, but if you’re planning the JMT and you get your permits 6 months in advance, talk to your boss then.


7. Make sure to request time and get approval in writing. Just in case, it’s good to have these things in writing.


8. Ask, don’t tell.


9. Help plan the workflow during your vacation. If you’re the only employee who knows how to program the time clock in the entire company, make sure to teach others how to do it.


10. Make sure that everyone who needs to know, knows. Put it on your boss’s calendar, let your coworkers know, let clients know, and most importantly let payroll know.


11. If your boss says no, DO NOT CALL IN SICK. They will know you’re not actually sick and you may cause a problem and possibly lead to getting terminated.


12. Send a reminder closer to the date to remind everyone.


If you’re job hunting, or just got an offer, make sure to let the employer know before you start! I had the High Sierra Trail planned for months before I started job hunting. When I got the job offer, I let the employer know that I already had a commitment for those certain days and would need the time off. I asked if they would agree to let me have the time off as part of my hire-on agreement. When you get hired you can also negotiate for more vacation time, it is part of your compensation package.


Also if hiking and traveling are a big part of your life and you want to travel more than once per year, have an open and honest conversation with your boss about it. Let them know that you are at the company to work hard but you value your time to explore the world. Make sure to be honest, and open with your boss and find a balance that works for everyone! After all, vacation time helps us come back more creative and productive after all!

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