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Writer's pictureEric Kaufmann

How To Overcome the Fear of Requesting Time Off (3 Steps)

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Hi Friends,


The holiday season is here—crazy, right? I, and hopefully you too, plan to take some time off from work. 


My family lives across the country, so I always try to book flights months in advance to get a decent price (is there even such a thing anymore?).


While I’m good about buying flights in advance, I’m not so good at requesting time off. I tend to procrastinate….a lot.


Every year was the same…I planned to ask during every meeting with my boss for months, but I couldn’t bring myself to ask or even send an email.


To be honest…I was scared.


And now I know I’m not alone. According to this article,


"25 percent of millennials feel nervous when requesting time off, with many feeling guilty, afraid, or ashamed when asking for vacation days."

If you also procrastinate requesting time off, this newsletter is for you.


Today, I’m sharing a strategy to help you confidently request time off, plan for your return, and fully enjoy your vacation. 


Let’s dive in!


Why Taking Time Off Feels So Stressful

Requesting time off can feel daunting, especially if you worry about your boss’s reaction or the pile of work you’ll return to. 


Maybe the thought of taking time off, along with the workload that will await you, keeps you from using your PTO. Or perhaps the anxiety around asking causes you to put it off for months. 


how to improve executive function skills adults
Me, overthinking my request for time off

These fears can lead to thoughts like, “What if something slips through the cracks?” or, “Do I deserve this time away?”


For me, the fear comes from the stories I tell myself:


  • What if my boss says no?

  • Maybe I don’t deserve that much time off…

  • What if I lose clients when I cancel some of their sessions?


The truth is, deep down, I knew my boss and clients would be fine with it. They were always supportive, even encouraging, about taking time off. Yet, I’d procrastinate, creating unnecessary stress, only to find the same response each year: “Of course! Enjoy your time with your family!” 


No questions asked.


But despite the relief, I’d feel a twinge of shame, thinking, Why do I do this to myself every year? 


Why create stress by procrastinating? 


Why can’t I just ask?


 

Want to learn more about executive function coaching for adults?

We know requesting time off isn't easy. That's what executive function coaching is for!


Schedule your no-cost inquiry meeting today. 👇

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How to Request Time Off Without the Guilt

If you also experience fear, guilt, or dread the mountain of work waiting for you after vacation, I have a few tips:


Afraid to Ask or Feeling Guilty?

Fear is one of the most common reasons people avoid using PTO. 


Maybe you’ve seen a boss react poorly to a coworker’s request or experienced guilt from a previous conversation about taking time off. This feeling of guilt or shame can prevent anyone from taking action.


If this sounds familiar, try this strategy:


  1. Make a list of the positive contributions you’ve made over the last six months. You provide big and small value to your organization. There's power in acknowledging that.


  1. Write down how you will feel after taking time off. Recognize that taking time off will allow you to return to work refreshed, with renewed energy and passion. Remember, you’ll be a better employee if you take a break.


  2. Practice the conversation or write a draft email and ask for feedback from that trusted friend. 


When fear or anxiety creates procrastination, practice develops a greater sense of confidence. This will make it easier to initiate the request. 


For More Tips, Check Out My Full-Length Blog

My full-length blog post covers these additional strategies:


  • How to request time off in an email

  • How to request time off in person

  • Out-of-office responder templates you can copy and paste

  • How to handle important emails while on vacation


Read the full blog here.


Summary 

In the past, requesting time off from work created fear and guilt, but it doesn't have to be this way.


If fear or shame prevent you from using your paid time off, these steps can give you confidence in requesting the time off you deserve:


  1. Make a list of the positive contributions you’ve made over the last six months. 


  2. Write down how you will feel after taking time off.


  3. Practice having the conversation or write a draft email and ask for feedback from that trusted friend. 


I hope you found this helpful, take some time off around the holidays, and truly enjoy it!


P.S. 

If you want to work on your adult executive function skills, consider joining dozens of others who graduated from our Adult Executive Function Skills 101 course. This course teaches you skills to strengthen your time management, personal finances, and more. Learn more.



About the Author

Eric Kaufmann is a Professional Educational Therapist and Certified Executive Function Coach. He is the Co-founder of UpSkill Specialists, an online adult executive function coaching company that guides adults in overcoming disorganization, procrastination, and productivity roadblocks so they can unlock their potential. He is also the founder of Elevate Learning Solutions, an Educational Therapy practice located in San Clemente, CA, that supports neurodivergent students in becoming independent and confident.

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