How to Actually Take Time Off From Work (Without the Guilt)

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Whether you are the Founder of your own company, a Senior Executive Assistant, or the Vice President of Operations–and whether you have three weeks of PTO, have a flexible work from home schedule, or have unlimited vacation and paid time off policy–I venture to guess that you’re still not taking off as much time as you deserve, or need, to live a well-balanced and fulfilling life. We were not designed to work all the time, no matter how much we enjoy our work.

Those of you who’ve been here for a while know I’m not all about that work-life balance life. However, I do subscribe to the idea of work-life presence and making sure I take the time to rest and recover when I need it, while also working my ass off or coming in on the weekends when work needs my attention. I enjoy my work and I enjoy my leisure time. And that looks a little bit different for everyone. I play present as much as possible and create white space time at work and at home. That in and of itself helps cut down on the guilt or distraction, and even the time it takes to accomplish each task. It also makes whatever I’m doing – binge-watching Dollface, working out, or writing a blog post – that much more enjoyable. Because I’m fully focused and fully present.

First, Why Do You Feel Guilty Taking Time Off Work?

Let’s just take a second to talk about why we even feel guilty about taking time off in the first place. I don’t want to tell people how to feel here, but feeling guilty about taking PTO that you’ve earned is never a fun way to feel. Guilt is a personal thing, so everyone may feel it a little differently. However, it often shows up in the following ways:

  • Undue burden and pressure put on you by your Executive.
  • You may be intimately aware of the financial struggles or staffing shortages at your company and don’t want to put any more stress or work on your colleagues while you’re out.
  • Maybe you’re already behind on a project (whether that’s your fault or not) and you don’t want to run the risk of falling even further behind.
  • It may be that you work in a culture that frowns upon taking time off.

Whatever the issue may be that is causing you the guilt, don’t be a martyr. PTO is designed to allow you to take time off to recharge and relax, which only makes you a better employee, leader, and human. So, the next time you start to feel guilt creep in, flip the script! By taking time off you are actually going to be even better at your job and you’ll be leading the way for others.

6 Ways Own Your Vacation Time

We’re not here to talk about the everyday work-life presence/balance/integration or whatever you want to call it. When it’s time to unplug and enjoy a long weekend with your extended family, take that week-long anniversary trip with your partner, or a two-week cross country road trip with your friends… how do you actually take time off–guilt-free–without being tied to your laptop or cell phone the entire time?

1. Do not be afraid to own your time off and set the tone for the rest of the company

I’ve known leaders and Force Multipliers who haven’t wanted to put up Out of Office messages because they didn’t want their team members or external parties to know that they weren’t working. Personally, I feel that perpetuates a culture of workaholism and guilt. Don’t slink off into that sunset cruise. Own that vacation! Take off the time you deserve! You will actually be setting the tone for the rest of the organization that you can be a badass business person and still enjoy your time off. That’s influential leadership.

2. Communicate with colleagues early and often

Assuming that your vacation isn’t last minute, start telling key stakeholders about it early and remind them often. I recommend at least a month out, if not more. While your colleagues may not be thinking about your time off as much as you are, it will help everyone get on the same page. Knowing when you will be out of the office will help you team drive towards deadlines, get their questions answered before you leave, and prioritize projects for when you return.

3. Set clear expectations with your colleagues and Executive

You may be completely off the grid. You may plan to check emails at 7am and 2pm each day (that’s typically what I do). You may answer texts on the fly. Or you’ll be away from your computer and email, but willing to take a phone call or two. Whatever you plan, make sure you communicate your availability clearly with your Executive, leadership team, and close colleagues. State your expectations and make sure that they (particularly your Executive) agree. You may need to negotiate a bit on this depending on your company’s PTO policy and expectations around availability. The key point here is to make sure you make a plan, communicate it, and make sure everyone understands. Depending on how much involvement you have with clients or key stakeholders, you may want to communicate your availability to them as well.

4. Manage your projects before and after your vacation

In a perfect world, you’d be able to finish all of your projects and tasks before you head out on vacation. But, unfortunately, that’s probably not going to be your reality. Instead, focus on getting your projects to a good stopping point that allows you to pick back up and hit the ground running upon your return. If you have a team, touch base with them on what to handle while you’re gone and where you expect various projects to be when you get back. Schedule check-in meetings or calls to handle new business for the week you return. It’s easy to fall into a week of catch-up after a vacation. But if you get your projects organized ahead of time and meetings scheduled for the week you’re back, you won’t really miss a beat!

5. Have a backup plan or bring in back-up

Depending on your Executive’s needs, how long you’ll be gone, and how unplugged you plan to be, you may or may not need backup. However, it doesn’t hurt to have some backup plans in place. Make sure there is at least one other person in the office who can cover anything that you can’t handle remotely (if needed). Consider creating a list of frequently asked questions or a “who to go to for what” document with all the necessary contact information. You may even need to bring in a temp or have a virtual assistant step in for scheduling while you’re gone. If you have a larger team, having a junior employee cover some of the basic responsibilities while you’re gone, could be a great solution for you and a career growth opportunity for them. You know, better than anyone, what your Executive and the company will need while you’re gone. Get clear on what you can (and are willing to) handle from afar and then either bring in back-up or create a backup plan to cover the gaps.

6. Schedule an out of office message

Last, but not least, get that out-of-office message scheduled, shut down your laptop, pour yourself a glass of rose, and start getting into vacation mode!

Don’t be afraid to share a little of what you’re doing (it can be a great connection point or conversation starter). And always include a way to contact you or someone else if they need immediate assistance.

Here are a couple of examples of Out of Office messages I’ve used in the past:

[OUT OF OFFICE] Making My Way to Music City USA

Thank you for your email!

I am currently enjoying some time with my family in Nashville (The Johnny Cash Museum, Lost River Cave, and Uncommon James are all on the list). I will be back in-office on Monday October 18 and I will return your email as soon as possible. 

If you need immediate assistance, please contact Kim Booska at

[OUT OF OFFICE] The Ocean is Calling and I Must Go

Thank you for your email! 

I am currently relaxing and recharging on the beach in the Bahamas with a book (or five!). I will be back in-office on Monday March 9. 

I will not be responding to emails as quickly as usual throughout the week. If you need immediate assistance, please send me a text or contact Kim Booska at

Looking for information about Project | U? Let’s schedule a call for you to learn more about becoming a part of the Project | U Class of 2021! 

P.S. Have you scheduled your vacations for the year? #workbetweenvacations 

As you can see, preparation and communication are the names of the game in order to take time off worry-free. What else would you add to this list?

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