jenna daykin | how to take stress free time off

Are you in desperate need of a vacation but, as a small business owner, think it is easier + less stressful for you to just immerse yourself in work? Vacation sounds like a dream but an anxiety attack waiting to happen?

I’ve been there. I’m practically describing myself.

Those feelings were not healthy at all + I lost sight of any sort of balance in my life. I firmly believe in the importance of self-care, time-off, + working smarter + not harder. I needed to make a change.

So today, I am excited to share with you my exact strategy for preparing to take time off! After implementing these changes, along with the systems I have in place, I was able to take a stress-free week off + that month also happened to be my highest in earnings yet.

That’s not a fluke!

It’s because I was intentional + strategic in my planning. It’s also because I RESTED. I took time away from my every day tasks. I was able to think outside of the box + consume different things so I came back with a sharper, rested mind + my days were notably more productive.

So, let’s dive in:


To set the tone early on, I suggest activating your autoresponder at least one day prior to your official out of office date. The more expectations that are set, the better overall experience for your clients or potential clients. Keep in mind, if you use a CRM like Dubsado, your respective email autoresponder won’t send to new inquiries that come through a lead capture form on your website. In order for the autoresponder to trigger, you must set-up a workflow attached to your lead capture form that includes your out of office email.


There are a few ways I handle this! First + foremost, I send a monthly newsletter to all my clients as a touch point + share any updates in my little world. In that email, I always have upcoming out of office dates. As soon as I have these dates, they go directly in there. Another place those dates go right away is at the bottom of my email signature. Last, but not least, I send an email to all my clients 7 business days before my official out of office date. Here’s an example email that I send:

Subject: Friendly reminder: Out of office starting [DATE]
Body: Hi, [NAME]!
I am writing as a friendly reminder that I will be out of the office next week. [ADD ANY DETAILS OF YOUR PLANS HERE]. I will officially be back to regular scheduling on [DATE].

To ensure I am present with [WHATEVER YOU MAY BE DOING], I will not be checking email during this time. I will be handling all to-dos due for next week that are on my list at this point by the end of the week + will handle the rest when I get back to my regular schedule.

Let me know if you have any questions at all!


Yes, it’s important that all my tasks + to-dos are completed by their respective deadlines but I also want to ensure that my list is manageable when I return. I don’t want to jump back into client work feeling overwhelmed from the start.

This seems like a lot of work, right?

Well, honestly, it is, but it is so worth it. I suggest starting to prep 3-4 weeks in advance by adding a few extra to-dos that are on the list for while you’re away or due a couple days upon returning. In some of these scenarios, gmail scheduler is my best friend. For example, I assist with sending VIP client welcome letters for my travel pro clients. Their clients may be traveling during or around the time I am out of office but you do not want to send them too early so insert the scheduler. It’s had a hand in increased productivity on my end!

Along with this, create a content calendar so it’s easy for you to stay active on whatever social media accounts suits you + your business. I suggest making sure to have at least two weeks of intentional content mapped out to help with the transition.


As you’re getting ahead, there will certainly be prompts along the way of to-dos you will need to tackle when you return. Instead of trying to remember all the things upon your return, document it all as you prepare for your time off. There will certainly be additions to your list while away but, by doing this, you will have something to work off of when you return + you can hit the ground running. My lists are created in Asana + in my planner.


How can you keep that vacation feeling as long as possible? For me, it’s to return to a cozy home. That means before I leave my home is deep cleaned, fridge is cleaned out, dishwasher has been run + emptied, all mail is tended to, + all laundry is complete (including bedding)! I also do one round of shopping for essentials as when you’re away, you tend to forget what you may need + it’s not fun to come home to needing paper towel or toilet paper.

Because we are friends, I will share something that may make me sound a smidge crazy. I also prepare all my snail mail that is set to go out in the week or two after I return. Think birthday + anniversary cards that have a notes in them, are addressed, stamps on, + ready to hit the mailbox.


If I return home on a Sunday, I always return back to work on the following Tuesday. Why? I use this as my catch-up day + helps ease back into my routine. If you’re traveling, sometimes that can be unpredictable so having this cushion is a comfort factor, too.

This day is used for enjoying a slow morning, handling any needs around my home, giving my pups a little extra love, + starting to tackle my inbox. This is another way gmail scheduler comes into place. I am not fully back + want to ensure I keep boundaries so I will work through my inbox + schedule all responses for the morning of my return. After working through my inbox, I make any adjustments to my to-do list created before vacation based on any emails that may have come in. Then the following day, my official back in office day, I am ready to tackle that list. This has also helped me limit my time mindlessly in my inbox.

Now, as a little bonus, I will share two of my tips for preparing to transition back into your daily routine from vacation mode. Starting with…


I’ll let you in on a little secret…I never have to do laundry upon returning from vacation! Relaxing on vacation is important to me but want to extend that vacation feeling for as long as possible. It helps me transition back into my routine. I never have to do laundry when I return because I make sure it is done before I leave. All I need to do when I return then is unpack my bags. How? I either do my laundry on the last day of vacation if where I am staying has the option. If it doesn’t, I will happily spend a little by having the hotel complete my laundry for me. This is a complete game changer when returning home. It’s one less thing + doing laundry is way better while care-free, sipping a chilled cocktail while on vacation anyways.


A bare refrigerator is certainly a pain point when returning from vacation so let’s eliminate this! Services like HelloFresh or Blue Apron can solve this! Maybe you need some general groceries like eggs + milk? Try Instacart – you can schedule delivery to show up right to your door. Not only do you save time, but money, because, let’s be honest, the emptier the fridge, the more likely you are to order your favorite takeout, right? And, if you’re anything like me, if I don’t meal prep at the beginning of the week, it’s tough for me to prepare meals throughout the week. An alternative option would to prepare some frozen meals. I love making frozen pot pies or raiding the Trader Joe’s frozen section.

Are you feeling confident with a plan for preparing for your next vacation? I hope so! It’s not easy taking time off but it is crucial for your health + wellness! With time being so limited + precious, it is important to be intentional to fully maximize that time. Need some tips on this? ↓

Download my guide for creating better balance in your business

Can’t wait to see how you implement to bring better balance into your business + life!

jenna daykin in the details, darling va and systems strategist for travel professionals signature


July 16, 2019

how to prepare to take stress-free time off

  1. […] an EPIC fail. So, this year, I’m starting early! And, I’m using my sweet business manager’s tips to prepare for time away (Jenna, from In the Details […]

  2. […] I know many of you are also small business owners and I’ve mentioned Jenna’s name numerous times over the last 2.5 years I’ve had the pleasure of working with her doing a lot of backend and sometimes front end business. She is a MASTER prepper for travel and with us being in the thick of the holiday season and with so many wonderful trips planned for next year, I thought you may find her blog post beneficial on how to prepare to take stress-free time off.  […]