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10 Steps to Totally Relax on Vacation

How to take the best break from your job and side hustles

Red hammock looking out at ocean and sky.
The Red Hammock. Author photo.

Like most creators and entrepreneurs, I find it nearly impossible to disengage from work. I spent my October beach week writing a revision of The Messy Planner. That trip wasn’t a vacation; it was just a week doing a different job in a gorgeous location. The change of scenery and schedule was helpful but not the full-on reboot a true vacation offers. That kind of reboot requires careful planning and a change of mindset. Here’s what I learned from my most recent vacation, which turned out to be the most refreshing time off I’ve had in years.

1.Before you leave, help your future self. Write and schedule posts for the time you are gone and work ahead in any other ways you can. Then prepare your to-do list so you know exactly where to start when you return. Make sure that employees and coworkers have everything they need to work without you. Delegate everything you possibly can — that way, when your mind turns to work while you are vacationing, you can remind yourself that things are getting done even though you aren’t there.

2. Take as much time off as you can. Two weeks is perfect for me. When I’m not sick, I find that I don’t completely let go of work for at least a week. If you work a day job and a side hustle (as I do), you might not be able to get away from both for a full vacation. If that’s the case, schedule a week or two off from your day job and then carve out days within that block for total relaxation.

3. Prepare your clients. If you have regular work obligations, let your clients know well in advance that you will be unavailable for a specific period of time. Most people are very understanding and can manage without you for a week or two. If you work in a business where you can’t leave them for a couple of weeks, hand clients off to a trusted associate. Either way, you need to be able to rest easy that they are fine while you are gone.

4. Use out-of-office messages on your email and voicemail to your benefit. Consider who might be trying to contact you and craft messages for that audience. Let new clients know that you are eager to talk to them, and you will contact them on x date. For ongoing customers (or your boss), provide one contact who can deal with emergencies. Choose someone who can field basic questions and will shield you from not-really-emergency situations. If you aren’t going completely off-grid, set your phone to “do not disturb” with that one contact being the only person who can get through to you.

5. Go offline. One of the reasons that I take annual cruises is that I don’t have phone or internet access on the ship. On most ships, it’s expensive to pay for WiFi, and I am not willing to do so. Vacationing in a mountain cabin can offer the same benefit. To be honest, my cruise this year did have free WiFi, but I simply made a rule that I wasn’t reading work email while I was gone. That’s not an easy resolution for me to keep, but Step 6 forced me into it.

6. Get sick. I wouldn’t have planned it, but a sinus infection was the perfect thing to slow me down and turn off my busy brain for a few days. By the time I settled into my cruise ship room, my brain was completely fogged in. All I could do was sleep, read, look at the scenery, and eat lovely meals. Luckily, that’s exactly what I planned to do. The bright red string hammock on my verandah was made for napping and watching the ocean, and I used it to its full extent.

If you aren’t sick, give yourself permission to act as if you are. My illness was my body’s way of telling me to slow down and do a bit of nothing. If you have been working two jobs, you are probably ready for an afternoon nap or three. Let yourself take them. In fact, luxuriate in them. This is not the time to push yourself hard to see everything a destination has to offer. Pick one or two things that interest you and go with the flow. If you don’t get to do everything on your list, that’s okay. You can save them for your next trip.

7. Do what most relaxes you. I’m an introvert, so I need plenty of downtime and limited socializing. If you are the life of the party, by all means, plan group activities. Most of us need a little bit of both. I spent those first few days napping in the hammock, punctuated with lovely meals at venues around the ship. Only later did I venture out to dance and attend shows. The important thing is to do what feels restful and rejuvenating for you.

8. Focus on the present. When your mind wanders to work-related issues, pull yourself back to what you are doing at that moment. Remind yourself that you did Step 1 you are ready to hit the ground running when you get home. (My librarian mantra comes in handy for me: “Nobody dies in a bibliographic emergency.”)

After you have pushed work out of your mind, replace those thoughts with mindfulness. Focus on each of your senses. Take a deep breath and smell the ocean. Feel the sun warm your skin. Savor every bite of a gorgeously-prepared meal. Gaze at a technicolor sunset.

9. If you are traveling with companions, be present and connect with them. If you have been working too much, you may not have been as attentive as you would like. This may be the time to have some deep conversations. Really listen. Most of all, relax and enjoy their company.

10. Set your date of return a day or two after your actual return date. On your out-of-office messages and when you warn clients (Steps 3 & 4), give a date that is actually a day or two after your flight home. That gives you room to sort mail and email, unpack, and transition back into the workaday world. It also allows for flight delays.

If you work a day job and need to hoard your vacation days, consider coming back on Friday to give yourself the weekend to catch up on your personal life and reset your sleep schedule. It means a shorter vacation but keeps your stress levels from spiking immediately upon your return.

11. Pick one thing you loved to do on vacation and schedule it into your real life. This might be something as simple as taking a bath, reading your favorite book, or taking a walk. I rediscovered yoga when I was on my trip, so I am adding that back into my daily routine.

This trip was very different, but I think that it actually gave me the template for successful vacations in the future. I didn’t even think about my job while I was gone, and I completely put my side hustles on hold, too.

Best of all, I’ve been able to carry that feeling of vacation back with me into life. I came back with even more energy than before (once the antibiotics took hold), and I’m loving my work and my side hustles even more than ever. The Wonder Woman tights are back in place, and I am ready to go!

Need help finding your own superhero life plan? Make an appointment for a free introductory coaching session with Marie. Mention this article for a discount on your first video, email, or text-based coaching plan.

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Marie Jones

Marie Jones

Librarian. Curious human. Writes about inconsistent organization, messy productivity, random thoughts, and living a happy life. messydeskconsulting.com