Breaking away from your business, even for just a few days, can be difficult, if not impossible. After all, what if a customer or team member needs urgent assistance? And how will the business keep running while you’re gone?

That said, many business owners have found smart strategies for squeezing in some R&R. We asked them their tips for taking a vacation, as well as technologies that have helped. Here’s how they responded:


Block off the days before and after your trip

I never check email while I’m on vacation, as I know that if someone truly needs me, they’ll call. However, certain other steps help me truly disconnect. I always block off the last day before my vacation and first day after I return on my electronic calendar, so that no one can schedule meetings with me on those days. I use the day before to wrap up loose ends and provide project updates to my team. On my first day back, I use the blocked-off time to play catch-up on emails and voicemails and get updates from my team.

Alexis Haselberger, founder, Alexis Haselberger Coaching & Consulting, San Francisco


Appoint a back-up contact

I’ve asked freelance colleagues to be my back-up contact while I’m on vacation, so my clients have someone to contact if they need help. They don’t usually call that person, but it gives them peace of mind. In terms of technology, I use Buffer to schedule my social media posts for while I’m gone.

Michelle Garrett, founder, Garrett Public Relations, Columbus, Ohio


Manage your clients’ expectations

As soon as I know I’m going on vacation, I write a short email to each of my clients letting them know I will be out of the office during that date range. I send a reminder email two weeks before and again three days before I go. That way clients know if they don’t ask me for something before then, they’ll have to wait until I get back. In terms of managing email, Boomerang is my absolute savior when it comes to letting myself be in vacation mode. I draft emails ahead to be sent on certain dates and times, and I can make sure unread emails that need a follow-up are circled back to the top of my inbox.

Kelsey Formost, founder, Magic Words, Hollywood, California


Work overtime before you leave

Before starting my own, one-person marketing business, one thing I didn’t think about was the challenge of taking vacations and making up for the lost income. So, here’s what I’ve done: A couple months leading up to a vacation, I work a Saturday every other week. After 10 weeks, I’ve accrued five extra days of work—allowing me to take a week off without feeling the pinch of lost income. While it’s not fun working on the weekend, it’s well worth getting to take a week off and not worrying about money.

—Jeff Moriarty, founder, JMoriarty Marketing, Naperville, Illinois


Hire fill-in help

I hire a virtual assistant (VA) to read and respond to my email and handle simple inquiries and requests to reduce the amount of digging out I have to do once I return. I give the VA a simple Swimlane diagram to help make great decisions about how to handle matters in my absence.

Bunny Young, founder and president, A Better Place Consulting, Henrico, Virginia


Remind—and remind again

I’ve made sure my colleagues and clients had months to prepare for my absence. I told them about my plans, reiterated the dates as we discussed timelines for projects and put it in emails, proposals, invoices and pay stubs. No one was surprised when I left, because I gave everyone ample opportunity to discuss backup plans and raise questions or get input. It ended up creating a sense of urgency before I left, and many projects that had been waiting for decisions to be made were actually kicked off so they could launch before I left town. (Note to self: Creating a sense of urgency is not a bad way to accelerate the sales cycle every now and then.)

Paige Arnof-Fenn, founder and CEO, Mavens & Moguls, Cambridge, Massachusetts


Take advantage of collaboration and communication tools

I’ll occasionally have to work while I’m on vacation.The most effective technology I use while on vacation is the Asana project management system, so I can track which projects have been completed, which are in progress and which need to be started. I also like to use WhatsApp, if I am traveling overseas, to stay in touch with my team and clients (if needed).

Kristin Marquet, founder and creative director,, New York City


Have an “anchor” reason for your trip

I find that I have to force myself to take vacations, so I do that by having an anchor—another purpose—for my trip. I do this frequently by extending my trips to real estate and vacation-rental conferences. They start as a great basis for my trip, because I meet new, like-minded people in my destination and set some roots in the area before the remainder of the trip.

Holly Gray, founder, East and Emerald, Issaquah, Washington


What’s your top strategy for taking a vacation? Share your tips in the comments section below!



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