Last month, Sean and I took a cruise around the Mediterranean. I visited 10 cities I’d never been to, tasted amazing local cuisine, and learned a ton about world history and culture.
It was perfect. It was beautiful. It looked like Linda Evangelista.
It also meant taking 13 days off from running Lightning Media Partners.
Could we have worked on our vacation? Of course we could have — but after scrimping and saving for this trip, I wasn’t about spend my time in Europe cooped up on a cruise ship with my laptop.
As appealing as the digital nomad life sounds to some, I’d rather fully unplug when I travel somewhere for leisure. Sean and I have both spent too many vacations checking work emails and cramming in last-minute projects in hotel rooms after a long, exhausting day of exploring. That’s why we decided to not work at all while we were away.
That doesn’t mean we didn’t work hard to prepare for it: The weeks leading up to our trip were jam-packed with long days, late nights, and weekend work to ensure that all our usual deliverables were scheduled in advance for the time we’d be gone. But it was well worth it to finally take the kind of vacation we always wanted to, but never could when we worked in the corporate world.
Tips for taking a vacation as an entrepreneur
As terrified as I was to walk away from work, I managed to do it (with the exception of one out-of-the-ordinary project that spilled over into Day 1 of the cruise). Here’s how I successfully hit the pause button on my business for two weeks without any major hiccups or angry clients.
1. Brief your clients well in advance.
The more heads up you can give them, the better. We started prepping our clients almost a month ahead of time to create an adjusted deadline schedule and work plan. For our retainer clients, we laid out everything we would prepare ahead of time and when they could expect it delivered. For our project-based clients, we simply said we wouldn’t be available during those two weeks, and we limited any new work we took on beforehand.
You should also check in regularly leading up to your vacation to remind your clients when you’ll be away. They have their own lives and businesses to worry about, so chances are they might forget!
2. Give yourself more time than you think you’ll need to complete pre-vacation projects.
Trust me on this one: You’re not going to have it in you to pull three all-nighters in a row right before your trip. You’re going to burn out and end up working on vacation (more on that below). Don’t procrastinate; make a plan to get things done at least 48 hours early, so you’ll have enough time to make changes/adjustments in case a project or two goes off track.
3. Put someone you trust in charge while you’re gone.
We are very fortunate to have a content manager, an administrative assistant, and a couple of talented writers on our team, so we trained them on some key tasks and projects that might need to be monitored in our absence. We then put our clients in touch with them so they knew someone would be available to help with any urgent matters while we were out of the office. The trick is to not overburden your team, but simply put them in place as backup after you’ve done your pre-vacation prep work.
4. Set clear communication expectations for your clients and your team.
If you tell your colleagues to “call or text you in case of an emergency,” somebody will take advantage of that. Don’t even extend that invitation to your clients — tell them you will be out of reach, and to email your backup person if they need something. Then, you can work out a system with your team (preferably one or two key people) to filter these requests so that only the items that truly need your attention get through to you.
It helps to define what constitutes an “emergency” and what can wait until your return. In 99% of cases, it can wait — and if it can’t, trust and empower your team to handle it.
5. Have a plan for the week you return.
If you’re taking a lengthy trip (a week or more), don’t expect to get back to your normal pace right away. If at all possible, plan to fully dedicate your first couple days home to catching up on your backlog. Then, you can dive back into your regular workload.
What would I do differently next time?
To be honest, my only regret is not giving myself a buffer day before and after the trip. Our flight out departed at midnight, so I planned to work a full day before heading to the airport and told my clients as such.
I worked up until the moment we had to leave for the airport. I packed everything with five minutes to spare, hopped in the car (completely flustered), and couldn’t stop thinking about the things I hadn’t finished. When I got to my gate, I immediately opened my laptop and furiously tried to wrap things up there and during part of my eight-hour red eye flight. By that point, I was so wiped out that I had no choice but to save those last-minute loose ends for “vacation time.”
While I did finally relax and enjoy myself after that final project was done, I was very unprepared for the whirlwind of catch-up that awaited me when I got home. I promised clients I’d be back and working the morning after my trip — when I’d gotten in the door at 10 p.m. AND was mentally six hours ahead. Jet lag destroyed me, and needless to say, I was not back to my usual routine and productivity for several days after I returned.
I thought it was in my clients’ best interest to make myself as available as possible before and after the trip. I thought they would be upset enough with us for leaving them for 13 full days — how dare I even consider asking for two more?
The truth is, not a single one of our clients cared how long we were gone, as long as we delivered what we promised them. They all knew who to get in touch with if there was an “emergency” (spoiler: there wasn’t a single one), and they also knew exactly when they’d hear from us upon on our return. I shouldn’t have been afraid to give myself that recovery time, and I’m not going to make the same mistake in the future.
The lesson I learned? Stop putting off that big trip or guilting yourself into working on vacation because you “can’t” take your eye off your business for a few days (or a few weeks). Unplugging is possible when you run a business. You just need to prepare for it.
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