What’s on your vacation to-do list?

If I were an email marketer going on vacation for three weeks, what would I do on my first day back in the office?

Everybody knows how great vacations are, but we email people truly appreciate taking a vacation amid all the craziness. As you read this, I will be holidaying in Greece and Thailand. I’ve never been to either before and look forward to a much-needed break. It has been a crazy year for me — and, I suspect, for many of you, too, because brands have rediscovered all the great things email can do. 

Since returning from the Christmas holidays on Jan. 5, I’ve been inundated with business, outside demands, client questions and a never-ending flow of activity. We had to forego the usual luxury of ramping up gradually in January. None of my colleagues has taken even the slightest pause.

That’s why taking time off is so important.

Just as we plan our vacations, we need to plan an exit and re-entrance that’s smooth and hassle-free. I don’t take work calls or respond to Teams or Slack notifications while playing golf or out on a boat. But before I leave, I wrap up as many loose ends as possible so no one has a reason to reach me. I have also planned for the work waiting for me on my return.

3 tasks to check off on your vacation to-do list

Technically, these are two things to think about when you return and one you should answer before you leave. But all three are important for a successful vacation reprieve.

Disconnection is important. You can’t truly enjoy your time off if you leave much work hanging. Either it’s on your mind or somebody is trying to reach you to talk about it. And whether that happens while you’re in your own backyard or halfway around the world, it punctures the holiday mood and makes re-entry more of a hassle than a triumphant return.

1. Did I do everything I could to reconnect successfully?

This is the one you need to think about now. I haven’t even packed a suitcase yet but I’m already thinking about what I’ll do when it’s time to plug back into my routine. And that’s the point.

You can’t expect to achieve post-vacation Nirvana if you leave things in a mess before you go. 

Right now, I’m meeting with senior management with plans to turn over my work responsibilities so they can run the business while I’m gone. Whether you’re the big boss or the most junior team member, don’t leave business undone as you rush out the door. That leads to frantic phone calls, emails, texts and notifications as people try to track you down. 

Give yourself the downtime you need to clear your mind, recharge your batteries and get a fresh outlook. And that means totally unplugging from work life. My wife deletes her work email from her phone and leaves her laptop in her office. I discipline myself not to get pulled into work things. But that’s possible only because I have prepped my team before I leave.

Fully embrace your vacation by not thinking about work. Americans are notorious for not taking vacations or combining work with time off. How often have you heard people say, “I had a great time. I only had to work a couple of hours a day.”? How about “I didn’t have to work at all!”

2. How will I leverage AI this holiday?

Even during a holiday, I think about work, just not as obsessively. I want to use this time to step back, but looking at the ocean gives me a clearer perspective that often helps me find solutions that elude me when I’m in the middle of work.

You might want to set some strategic goals when you’re gone. I have a list of 3 things that I want to figure out. Again, while looking at the ocean. These are higher-level objectives for the business and how to affect change. Your list could be anything, but goals are important while your mind is clear.

In a recent column, I talked about coming up with a plan for using generative AI in your email program, developing a testing plan and using it for more than subject lines. 

Dig deeper: 3 steps to make AI work for you 

If you didn’t take the time to think about how you can extend your email program with AI help … Well, shame on you. Don’t you do what I tell you to do? But seriously, maybe you didn’t have time with everything else on your plate or you just don’t know enough about it to see how to apply it to email. 

If you plan it right, you’ll come back from vacation with an open, refreshed mindset and a blank sheet of paper or a whiteboard that you can fill up with ideas for looking at things differently in your digital marketing program. That can give you the mental space to tackle a complex topic like AI in general and generative AI in particular.

Ask yourself two questions: “How will I leverage AI in my holiday campaigns this year?” and “How can I leverage it today?” You could try creating AI-driven testing plans in Q3 that would pay off in Q4. Look at ways to use the technology and insights to guide production, strategy and messaging.

Take time to look across your industry and discover what other marketers are doing. What could you borrow and improve upon? What could you use as a base? Generative AI gives you the capacity to help people and programs overcome deficiencies. 

During a recent industry discussion group, Dela Quist, an email industry veteran with Alchemy Worx, said this about AI: “It helps fill gaps for people, teams and companies.” That’s a great point. To that point, I would add this: AI can up-level everybody by filling in deficiencies and spurring improvement. 

Use the week after you get back to take some time to write down how you could test into AI to have a program ready to go for Q4. 

3. Am I ready for the holidays?

And by “I,” I mean “you.” When you return from vacation, the holiday marketing plan is the last thing you want to consider. But now is actually a great time to start fleshing out plans before the holiday crunch arrives and the screaming-down-the-hall moments begin.

Maybe you don’t have the specifics for each campaign, but you should have a production schedule and rough ideas in your head. If not, dust off your notes from 2022 and look at what worked and what didn’t and how the numbers added up. Then think about what you’ll change this year.

Dig deeper: Email: An early check-in before the holiday madness begins 

If you’ll be working on holiday marketing for the first time this year or the first time with your company, talk with your team members about last year. Look for webinars and peer discussion groups to discuss what others have done. This is your time to get up to speed. 

And if the holiday season is a slow time for your company, you can still use your time now to come up with ideas for using that time productively, whether to create a sales plan, work on a new strategy or map out goals. 

When I was an email strategist, the last two months of the calendar were slow. I no longer had endless planning sessions with clients because they were deep into execution mode on those plans. So I spent that time on my own planning.

Naturally, you can’t anticipate everything in Q4, especially if you’re a retail email marketer. But if you have plans to act on and anticipate the “what ifs” and pivot moments that usually crop up in the busiest quarter of the season, you won’t have to scramble for solutions.

Wrapping up

Vacations should be fun, but they’re hard to pull off. Many people don’t take the time due to them because they fear they might not have a job when they come back. Or they work for people who don’t respect their time off. 

If you stick to your pre-vacation regimen, you can disconnect without fear or anxiety and enjoy spending the money you earned all year. So, go ahead and order another mai-tai. Spend an extra hour on the beach. Hike an extra 20 miles if you must. These activities will help you tackle the tough stuff when it’s time to plug in again.