Issue #12: On Taking a Productive Vacation

Revue
 
Imagine you're on a boat. Relaxing somewhere in the middle of the Caribbean. Enjoying your strawberry
Revue

James Costa

May 30 - Issue #12 - View online
A batch of thoughts, resources, and motivation from a friendly digital agency owner delivered every Monday at 6am ET.

Imagine you’re on a boat. Relaxing somewhere in the middle of the Caribbean. Enjoying your strawberry daiquiris (or maybe being adventurous and mixing them with pina colodas) while consuming copious amounts of food. You’re looking out onto the waves thinking about how beautiful they are and how at a certain point they blend into the sky. You may be on your honeymoon, vacationing solo, or with your family, and you’re so present.
But then, 5 seconds later, your brain goes back to work mode and wondering whether something got resolved or done. You second-guess about cash flow, wonder if clients have been continuing to pay on time, and debate an upcoming expense. You worry about a particular hire and whether they’re doing what they’re supposed to, or whether a client is still driving your team up the wall.
Ladies and gentlemen, welcome to vacationing as a business owner. (Also, hey! I missed you for two weeks.)
16 days ago I married my best friend, and proceeded to taking a short cruise in the caribbean. This is my second time in less than a year that I’d consider being on a true vacation (which I define by the amount of time I end up working, whether or not I take meetings, and whether I bring my computer). The anxiety doesn’t subside, but I’ve found some important things that have made the vacations better:
  1. Bring books. I’m not a big reader regularly (I read so many emails and messages due to being on a remote team that reading can be hard to do in my spare time), but when I’m on vacation this is one of the few things that can calm me down. In particular, I bring all of the books I’ve been wanting to read on business and work. Through reading and reflecting on what I read, I end up feeling like vacationing is actually some sort of personal improvement time that benefits the team. This time I read The CEO Tightrope, You’re My Favorite Client, Just Enough Research, and got halfway through Delivering Happiness. (And for lighter reading I always have a couple issues of Offscreen.)
  2. Write a message and tasks for your team to do or things you’re concerned about, and delegate things to people. Even though the team might know what they need to do, giving them some things to focus on while you’re away is important so that you don’t have to worry if something has been forgotten. While I didn’t write one for this vacation, last time it took me a few days to put together as I kept adding things to it (up until the point I was boarding the plane).
  3. Give your team a few goals for the week. I’ll admit it was really cool seeing the team striving to achieve some of the goals I laid out and mentioning it in Slack messages. Overall, keep them simple and save rewards for big wins. They’re keeping the lights on for you, so they deserve it.
  4. Block out an hour (but not much more) to catch up on emails close to the end of the vacation. Coming back from vacation can sometimes make you want to take another vacation. I found that clearing out some of my inbox (especially low-hanging fruit) and getting a pulse made me relax a bit. Unfortunately, though, the Internet package on the cruise was for 24 hours, so I ended up extending my check-in time because it was hard to break away. I think the pro tip for next time will be getting the Internet package on someone else’s device so that they can manage your consumption.
  5. Get your team to write you a message for when you get back to catch you up. Our operations team has found this pretty key when anyone has been away. It doesn’t take long for them to put together, but makes sure that anyone who has been away knows about any actions they need to take.
  6. Write (at least) one actionable thing you want to change, do, or improve on for every day you’re away. This one has been key and has been something I’ve done regardless of whether I took a true vacation, or ended up just being out of town and continuing to work. It forces you to 
  7. Always have a notebook with you. When you forget something, you can often remember it when you let your mind wander to other things. Similarly, when I’m on vacation I find I have my best ideas because my mind is relaxed. Having a notebook is extremely important to make sure you capture those ideas and turn them into actionable things when you get back.
  8. Don’t expect your first week back to be normal. There’s no such thing as “getting back to normal” from a vacation right away. I find it takes a couple weeks, and you should expect that. The anxiety of being back at 100% your first week back is unreasonable, so give yourself some slack. That being said, the benefit to taking time off is long-term, not short-term, so expect to see the benefit from relaxing in the weeks to come.
This might all seem like a lot, but I find taking a vacation properly is a mental preparation game. Making it productive and work-oriented helps me manage anxiety, and means that coming back I can really make an impact. These tips are simple, small actions that I’m adding to each time I take time off (as I’ve been learning is important), and will keep updating you on as I strive to strip away the idea that not taking time off is an okay thing to do in our industry.
Here’s to an awesome, productive week that gives you everything you deserve!
P.S.: If you have a moment and enjoyed this week’s issue, I’d really appreciate your support sharing this newsletter. Whether it’s a forward, a Twitter post, or naming a culinary food dish after it, it would mean the world to me.

Good Reads
How to create fast, impressive proposals that sell
Find, Vet and Close the Best Product Managers
A Manager’s Job Is Making Sure Employees Have a Life Outside Work
We’re Way Too Nice At Work
The art of being agile in an agency
62 Actionable Ideas for Getting More Clients From 13 Top Marketing and Sales Leaders
Inspiration for the Week
“People who are crazy enough to think they can change the world, are the ones who do.” — Apple Computers
In Closing
For those of you who’ve been following my raccoon tales since the last issue, my team created a few accounts to troll me while I was on my honeymoon that you might find entertaining: a raccoon, a skunk, and a moose. They also got me a couple little raccoon figures as part of my wedding gift. Needless to say, I’m pretty proud.
(Oh, and that account that was trolling me last week? That was being controlled by my wife.)
If you have any questions or I can help you in any way, all you have to do is respond to this email.
🖖
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Carefully curated by James Costa with Revue.
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