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Issue #17: Getting Through Working Vacations

Last week I spent time with family at a cottage and attempted a working vacation. We were spoiled wit

James Costa

July 12 · Issue #17 · View online
A batch of thoughts, resources, and motivation from a friendly digital agency owner delivered every Monday at 6am ET.

Last week I spent time with family at a cottage and attempted a working vacation. We were spoiled with a private dock, massive house with Internet, satellite TV, and a dishwasher while being 15 minutes from town (i.e. the “essentials”). There were three (tired) adults, three (excited) kids, and I had a pile of work to get through.
I’ve talked about taking time off before, but sometimes unplugged vacations aren’t possible and you need to compromise. For the last 7 years, the majority of the vacations I’ve taken have been working ones. I don’t admit to have it down to a science yet, but here are some of my key findings:
  • Expectations are key. This is the number one most important thing to do when going on a working vacation with others (especially family and friends). Making sure people know that you’ll be working, but also giving them a sense of your general schedule is important. For me, this was letting everyone know I’d likely be working 2-3 hours during the day, and another hour in the evenings. I set this expectation before the cottage was booked as a condition and it helped a lot. Additionally, I gave everyone a sense of when any meetings I had planned were daily so that plans could be made easier. Don’t try and undersell how much work you’re doing - it’s always better to under-promise and over-deliver.
  • Expectations are key for customers and your team as well. Setting the same expectations with your team and clients are important as well. It also means that the team will try and lean on you less than they might normally because they respect your need for time off.
  • Try and schedule as few calls as possible. Calls are the hardest to deal with while away. While you might be able to take calls, they can often get in the way with other activities whereas other forms of work are more flexible.
  • When you’re not working, be fully there. While people might not mind your working for a few hours a day and being distracted from time to time, when you’re there you should be totally there. Oftentimes work can simmer into our conscious and distract us, but setting it aside is extremely important.
  • Replace your computer with a notepad (or tablet) when possible. If you do the majority of your work on a computer, your computer will have “work” associated with it both by others with you, as well as yourself. Switching things up and using offline tools to still get things done while being perceived as more social can help (while still making you feel productive).
  • Get work done when nothing is happening. I generally try and get the majority of important work done in the morning and evening because most of the time it’s when the least is happening. It’s your vacation too, so make sure you adjust to get the most out of it.
A lot of this has to do with making sure that people you’re with aren’t upset. It’s their vacation too, and keeping them happy is important to make sure you can balance work and play while there. Ultimately, being respectful and aware is crucial.
Taking with tradition around my time “away” (which is ironic given the remote nature of the team), I always come up with a few ideas on how to improve the team when I get back (usually one per day I’m away). Here’re the ideas I came up with this time in case they help:
  • Core values survey: I want to send out a survey to find out how many people remember what our core values are, and what other ones they think we have. Zappos does this yearly and creates a culture book out of it, and I’d love to explore doing something similar.
  • Sub values. We have an awesome set of three core values (authenticity, collaboration, transparency), but I’d like to create some more tangible sub values that are more specific.
  • Set of interview questions based on values. I want to make sure we’re hiring people for culture fit in a more conscious way while hiring. Also, having a set of predetermined questions can help to make sure we’re consistent in interviews and can compare applicants more effectively. This is especially important to me as I become more removed from hiring.
  • Recommended reading for departments. In our spirit of always learning and growing, having a solid list of things for our team to read and contribute to (for our three core areas: design, development, and operations) is helpful. (It’ll hopefully also mean more people using the stipend we give them every year for Education.)
  • List of recommended vendors. We’re a specialist team and don’t position ourselves as a full service agency. Because of this, we often refer people to others who have been recommended to us or who we’ve worked with before. Often, it’s hard to remember names and companies, as well as their core competencies. Having a list we can maintain internally and the whole team can access would be helpful.
  • Getting rid of Dropbox, just using Google Drive? I don’t know about anyone else, but we use both Dropbox and Google Drive for different needs. It would be helpful to drop one and just use the other (not just for cost reasons, but also to make finding things easier). This might be a big one, but it’s certainly something to think about as we try and streamline to be more efficient.
That seeping guilt of taking time off is hard to get over, but hopefully some of the above might help you out the next time you plan on taking a working vacation with others. Regardless of how you work or how long you do each day, make sure you’re using the time off effectively and getting some rest out of it. I’ve said it before, and I’ll say it again: you deserve it.
P.S.: If you enjoyed this week’s issue, I’d really appreciate your support sharing this newsletter. Whether it’s a forward, a Twitter post, or starting a chain email threatening bad karma and evil omens, it would mean the world to me.

Good Reads
Under the Radar: How Floorplanner Used Money From Cash-Flow to Buy Their Highly Funded Competitor
Real-time dashboards considered harmful
Introverts: This 75/25 Networking Formula Makes Small Conferences Enjoyable
A Manager’s FAQ
Why you aren’t getting the best digital staff
Weekly Motivation
In Closing
I’m pretty proud of my Portuguese heritage, especially in this past week. If you hadn’t heard (and I mean that literally for those of you reading from Toronto), our national team just won the Euro Cup (⚽️). Whatever you think about Cristiano Ronaldo (“he’s a jerk,” “those abs, though *swoon*,” and “he’s the greatest soccer player in the world,” are all widely accepted thoughts), the team pulled together and showed we’re not dependent on him. How would your team work without it’s “best” player?
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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