Top Tips for Vacation Planning

Vacations are important. Spending time away from the hustle and bustle of the office, last minute requests, office politics and late nights is crucial to retaining any semblance of sanity and to prevent burn-out.

All high-level sports stars can see the benefits of rest so as a high performance business worker, so should you.

Last Thursday, I set my out-of-office assistant, shut down my lap-top and stepped onto a flight to Mexico for a well-deserved week in the sun. However, before I could do that, I tried to cram 10 days of work into the four I worked.

Not good. So here are some best practices I’ve gleaned from that last week. Hopefully these will ensure you go on holiday as refreshed as you intend to return:

1. Inform your clients two weeks in advance that you’ll be taking significant time off.

2. Inform your clients again, a week in advance that you’ll be taking significant time off.

3. Make sure you set deadlines for client deliverables at least two days before your last day in the office. This will give you some leeway and make sure you aren’t in office until 9 or 10pm every night before you leave.

4. Schedule handover meetings with everyone on your teams. Make sure people know what they need to do and how to do it while you’re away.

5. Write a handover document:

5a. Break up each client’s account into projects and go into too much detail on each project.

5b. Assign a lead and back-up for each project.

5c. Provide contact details for the client (who should know who is working on their account – see 1 and 2)

6. Let go. As one of my new colleagues says, we’re all control freaks but sometimes you just have to let go.

7. Write your out-of-office auto reply (Outlook: Tools > Out of Office Assistant) and proof thoroughly. I use the following template:

Thanks for your email – it’s <Date of your last day> and I’ll be out of the office on vacation until <First business day you return>.

I will get back to you as soon as possible when I’m back in the office but if you require urgent assistance, please contact either <Contact One> or <Contact Two>.

Contact One

Contact Two

Many thanks,


8. Enjoy! Lock the BlackBerry in the safe and only check it a couple of times a day. When I was away, I would check mine while reserving our cabana at 6:30am (updated: my view below) and then when we got ready for dinner 12 hours later.


God, is there anything sweeter than setting your out-of-office assistant for a vacation?


5 Responses to Top Tips for Vacation Planning

  1. Hi Ed.
    Great meeting you. I enjoyed this post; it made me wish I was about to embark on a vacation of my own. Alas, that will have to wait till summer.

    I do have one more suggestion for your list: Ask colleagues to stop cc’ing you on emails when you’re away. Instead, suggest they provide you with a single email update detailing what transpired when you were gone. Then when you get back, you don’t have to slog through an inbox filled with matters long since resolved, but can ease into work and even have time to share a vacation story or two.

  2. Vacation? Not ‘holiday’?

    Queen’s English mate. 🙂

  3. When I went to Mexico last year, I had absolutely no contact with any computer or mobile device. (Although the latter was because my phone was stolen). It was absolutely the best thing I’ve ever done. The only true way to get away from the office! I’m going to try to do that at least once a year.

  4. Megan Ramsay says:

    Hi Ed,

    As someone who loves to travel I am very much in support of people taking time away to relax and recharge. You list offers some great suggestions, however I have a problem with tip #8.
    I was also in Mexico last week (lovely weather wasn’t it?) and I did not even bring my phone. I should note that I am an intern at a PR agency, and I only missed school and not work, but I feel the purpose of a holiday is to relax, not to be concerned with what is happening at the office. I’m not suggesting you ignore prior and important commitments, but I checked my e-mail 3 times the entire week, and it was fantastic.
    Understandably not everyone has that option, but I would try to separate work and holiday as much as possible. If you’re doing work, then it’s not a holiday.
    I hope you had a great time though!

  5. Excellente! You know Ed, I just started planning my first summer vacation after having become a business owner. I must tell ya – it’s been pretty scary man. First thing I did was find out how to get hooked up with wireless broadband in the Dominican Republic as well as see if my crackberry would work out there or not.

    Your timing with this post is right on point man. It makes me really want to just go and leave it behind for a week or perhaps two. With your tips I think I am one step closer to actually taking a ‘real’ vacation; one where my wife and kids do not yell at me for being online 1/2 the morning, 1/2 the afternoon, and 1/2 of the evening!

    Felix –
    Nicasio Design & Development

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