QUESTION: While on vacation, how do you juggle work and play? How much time should you allot each day of your vacation to 
reading business email, checking up on projects, etc.? What’s the best balance of work and play? When is the best time of the day to spend on work? What organizational tools should you always bring along on your vacation?
DAVID ALLEN: My main purpose for a vacation is to change pace and environment to refresh perspectives and energies. Things that support that are on purpose. Things that don’t, aren’t. I like to think of vacation as re-creation, i.e. an opportunity to shift gears and balance my activity and focus mix (mental, physical, emotional, spiritual, social, relationships, family, etc.) If I’ve been spending a lot of energy thinking, writing, and speaking, then I want to spend some time getting physical–going for walks, exploring, swimming, jogging, etc. If I’ve been engaged in lots of physical work, then I want to read adventure novels, do some creative writing, and just hang out and socialize. Sometimes, when I’ve really been in the turbo fast lane for a while, I just like to do nothing, with a vengeance!
The main thing I want to keep on a vacation is a clear head–lack of distraction. That should be the criterion for how much of what kind of “work” to take with me or to stay connected and current with. If I’m lying on the beach and I keep thinking about what’s in voicemail or email, then I’d better check it so I can tan with a clear head. There’s a fine line, though, between checking in with the office to stay clear, and checking in with the office as an addiction or comfort zone of the pressure and pace of professional engagement. Because most people have some version of that habit, I would suggest erring toward the unplugged side of the equation. But if you must, to keep a clear deck, then of course do them as soon as you can in the day so that all those things can be put to bed early.
Many times we actually can afford to take off for mini-vacations, not constrained to “be in the office”, simply because we have the ability to be in touch from wherever, handling the necessities of our commitments with our clients and companies. Complaining about “having to do work” in those situations is a bit absurd. I have made business calls from my sailboat, so that I could actually go out sailing all day. You do as much as you need to do, to be able to keep doing what you’re doing!
Some specific suggestions:
1. The last place in the world to have a thought twice is on vacation. That’s why you should always have at least a low-tech “capture” kind of tool with you, even in the most remote places, doing the most remote things. I have a small wallet for credit cards and driver’s license that also has a tiny notepad and pen. I may not process the note (decide actions and input information) until I’m back in the groove, but the potential value that the thought might add is not lost. I also travel with a file folder or large envelope labeled “IN” for tossing notes, business cards, receipts, etc. for dealing with back at the office. The more senior and sophisticated your professional roles, the more likely your best thoughts about work won’t happen at work! They may happen on the vacation. And invariably people meet others to expand their network, and get new ideas and good information while socializing. And if you’re traveling it’s great to keep track of places to go, things to do, in case you want to go there again. If a key benefit of recreation is to get a fresh perspective, then protect your investment and be ready to take advantage of it’s outputs.
2. It is common sense to do your best before you start a vacation to catch up, clean up, and get proactive and current in all your work-related agreements and commitments, handling all the details in plenty of time. Be sure that you identify “Vacation” as a project as soon as it’s on your radar, and that you continue to define and complete all the action steps as soon as they can be done. Too many people need half their vacation to recover from the last two days before they leave!
3. If you have support and admin staff, give them relevant contact information and clarify what might constitute an “emergency” ahead of time to use it, and allow them to filter all communications.
4. Block out at least a full day or two on your calendar for catching up when you return. It is just shy of stupid to not prepare ahead of time for the invariable accumulated pile of details to adjudicate.
In conclusion, there’s nothing inherently good or bad about being involved with professional things on a vacation. It all depends on the many variables in your situation. But the assumption that work and fun are mutually exclusive is not a healthy one. If you have to have a vacation because your job is too stressful or no fun, you might want to change jobs, career, or your mindset about it all.