CoolTimeLife Podcast: Planning for a Successful Vacation

This blog comprises show notes for my CoolTimeLife podcast entitled Planning for a Successful Vacation. Vacations – we all dream about them, but are they being put to the best use? Half of the therapeutic value of a vacation comes from planning – not just where you want to go, but planning the days leading up to departure date as well as your return to work after it’s done. If you do these right, your vacation will be doubly beneficial.

From a productivity perspective, vacations are huge. They are a major contributor not only to health and life balance, but to productivity, and that’s something that many people have a hard time getting their minds around. It’s impossible for people to imagine going on vacation for 2 weeks – or even 2 days without checking email or touching base with the office. Most people can’t even imagine going on vacation, and actually don’t.

There are stats available everywhere of course, but here are a few pulled from a story in The Guardian, written by Jana Kasperkevic.

Jana writes that in the U.S., the number of unused vacation days in the US recently was 169 million days, equivalent to $52.4bn in lost benefits. The reason for this, she writes, is that “many employees are afraid to take it, while others just don’t get any at all, in fact she points out that only about 77% of Americans working for privately owned companies got paid vacation days. Those who choose not to go fear the face time problem, and they also feel that too much work will pile up while they are gone and they will be so stressed when they return that time off won’t be worth it.”

Clearly there’s a problem here. You need only look at your cellphone or the gas gauge on your car to see that the tools we rely on most need to be recharged or refilled regularly if they are to stay useful. You can’t use something once it has exhausted its power supply. So why do we think we can?

Well, first, there’s fear. Fear of missing out on work that’s going on, and worse, fear of being discovered as expendable. If you vanish for a week and people just go on without you, then just maybe, you think, they won’t need you at all, or someone else will sneak in and take your place. The fear of losing out negates the perceived pleasure of any type of vacation.

Secondly, there’s compulsion, specifically, the compulsion to stay in touch through email and messaging. We have become so used to constant bombardment of incoming information, that a few days without it seems to not only be an impossibility, it also appears to be quite scary. Absolute silence after so many years of noise.

Thirdly, there’s fear again. This time, the fear of the backlog, the huge mountain of work and emails waiting for you upon your return, and even the fear of the departing – the rush of work needed to get finished before you walk out the door.

But all of these fears can be countered and vanquished with just a little planning and communication. I will share with you how to do this in just a moment, but before I do, let’s first look at the three, yes three distinct ways in which vacations work as a productivity and time management tool.

The most obvious is the vacation itself. It is supposed to be a time when you let go of all of the stresses and pressures of the working year and do the things you really want to do. Most people find the first three days or so to be a major period of transition as they catch up on all the sleep they have missed, and actually gear down from the pace of business. After those first few days, the restorative effects of the vacation start to take shape, and like so many other areas of life, this does not exist only in the mind. It has profound effects on the body, particularly the immune system, as you start to actually feel relaxed and feel good.

But the benefits of a vacation do not – or should not – start and end with the dates of the vacation itself. There is also the anticipation of a vacation to consider. If you find yourself in a stressful work situation, putting in extra hours and dealing with crisis after crisis, one of the best ways of mitigating the stress of that moment is to look forward to a break or vacation on the horizon – this is the light at the end of the tunnel. Knowing there is an end in sight has both a motivating and calming effect on your mind and body. For more information on this, check our shownotes for information on our podcast dealing with fear.

For example, I work with a lot of accountants, many of whom are tax accountants. When tax season starts in earnest, which is pretty much now – January/February time, they face weeks of long, frustrating days, racing against the clock to file on behalf of their clients, many of whom were responsible for the stress in the first place. For tax accountants, there is no way to defer this work. It has to get done now. It’s a crunch period. OK, fair enough. But when I ask them what they plan to do after they have filed that last return, most of them shrug their shoulders and say, “I don’t know.” I will just go back to the regular work.

Wrong. This would be a perfect time to look forward to your vacation, scheduled for immediately after that last return gets filed. Anticipating the vacation, knowing there’s a break coming, allows your entire body to meter out its energy and stamina accordingly. It’s inbuilt. When you know a break is on the way. You will be better suited to survive the current stressors much better. And this has both short-term and longer term health benefits.

Finally, there’s the memory of the vacation. Once you have had some time off, hopefully you have done something great with that time, those pleasant memories of the activities – or just the rest – will stay with you forever. Those are good memories, and feeling good always has long term physiological rewards. As the old expression goes, no one on their deathbed ever wishes they had spent more time at the office. Great memories flood your brain with endorphins. They make you feel good, and this too serves as insulation against the stressors of the workday.

So How Can You Prepare For a Vacation?

Your vacation should be treated as one of the most important parts of your job, because that’s just what it is. Consequently, vacation days must be defended if year-round productivity and achievement are your goals. This means you must take the time to plan your vacation period carefully to help ensure a smooth, stress-free departure and a smooth, stress-free return.

First, plan ahead to avoid that pre-vacation crunch. The last few days at the office before a vacation can actually be more stressful than usual, because it seems that all the work that you would have done if you were not going on vacation becomes immediate top priority. Everyone around you feels you absolutely must get it all finished before your departure.

But this is a completely avoidable situation, since vacations rarely come as a surprise. Most vacations are reserved many months in advance, just to ensure that everybody doesn’t take off at the same time. Therefore, if you start planning your departure a few weeks or months before the actual date, you can influence the timelines of your projects, meetings, and other office events.

Remember, a vital component of Cool Time Life – the most basic rule of all is that success comes from just two words: planning and communication.

It’s essential to draw a protective barrier around the period of your vacation, especially including the ten business days leading up to it and the ten immediately following it. Make sure those days before your vacation are carefully planned, so that you can hand off responsibilities to others and wrap up your projects. The days preceding a vacation should not be just business as usual for you. They should be about winding down and handing off.  If you try to keep on working on your normal tasks at your normal pace on these days, you will simply generate more stress and overwork than the holiday could possibly alleviate.

To use a boating analogy, very few people will try to bring their boat to the dock at full speed. Stopping a boat by crashing into the dock is not advisable. Instead, you learn to bring a boat up alongside using momentum and physics to allow it to come to an approximate stop just where you want it. This maneuver starts much further out in the water. It is not sailing as usual. It is a practiced procedure.

Here are some pointers:

  • Draw up a list of colleagues who can be counted on to perform small tasks on your behalf, such as returning a call to a key client, or ensuring delivery of a package on the first Monday of your holiday.
  • Set up instructions on your outgoing voicemail message, and on your email auto-reply, and any other messaging system, letting everyone know you’ll be unavailable. Ask them to contact you back after a certain date rather than leave a message, and make sure this a date that is definitely not your first day back in the office.
  • Avoid leaving a contact number at your vacation place for everyone’s knowledge. If your position is such that you must be reachable for the highest-level emergency, leave your number with someone you trust.
  • Keep your priorities in view. Not all work is going to get finished by the time your holiday starts. Some things can wait, or can be delegated. The company will survive without you, at least for a couple of weeks, and you can survive without it. Remind people that you will soon be back, and that life will go on.
  • Leave an hour early on the last day before your vacation. This is pure self-indulgence, and it feels absolutely great, which in itself goes a long way toward establishing balance in your life and getting your vacation off on the right foot. Enjoy the freedom of that stolen hour. Definitely avoid working late on your holiday eve. This robs you and your family of the good feeling that a holiday should bring. It is unfair, and is completely avoidable. Take off. Go and have a great time.
  • Most importantly, plan your return before you leave. Though most people don’t want to even think about their return to work as they start their holiday, a smooth return will help to ease the stress of stepping back into the rat race. The day of your return should not include any meetings. It should be a transition day, in which time is given over to catching up on the events that happened during your absence, returning returning calls and emails, updating your agenda, and getting back up to speed.

Why is this so important? Because too many people simply return to the office and hit the ground running, trying to immediately regain the pace they were at when they left. They return straight away to the stress levels and pressures that they left behind, erasing much of the therapeutic benefits that a vacation brings. Remember: your vacation is a tool for relaxation and rebuilding. It is part of your job. You benefit, your family benefits, and your company benefits. Ease your way back into the momentum of work, just like a runner warming up before a marathon, and you will be better prepared to handle it. Start planning your next vacation immediately.

  • Consider spending part of your vacation at home – a staycation. A two-week vacation in the Caribbean sounds great, but a ten-day island vacation bracketed by four days at home may be even more relaxing. Spending some time at home while everyone at the office thinks you’re away gives you the time to get a few things done, to enjoy a certain quiet that the house seldom sees, to catch up on a few overdue tasks, and put your mind at rest. A couple of days at home before you depart for your holiday trip, followed by a couple of days after, also allows you to prepare for your trip and travel to the airport without stress, hurry, or forgetting anything. The secret here is to have a comfortable holiday and not let anyone know you’re back until your second day back at the office. Plan your vacation as you would plan any other project. Make room for contingencies and delegate authority to others. Work diligently to ensure your return to work is as stress-free as your vacation itself.

Now, there are those who would argue that the only way they can relax on holiday is to check work email regularly. This is always going to be your choice, of course, but the problems is that emails have a terrible habit of pulling you back into work mode, both mentally, therefore diluting true relaxation, and physically by demanding your attention. Emails always create new tasks and new emails. Pretty soon a large part of your vacation day will be spent in the hotel room back on your laptop while your vacation minutes tick away.

It’s your choice, but in the end, your value to your business, whether you own it or are employed by it, should not be determined by face time. It should be determined by your obvious value as an expert a team player and a resource. This can be achieved through a combination of planning and communication, with a couple of spoonfuls of influence thrown in.

This is the transcript of the CoolTimeLife podcast entitled Planning for a Successful Vacation. If you would like to listen to it, you can check it out at our podcast site here. If you would like to review other podcasts in this series, visit my podcast page at

If you feel you derived value from this blog or the adjoining podcast, please consider supporting our work by sending a small donation of $1.00, $2.00 or $5.00. It helps us give more time to research and prepare the episodes. The secure PayPal link is available on the podcast page at