Taking proper vacations

Taking proper vacations

This is one of most contested topics I get to chat about with founders.

At this point in my life, my opinion is formed, after many debates and many experiments. Ending in a hospital bed, settled this debate for me once and for all.

You can get to the same conclusion when you are: by the pearly gates of heaven, in a hospital bed, or before any harm is done to you. It’s your choice.

Here is the rationale to what a proper vacation is, and what it isn’t – so you can test if you ever took a proper vacation.

Wait, what?

Yep, you heard me. You may have NEVER taken a proper vacation, ever. You may have been physically away from the office… but you were not on vacation.

This article is written for the US workforce mostly, although, many countries follow the same insane work schedule an norms.

For founders of VC-backed start-ups, this topic is more critical than anyone else. But if you work in a Western society economy, whether you are the CEO, executive, manager or employee – heed my call.

Let’s start with the facts. If you know what inertia is, then you would agree that if you are operating at 100 thoughts a minute on an average work day, it takes time to slow down when you stop.

If you see that it takes time to slow down your thoughts to truly relax – than you can see the point that you can be away from the office, but not on vacation.

Most founders, especially first-time founders, are worried about making a mistake that will ruin their company. Its natural, its an instinct, it will not change. What this means to them, is that they need to supervise EVERY decision, thus, they need to be involved ALL THE TIME.

If that is the case, then the founder never shuts down, never relaxes, thus never going on vacation. Does this describe you? Do you think that is a recipe for success?

If you are an employee at Corporate America, you may be operating under the norms, and assume that taking real time off is going to look bad. Its going to make you seem like a slacker, or someone who is not hardworking.

In order to function well, over a long journey – everyone needs to take a break. Take a REAL break, and not just pretend to do so.

If you were a basketball player, and you played every minute of every game, the entire season – would you be great?


Good coaches know how to optimize their players, and that means, by design, getting them to STOP playing and rest, relax and recharge.

Imagine a coach sending a player to the bench to rest – and instead, the player is going to the locker room to do an extreme cardio workout… Do you agree that it defeats the purpose of resting?

While I am not going to evoke the word “workaholic” in this post – I will say that most of us spend time working during our vacation. It could be as little as just checking emails, or just taking a conference call, or just signing one document or just [fill in the blank]. Some of us, trying to be clever, do this while their family is asleep. Rationalizing it with “if they don’t see me work – then I am with them, and I am on vacation.”

Being away from it all, yet working from afar is NOT taking a vacation. It is not. Its called working remotely.

Ask yourself this question while you are on vacation: Did I manage to get away physically, but my mind and spirit are still in the office?

If that is the case, and it is the case for many – then you are cheating. You are taking time off the basketball court, but you are still exercising vigorously in the locker room. It’s that simple.

Take a deep breath (pun intended).

So what to do? How can you take a vacation and be in a ‘vacation state of mind’? How do you take a proper vacation?

Let’s start working our way backwards from a typical ‘fake vacation’. You go for a week usually, and you may have a family of four.

Day 1 is all about getting there. It could be filled with ‘adventures’, airport delays, lost luggage and what not. Even if its 100% uneventful, its not a vacation day. It a hassle day, to get to the location in which you MAY be in a vacation state of mind soon.

Day 2 is all about settling in, getting to know what is around you, some planning of what to do etc. Because of inertia, of operating at 100 thoughts per minute, you are still not on vacation. You are still running 100 thoughts a minute: a combination of your work worries AND vacation planning.

Day 3 could be the first day of your vacation, but for most people its not. Because you feel compelled to check back with the team, to make sure you did not miss anything critical. Heck, let’s be honest, you just check to verify everything is fine – right? You are not WORKING… you are just checking.


You are not letting go, and you are still on the hamster wheel, just praying that no one catches you. This is exactly what most of us do, and its not considered taking a proper vacation.

Day 4 is probably the first day that the inertia of work thoughts and getting to your vacation and acclimation thoughts are stabilizing. So consider this DAY ONE of your real vacation, assuming you are not doing work, and that you just pretend to relax.

Day 7 – heading home day, not a vacation day. You may experience a minor depression that comes with the realization that it was GREAT to be on vacation – but it was too short. Your body and soul could use more R&R.

You were a week away, but clocked only three vacation days.

To go on a week vacation, you need to get away for at least ten days. Try it. Then upgrade to two weeks away, which are ten vacation days and see the effects. Most people never went on a week vacation based on this definition.

So how do you get to break the mold, and take a proper vacation?

1) Before you go, nominate one of your senior staff members, to be the acing CEO, while you are out. Delegate your role, so you can disconnect. It will give the person some responsibility, a taste of what its like to be you, and they will appreciate what you do even more.

2) Establish a ‘bat phone’ protocol, where the acting CEO can get to you, if there is an emergency. You can do it with agreeing to text messages, and not over email (as you will be tempted to check every minute if there is an emergency email, right?)

3) Hand your smartphone to someone else, like your spouse, or your kid/s. Tell them “as long as I stare at this screen, I am not on vacation. I am not with YOU. I am not in the moment. Please keep this for me, until you think I should have it back. If you hear the text sound, please check if its from [the person you delegated the CEO role to], as it could be an emergency. Otherwise, I am on vacation.”

Much to your surprise, you family already knows that while you have your smartphone – you are more committed to it, than them. Its a sad truth of 21st century business culture – and it robs families from having real quality time.

Just like you mark your calendar for an important meeting with a client/investor, you should mark your calendar for the MOST important people you work for… your family.

Ask yourself this: would you take a call with a telemarketer while you are on vacay?
Of course not.

Would you take a call with a prospect while you are on vacay?
Of course not, this was not a trick question. You should NOT be taking calls, making calls, thinking about calls…

You should be meeting with those who are on vacation with you. That is your JOB now, and you should do it well. You should do it properly, as in taking proper vacation.

Otherwise, you are doing a lousy job at resting, relaxing, recharging, recuperating. A lousy job being with those who do not get to be with you every day.

When you take proper vacations, and really disconnect, something else happens. During the daily routine of being busy, great ideas are hard to come by. One way to think about it, is captured by a Kleiner Perkins law: its difficult to see the picture from inside the frame.

Only when you are truly away from it all, you can see the bigger picture. You do not see the minute by minute, play by play of your business. You can see it, including seeing yourself in it. It may give you ideas that otherwise would not come to you, if you were in the office working.

So taking proper vacations is actually, good for the business at the end of the day.

If you want a mental model to help remember this article:
Work hard. Play Harder.

See this video taken during a Georgian Partners CEO Group about this topic

Neuroscientists Strongly Recommend That You Visit The Beach Regularly – Blue Space

22 Awesome Vacation Quotes You Need to Read ~ World On A Whim

Prayer for a good vacation
Recited before going on vacation:

God, our heavenly Father, whose glory fills the whole creation, and whose presence we find wherever we go: preserve those who travel on this vacation to Turks & Caicos; surround them with your loving care; protect them from every danger; and bring them in safety to their journey’s end;

Please make the sunshine not too hot, to protect their skin

Please make the food as tasty as possible

Please guide the fish to the lures

Please let the neighbors be quiet in the morning, and the sounds of babes be silenced
Please let no sand get stuck in any crevice or crack unwanted

Please let all thy water drain from our ears, and back into the ocean

Please let our bathing suits dry gloriously in the air you have bestowed upon us

Please let our minds relax, our bodies recharge, and our spirits rejoice

Please let our car take us only into neighborhoods known and well lit

Please let our local citizens not cast any spells unto us

Please let our vacation end with the least amount of tears and sorrow as we embark on our way home