Save butterflies, Switch to portrait mode.

An Entrepreneur's Guide to Taking a Holiday

Posted on December 5, 2018 by Sheila Vasan Singla

A holiday is a time to unplug and recharge at the same time. It is the time when we reconnect with people who are the most important in the world, and when we take the time to make new friends. It is also when we rejig our mind while stopping to smell the proverbial flower.

But for entrepreneurs, it is never a holiday - the businesses we run are more than just work for us - they are our babies - our passion, and sometimes, our obsession. In this all-consuming fervor for our businesses, how can one truly disconnect? In the two decades and more that I have run a business, I have been equally passionate about my annual vacation and have always scheduled it at the same time every year.

This is my countdown to ensure that I make the very most of the time I take off annually:

10. Twelve months to go: Identifying the location of my vacation.

I have a note to myself which has locations for holidays for the next 10 years. Of course, the destinations are not cast in stone, but that list gives me a long-term perspective on my holidays. With the people I travel with - We decide where to travel - it could be an “off the beaten path” country or could be a “just let’s chill” vacation.

9. Six months to go: making those reservations.

About six months ahead of the dates - I start making travel and hotel bookings. Very often, the sheer inconvenience of cancelling and re-booking has twisted my arm into going for the holiday. I have, of course, come back with the realization that the world continues to spin without my help.

8. Four months to go: steeping myself into the culture of the place I am visiting.

I like to understand the country or the place. I start reading up about the country - it’s history, politics and social structures - I read iconic books from there and watch the “great movies” - I immerse myself in the art over the years. I learn about the food and customs. This acts a “trailer” to the main vacation. By now I have invested so much of time and effort in discovering the place - it keeps from wanting to ditch my vacation. (because my business needs me!! Oh really?)

7. Three months to go: itinerary Planning.

I personally plan my itinerary - making sure that I have identified what each day will unfold into. I shortlist places to visit, restaurants to eat at, things to do and routes to walk - I make reservations at the restaurants we will be eating, find professors of history and archaeology who is ready to walk us through the places we visit and also identify alone time for myself on each day. I have friends who have asked me if I don’t like spontaneity in my holidays - of course I do!!! A plan does not mean you can’t be spontaneous- it just means that you have everything worked out before hand and you can still deviate if you want to be spontaneous. A plan becomes important to me because I pencil in about an hour of work every day at times when it won’t impinge on the people traveling with me.

6. One month to go: connecting with clients.

I make it a point to meet my clients before I proceed on holiday and I do it when I have ample time to work on their requests. I also share with them that I will be on vacation and let them know who they can get in touch with in my absence. I always tell them that I will be available to them anytime they want. I make it a point to not change my telephone number - the extra cost of roaming is worth comfort my clients get out of knowing - I am just a call away. But having said that - I have come to realize that my clients don’t really need to reach out because I have an amazing team that is more than capable of handling any situation. In all my years as an entrepreneur- I have found only 1% of my clients have called me on a holiday.

5. Two weeks to go: getting my bags packed.

I get my bags packed two weeks ahead of time - and keep them ready. In the early days of travel - I would pack to prepare for all contingencies that may occur - right from a sudden big fat Indian wedding in the middle of an equatorial forest to snowy blizzard in the desert. I would justify it by saying - I am a woman and I am allowed to carry 10 pairs of shoes on a 12-day vacation. Since I have deactivated all my personal social media platforms - I am no longer driven by the urge to be seen in different clothes in the photos I would have uploaded. Today I travel lighter than ever before. Having my bags packed takes away the last-minute rush and I can ease into my vacation.

4. One week to go: tying up loose ends.

I spend the last week tying up loose ends at my home and at work. At work - this involves bucketing my work into “if I don’t this - the business will collapse”, “if I don’t do this, it will impact client experience” “if I don’t do this, my people will be clueless. I have come to realize with time - that I am completely dispensable to my business and there are very few items in the three buckets mentioned above. If you have built a strong business with equally strong processes and if you have built a great team - then you will find that you will not be missed.

3. One day to go: cleaning up my work space.

I spend the last but one day cleaning up my work desk - both virtually and in real time. This allows me to get a sense of control and also recheck on anything that I may have missed. Just the process of clearing and sorting out things gives me a sense of order and helps me establish an environment that I can return to with least amount of disruption. For example, I go over all my passwords and change them if required in order to ensure that it will be on the top of my mind. I also like to set my home in order before I leave - whether it is paying bills or stopping the newspapers or milk supplies. Sometimes the stress of not handling something at home can start off the holiday on a bad note.

2. On the day of Departure - going into the chill zone.

I start relaxing and taking it easier. Earlier on - my last day would be a flurry of activities related to work - last minute instructions and last-minute calls and reviews. Now I have come to realize - since I am always connected - something that I have forgotten can wait 24 hours. I can always address it when I spend my daily shot at work every dayof my holiday.

1.The holiday itself - unplugging and recharging.

Life is too short, and one does not know what tomorrow brings. Children will grow up in a wink and age will catch up sooner than we can think. What stays are the memories of great times and stolen kisses and laughter shared. So, breathe in deep and enjoy.

I believe that it is crucial for every entrepreneur to understand the responsibility they have to their organization. We must understand that if we are not recharged - we will not bring the best of ourselves to our organizations - we will be doing a great disservice to our teams and ourselves.

I always remember a saying - A well must have water before it can give water to others. So, I guess, it is time to fill up the well.

This article was originally published at LinkedIn



Sheila Vasan Singla


Sheila is the Founder & Principal Associate of Chrysalis. She is a pioneer in Human Performance Improvement in India who has been passionate about driving business impact through Results Based Learning™.


The Short Road to Excellence


The Lessons of Humility