12 tips for a stress-free vacation from a SaaS entrepreneur

“A man should never neglect his family for business.” - Walt Disney

Vacation is a good time to disconnect from work and take a break to relax, rejuvenate and refresh. It is extremely important (for your sanity) and I can’t believe that some entrepreneurs actually preach working all day and slogging it out without a break. That would be being a slave to your business. The whole point of building a business is to have it run without you. If it can’t, then you are as good as self employed.

I have had a very busy time with Brightpod in the last couple of months and taking a break last month was a great call. Although, you don’t want to think about business while in the pool or at the beach but there are thoughts that creep into your mind about your business. It is normal to think about how the web app is functioning. Being an avid traveller, I used to get a bit anxious about my business. However, over time I have trained my mind to let go of work and instead enjoy a stress free vacation.

Plan before you head out

Spend the last week with each of your team members (assuming its a small team) and plan out deliverables for when you return. I normally plan a 3-4 important tasks for everyone with priorities. Also discuss worst case scenarios so key employees know what to do in case they need to handle a crisis.

Daily automatic standup

We are experimenting with an automated daily standup for our small team. Every evening we all get an email asking us to reply back with stuff done that day. The next day each one of us receives a digest of everyone’s work for the previous day. This helps all of us to be in the loop - especially important when you have team members who work remotely.

Everyone handles support

Answering customer emails is not just for a single “support” person. Everyone, especially developers, are looped into incoming emails from customers through Intercom.

Managed hosting

I have always hosted with Rackspace. Just love their level of support if something goes wrong. I want my team to focus on building "gracious" software and not worry about network and server issues.

Daily backups

We backup all data daily so in the event of a failure everything can be restored. This helps me sleep better at night and of course, enjoy my vacation.

Are the bills paid?

A week before, I do a quick check to make sure all our bills are paid (e.g. hosting) and a quick check to make sure my credit cards are not expiring while I am away (and that they have sufficient balance for automatic business expenses).

Ditch the laptop

The laptop is always going to be a symbol of work. However, a tablet can not only help you get work done (crank out some emails) but can also be a source of entertainment while you are away.

Schedule email checks

On vacations, I check mail twice. Once, after breakfast (so I don’t think about work during the lavish buffet spread) and once in the evening. Honestly, if shit were to go wrong you would get messages and frantic calls - or your team will track you down.

No devices on the beach or pool

This is a strict rule I follow not to mention the paranoia of having sand and/or water get into my devices :) I don’t want to be that workaholic guy on a vacation constantly looking down at a screen. That is just sad.

No Notifications

I turn off all notifications on my phone and tablet. The only 3 things that matter are phone calls, messages and emails. I don’t give a damn about Twitter, Facebook, Quora, Feedly, Pocket etc.

News Free

No newspaper, Twitter, or even TV news. Trust me, you won’t miss a thing because the same news gets recycled over and over again. You come back from a vacation and it is the same crap. Once back, I always come to realise how much of the day we waste on non-important things just to stay busy.

Say f$$$ it

Being on a vacation is MY TIME that I have earned it. No one can take it away from me. Sometimes you just have to say f$$$ it to everything that is nagging you and just enjoy the present moment.

"The secret of health for both mind and body is not to mourn for the past, worry about the future, or anticipate troubles, but to live in the present moment wisely and earnestly." - Buddha

Enjoy your next break and thanks for reading! Would love to hear your comments on how you manage a stress free holiday.