Holiday Hacks for Founders

I blew it. Everything was going so well. I started a 30 day blogging challenge, and was religiously disciplined about posting every day. I even posted after a 2-hour visit to the hospital when my daughter accidentally scratched my cornea (it only hurt when I blinked, if you know what I mean).

But then I went on holiday and things really started slipping. I would start a post and not finish. The pool and jetlag got me so tired that I’d pass out on my phone or while reading a book. And, it was so hard to find a block of time to focus on writing a post. This made me think it’s something many of us struggle with. How can one enjoy a holiday when we have so many commitments (to work, family, ourselves)?

I dug up an old thread with some founder friends and wanted to share their advice anonymously. Getting it right means coming back refreshed and full of energy. Most of us unfortunately get it wrong…

There are no silver bullets, but below are the 10 tips for hacking your holiday:

1. Set the right expectations

Going on holiday doesn’t mean automatically getting rid of all the stress and anxiety. They’re coming with you in the suitcase and you need to slowly unpack them like the rest of your baggage. As one founder put it:

People often go on holiday to ‘get away’ from their day-to-day life, but really what they want is to get away from themselves (thoughts/problems/feelings).

Don’t beat yourself up for checking email about what’s going on in the business occasionally. Some suggested setting an hour a day when you allow yourself to be connected and check things up on your phone.

2. Boredom can be good for business

Some of our best ideas come while we’re in the shower. Researchers are fascinated with boredom and have found it comes with surprising benefits. It turns out that by encouraging contemplation and daydreaming, boredom can inspire creativity. So putting away that phone on holiday might be ‘boring’ but also inspire your next great idea.

3. Keep a journal

Journaling every day has been linked to several health benefits. A study by University of Texas at Austin psychologist and researcher James Pennebaker found that regular journaling strengthens immune cells (T-lymphocytes). It’s also been found that writing about stressful events helps us come to terms with them.

So buy a notebook, and spend 10 minutes a day writing whatever comes to your head. It may be business or a description of the sunset you’ve just watched. It will help you get your mind organised (and body’s defenses stronger).

4. Reading fiction

In the day to day, I mostly read non-fiction and try to learn from smart, experienced people about business and tech. I read articles and books and listen to podcasts. When you go on holiday, you may want to pick up a fiction book that will let your mind wonder, amplify your empathy and improves your brain connectivity and function according to a study discussed in Psychology Today.

5. Replenish your energy

It’s surprising the effect that eating well, sleeping well and enjoying a good conversation can have on our bodies, even in a short period of time. There’s no need to set an alarm clock, or eat junk fund when you’re on holiday. Take care of your physical self and you’ll relax more than you realise. Nobody is designed to work non-stop.

6. Get active

Several people recommended a hike, bike ride or group activity to get your mind off work. I mentioned the benefits of sports in my post on Flow and peak performance.

For me that is activities that can bring a flow state i.e.
skiing, surfing, water sports etc. When doing them you can’t focus on
anything else and when finished you are knackered in a good way.

7. Trust the people you left in charge

It can be stressful to leave on a two week holiday and not include every method of contact. If you’re a control freak, taking a vacation may sounds like a nightmare because you don’t know what’s going on. Set an out of office and give your team the hotel number if they REALLY need to reach you. You may be positively surprised and realise that all those emails you didn’t check have largely been resolved when you got back.

8. Phone settings and notifications

Stress and anxiety on holiday aren’t always phone linked, but removing the temptation can help.

Ideally- no phone
Failing that—no notifications
Failing that—airplane mode and just check when you get wifi
Failing that—silent mode
If possible, put the phone on calls only.

Other tips include putting some restrictions on phone usage. i.e. only check your phone after 8pm or on the weekends while on holiday.

9. Create a little ritual

Rituals can reduce anxiety and increase people’s confidence. From Scientific American:

While some rituals are unlikely to be effective—knocking on wood will not bring rain—many everyday rituals make a lot of sense and are surprisingly effective.Take a ritual with you on holiday. It can be as simple as you want it to be.

The rituals on holiday can be something you bring from home or a a simple behaviour like a walk at a regular time that helps us increase emotional stability and confidence. If meditation works for you, this could be your daily ritual and the holiday setting could put a different setting to a familiar feeling.

10. Pick the holiday that’s right for you

For all of you go-getters-high-performing-smart-creative-hustlers, sitting on a beach for two weeks may be the opposite of a relaxing holiday. As one founder put it, the purpose of building their dream, getting things done and getting over hurdles makes them happy. Sitting idly on a beach doesn’t. So do whatever makes you happy. At the end of the day, that’s the whole purpose of holiday, no?

I’d love to hear other tips, if you have any, on how to disconnect and use the holiday to serve its purpose, rather than feeling guilty checking emails, or taking conference calls while roaming. If you’re interested in reading more about holiday etiquette, the FT just published a management supplement on how to take a holiday from work.

The post was originally published on VC Cafe. This was day seventeen of my 30 day blogging challenge. If you’d like to see more content from me, sign up to my newsletter and follow me on Twitter | Linkedin | Techbikers | VC Cafe | Medium.