Engineering a Vacation

2014 was the first and last time I took a truly relaxing vacation. I traveled a lot for work and for pleasure before then but that was when work meant work and pleasure meant partying like a maniac. Neither is truly relaxing.

That particular vacation in 2014 was special because I had just sold a startup I was working on for 6 years and for the first time as an entrepreneur and an adult, I allowed myself a complete digital detox for two weeks. It took a while to take effect (almost the entire first week) but when it did, it was a life changing experience. I was alive in the present moment like never before and every breeze, bite, and beverage was the best thing I have ever experienced.

Unfortunately I have not been able to replicate that state of presence, enjoyment, and relaxation in the five years since that epic trip. Each vacation since has been mired in stress, boredom, and depression. T-mobile’s free global roaming data plan doesn’t help either. (although it is freaking amazing).

For my most recent vacation, I decided to engineer a process to achieve that same state of tranquility I briefly felt 5 years ago. This process is personal and not meant to be a “how to” for anyone else, but it worked well for me given my current work and family obligations. In my never ending quest for self awareness, I have realized that for me even relaxation needs to be a process. You could argue that I’m not really relaxing and maybe it is not possible for me to be truly relaxed ever (way deeper and darker post in the works for that one). While a pure detox works wonders, it is no longer feasible for me to completely disconnect given that I have a family that I need and want to take care of. With that, I share with you my process and results.

Process

Two weeks before the vacation:

• Block off the entire last day before your vacation on your calendar.
• Keep your calendar light for the days leading up to the vacation.
• Clear your calendar of all recurring meetings for during your vacation.

The week before the vacation:

• Get to inbox zero (if that is your thing).
• Unsubscribe to newsletters or set filters to keep them out of your inbox.
• Separate work and personal email apps. I use Gmail for work and Apple mail for personal. Separation is key to avoid accidental openings.

Day before the vacation:

• Shut of all notifications on your phone.
• Set a blunt Out of Office message.

• Change your phone’s home screen to have no apps, just a nice picture.
• In the dock put essential travel apps.
• Change the second screen to personal communication essentials.
• The third screen can be your folders and apps as you usually keep them.
• Remove all widgets that can take you away from the present moment.

During the vacation:

• Give yourself four work email triage sessions per week. I chose Monday morning, Tuesday night, Thursday morning, and Friday night.
• Time-box these sessions to 30 minutes and never reply to any emails. Use the time to quickly archive or snooze emails.
• Try to find alone time and space to do these sessions. The goal is not to think about the email content but to organize your inbox and only reply if something is unbelievably urgent.

Results

I was worried about coming back to “thousands of emails.” That wasn’t the case. Here are the raw numbers:

• 451 emails came in over the two weeks, not including filtered emails. I snoozed 88 of them. That means only 20% of all emails felt important enough to save for later.
• Only 54 of the 88 snoozed emails still mattered when I returned. That means less than 12% of all emails actually mattered. 40% of the emails that I thought were important resolved themselves within two weeks.
• I replied to 6 emails while away. Only 1% of all emails were actually urgent. Nothing bad would have happened if I didn’t reply at all.

Conclusions

• A calm inbox made returning to work less overwhelming and peaceful.
• Put the burden of urgency on the sender. I did with my OOO. It worked.
• I am addicted to being connected, but you don’t need to completely disconnect to build a healthy relationship (on vacation and at home) with technology and connectedness.
• If you choose the triage route for your vacation, make sure you give yourself space to do it. Go away from the family and distractions for the sessions and strictly time-box it.
• The triage sessions lost their appeal very quickly. I didn’t care after the first few and by the second week missed all four of them. The sessions got quicker each time as I was doing less thinking and more archiving. My metric for importance also changed as the vacation progressed. Most things just didn’t matter and time proved that.
• This process is a form of Cognitive Behavioral Therapy (CBT): recognizing thoughts and patterns (without judgment) and then reframing them to serve you better. CBT has proven to be a very effective mental and emotional tool for me.

Pro Tips

• Avoid the urge to connect to free wifi. No internet is a great deterrent.
• No phones at meals. This is a great rule for vacation and for life.
• Don’t charge your phone midday. A dead battery forces disconnection.
• Sleep. A lot.
• Keep a log of your thoughts. It helps to stick to a process.
• Take long road trips (and don’t text while driving!).
• Triage email at off hours. This limits incoming mail while you triage.
• If you need a phone so that family can reach you, leave your phone behind and hold your partner’s phone in your pocket. This way neither of you is inclined to check it.

My Raw Log

I kept a running log of my thoughts, feelings, and observations on my trip. I kept it as original as possible, only editing formatting and adding helpful labels (and some pictures) to each entry. Please feel free to comment!

Click here for my raw notes

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