Lessons from a “Relatively” Digital Free Vacation

The salt marsh walk from the beach to town

I am just back from a semi-regular sojourn to Provincetown, MA better known as P-Town. My partner and I have had a pretty stressful 2019 dealing with a variety of family and professional challenges climaxing with the passing of one our parents a few weeks ago. Knowing that we needed some serious recharge time, I decided to make it a digital free vacation and left my laptop at home.

Okay so what’s the big deal? Well this is the first time I’ve left the laptop behind in the past 20 years of traveling. Regardless of destination the laptop always went with us. Before I had a SurfacePro it was a bit like carrying a child strapped on my back through airports, trains, buses and ferries. I had rationalized the need to have it. I needed to stay ahead of emails or really important things were happening and I needed to be able to respond to those things immediately or Rome would burn. I needed to be at the ready…always. I would always be a little cute with my excuses and say “Hey I am only going to check it 1–2 times a day” but that really meant I was never really turned off or tuned out. It was so ridiculous that once I took my old 10 lbs beast wrapped in plastic on a sailing charter from Puerto la Cruz, Venezuela to Grenada. Really, how much internet did I have tooling across the Caribbean…

This trip I decided that I would turn my OOO on with a declaration that not only was I away but I didnt have my computer or phone and you werent going to hear from me unless yes Rome was truly engulfed in a conflagration. I admit that I DID have my phone with me so I could see the emails and Slack’s and WhatsApps but I solved that by keeping it in a drawer behind the passport and books. I looked at my phone maybe 2–3x a day and that was it. Thus the “relative” digital free statement. Yeah not having the phone meant that I couldn’t take photos or communicate easily with my friends around town about drinks or sightings of Alan Cummings but that was okay as I was mostly in the moment of the day whatever I was doing at that time.

I am going to admit that I did send one email, did two calls from my phone and executed two Docusign agreements (yep I did it). I actually caught myself falling back into the mix (it was the end of the month and blah blah blah) and quickly kicked the issue over to one of my team members and put the phone back in the drawer.

We returned home after a week rested and recharged. I was somewhat apprehensive about the volume of stuff awaiting me but that didnt keep me from ignoring the laptop for another 12 hours while I focused on more important things like walking our neurotic dog. When I finally looked at the inbox I was really pleased that only about 20 emails of the 600 were direct emails from team members. They respected me enough to limit their interactions while I was away. What was really disturbing was the number of newsletter type emails that had piled up. I started writing rules to curb that stuff right out of my main box for future sanity. Yeah Yeah I could use Superhuman to manage this but apparently I’m not cool enough to be invited to sit through one of their video tutorials to learn how to better manage my inbox.

Here are a few things I learned from my experience without the laptop that might be useful for you in the future:

Lesson #1-It’s okay not to be 24x7 available or responsive. Regardless of what you do or the size of your business if you are doing things right the world will keep spinning while you sleep, eat, read and do well other things. Dont set the expectation that you are there waiting to pounce on that email, sms, Skype or whatever. People will take advantage if you do.

Lesson #2-Empowering your team means giving your team power. Take a break and let them drive. A vacation is a great way to assess how they performed without you looking over their shoulder. if you have the right people things will be fine. If you don’t then you should look at your hiring skills and adjust.

Lesson #3-Sometimes your team needs a break from you as much as you need a break from your team. Giving people the space can be a great reset button for better internal communications.

Lesson #4- Ease back into the fray. Bake in a extra day to the vacation to get caught up on all of those emails. digest, assess and decide on how you want to handle things versus jumping back in at warp speed. Much healthier approach this way.

Lesson #5- Don’t jump in, rather jump ahead. Don’t get into decisions that were made in your absence rather figure out how to engage with the next set of decisions to be made. I suffer from the classic “I would have done it this way” mentality but guess what I wasn’t in the chair and a decision was made so back to Lesson #2 if you’ve empowered the right people then Rome isnt close to burning in fact they probably conquered the Britons while you were away (okay I wonder if this is my Dave Chappelle pc moment that I will hear about later…).

Lesson #6-Nothing is more important than your own mental well being. You cant be truly effective for yourself or your family or your team if you don’t talk a minute and recharge the batteries on a regular basis.