How to take a vacation

This Tweet from Samuel Pollen couldn’t be more true (especially for us work-hard-die-hard US Americans).

It says so much in 39 words, no?

Let’s focus on the ‘American section’ real quick (I’ll skip the ‘European section’).

It is a little ridiculous (US-centric view here), that we have this unattainable responsibility to continuously ‘be on’. I wrote a separate blog post on how to achieve inbox zero (tangentially related).

I can’t talk about fixing that unattainable responsibility, as it’s a systemic issue of the work environment we’ve built. We try to curb some of that at Sutro through management decisions, but it's what gave us that US flavor of capitalism & competitive edge (or at least until most recently) reference: Principles for Dealing with the Changing World Order: Why Nations Succeed and Fail by Ray Dalio. And this continuous ‘being-on’ affects your ability to vacation.

I will write about why vacations are important and how to make them most efficient.

So, why take a vacation in the first place?

You may…

• …be burnt out
• …need to decompress
• …want to explore a new place
• …take time to think about a problem that’s been bugging you (work or personal)

First, understand why you’re going on vacation.

Sometimes I’ll go on a vacation to write, brainstorm, or read. I’m a sucker for these solid wooden tables that are overlooking snowy landscapes. I generated this from Dall-E.

Or visit a dark sky sanctuary to look at the stars (I wrote a post on why every Founder should see the stars).

Or hit up a silent retreat, another post I wrote a few months ago.

Or visit family and friends with my significant other.

Or sail between Colombia and Panama with my buddies.

A few points on the reality of your vacation:

• ~7 days is about the minimum time that you’ll need to fully disconnect
• ~3 days to fully get into ‘vacation mode
• ~1 day (your leaving day) you’ll be packing, traveling, getting on the plane, driving to the airport, etc.
• ~1 day (buffer day) to unpack, clean, prep for the week, and clear out your emails
• ~2 days to actually enjoy your vacation. Crazy huh?

Long story short — you’ll need a system to make the most of your vacation, or you’ll be a stress ball and screw up your vacation. You don’t have that much time!

Here’s a diagram of a 7-day vacation, you can see days 4 and 5 are when you’re really vacationing.

What should you do before you go on vacation?

2 weeks prior:

Communication is the name of the game.

• Create an escalation plan with your team. Who will handle what while you’re gone? This is most important if you’re a founder. Create a joint document and share it with all of the notable team members. List out names, tag people, and put email addresses for the connective tissue that you are.
• Assign one person to be the point person. This person has all rights and responsibilities to call you if they need to. They can push the ejection switch and text/call. But having this point person allows the rest of your team to have one distinct point of contact.
• Create a joint calendar invite with the notable folks who should know that you’ll be gone (actually do this as early as possible). It’s your job to notify them that you’ll be gone, not for them to remember that you’ll be out. In the calendar invite description put your cell phone number, in case there is an emergency, and link to the escalation plan (in point 1), as well as your point person.

1 week prior:

Start prepping for your vacation.

• Run a limited-issue ‘fire drill’ and see if the team is able to handle the vacuum of you not being there. Pick a benign problem and see how they handle it. Iterate and edit your escalation doc if it needs to.
• Pre-set your away message to automatically enable itself on your scheduled vacation date/time (not on day 1 when you’re off).

Here's an example away message that I use:

The day before you leave

• Email, Slack, or Teams message to remind the team of the escalation plan and your absence. Again, this is most important when you’re the founder. I’m harping on over-communicating here because that’s what sets everyone's mind(s) at ease.

While on vacation

• Turn off notifications unless needed. Turn off your email, Slack, Teams, Facebook, and Instagram notifications. If you’re traveling internationally and you use WhatsApp or FB Messenger — sure, keep that on. The goal here is to limit how much ‘at home noise’ gets through to you.
• If you need to check your emails do it at a pre-ordained time (no more than 30 mins). I get it, you may be a control freak, and not checking your emails gives you more stress than checking them. Don’t just bring your computer to a coffee shop (unless you’re going to write something or ‘problem solve’), to sit there and answer emails. You could have done that at home, you’re wasting precious vacation hours.
• Don’t answer any emails. More than being an egotistical micromanager, flip the script around. By answering emails while on vacation, you’re not allowing your team agency & responsibility. You’re stepping on their toes. Stop. You set up your escalation plan for a reason — let them (and you) follow it. If they absolutely need you, you put your phone number in the calendar invite (remember?), and your point person will call you if they need you. If you have an external email from a client or something that needs to get paid (that only you can authorize), or you forgot to process payroll — obviously, do that.
• Don’t bring your laptop if you can avoid it. Leave your laptop at home, you have your phone. The small screen size makes it uncomfortable to do real work. So in a sense, you’re giving yourself that fishing line to not totally stress out, but also changing your environment so you can actually vacation.
• Your first few days will be rocky. It naturally takes your mind 2–3 days to fully disconnect from the race you were running. It’s like running a marathon, and then you stop all of a sudden. You have lactic acid build-up that you need to get rid of. That's the first few days — the purging of said build-up.
• Spend days 4 and 5 really disconnecting. Use days 4 and 5 to really disconnect. Try to not open your computer or even check emails on your phone. Enjoy the sights and scenes, spend time with the people you’re with, find new ones where you’re at, read a book, or sip Mai Tais alone on a beach (whatever your flavor of ‘experience’ that you’re on vacation for).
• Plan a buffer day after your vacation. On the last day of your vacation, plan it as a buffer day when you come back. You’ll need time to unpack, wash your clothes, get some food for the week, and maybe spend a bit of time answering some emails that are awaiting. Washington Post had a great post on the buffer day if you desire to dig deeper.

Corollary, a 3–4 day jaunt.

Taking a long weekend also is great. If you can get a Friday and Monday off and sandwich the weekend — that’s amazing. These little ‘adventures’ also really help you come back recharged and refreshed. If you’re doing the 3–4 day jaunt, just turn everything off from Friday to Sunday. Have the ramp up back on Monday, or even on Tuesday.

Music I was listening to while I wrote this

Just a feeling from the Martinez Brothers. I’ve been hooked on this Spotify Hi Ibiza Playlist.

This is day 34 of my #90DayOfProse challenge.