[Vacation Series] Stop Dreading Your Return to Work! 7 Pro Moves for an Easy Reentry

⬆️ Mindset Shift:

Invest the time to build a pre- and post-vacation plan to maximize your time off. Lack of planning leads to waves of unneeded stress and hassle, often tanking the overall quality of the vacation. Flip the script. Use this guide to apply the right amount of discipline and intentionality, delivering a much better vacation experience for you and your team.

📋 Setting Up a Great Vacation:

Vacation time is sacred, or at least it should be treated that way. 

Fitting into the popular ‘self-care’ or ‘soul-care’ categories, proper vacationing is something we Operators need to work on.

And it turns out NOT vacationing is costing US companies billions and making the lives of many fellow citizens miserable. 

If we don’t follow proven steps and architect the time before and right after vacations, and encourage our team members to do the same, the chances for burnout go up, as do the chances for pre and post-vacation stress that can ruin parts of the hard-earned time off. 

Consider the following excerpt from this Forrester Research article titled ‘Americans Vacation Less Than Ever, Costing Companies Billions:’

“The cost to companies is significant. The report estimates that unused vacation time costs U.S. businesses $61 billion per year in lost productivity. This is because employees who don’t take vacations are more likely to be stressed, disengaged, and less productive.” Source

Instead, let’s choose a better path. Let’s plan to leave the office with confidence. 

When returning from vacation, let’s achieve these three things:

1. Driving down and eliminating work-related vacation stress.

2. Getting back up to speed as efficiently and effectively as possible.

3. Returning rested, restored, and ready to bring renewed innovation. 

I invite you to be more intentional and disciplined in setting up your next vacation to deliver what it should - a rested and recharged Operator ready to impact the world.

Consider following the seven steps outlined below to improve work-life harmony. 

💥 7 Key Moves to Make Before & After Your Next Vacation:

(1) Reentry Point Person Assigned

Let’s start with the end in mind. Just as important as it is to visualize a successful work departure, orchestrating a simple plan for when you return will bring a higher level of peace of mind.

Power move: Assign a leader and ‘Chief Summarizer’ in your absence. 

With your aim to eliminate returning or ‘reentry’ stress and minimize the time to get back up to speed, you identify a Reentry Point Person defined as…

Reentry Point Person - Before leaving, you have assigned a team member, or in some cases, it may be a few team members, to keep track of key decisions and situations in a shared online Google or Word doc. Sometimes, this role may be split among your direct reports or peers.

This temporary role also has defined decision-making and spending authority in your absence, giving your team a clear indication of who is running the ship in your absence. The empowerment also gives your Reentry Point Person a time to grow as a leader. 

⚡ PRO TIP: By piloting this approach with your team utilizing peers, you create a mutually beneficial ‘buddy system’ that benefits other team members when they go on vacation. 

Power Move: Ask for a summary of key events while out. 

Reentry Highlight Reel - Usually sent the workday before you return, a screen recording put together by the Reentry Point Person recaps and summarizes all key decisions, situations, and outcomes while out. Your Reentry Point Person records themselves reviewing the shared online document with each highlighted item. Your Reentry Highlight Reel will cut through the clutter and dramatically help you get up to speed lightning fast. 

💡NOTE:  Your Reentry Highlight Reel will often be a video created using tools like Loom, Vidyard, and Snagit (what I use), or one can record a meeting (with themselves) using Zoom, Teams, or Google Meet. Zoom has also recently launched Zoom Clips, which are easy to use and work well for personalized video applications like creating a Reentry Highlight Reel. 

Okay, now, it’s demo time…

Here is an example of a Chief of Staff created Reentry Highlight Document made for the pretend vacationing COO ‘Mark Everett’ of a fictional AI software company called ‘CogniForge Technologies.’

The COO has been out for seven business days enjoying a fully unplugged ski vacation in the Lake Tahoe area. The COO can fully detach from work because of the company’s ‘Communication Escalation Policy.’ 

The Chief of Staff created the following 3-minute video from their Reentry Highlight Reel document mentioned above. See it in action…

(2) Reentry Meeting(s) Scheduled

Power Move: Get up to speed swiftly and confidently when returning.

Reentry Meeting - a proactive 30 to 45-minute meeting you schedule before leaving for an extended period of time. The meeting normally occurs on your first day back at work. Before leaving, you assign a Reentry Point Person, as mentioned above, who updates a shared online Google or Word document of important events, situations, and decisions made in your absence. 

When you return, your Reentry Point Person is ready to elaborate on the provided Reentry Highlight Reel mentioned above. You also bring forward key ideas and insights you had while away. Overall, this process dramatically reduces Reentry Stress and reinforces the confidence that you are immediately focused on the right things when back in the saddle.

(3) Communication Catch-Up Day Planned

Power Move: Avoid communication overload stress by blocking out a dedicated ‘Communication Catch-up Day.’

Imagine you will be enjoying an unplugged sunny beach vacation Monday through Friday, returning the following Monday. 

With an average of 200 weekly Slack, Teams, or Twist messages (Source), the average knowledge worker also receives 121 daily emails (Source). Knowing this, you dedicate the first day back to working remotely while focusing only on catching up on digital communications (and having your Reentry Meeting).

Here’s how to operationalize this critical buffer day. Even though you are back the following Monday, your OOO message accurately states that you will return to the office the following Tuesday. This gives you a full day on Monday to clear out all your communication debt. 

💡 NOTE: If you are out for two weeks, you may want to tack on another and have two dedicated Communication Catch-up Days. 

Do you see how powerful this will be in helping to eliminate your work-related vacation stress? 

(4) Calendar Blocked & Cleared

Power Move: Calendar housekeeping that many forget to do. 

Step 1: Block out your calendar for the entire time you will be out using a ‘Busy’ all-day calendar event. This way, you won’t get scheduled for a meeting while out of the office.

Example:

How this appears on your calendar when saved:

Step 2: Clear out/cancel/delete all recurring or scheduled meetings during your time away, notifying the meeting attendees of your absence. You are finished when your calendar is clear for all of the days out. 

(5) Travel Calendar Events Scheduled

Power Move: Reduce stress by having all travel/flight information already scheduled in your calendar.

Example:

⚠️ HEADS-UP: I carefully delineate between Mountain and Central time in the example. Hence, my calendar reflects the accurate time when my phone automatically adjusts for the time zone changes. Carefully triple-check your calendar events, as getting them wrong can be time-consuming and costly. 

(6) Vacation Checklist Complete

As an Elite Operator, you understand the value of an experienced-based checklist. There are rewards for having the discipline to use and improve key checklists, especially with the complexities of travel and vacations. 

Using the Paperless checklist app on my iPhone with my travel-focused checklists, I get a distinct level of planning confidence and added peace.

Here are the main ones I use when gearing up for a vacation, confirming I have planned for and packed properly.

💡 NOTE: A key checklist item is setting your Out of Office Message, which is reflected in my main Travel checklist as per this screenshot. 

To dial in your OOO message, see the other post in this series: Mastering Out of Office Messaging: Set Expectations so You Can Finally Vacation Well.

(7) Reentry Steps Complete

Power Move: Finish the vacation and return to your normal work rhythm.

Here is a short list of 5 key items you will want to accomplish when you are back:

1. Update your Travel checklists with anything you learned.

2. Update your Travel journal, noting what you learned to make the next outing more successful. 

3. Your Reentry Highlight Reel detailed above is reviewed and commented on for the upcoming meeting.

4. The Reentry Meeting, also mentioned above, is completed with any follow-up and action items assigned.

5. Email communication debt cleared.

⚡ PRO TIP: For newsletter-type information that comes in daily to your inbox, I recommend sorting by sender only, keeping the latest newsletter, and deleting the rest to help you clear out your communication debt more efficiently. 

Finally, avoid the ‘Post-Vacation Blues’ by identifying your next getaway and getting it on your calendar. 

💥 Operational Action:

So everyone can benefit from significantly better vacations, socialize this post with your team, and seek alignment on the approach. 

🔎 Want to Go Deeper?

Also listed above, to learn about key and important nuances in your OOO message, see the other post in this series: Mastering Out of Office Messaging: Set Expectations so You Can Finally Vacation Well.

💡 What Do You Think?

Consider leaving a comment or asking a question below so others can benefit and learn. 

🛠️ Tools Mentioned:

Microsoft 365 and Google Workspace for creating a Reentry Meeting Highlight document. 

☁️ AI Content Disclaimer:

Bard offered some help with supporting research. I used Midjourney for the CogniForge Technologies logo referenced in the Reentry Highlight Document. ChatGPT generated the CogniForge Technologies name. Everything else is 100% human-created content. 

✅ Mind Break:

Check out the first 5 seconds of this video showing a barn owl gliding through tiny bubbles and see the vortex left. Wow.

🗓️ What’s Coming Up Next:

Next week, be on the lookout for my thoughts on why you must consider a ‘Communication Escalation Policy’ if your culture values deep-thinking work cycles. 

Let’s eliminate all of your returning-to-work anxiety,

Steve Kahle |  ELITE OPERATORS

🔵 P.S.

P.S. If you find value, consider signing up for The Elite Operator Report if you haven’t already. I encourage you to share my content with others, which is a great way to help me build a growing community of elite operators. Also, check out my no-cost resources, like the Ideal Recurring Week Mini-Course. You can also apply for my next Productivity Accelerator, become a paid subscriber, or recommend me for executive coaching, operational and technology consulting, or speaking opportunities like this interview called Time Architecture, Transition from Stressed, and Distracted to Focused.

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