Crush the vacation wind down - Five steps to set your future self up for success

holiday vacation wind down Dec 14, 2021

2021 is coming to a close, and for many of us that means getting ready to shut off our laptops for a bit of time off before the hustle and bustle reboots in 2022. You might be thinking “it’s about time”, and “I swear if anyone gives me one more thing to do I’m going to lose my mind”. We know the feeling. 

Have you ever come back after a week or two away and had vacation amnesia? Symptoms include wondering “What was I working on again?” and wondering “What should I be doing now?”. 

We know you’re eager to get to the eggnog (or whatever your holiday beverage of choice might be), but before you set your Out of Office responder, give your future self a big gift. Prepare for your return by following these easy steps to save serious time, confusion and searching when you come back.


Step 0: Create your Crush 2022 Document

We love using Google docs, but anything you commonly use will do. Name it something helpful like “Crush 2022” or “Open this first in 2022”, and follow along with the steps outlined below. Click ---> HERE, we made you a template.


Step 1: Create a current project inventory. 

GOAL: Make it easy to pick back up where you left off on your current work 

What projects and initiatives are you currently working on? Spend a few minutes jotting down any workflow you expect will continue after you return, as well as the current status of that project, planned next steps and links to relevant files. Aim for high level but descriptive bullets. This isn’t meant to be an exhaustive list of absolutely everything, but it should contain the essentials.

If it’s helpful, you can follow this template and use the examples for inspiration, and copy and paste it into your “Crush 2022” file:  

Project Name


Current Project Status


Anticipated Project Next Steps and Known Upcoming Deadlines


Key Documents/Email References

Name of the project, ex. “2022 Revenue Forecasting”


Note where the current project stands. Ex. “Completed v1 of 2022 forecast based on Q3 2021 data. Agreed on Jan 15 for next release”


Note any known or anticipated upcoming steps or deadlines. Ex: “Update forecast based on Q4 2021 data. Prepare for Jan 15 release. Set up meetings and draft release email.”


Link any relevant working files or draft documents. Ex. current version of forecast, meeting minutes, project trackers, etc. 

 P.S. This is in the template Click ---> HERE.


Step 2: Capture important emails and documents

GOAL: Know how to find your stuff, and close it all down in peace

Add a second section to your “Crush 2022” document. Name it whatever you like, we usually go for something like “Reference materials” or “Follow up items”. 

Include any important or relevant files you may want to reference early in the year, and either directly link to them or note where they can be found. 

We’re not going to name names, but most people we know have at least 30 tabs open on their computer at any one time…usually things they’re working on, may need later, want to provide feedback on, need to act on…

This is where you put that stuff, and then you shut them all down, so you can start fresh when you come back and intentionally decide what you want to reopen. Examples could include presentations you’d like to review, recordings you’d like to watch, or a list of emails you want to reference (we recommend also labeling any such emails directly in your inbox). The goal again is to make it really easy to find things you think will be important, and to give you peace of mind when you shut it all down. 


Step 3: Plan for future priorities

GOAL: Set yourself up to be proactive (vs. reactive) when you return

Your reflex will likely be to jump into reaction mode when you get back: answer emails, show up to meetings, and put out whatever new fires might have emerged while you were away.

That’s a missed opportunity. 

Time away can be a powerful moment to reset and reassess. 

Step 3 is therefore to think about your role, your team, your function and your organization’s most important problems and highest priority goals, and how you can uniquely contribute to them. 

Add a new section in your “Crush 2022” file, and add any new priorities you might want to focus on. Not sure what that might look like? Here are some thought starter questions to consider: 

  • What are the biggest challenges to tackle, or biggest problems to solve?
  • What are the biggest opportunities? 
  • What actions would have the biggest impact? 
  • What are my unique skills, talents and capabilities that could impact these? 
  • What would I need to do in order to move the needle?
  • What am I most excited about working on? 

Answer the questions that might be relevant to you. 


Step 4: Align your Calendar to your intentions

GOAL: Set yourself up for success before you leave

Now that you know your current projects that are likely to continue, as well as potential future priorities, align your calendar to give yourself the time and space to kick off right. If you don’t actively use a calendar to help manage your time and priorities, you can apply these principles to whatever method you use (project management software, writing in a paper agenda, post its, whatever works). 

Here’s how we propose approaching this BEFORE you leave

  • Block the first 90 minutes of your first day back in the office to do two things: (1) Quick email scan (30 minutes or less) and (2) Crush 2022 document review. Link your Crush 2022 document to the calendar entry so it’s easy to find. 
  • Identify what projects you will need to tackle in your first week back and block off “catch up” time for each priority project in your first week back. Decide whether this time needs to be solo or with the project team and schedule accordingly. 
  • If you have any known deadlines in your first week back, make sure that you have planned for sufficient working time to nail those deliverables. When this happens, we like to have a calendar entry on the first day back focused on this project, and that includes in the calendar invitation project context, upcoming deadlines, and links to any relevant files. 
  • Plan for the unexpected: Try to block off at least one, but ideally a few working blocks of 2+ hours to focus on your 2022 priorities, or for any unanticipated new work. 


Step 5: Run the Day 1 Return Routine

GOAL: Start strong after your time away!

Welcome back! 

The tried and tested “Day 1 Return Routine” to start your year strong…

  • 15-30 minute landscape scan: Open your inbox ONLY to scan for any urgent or time sensitive updates that may have occurred during your absence. Resist the urge to open any email that is not clearly urgent or a change of direction. DO NOT act on any of the urgent matters now, simply take inventory. Set a timer for 30 minutes. Do not exceed it. 
  • 30-60 minute priority assessment: Immediately after your landscape scan, plan to spend 30-60 minutes of your first day back to review your “Crush 2022” document. 
  • 30 minute prioritization: Create your top 3 priorities for Day 1 and Week 1. Then look at your schedule for the week. Take a few minutes to make any adjustments that might be needed based on what might have changed while you were away. Ensure you’re up to speed on any upcoming deadlines or deliverables. 
  • Ensure your time reflects your priorities: Look at what’s ahead, and align how you’re spending your time to those priorities. 
  • BONUS: Plan a 2022 goal working session. The first week or two after coming back, is a great opportunity to more broadly plan your objectives for the year. 


The takeaway: Take the time to set yourself up for success

The “Crush 2022” wind down doesn’t have to take long. You can do a pretty decent version in less than half an hour. You can even do a skeleton version in 15 minutes. This doesn’t have to be a huge lift, but any time you invest in this process now will pay back in multiples when you return. 

Knowing you have set your future self up for success might even help you relax as you head off the clock. Give it a try, and let us know what impact it had on you!

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