10 Questions you should ask yourself before going on holidays

10 Questions you should ask yourself before going on holidays


Holidays aren’t just a break from your schedule: they can be a transformative opportunity if you take them seriously. Below is a list of essential questions—practical and personal—that can help you close the cycle with intention and open the door to a truly restorative break.

  1. What do I need to complete before I leave? Prevent pending issues from becoming intrusive thoughts during your break. A clear and decisive checklist is your best ally.
  2. Have I communicated my absence correctly? My team, clients, and contacts should know you’re leaving. A good “Out of Office” message avoids unnecessary emergencies.
  3. Have I anticipated what will happen during my absence? Are there any deadlines or meetings that fall on your days off? Delegate strategically and get everything under control.
  4. What kind of disconnection do I want? Will you be without a phone, available only for emergencies, or somewhere in between? Define your level of connection… and stick to it.
  5. How do I want my return to be? Avoid post-vacation chaos. Plan a gradual return with space to recover.
  6. What do I need emotionally during this vacation? Physical rest? Personal connection? Adventure or introspection? Be honest with yourself.
  7. Am I satisfied with the professional direction I’m on? A little distance can give you perspective. What’s working? What could evolve?
  8. What purpose drives me right now? Reconnect with what inspires you. Does what you’re doing make sense to you beyond the outcome?
  9. What would I like to learn, discover, or experience during this break? Vacation can also be fertile ground for curiosity. What would you like to explore?
  10. How can I return with more balance? Think of small changes you could integrate into your post-break routine. More presence, less autopilot.

I’ll share a quote from Robert Orben I love that perfectly sums up what vacation is all about.

“A vacation is having nothing to do and all day to do it.”

And I’ll end with one last thought:

“Going on vacation isn’t just about getting away from work. It’s about getting closer to yourself. And for that, these questions may be the best suitcase you pack.”



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