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Planning a Sabbatical? Ask ChatGPT These Essential Questions!

Are you dreaming of taking a sabbatical from work? Perhaps you’ve already begun the information-gathering process, trying to figure out if it’s even possible for you.


While you may not be ready to quit your job just yet or even have a clear timeline in mind, you’re probably starting to realize that taking a sabbatical is something you want to keep on your make-it-happen list… or you’ll forever regret it!

Planning a sabbatical - questions to ask CHATGPT

The initial research phase is important!

It gives you the time and space to start thinking about making your dream a reality, to list all your questions and doubts, and to get inspired about what (and where) it could be. Little by little you start believing that you too can take an intentional break from your career and explore the world! 

“When you’re at the beginning of any big new project, like planning for a sabbatical, asking for help is key. But the problem is that we don’t always know WHAT questions to ask.”

So if you’re not sure where to start… no sweat! To help you kickstart your sabbatical planning process, we’ve compiled a list of questions below that you can use to get the brain juices flowing.

Now, how to find the answers to these questions? 

  • Google them (obviously)! There are lots of travel bloggers and vloggers out there that share interesting travel stories and tips to help you get inspired!
  • Ask other people who took a sabbatical >> Read the interviews we’ve done with other sabbatical takers. They’re chock-full of helpful real-life insights and lessons learned
  • Last but not least, ask your smartest friend – ChatGPT!

What is ChatGPT?

ChatGPT is an AI tool that engages in natural language conversations and generates human-like responses based on the input it receives. Trained on vast amounts of text data, ChatGPT can be a really valuable tool to get quick answers to your sabbatical questions, rather than spending hours going down internet rabbit holes, like forums and youtube videos (don’t get us wrong – there’s a place for that too!).

It’s free, give ChatGPT a try now!

Important Note:
Please keep in mind that ChatGPT is not designed to provide professional advice. Instead, think of it as a source of inspiration and initial information to support your planning process. Imagine talking to a friend who just knows a lot about pretty much everything – that’s ChatGPT!

Questions to ask when starting to plan a sabbatical:


If you’re unsure where to start with your sabbatical planning, here’s our initial non-exhaustive list of questions you can ask ChatGPT. Give it a try!

New questions will probably start popping up in your head as you go along too, so make sure to write them down.

  • Choosing Destinations:
    • Considering I really want to do [insert your must-do activities] during my sabbatical, which countries would you recommend?
    • What are the safest countries to travel to in [insert continent or area]?
    • What are some affordable places to visit during a sabbatical?
  • Gathering Information about specific countries you’d like to visit:
    • What are the visa requirements for visiting [insert country]? And how long can I stay there as a tourist?
    • What are the local customs and cultural norms of [insert country]?
    • What would be the average daily budget for living in [insert country]?
  • Defining Sabbatical Goals:
    • I’m currently experiencing [a lack of meaning, tiredness, burnout, etc.], and I would like to take a sabbatical. How would you recommend I make the most of my free time?
    • What are some popular activities or projects people pursue during a sabbatical?
  • Accommodation and Transportation:
    • What are the best accommodation options in [insert desired country] for long-term stays?
    • Are there any reliable platforms or resources for finding affordable housing while traveling?
    • What are the most cost-effective and convenient modes of transportation in  [insert country or city] for long-term travel?
  • Health and Safety:
    • How can I ensure my health and safety while traveling in [insert country or city name]?
    • What are some essential travel vaccinations or health precautions to consider before traveling to [insert continent or country] on a sabbatical?
    • Are there any specific travel insurance policies or providers you would recommend for sabbatical travelers?
    • Are there any cities to avoid for safety reasons in [insert region name]
  • Work-related Considerations:
    • How can I negotiate taking a sabbatical with my employer?
    • Are there any remote work opportunities with [insert your skills] available for individuals on a sabbatical?
    • What are some options for maintaining professional skills or learning new ones during a sabbatical? [share more about what you are currently doing and what you would like to learn]
  • Cultural Immersion and Learning Opportunities:
    • How can I make the most of cultural immersion experiences during my sabbatical in [insert country]?
    • Are there any language learning programs or resources you recommend for sabbatical travelers?
    • What are some unique learning or educational opportunities available in [insert countries] during a sabbatical?
  • Volunteering and Community Engagement:
    • Are there any meaningful volunteering or community engagement opportunities for sabbatical travelers?
    • How can I find and choose reputable volunteer organizations or projects?
    • What are some examples of impactful projects or initiatives undertaken by sabbatical travelers?

By asking the right questions, ChatGPT can help you efficiently cull through information and insights to shape your sabbatical plans. 

sabbatical planning: questions to ask ChatGPT

Remember to use ChatGPT only as an initial idea generator – and just like talking to a friend, you always want to double-check any information that can have a critical impact on your sabbatical (such as visa requirements or travel insurance for example). 

sabbatical planning: questions to ask ChatGPT

Your Non-Negotiables


Once you have a clearer idea of what your sabbatical could look like, start filling in the gaps with your list of non-negotiables that you can find here


Your non-negotiables list can help you narrow down what ChatGPT information will be most helpful to you, so you can design your sabbatical to be one that aligns with your passions and your priorities – completely unique to you!


The non-negotiables list is also the first step to start building your sabbatical budget. Click here to learn more

About Us

We both had amazing and memorable sabbatical experiences earlier on in our careers (if you’re curious you can learn more here). Our time abroad shaped the humans we are today as well as the business we are building!

As financial planners, we now help you get that experience too! 

Our mission is to make sabbatical breaks not only possible but also an important, intentional, and rich part of your career through smart financial planning!

Once you’ve committed to taking a sabbatical and have an idea of what you want it to look like, contact us! We can help you to better understand your current financial situation and what it would take to make your sabbatical dream a reality. 

With smart planning, you really can have it all!

Kailie & Taylor

Kailie and Taylor Middleton - Sabbatical & Financial Planners

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sabbatical planning: questions to ask ChatGPT
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