Future Planning Would You Rather Questions

Question 1

Would you rather travel the world for 5 years with no permanent home or settle in your dream home and take shorter trips?

Question 2

Would you rather run a business together or have completely separate careers?

Question 3

Would you rather have a lavish wedding with 300 guests or have an intimate ceremony with just 20 people?

Question 4

Would you rather retire early and live simply or work longer and retire in true luxury?

Question 5

Would you rather raise kids in the city or raise kids in the countryside?

Question 6

Would you rather live in another country for a decade or stay in your home country your whole life?

Question 7

Would you rather build your dream home completely from scratch or renovate a charming fixer-upper together?

Question 8

Would you rather live by the mountains or live by the ocean?

Question 9

Would you rather have a vacation home you return to each year or put that money into different travel experiences every year?

Question 10

Would you rather both work remotely from anywhere in the world or have stable careers in one city you both love?

Question 11

Would you rather have a large house with a big garden or have a smaller home in the most vibrant city you love?

Question 12

Would you rather spend retirement volunteering around the world or live quietly and peacefully in a community you love?

Question 13

Would you rather have several pets or no pets, but travel completely freely whenever you want?

Question 14

Would you rather save aggressively now and splurge later or enjoy life fully now and save moderately?

Question 15

Would you rather move somewhere new every few years or put down deep roots in one community forever?

Question 16

Would you rather grow old surrounded by a big extended family or grow old quietly, just the two of us?

Question 17

Would you rather live on a boat for an entire year or take an RV road trip across the continent for a year?

Question 18

Would you rather adopt a child or have biological children?

Question 19

Would you rather one big international adventure every year or lots of small local adventures throughout the year?

Question 20

Would you rather be together almost all the time or have independent pursuits that you bring back to each other?