10 Questions to Ask Yourself When Making a Big Decision

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Facing a big decision? Here are 10 questions that will help you see the bigger picture and make a choice from a place of self-knowledge.

Facing a big decision? Here are 10 questions that will help you see the bigger picture and make a choice from a place of self-knowledge.

“The more I think about it, the more it seems we don’t really have a decision-making crisis. We have a self-knowledge crisis. How can we decide who or what to say yes or no to until we know what matters to us?"'How to Live a Good Life' by Jonathan Fields

We tend to think of big decisions on a 500-foot view level: it’s either this or it’s that. You take the job or you don’t. You leave the relationship or you stay. You apply for the course or defer it until next year. You book that ticket for the trip of a lifetime or keep saving for a deposit on a home.This kind of microscopic X or Y thinking can make these decisions feel impossible because you don’t have a crystal ball that will tell you how things will work out. Moreover, many of these kinds of decisions aren’t about the situations themselves, but about you.Many of the path-not-taken decisions we end up making (or avoid until they are made for us—not the best approach!) are less about the practicalities of the choice that’s in front of you, and more about questions like: What matters to you? How does this decision fit within the broader scope of your life? How can you tell the difference between what you think you should do and what you want to do? What motivations and desires are driving this decision? In other words, they require you to zoom out from the 500-foot view to the 35,000-foot view. Instead of limiting your vision to the individual cars and houses below you, you expand your sights to the swathes of countryside and towns, stretching for miles towards the horizon. As Jonathan Fields describes in the quote above, issues with big decisions are less about the details and more about self-knowledge.With that in mind, I want to share ten questions I’ve found helpful for making big decisions. You can answer all ten or pick the ones that resonate most for you. Either way, I hope they are helpful!

  1. Does this bring me closer to or take me further away from my values?

  2. How will I feel about the potential outcomes in 10 years time?

  3. What will my future self thank me for?

  4. WWXD? Think of a person you admire or a role model. What would they do and why? You don't have to do the same as them, but this can be a useful thought experiment.

  5. What is my ideal outcome here? E.g. “I want to move in with my partner and have the independence to take trips on my own, pursue my hobbies, etc.” Thinking about your ideal outcome in a given situation can open up possibilities you haven’t yet considered.

  6. What strengths am I bringing to this decision?

  7. What internal motivations are driving this decision? And what external motivations are? Internal motivations are things like wanting a sense of mastery, wanting to meet certain needs, and about your relationship with yourself etc. External motivations are more about how other people see you and your relationship with the external world. So an example of internal motivation would be: I want to feel accomplished at this skill. An example of external motivation would be: I want people to think I’m great at this skill.

  8. If I were free to do whatever I wanted, with no judgment or repercussions, what would I do?

  9. What will change in other areas of my life because of making this decision? And what will stay the same?

  10. What would happen if I did nothing?

What questions do you find helpful for tackling big decisions? Leave a comment and share your thoughts.Photo by Burst on Unsplash