How To Become Wiser: 25 Questions To Ask Yourself
You can’t become wiser by consuming wisdom. You become wiser through taking action.
Wisdom is something that develops with time and effort, through challenging yourself to look at situations from different perspectives in order to learn from them, examining your own behavior, and developing compassion for wider circles of beings.
Written wisdom can give you powerful and inspiring ideas about how to direct your action, serving like a North Star. But there’s no way to skip the work of becoming wiser. We need to grapple with these ideas, test and try them in our lives, and internalize them through trial and error. As Seneca said, “No man was ever wise by chance.” It’s a relatively rare attribute for a reason!
Here are 25 questions you can use to help you develop your own wisdom. Use them to pause, reflect, realign, and help you take the next, wisest action.
Seeking perspective
What’s another way to look at this?
What assumptions am I making right now?
How would an objective observer describe what happened?
Who is this benefitting and who is it hurting?
What would my wisest mentor advise me to think, ask, or do at this moment?
If everyone made this choice, how would it affect the world?
What are the ripple effects of this choice in the immediate moment, short-term and long-term?
Examining yourself
What would I do in this moment if someone was watching me?
What can I learn from this situation?
Where am I failing to uphold my values?
Is this choice helping me move closer to my values or further away from them?
How are my personal experiences, biases, fears, and goals affecting the way I am looking at this?
Are my words and my actions aligning (living with integrity)? If not, what do I need to do differently?
What is happening within me that I might be projecting onto another person or this situation?
How are my strengths and weaknesses affecting my response in this moment?
How have I contributed to this situation?
Developing compassion
What do I need in order to see this situation from a wiser perspective?
What would constitute a good outcome for everyone involved?
What’s the most caring interpretation of this person’s actions?
What needs is this person trying to fulfill right now?
How might this person or group be suffering right now?
What’s the choice that benefits the greater good?
If I’m judging someone, have I behaved similarly before? What was going on for me at that moment?
Is the choice I’m making leading to more love and compassion in the world?
