14 Questions to Ask Yourself Again and Again

There’s life-changing power in regular self-inquiry

Photo: m-imagephotography/Getty Images

In school, we’re typically only rewarded when we give the right answers. That’s too bad because it prevents us from learning a critical lesson: that the real power lies in asking the right questions.

Over the years, through reading books, talking to my mentors, and interviewing those I admire, I’ve realized that the people with the most meaningful lives are the ones who never stop asking questions — to others, but just as importantly, to themselves.

It’s a realization that led me to develop my own practice of self-inquiry, which I now do regularly. At least once a month, I’ll pull up a list of questions I’ve written in my Evernote app, and check in with myself. The results have been profound. Based on my answers, I’m able to constantly make positive adjustments, check in on my progress, and reflect on my growth.

Here are the 14 questions I ask myself.

1. Am I happy?
   I like to start with some yes or no questions to assess how I feel. I don’t spend too much time answering these — I know that my first response is usually my truest one.
2. Am I grateful?
   I remind myself all the time to appreciate what I have. This question prompts me to do that.
3. Do I like my job?
   We spend most of our time at work, so it’s important to feel good about what we do.
4. Do I feel good?
   When I’m in a good mental and emotional place, I’m better equipped to connect with the people in my life. That’s why I work on my own energy before trying to help others.
5. What new things am I learning?
   If I don’t have a good answer for this one, I know it’s time to make a change. When I’m not learning, I’m not growing, and when I’m not growing, I feel frustrated and weak.
6. Where is my career going?
   I want to wake up excited every day for what’s ahead. Some advice: If you can’t identify your long-term goals, start thinking about them. You don’t need to know exactly what you want to do, but you should have an idea of the direction you want to take.
7. How meaningful is my work?
   This is very simple: I want to feel like my work matters.