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14 Questions to Ask Yourself Again and Again
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.
- 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.
- Am I grateful?
I remind myself all the time to appreciate what I have. This question prompts me to do that.
- Do I like my job?
We spend most of our time at work, so it’s important to feel good about what we do.
- 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.
- 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.
- 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.
- How meaningful is my work?
This is very simple: I want to feel like my work matters.
- How can I get better at what I do?
The better I become at what I do, the bigger impact I can make, which leads to both more satisfaction and more income.
- What’s my number-one priority right now?
I probably ask myself this question every day. When we focus on too many things at the same time, we don’t make much progress at all.
- How can I achieve that number-one priority more quickly?
This question is not about being impatient — it’s about being creative. Imagining how I might achieve my goals faster pushes me to come up with new ways to get better results.
- What tasks should I stop doing?
We all waste time. It’s important to identify the tasks that distract you from your real goals, and stop doing them.
- What tasks am I procrastinating?
It’s always tempting to avoid difficult or uncomfortable tasks. But putting them off until tomorrow (or months from now) will only make them that much more unpleasant when you ultimately do tackle them.
- How can I help one person today?
My life has more meaning when I do something generous with my time. A simple gesture is enough. I might decide to call a family member, or cheer up a friend.
- What questions am I not asking myself?
This list of questions will always be changing — because I myself am always changing. Try coming up with a list of your own, and then bring it out every month or so. After a while, you may just find that your life is better simply because you took the time to ask yourself how things were going.