68 Thought-Provoking Questions To Ask Yourself

In order to figure what would constitute a truly fulfilling and happy life, we need to have a clear sense of who we really are. Not who our parents, friends, spouses, colleagues, or the world at large thinks or demands that we be. Discovering and being our true selves can be a challenging task – after all, advertisers make money when we buy into their message that unless we have x, y, or z (namely, their product), we aren’t complete.

So, while you probably would agree that happiness is one of your top priorities, what does true fulfillment really mean to you? What are the essential ingredients? Without a clear sense of your bottom-line wants, needs, preferences, and personality, it’s quite possible that you may find yourself chasing items, people, and lifestyles that won’t bring you even one step closer to being truly happy and content.

After all, someone else might prize their relationship with their friends, whereas you place a higher importance on your spouse.

Some people feel most alive when they have a lot of proverbial plates in the air, while other people feel most centered and fulfilled when putting all of their attention on one project.

You may cherish time alone or with one other person, whereas most of your contemporaries live for large, lavish parties and being social butterflies.

Do you have a good sense of what makes your life worth living? And if not, might it not be wise to spend some time contemplating this? After all, you don’t want to wear yourself out climbing the ladder, only to realize years (or decades from now) that the ladder’s been leaning against the wrong wall.

If the very idea of looking within strikes terror in your heart, don’t worry – you’re certainly not alone. We’re evolutionarily wired to seek inclusion in social groups. Yes, this is true, even if you consider yourself a loner. For as long as the human race has existed, belonging to a group has meant (at least in theory) access to food, protection, and other shared resources. In addition, a sense of belonging is vital to our emotional and spiritual development. So, there’s a pull within us to get along and go along with the tide.

However, it’s also true that each of us is unique, with our individual, highly specific wants and needs. And it’s inevitable that at times these will be at odds with those of the people around us. This can feel threatening, and as a result we may either stifle our true wishes in order to “get along” or become angry or feel threatened if other people’s priorities don’t align with our own. There is also a third alternative – that of being honest with yourself (which is a lifelong journey), yet respectful of other people’s values.

But, first, get clear with yourself on where you stand today (not last month or last year) on what really makes you tick. It can help to block out an hour or two on a regular basis, such as weekly, to sit with your thoughts and ponder the following questions.

What are the three things I’m most grateful for?
What am I looking forward to today?
What keeps me motivated?
What would my perfect day look like?
What do I enjoy doing?
When was the last time I laughed really hard?
When was the last time I cried?
Do I surround myself with people who bring out the best in me? Do I bring out the best in them?
What qualities do I admire most in other people?
What qualities do I admire least in other people?
Do I prefer a small or a large group of friends?
What does my ideal intimate relationship look like?
How did my parents’ relationship influence my current feelings about relationships and marriage?
Do I like who I am right now? If not, what adjustments do I need to make?
What is my biggest strength?
What is my biggest weakness?
What does my ideal self look like?
What are some of my favorite pieces of advice?
How would I answer the question “I’ll be happy when…”?
Am I good at standing up for myself and my beliefs?
Am I self-destructive in any way?
What would I do with my remaining days if I had only one year to live?
How is the current pace of my life? Is it too fast? Too slow?
What am I curious about? If I could learn a new skill, what would it be?
Do I like surprises, or do they throw me off-balance?
Do I need to have a lot of control over my life, or am I okay with releasing control?
How do I define my spirituality? Do I have spiritual beliefs that help guide me?
What’s the one thing I can’t live without?
What could I easily live without?
How would good friends define my character? What three words would they use that would best describe me?
How would I like people to describe me?
Am I a leader or a follower?
What would I be doing if financial considerations or other people’s opinions didn’t hold me back?
Have I done something recently that I’m proud of? If so, what?
What talents and skills do I have to offer? How am I using these to enrich other people’s lives? What gifts do I want to share with the world?
What habits, relationships, possessions, or wishes can I let go of to simplify my life?
Am I more of an introvert or an extrovert? Do my lifestyle choices reflect this?
How do I recharge?
How and where in my life can I relax and take it easy?
If I could travel anywhere in the world, where would it be and why?
What makes me feel truly alive? When was the last time I felt like this?
Who do I look up to? Why?
Who was the biggest influence on me when I was growing up?
What three life lessons have I learned the hard way?
How can I look at past mistakes with more self-compassion, so I can forgive myself and drop this excess weight of self-condemnation?
What less-than-ideal aspects of my life do I need to accept and make the best of, rather than lamenting? How can I practice acceptance, resilience, and gratitude in these areas? How can Ibe more grateful for what I have?
Do I focus more on solutions or problems?
When was the last time I found the “silver lining” in a bad situation?
What are some of my limiting beliefs that might be holding me back?
What’s draining my energy?
Do I drive myself too hard?
Do I challenge myself enough? Or do I live too much within my comfort zone? Are my self-expectations too high? Too low?
If money weren’t an issue, would I still be in my current job? If not, what would I like to do instead?
What’s my career goal for the next five years? How does this line up with my ultimate goals for my life?
Do I learn something new every day? If so, what was that today?
What new thing do I want to learn in the next year?
What does self-care look like to me?
How important is my health to me, and why?
How well do I treat my body?
How is my relationship with food?
What does my exercise regime look like?
How are my sleep habits? Am I a night owl or a morning lark?
What five things can I start doing to take better care of myself?
How do I define success?
What do I want my legacy to be?
Would I like to be proudest of my accomplishments or of my character?
What’s one motto I can live by, which my future self will thank me for?
What can I do this month to take action on that choice? This week? Today?

Now what? First of all, it will help to revisit these questions from time to time, since your answers are likely to change. Which is as it should be, as we are constantly growing, changing, and making appropriate adjustments.

Also, try to rearrange your life and how you spend your time, energy, and resources, so you’re living more in line with your values and what brings you joy. For instance, if you’ve listed “my family” as your top priority, how has this been playing out in your life? Do you spend sufficient time with them? And when you’re with them, do you put aside distractions so you can really be there 100%? Do you feel close to your family emotionally, and if not, what could strengthen your connection? Can you show more interest in them or share more of yourself with them?

Another example: If being physically fit and healthy is a major determinant of your happiness level, what are you doing to promote wellness? Do you have an exercise regime that maintains or increases your strength, flexibility, and endurance? If so, is it sufficiently enjoyable, so you don’t get bored? If not, what can you do to change things up? Would teaming up with an exercise buddy help to get you to the gym, tennis court, or yoga class? Or do you prefer working out on your own, such as taking a long jog, to clear your thoughts? Whatever the case, as you more closely align your preferences with your actions, the more content you are likely to feel.

You’re likely to find that the better you know yourself, the more fulfilling your relationships will be. Another benefit from self-knowledge is that you’ll use your time, energy, and resources more effectively. Why? Because you’ll be able to distinguish between what really calls to your soul (and thus what to say yes to) and to what you can politely say, “No, thank you”.

Record your answers in a journal. This way, you’ll have a record which you can review at a later date, which can be illuminating. It’s common to find that some of your answers will change over time.

Keep in mind that there are no wrong answers. What’s important is your intention to explore your personal truths. These may take awhile to surface, so don’t worry if you initially draw a blank when trying to answer these questions. Maybe you jot down just a word or two. Or doodle. Or draw a picture. Just give yourself a specific length of time to sit with a question or two – the success is in providing yourself the space to listen to your heart.