4 Of The Most Important Questions You Can Ever Ask Yourself

When was the last time you gave yourself a self-development checkup?



Life is short, and only those who take time and effort to invest excellence in themselves will ever produce quality results. In this world of instant gratification, 24/7 entertainment and thousands of options for any choice, it is almost a given that we all occasionally overlook the most important parts of our lives. Here are four big-picture questions to ask yourself that, when answered, add exponential value to the purpose and clarity of your life.


1. How Does My Health Affect My Life?

Whether you have been blessed to experience full and vibrant health most of your life, can generally make it through the day or have major health goals you are still working on, most of us would agree physical health is important. It is one of those essential life factors that, when ignored, usually spells disaster for other areas of life. Few people question the value of striving for good health, but we rarely stop to ask ourselves: “How does my health affect the rest of my life?”

For better or for worse, your current state of physical health is the sum of all previous choices you have made. If you have trouble getting out of bed in the morning, this is due to habits that were created in the past. If you are able to enjoy sustained energy throughout the day without heavy dependence on caffeine or snacks, this is also because of previously created habits.

Take some time now to answer the following questions:

  • Do I feel comfortable in my own skin? If not, why is this?
  • Does my current level of health allow me to enjoy most days?
  • Are there persistent health troubles that, if remedied, would create a brand new level of health for me?
  • What is the single largest health step I can take this week that will dramatically improve my habits?


2. Am I In Love With Money?

This may sound laugh-worthy at first glance, but looking deeper this question reveals a stark truth. Yes, we all need money to live decent lives (and no one should be struggling to make ends meet at 60 or 70), but life has always been about more than money at the end of the day. Financial independence is necessary for a fulfilling adulthood, but money does not spell satisfaction in and of itself.

As we grow up, we are encouraged to “get a good job that pays well” so we can support ourselves and begin to craft a livelihood. But it is all too easy to overlook genuine fulfillment in the name of money, if we fail to take time to examine the experiences and skills that feel most natural to us.

  • Am I neglecting what speaks to my soul in favor of just getting paid more?
  • Do I find myself merely looking to “get ahead” instead of dedicating time and resources to helping others become successful?
  • Do I spend my free time with busywork or side jobs instead of creating something of value that will outlast time and money?
  • Am I concerned with just making more money in the present instead of building financial vehicles for the long-term?


3. What Does The Word “Work” Represent To Me?

Getting up (almost) every day to work is a reality we all face, at least in different formats. Everyone has bills to pay, leisure time to save for, clothes to buy and food to eat. So why is it that work itself is often a point of contention or personal dissatisfaction?

It is because we as a society have, in many ways, lost the vision of what work ought to produce, and what it means to be fulfilled by work. Tim Ferriss’ definition of work is my favorite. He says work is not what you do to earn money in order to cover expenses; at the end of the day that is more like slavery. Work is what you do – or what you could do – if money were no option.

Granted, not everyone can simply quit their job right now and run off to chase their dreams with full vigor. In fact, it usually takes anywhere from a few months to a few years to create a business that allows you to live life with full freedom and fulfillment with work. So, in the meantime (or before you get started on your business), answering the following questions is ideal:

  • What would I do for 20-40 hours per week if money were no object?
  • Am I working on slowly but surely making my passion my paycheck? Why or why not?
  • Am I completely content in my daily work as of today? Why or why not? What could I be doing better?
  • Am I jealous of others who seem to have the world at their fingertips? Why or why not?
  • Do I have regrets of what I have not done yet in life? Why or why not?
  • Have I experienced success with what I love? Why or why not?
  • What is success to me, at the end of the day?


4. Who Are My Closest Friends?

From the perspective of author and thinker C.S. Lewis, friendship is not a tangible essential in life, but it is one of those blessings that helps make the rest of life tolerable and livable. While friendship is a two-way street, the friends we choose often have different effects on us than we may expect.

Friendship is one of those rare areas in life where you have tons of control over what happens and when. Naturally, mistakes and accidents still occur, but you can always learn something from unexpected events. Trying times and challenging seasons bring out everyone’s true colors, which means it is important to know who your closest friends are. A friend is someone you can lean on when you have no other source of strength, so take some time and examine your closest friendships through these prompts:

  • Are the five friends closest to me people I can rely on when I’m facing a difficulty?
  • Do my closest friends mirror the values I want to live by in my own life?
  • Do I have friends that encourage me to be my best, rather than simply skating through life?
  • Do I have friends I can trust deeply – both in sharing about myself and hearing from them? Why or why not?

Use these four big-picture questions and their smaller prompts to bring about unprecedented clarity in your life. Life will always give you back what you first put in; excellence and fulfillment come to those who examine their roots in order to maximize their fruit.

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