5 Critical Questions To Ask If You Want More Success

Everyone wants answers, but have they really considered the question?

Below are the 5 critical questions to ask if you want more success and happiness in your life.

“Judge a man by his questions, rather than his answers.” – Voltaire

“The question isn’t who is going to let me; it’s who is going to stop me.” Ayn Rand

5 critical questions to ask if you want more success

Everyone wants the answers, but few have considered the question.

This week a young person asked me for some advice about a career move that he was considering. He was thinking about making a lateral move to another department of his organization and he wanted to know if I thought that his move would negatively impact his career in the long run.

I gave him the most considered opinion that I could conjure up at a moments notice. I suggested that;

  • he deeply consider his motivations for wanting to move as well as what he hoped to achieve in his career,
  • if he was feeling stagnant in his present role he should most certainly consider a move but he could also investigate opportunities for growth within his present position,
  • adding new skills and experiences in life is rarely (maybe never) a bad thing.

But since then I have been wondering if he was even asking the right questions. We will never get the right answers until we begin asking the correct questions.

Since that time I have been pondering which questions, that if answered truthfully would point us (or me) toward a completely new way of  living.

Following are;

5 Critical Questions To Ask If You Want More Success

1.  Why don’t you do the things you know you should? (Or stop doing the things you shouldn’t do?)

Most of us have things in life that we know we should do, but we simply don’t do them.

These may be major things, like leaving a job we dislike, breaking off a bad relationship, losing weight, starting a company, writing a book or quitting smoking. Attending to these things could have huge positive impact on our lives, but still we don’t act.

We also delay or avoid multiple smaller items, which have a funny way of growing into much bigger projects. For instance, I have been putting off cleaning out my garage for far too long. This minor task is now looking like a major chore, which, if not tended too soon will become a significant project

But the point is we all seem to have things that we should do, but don’t and I am left wondering why.

2.  What are you afraid of?

If there is one thing I am certain of it’s that the vast majority of our potential lies on the other side of fear. But before we can overcome our fears we need to know what that they are. Naming our fears takes away their strength.

Truth be told the majority of people are held back mostly by the fear of rejection. Our fear of failure and our fear of ridicule are really just the fear of rejection in disguise. These are all ego based fears and I know from decades of experience that injuries to our egos, while painful, are never life threatening.


And I will let you in on another little secret; most people are far too worried about how they look to worry about how you look.

If someone goes out of their way to try to make you look bad they are usually compensating for the fact that they feel they look REALLY bad and the only way they can feel better about themselves is by making someone look worse.

So if you are in any way held back by your fear of how other people perceive I invite you consider the following quote from the late, great Steve Jobs who said;

“Remembering that you are going to die is the best way I know to avoid the trap of thinking you have something to lose. You are already naked. There is no reason not to follow your heart.”

On the very rare occasion that I start to let my fears of rejection get hold of me I try to think about Steve’s quote to remind me that most things in life are just not that scary compared to death.

I invite you to closely examine the things that you are afraid and ask yourself two more questions;

Is what you fear truly something to be afraid of?

Is there any way that you can face your fear?

Another fantastic quote came from Nelson Mandela who said;

“I learned that courage was not the absence of fear, but the triumph over it. The brave man is not he who does not feel afraid, but he who conquers that fear.”


3. Is this how you really want to spend the rest of your life?

For a moment consider the trajectory of your life and ask yourself this question.

Is the way you are living your life truly sustainable?

Look at your career, your health, your home and your relationships and ask yourself if this is really how you want to spend the rest of your life. Life is not meant to be a struggle, but on occasion, we simply have to take one or two steps back in order to move forward.

If there is an area of your life that is truly unsustainable then some how you have to find a way to summon up the courage to make a change.



4.  What is your true purpose?

As Victor Frankl said; “Don’t aim at success. For success, like happiness, cannot be pursued, it must ensue, and it only does so as the unintended side effects of one’s personal dedication to a cause greater than one’s self.”

People can only achieve happiness and true success when they feel they are contributing to a greater good.

The nature of the greater good really doesn’t matter – it could be saving the rain forest, feeding the hungry, helping the elderly, healing the sick, serving the poor or climbing a mountain.

Being attached to a greater good gives us an increased feeling of personal value but we must be in active pursuit of that greater purpose.

5.  What do you have to be grateful for right now?

We live in a world of delayed gratification and postponed happiness.

We often fall into the trap of attaching our happiness to future events. We commonly say things like; I will be happy when I get a new job, a new car, a new house or more money. The problem is that none of this is true. New possessions or accomplishments make us happy for a short time, but not for long.

As referenced below at least one study has proven that, through a process called hedonic adaptation, people who win lotteries and people who become paralyzed through an accident both return to their original states of happiness within about a year.


Brickman, P., R. Janoff-Bulman, and D. Coates. Lottery Winners and Accident Victims: Is Happiness Relative?  1978.Http://pages.ucsd.edu/~nchristenfeld/Happiness_Readings_files/Class%203%20-%20Brickman%201978.pdf. Journal of Personality and Social Psychology, 1978. Web. 28 Oct. 2014

Given that few of us experience major lottery wins or serious accidents the majority of the things we look forward to have with longing or dread have little long-term effect.


Here is a great article from Wikipedia about hedonic adaptation if you are interested in further reading.

It is my opinion (supported by science) that It is a far better strategy to look for things in  our lives right now that we are happy about and grateful for – chances are you have a lot of them. While the pursuit of future goals is a truly worthy task, we all have to be realistic about their impact and learn that true happiness exists in the present, not in the future or the past.



So what about you? While looking for life’s answers have you really thought about the questions?

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Thanks for reading