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Reassessment of yout life – 20 Questions

The 20 Questions That Can Change the Way You See Your Life

Every now and then, we need to stop.

Not because something is necessarily wrong, but because life has a way of carrying us forward without asking whether we are still heading in the direction we actually want to go.

We wake up. We work. We take care of responsibilities. We maintain relationships. We pay bills. We solve problems. We make plans.

And somewhere along the way, we can become so busy living our life that we forget to examine the life we are living.

Perhaps the most valuable thing we can do from time to time is pause and ask ourselves:

“How am I actually doing?”

Not how successful do I look.

Not how much money do I have.

Not what do other people think of me.

But genuinely:

Where am I in my life?

Here is a simple exercise.

Take a piece of paper and score each area of your life from 1 to 10.

1 means: I am deeply dissatisfied, disconnected or neglecting this area.

10 means: I feel deeply fulfilled, healthy, connected and aligned in this area.

Don’t try to impress yourself with your answers.

Be honest.

Because self-awareness begins where self-deception ends.

1. How is my physical health?

Am I looking after my body?

How are my sleep, nutrition, movement, energy and general physical wellbeing?

Score: /10

2. How is my mental and emotional wellbeing?

How often do I experience peace?

Am I emotionally balanced, or am I constantly living in stress, anxiety, anger, fear or overwhelm?

Score: /10

3. How is my relationship with myself?

Do I actually like the person I am becoming?

Do I respect myself?

Can I accept my imperfections without constantly attacking myself?

Score: /10

4. How is my experience of love and intimacy?

Do I experience genuine love, affection, companionship, vulnerability and emotional connection?

Am I giving love as freely as I want to receive it?

Score: /10

5. How are my family relationships?

Are my relationships with the people closest to me healthy and meaningful?

Are there conversations that need to happen?

Are there wounds that need healing?

Score: /10

6. How are my friendships and social connections?

Do I have people with whom I can be completely myself?

People I can laugh with?

People I can be vulnerable with?

People who know the real me?

Score: /10

7. Do I have a sense of purpose and meaning?

Do I understand why I am doing what I am doing?

Does my life feel like it has meaning beyond simply getting through another day?

Score: /10

8. How satisfied am I with my work or career?

Does my work utilise my abilities?

Does it challenge me?

Does it give me a sense of contribution and fulfilment?

Or am I simply working to survive?

Score: /10

9. How is my financial wellbeing?

Do I feel financially responsible and secure?

Am I living within my means?

Am I building towards greater freedom, or am I constantly experiencing financial pressure?

Score: /10

10. Am I still growing?

Am I learning?

Am I challenging my beliefs?

Am I developing emotionally, intellectually and personally?

Or have I become comfortable with what I already know?

Score: /10

11. How is my spiritual life?

Do I have a connection with something deeper than myself?

Do I have faith?

Do I make time for reflection, prayer, meditation or spiritual awareness?

What gives my life its deeper meaning?

Score: /10

12. How am I using my time?

This may be one of the most important questions of all.

Am I spending my finite time on what genuinely matters to me?

Because time is the one currency we cannot earn back.

Score: /10

13. How much joy is there in my life?

When was the last time I laughed until I couldn’t stop?

When was the last time I did something simply because it made me happy?

Am I allowing myself to experience joy, playfulness and fun?

Score: /10

14. Am I still experiencing life?

Am I exploring?

Am I trying new things?

Am I travelling, learning, meeting new people and stepping outside my comfort zone?

Or has my life become predictable?

Score: /10

15. Does my environment support me?

Does my home feel peaceful?

Does the environment around me reflect the person I want to become?

Do I feel safe, comfortable and at home in my own space?

Score: /10

16. Am I contributing to something bigger than myself?

Am I giving something back?

Am I helping another human being?

Am I caring for an animal?

Am I doing something for my community or the planet?

A meaningful life isn’t only about what we accumulate.

It is also about what we contribute.

Score: /10

17. How emotionally free am I?

What am I still carrying?

Resentment?

Anger?

Guilt?

Shame?

Fear?

Grief?

An old relationship?

An old version of myself?

Sometimes the greatest weight we carry isn’t something in our present.

It is something we refuse to release from our past.

Score: /10

18. Am I living authentically?

Am I living according to my own values?

Or am I living according to what my family, society, friends or other people expect from me?

There is an enormous difference between living your life and performing the life other people expect you to live.

Score: /10

19. Where am I heading?

This question can be confronting.

If I continue living exactly as I am living today, where will I be in five years?

Will I be happy with that destination?

If the answer is no, perhaps something needs to change today.

Score: /10

20. Overall, how satisfied am I with my life?

Forget what you own.

Forget your job title.

Forget your social status.

Forget what other people think.

If you could stand outside your own life for a moment and simply observe it…

How satisfied would you be with the life you have created?

Score: /10

Now Look at the Numbers

Don’t become obsessed with your total score.

The total isn’t the point.

Instead, look at your five lowest scores.

Those are the areas that may be asking for your attention.

And then ask yourself:

What is missing here?

What am I tolerating that I know needs to change?

What have I been avoiding?

What is within my control?

And most importantly:

What is one small thing I can do this week to move this score from a 4 to a 5?

You don’t have to transform your entire life overnight.

You don’t need to fix everything.

Sometimes transformation begins with one honest conversation.

One boundary.

One apology.

One doctor’s appointment.

One walk.

One night of proper sleep.

One phone call to someone you love.

One decision to forgive.

One decision to let go.

One decision to finally begin.

The Purpose Isn’t Perfection

We often think that a successful life should be a 10 out of 10 in every category.

I don’t believe that is realistic.

Life moves in seasons.

There will be times when your career is flourishing but your relationships need attention.

There will be times when your finances are difficult but your spiritual life is incredibly strong.

There will be seasons of grief, rebuilding, growth, adventure and rest.

The purpose of this exercise isn’t to judge yourself.

It is to see yourself.

Because we cannot change what we are unwilling to acknowledge.

And we cannot intentionally create a different life while remaining unconscious of the life we are currently living.

So perhaps once or twice a year, stop.

Put the phone down.

Turn off the noise.

Sit quietly with yourself.

And ask the 20 questions.

Not with judgment.

With curiosity.

Not with shame.

With compassion.

Not asking:

“What’s wrong with my life?”

But asking:

“What is my life trying to teach me?”

Because perhaps the greatest form of personal growth isn’t becoming somebody completely different.

Perhaps it is becoming increasingly conscious of who we are, what matters to us, what we need to release, what we need to nurture, and where we want to go next.

Your life is happening now.

Don’t wait until something breaks before you stop to ask whether it is working.

Pause.

Reassess.

Listen.

And then take the next step.

One point at a time.

Gerald Crawford in Stellenbosch

Gerald Crawford in Stellenbosch

My Personal Motto Is: With experience and study comes insight with insight come wisdom with wisdom comes moments of absolute clarity, transcendence then follows.

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