Challenges are part of life. We all have them. It’s overcoming challenges and growing as a result of them that help us progress in life. End of year is a good time to reflect on your challenges (though of course, reflection with a purpose is powerful at any time of the year!)

Reflection can lead to us taking empowering action. Reflection with purpose can lead us to make ground-breaking changes in our lives.

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Important Disclosure – I am not a trained medical professional, therapist or counselor. If you need help with depression, anxiety or suspect you may be struggling with a mental illness, please see help from a medical professional.

Never be ashamed to reach out for help and assistance. Everyone needs help from time to time. I’m currently working short-term with a counselor about a particular issue that I have been struggling with and it’s helping a lot!

20 Questions to Reflect on Your Challenges

Now let’s talk about our questions.

Don’t worry if you don’t have an answer for every question but definitely give some thought to each one. If you didn’t have a challenge yourself, you might have been known someone close to you who did.

After each question, I’ve added some ideas to get you thinking but again if they don’t relate to you, don’t worry.

You’ll get more out of this exercise if you write down your answers, so grab your favorite journal or notebook and get busy. Think about and dig into each question.

Let’s get started.

What were your greatest work challenges?

You might have dealt with crazy deadlines and heavy workloads or you might have had to deal with a challenging co-worker or boss.

Remember work doesn’t have to mean working as an employee in a company – you could be a stay at home parent, self-employed, a student or even job hunting – because let’s face it, it’s all hard work at times!

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What were your greatest financial challenges?

You may have struggled with debt problems, bad investments, not enough money for retirement, not being able to pay the bills, spending more money than you earn, or not having a budget in place.

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What were your greatest relationship challenges?

Perhaps you were single when you didn’t want to be? Perhaps you are in a relationship but want to be single? Or perhaps your relationship or marriage is struggling?

You might want to improve your relationship with your family.

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What were your greatest health challenges?

Unfortunately, our health can be one of the things we put on the back-burner when we are busy.

It sometimes takes a health crisis or emergency of some kind, to remind us just how important our health is.

Without good health, everything else suffers.

Perhaps the question should be, what health challenges have you been avoiding this year? (I can relate to this one because I’ve been on the avoiding side of things myself. Thankfully, I recently found a great new doctor and we are working together to improve my health.)

What were your greatest personal challenges?

Did you struggle with self-doubt? Were you held back by feelings of not being good enough?

You might have felt unmotivated or struggled with feelings of overwhelm.

A fantastic book for self-doubt and not feeling good enough is You Are a Badass by Jen Sincero.

I have read this book multiple times and it has helped me a great deal. If I’m having a rough day, I throw it in my handbag, read a chapter on the way to or from work and it picks me right up and gets me back on track!


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How did you take care of yourself when going through a challenge?

Unfortunately, the answer for many of us is – I didn’t!

When we are busy, stressed and dealing with a big problem, taking care of ourselves can fall by the wayside. Of course, the truth is dealing with a challenge is when we need self-care and self-love the most.

Your self-care could be something like getting regular massages, eating healthy food, spending more time with family and friends or spending time with a pet. Caring for yourself could be about reaching out to others for help.

What challenges did you have no control over?

These sorts of things usually involve something like a family member falling ill, losing your job or being involved in a car accident.

This can be some of the hardest stuff to come to grips with because we have no control over the initial incident.

We do have control over how we think and feel after the incident, however.

Which challenges did you have more control over than you thought?

Give this one some serious thought. Often we feel powerless or trapped in a particular situation but in fact, we have more power than we realize.

Often the true power lies in adjusting our attitude and our mindset.

Often we know the answer to a problem. We know what needs to be done to fix the problem, but we struggle taking action.


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Did you make a particular challenge (or drama) bigger than it actually was?

Be totally honest with yourself on this one!

Sometimes we can make a huge drama out of something that isn’t one. By stressing, worrying and catastrophizing we turn a small problem into a huge drama.

Related post – How to Stop Creating Drama in Your Life

Did you create a challenge that didn’t exist?

This is a follow on from the previous question but we’re ramping things up a notch.

Did you create a problem or challenge that didn’t even exist?

In other words, did you stress yourself out big time over something that DID NOT HAPPEN? 

If you did, don’t feel bad, many of us (me included) do this from time to time. Some people do it more than others.

As I often say to my Mum – let’s focus our energy on fixing the problems we currently do have, instead of worrying about the ones that haven’t happened and probably never will.

Related post3 Ways to Stop Bringing Negative Energy into your Life

What challenges were caused by self-sabotage?

While we are often quick to blame our challenges on other people, the truth is many of them are created by ourselves.

We self-sabotage and create our own challenges.

We get in our own way and create our own obstacles.

Did you struggle with procrastination, laziness, self-doubt, lack of self-discipline or comparing yourself to others?

We often know our favorite self-sabotaging techniques but we choose to ignore them and let them run amok in our lives. Now is the time to get honest about your self-sabotage!

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Were some of your challenges self-inflicted bad habits?

Think along the lines of smoking, drinking too much, overeating, choosing inappropriate relationships, gambling,
overspending or drug use.

Are some of your challenges fuelled by bad habits?

The good news is that bad habits can be changed, which means you can replace your bad habits with good ones and significantly reduce the challenges in your life.

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Did you face challenges that were a result of a values conflict?

For example, you may value family over work but you spent most of your time at work and very little quality time with your family.

This would create conflict and a challenge because your life is not aligned with a core value which is your family.

Challenges can be created when we take action against a core value. Once you are aware of your values being out of whack, you can work towards correcting them.

Related post – What do you Value Most – Experiences or Possessions?

Do you know what your core values are?

Perhaps the problem is you aren’t aware of your core values?

If you aren’t aware of your values, you will face challenges.

Not knowing your values, could give you a feeling of being unhappy but not really knowing why you are feeling unhappy? When it comes to your values, it is vitally important that you are living your values and not someone else’s.

Related postKnow Your Own Values

What challenges did you face that was caused by not having better boundaries in your life?

If we don’t have boundaries in our lives, we live a life of chaos.

Boundaries are an important part of life. Having strong interpersonal boundaries is one of the best ways to show respect for yourself and for others.

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What challenges are you proud of yourself that you overcame this year?

Overcoming challenges can be tough. Working through challenges can be hard and draining and can make us feel like we are not coping very well with life.

But we are always much stronger and braver than we give ourselves credit for, so what are you proud of yourself for this year?

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Do you need to forgive yourself in regard to your challenges?

Perhaps you are struggling with a forgiveness issue?

Are you having trouble forgiving yourself with how you dealt with a particular challenge or is not being able to forgive yourself (or someone else) causing challenges in your life?

Forgiveness is a powerful, powerful force. Forgive yourself, forgive others and stop holding yourself back.

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Who is the person (or people) who most helped you through your challenges this year?

It’s always important to remember those who help us when we need it the most.

It’s important to remember the people who stand by our side when we are struggling. It can be easier to have a lot of friends when life is all fun and games, but it’s the tough times that show us who our true friends really are.

Sometimes it can be the people we least suspect!

It could even be a complete stranger showing us a simple act of kindness.

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Which challenges were blessings in disguise?

Yes, you read that correctly. Often our challenges can lead us onto bigger and better things!

You might have been made redundant but then gotten a much better job or started your own business. A relationship
might have ended but you find yourself loving the single life and enjoying our freedom.

What valuable lessons did you learn from your challenges?

This is where the whole personal growth through challenge kicks in. This is where the rubber meets the road as they say!

We have challenges so that we can learn and grow from them.  

We learn from our challenges so we can make better choices and decisions going forward. We get better at taking actions as we learn from our challenges and our mistakes.

A gentle reminder – these reflection questions aren’t about getting angry or bitter about what has happened to you or wallowing in misery about the past, so if you feel yourself getting bogged down and getting stuck in the past, take a break, get yourself in a better mindset, than come back and continue.

Reflection isn’t about blaming others, it’s about being honest with ourselves and taking responsibility for our thoughts and actions.

Reflection is about healing and growth.

Head back and read through each of the questions again, with a specific focus on what you have learned (not just about what happened).

Ask yourself what were the lessons learned from your challenge and how can they help you moving forward?

If the challenge is an ongoing one, ask yourself – what are the next 3 steps I can take to fix or work through this issue?

If you know you played a large part in your problems, ask yourself – what can I learn so that I don’t make the same mistakes or find myself in the same situation?

Overcoming our challenges fuels our growth. Challenges make you a stronger, better and hopefully a more caring person. When we honor our struggles as well as honoring other people’s challenges, we all move forward together.

Because life is about balance, my next post will feature questions to reflect on your joy and happiness throughout the year because we must always acknowledge both the struggle and the joy.

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Read Next – 20 Questions to Ask Yourself if You Had a Tough Year