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5 Strangers Reveal Their Biggest Regret To Date

Do you ever wish for a do-over? A chance to go back in time to seize an opportunity you were too scared to take?

In life we have many ultimatums and options and choices. Sometimes we roll the dice and get it right. There are some cases where our logic is thrown out the window. We clam up, get afraid and do nothing. Or we naively think something better is coming along. It is hard not to kick ourselves with regret, wishing we could reverse time and do it all over again. The could haves or should haves and what ifs, haunt us terribly each night.

“It’s better to look ahead and prepare, than to look back and regret”.

Jackie Joyner-Kersee

According to Psychologist Professor Shai Davidai, regrets about inaction haunt most of us for longer periods! Sadly, in life there is no reset button and time travelling is still a work in progress (said no-one ever!). We can only hope we will learn from our mistakes and pass the lesson on to those none the wiser.

Regrets come in different magnitudes and vary in effect. We must learn from our mistakes and share the insight.

5 strangers tell us their biggest regrets in life and what they would have done differently:


Anonymous, 26 years old. Occupation: Legal Assistant.

“My biggest regret so far has been my lack of faith in myself. For too long, I accepted people’s view of me as my own. I accepted they knew what my capabilities were and lived to their expectations. Because of this I lacked the confidence to pursue my dreams and I became too dependent on others views of me. I am now trying to find the courage to do things I have always wanted to do”.

“My advice to someone going through this would be to listen to yourself, because only you know what you are capable of. If you don’t, you will risk losing out on a lot and will spend years trying to overcompensate for it. Also, you will lose everything you once liked about yourself. I have accepted now, fear is the only thing standing in my way”.

woman writing on a notebook beside teacup contemplating biggest regret
Photo by Tirachard Kumtanom on


B, 27 years old. Occupation: Teaching Assistant.

“My biggest regret [in life so far] was not being focussed from the ages of 18 to 24. I was far too social during that period and surrounded myself with negative people who complained about their jobs and were envious of other people. I learned you are the company you keep. As a result of this, my pursuit towards a legal career failed and I am now in my late 20s not making much progress.”

“My advice to younger men and women is to focus on your career at an early age or you will go into your late 20s, 30s or even 40s struggling to make ends meet.”

young woman using laptop in bed and resting. Wasting time is her biggest regret
Photo by Ketut Subiyanto on


Anonymous, 24 years old. Occupation: Finance.

“My biggest regret in my life so far is being too lazy. I have spent my early years being quite passive and thought things will just fall into place. I would settle for average and not push myself to achieve the best. I have now bettered myself; I seize opportunities and look for them. It is a good way to grow, and I am excited for the journey to continue”.

“My advice to someone who is going through this is to reflect. Reflection is important for growth. I would suggest they seek opportunities, set goals, and find the motivation to stick to them”. 


N, 27 years old. Occupation: Employment Advisor.

“My biggest regret to date is not letting people get to me. I felt like when people would make me upset, I would react irrationally, and I failed to cope better.

If anyone was going through this, I would advise them to think before they react. You cannot control other people and the things they say but you can control your reactions and how you let things affect you”.


H, 24 years old. Occupation: Student Recruitment and Support Advisor.

“My biggest regret is not completing my degree in full and changing over to an apprenticeship. To anyone out there that is struggling with their degree and feel like giving up, my advice would be to put your head down and find motivation to complete the degree”.

all we have is now neon signage on black surface eluding to biggest regrets we may have
Photo by Daria Shevtsova on


When you are at the end of the road with a choice to turn left or right, don’t be afraid of taking the path you want. We know it can be risky and difficult. Or sometimes it could be scary! Learning to do things you want can be hard. Especially, when you are afraid of falling flat on your face.

Instead of being afraid of what could happen accept, if you don’t snap up what you want now, you may not get the same chance again. Find the courage to say “yes”, just remember making mistakes is part of the journey!

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