When I posed this question on Twitter, the stories poured out and patterns emerged. Real regrets are about bad choices in love, learning and loss, being held back by fear – and self-blame

My 20-year-old son just moved into a fraternity house at his college in the US. Last month, I spent three days there trying to turn his bedroom from a fluorescent-lit hellhole into a page from an Ikea catalogue, and while making up flat-packs, we discussed his hopes and plans for the next three years … what he wanted from life, from love, his strengths, his fears, and how to approach his college years so that he could set himself up for a life well lived. On the final evening, I found myself alone in a horrid Illinois hotel, still thinking about my boy’s apprehensions for his journey into adulthood and how I might help him make decisions he would never regret.

I went to Twitter and typed: “What is your biggest regret. Asking for a friend.” The response was huge. It wasn’t just big in volume – more than 300 replies – but the tweets were devastatingly honest. I had casually asked a question that, surprisingly, a lot of people really wanted to answer. These were sad, sobering, enlightening responses – big stories told in 140 words to a stranger on a Saturday night. I don’t know why so many people had such strong regrets living so close to the surface – but by the end of the evening, I felt I might have learned more about life through what people regretted not doing, than through 55 years of being given advice about what to do. I’m clearly no authority on this subject, but I’d love to tell you a bit of what I saw that night.

Very few replies were lighthearted – though I loved the ones that were …

“Being sick in my father-in-law’s hand”

“Not flying on Concorde to New York with Lionel Richie. He wanted to take me for dinner. I was working. #muppet”

“#TossUp between joining the Jehovah’s Witnesses at 14 & living in a high-control group for years - OR - not seeing Patrick Swayze in Guys & Dolls”

But what emerged is that real regrets are about bad choices. Not bad things happening to you, or the way that life has punched you in the face: regret is a deep sorrow about something you did, or something you failed to do. It’s anger at yourself for having enough information to have made the right decision, but making the wrong one – ie it’s about self-blame. All I had expected were a few variations of the classic “I regret working too hard – should have spent more time with the kids”, but nobody said that – not one person. And most of the replies divided into six specific categories. By far the most frequent were regrets about not doing the right thing when someone died.



“Not being with Mum at the end. She died 2 hrs after I left her, it haunts me still”



“Not calling my Dad the night before he suffered a fatal heart attack, just because I had only lost ½lb and I didn’t want him to be disappointed”



“My cousin rang me on Christmas eve and I really rushed the convo because I was cooking … she killed herself on Boxing Day”



“Not staying with my mum to the very end. I was afraid and needed to go home to my kids. She died overnight. I forever fear she was in fear. The hardest part was not the decision, but coping with the ‘what if’ afterwards”



The truth is that a) we all try to make the best decisions possible using the information available at the time, and b) we all mess up. But it doesn’t help the pain to point that out.



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The saddest stories were from people who had been abused – and even in 140 characters, they were terrible. The damage, trauma and pain came from a range of different circumstances, but the “regret” in all of them seemed to be the same – that the survivor hadn’t spoken up sooner. It was one area in which the abused had control, and they regretted not exercising it.



“Not having the courage to speak up as a teen victim of sexual abuse”



“Not speaking up sooner about stepfather. Took the Savile situation for me to realise I would be believed.”



“Biggest regret.... my Grandad... abusing my brother and I ... not having the courage to disclose so I could have protected him ...”

They all had the same message. Maybe these survivors passing on this single regret with such unity and clarity will encourage others to exercise that one vital control. I was humbled by their honesty.

Education was high up the list – there were many more regrets to do with school and college than I would have expected.



“Never going to University. Left me disadvantaged all my life. Never lived my potential”



“Not getting a better education and working full time from the age of 16”



“Leaving school in 80s & not going to art college. I wanted to get a job. Found one. Still at the same workplace now”



And then, as if in reply, I also got a set of tweets filled with big solutions.



“My regret: listening to teachers who said I was stupid because I can’t spell. After 2 degrees was told I’m dyslexic. Am currently on 4th degree”



“For me it used to be going into teaching instead of law. I righted my regret. Best choice ever. I was a wimp in my 20s. Changed for better”



“Not finding the Open University earlier”



In an age of teen entrepreneurs and endless messages telling children to “follow their dreams”, these feel like crucial lessons. I’ve read them out loud to my teenage sons. More than once. As well as the many tweets like this:



“That my mum died too young to see me turn from an ungrateful, truculent teenager into a person and father I hope she’d be proud of”



Might even get that tattooed on to their arms.



Career-choice regrets made me realise a pattern was developing … regret seems most often to be about fear. Fear of getting it wrong, leading to an unfulfilled life, followed by self-blame for being fearful.



“Too scared to risk failing at something I loved, so I succeeded at something I had no passion for”



“Not following my dream to work in radio”



“Listening to my dad when he said my voice was too weak to be a singer”



“Not taking the job in Paris”



Also – a lot of lessons to be learned here:



“My regret: Going to the office Christmas party and then having to look for a new job the next day … Not my fault the boss’s wife turned out to be more than just a flirt”



And then, perhaps less surprising, there was love: a few tweets from people regretting that they had declared their love and ended up having their heart broken, but many, many more regretting not being braver and not risking vulnerability – the regret of having been afraid. There’s definitely a lesson in there: while there’s always the possibility of regrettable rejection, it’s better than the regret of not having tried.



“Not telling someone I loved them. 20 years too late now”



“Marrying the first person who asked because I thought no one would ever ask me”



“Not following my heart many times over the years, and allowing my limited expectations to define my life and decisions. After reading many answers in this thread, I’m about to change that”



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In a way most complex, there were a lot of tweets about anxiety, and what intrigued me was the self-blame. If a regret is defined as “feeling sad or disappointed about something you have done, or failed to do”, then it would imply these tweeters feel that living in fear is some sort of choice. Nobody said, “I regret that I got cancer”, because nobody chooses to contract the disease, therefore it’s not technically a regret. But mental health still carries the stigma that it’s a “weakness” of some sort – and the regrets played that out:



“I regret being scared all the time”



“My regret: being too anxious and not assertive enough”



“I regret not coming out sooner. Wasted years worrying about it”



“Worrying. About pretty much everything. All the time”



“Being too afraid to live”



Mental health is tough enough to handle without adding self-blame – but anxiety and self-reproach seem to be a “buy one, get one free” package. Depression’s most successful con trick is to convince its victims that it’s their own fault. The tweet “I regret allowing depression and anxiety to rule my life since teen years” could have been reframed as “I have a mental illness against which I have felt powerless since my teens”. But her tough life had been turned by her head into a personal failing and therefore a “regret”.



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It was encouraging that right alongside the people who regretted a life lived in fear were others who had made a change – now regretting the time it had taken to find their solution for this exact problem:



“Taking far too long to realise that everyone else in the world is also imperfect and winging it – just like me”



“Worrying too much about what other people thought of me – trying to uphold what I thought were their beliefs not mine”



“I regret not getting antidepressants 20 years earlier”



“Being scared all the time. Moved to France – still scary but food and life is good!”



“I used to worry about keeping up appearances but when I had a crisis ppl were so supportive”



Where there’s life, there’s clearly time to turn regret around.



Intriguingly, of all the replies, only two people mentioned money – one regretting a flat they hadn’t bought, one regretting a sale. And there were some beautiful stories.



“didn’t know I could be an athlete til I saw London 2012. This weekend I became World Champion Kettlebell Lifter in 55-59 age group. Regret … perhaps I could have been an Olympian”



But my favourite of all the replies was from @dorey1414. She tweeted me this:



“I’m 54, no friends, or family, only 18 followers – the least on here – but I have everything I need. Biggest regret – not listening at school”



At last, here was one tiny area I could be useful … I retweeted her words and asked Twitter if they could help. Ten minutes later her follower count had gone up to 24. By the morning it was 360. She now has more than 900 and is massively excited about it, starting enthusiastic conversations with dozens of her new followers. Having left school before her exams and worked for 38 years in a job she doesn’t enjoy, she’s using this moment as a chance to address the regret, and has just bought her fourth book …



“The last 20 years have been particularly bad, no one should wake up dreading the day ahead, I thought it was all I could do, but maybe not …”



Before I flew home from Chicago, I texted my college son with this advice: “The most debilitating enemy you can have is your own fear. Own your mistakes but don’t dwell on self-blame. Be confident. Learn from your teachers – you’ll never regret that. Take risks – they may go wrong but it’s better than regretting not having tried. Ring your mother, be kind to everyone and FFS change your sheets.” I’m already regretting the shallowness of the “change your sheets” bit.

