Okay so we need to talk. You know that 2am spiral where you’re lying in bed doing a full forensic audit of every decision since 2019? The life before everything led to a snowball effect in 2020, that online dropped major, the situationship you definitely should’ve ended in month two, the job you took ‘just for the paycheck?’ These books are the group chat intervention you didn’t ask for but desperately need.

Do not let the title fool you, this has nothing to do with anything you are thinking. It’s actually about a farm kid who becomes a quiet, unremarkable English professor, and on paper it sounds like the most boring plot synopsis of all time. But it’s devastating in the best way, it makes the case that an ordinary, ‘unimpressive’ life spent doing something you actually cared about was never a waste. If you’ve been comparing your career to a LinkedIn influencer’s, this book will humble you and heal you simultaneously.

This one follows two best friends who build video games together across decades, through fallouts, disability, grief, and everything in between. It’s not preachy about regret at all, it just shows you that the ‘wrong turns’ in a friendship or a creative path are usually just… part of walking on the path itself. Also it’s genuinely one of the best books published this decade, so this is not a filler pick, it’s the main character of this list.

A botanist and Indigenous scientist writes about plants, reciprocity, and what it actually means to live in relationship with the world instead of extracting from it. This sounds unrelated to ‘regret’ but trust the process, it reframes what a meaningful life even looks like, and it’s not about ambition or achievement at all. It’s the antidote to hustle-culture brainrot and you are definitely going to love it more than that hour of doomscrolling.

This is a novel disguised as a philosophy lecture disguised as a relationship you will absolutely see yourself in. It follows a couple from meet-cute to marriage to kids to the mundane, unglamorous grind of actually staying together, and de Botton keeps pausing the story to drop devastatingly accurate commentary on why you thought ‘the one’ would fix everything. If you’ve ever regretted a relationship, or wondered if you picked the ‘wrong’ person, this book gently informs you that the fantasy of effortless love was the actual problem, not your choices. Painfully wise and a little bit savage.

This one’s for all the overthinkers out there! Kundera basically asks: if you only live once, do your choices even matter, or are they all equally weightless? It’s dense, it’s philosophical, it will make you feel smart at brunch, and it will absolutely wreck your sense of certainty about anything you’ve ever decided. In the best way. Read with a highlighter and a friend to text about it at 1am.

Bottom line: none of these books tell you your choices were perfect, because, in all honestly there is no definition of a perfect decision. These books just gently suggest that ‘wrong turn’ might be doing a lot of unnecessary emotional labour in your head. Pick one up before your next spiral.