Why articles like “things I wish I could tell my younger self” don’t work

If you Google “things I wish my younger self knew” or “open letter to my younger self”, you will not get a shortage of answers/links.

Even on Medium, I have seen more than a few stories along this topic.

Yet when I read through them, I can’t help but think of one thing: “my younger self did know many of these things.”

But did she do anything about them?


For example, one common advice is “don’t care too much what people think about you.” (i.e. give less fucks).

My younger late-teen/early-twenties self have indeed come across countless articles on this topic. Not only that, but I have heard it from friends and family as well.

But here is the thing, when we are young, we are also more insecure. We don’t yet have the experience, the wisdom, and the self-confidence to grasp the value of this piece of advice. As a result, we often fall short of following it.

“The older we get, the less fuck we give.”

You’ve probably heard this saying before. This is something I have observed in myself. This is something many of my friends agree with as well.

Most importantly, this is something that came gradually with life experience, not after reading some article that someone else wrote.

My younger self could have read over and over “don’t give a fuck” and it wouldn’t have mattered. She would still have been the insecure little girl who constantly worried about whether others liked her, what others thought about her.

It is only through growing older and experiencing things that I have gathered the wisdom to understand WHY I should care less. No amount of reading could have ever convinced me when I was younger.

That’s not to say these types of articles are wrong. They are, more often, than not, extremely correct and insightful.

Here are a couple lines I can relate to:

Always be willing to walk away. Never want something so badly that you’re willing to sacrifice everything for it. Have faith that if this doesn’t work out, something else will. — 40 things I’d tell my younger self now that I’m 40

If you aren’t getting done what needs to get done, there is a fear. We avoid the things we don’t want to do — or worse, wonder if we can do at all. This is why startup plans and book ideas get pushed to the back burner so often. To get the work done, you have to confront what’s holding you back. — 30 things about life everyone should learn before turning 30

Unfortunately, the people who can relate the most to these lessons aren’t the people for whom these writings are intended.

Without real experience to understand the value of those words, those words are, more often than not, mere empty shells.

However, when you reach an age where you can truly relate to these sentences, you no longer need to hear them.

Telling the 20 years old me “always be willing to walk away” would have been useless because she wouldn’t have understood and wouldn’t have listened. Telling the now almost 30 years old me this would also be pointless. She already went through sh*t and now knows the importance of walking away when the time comes.

Perhaps that’s simply a bittersweet fact about growing older.

On the one hand, I’m wiser, more confident in myself, and more comfortable with who I am. On the other hand, I’m no longer the early twenties girl who still had her whole best decade ahead of her, who can still make expensive mistakes and learn from them.

Machine learning enthusiast

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