I think one of the most useless questions people get asked is, “What would you tell your younger self if you could?”

The answer, of course, is always some bit of wisdom that was acquired through mistakes and failures. I am in favor of learning from mistakes and failures. It’s the most thrilling kind of learning there is.

But, while I am in favor of reflecting on what you’ve learned in your life, I have three problems with the question, “What would you tell your younger self?”

1. Your younger self already ignored the lesson

Your younger self almost assuredly was presented the lesson and chose to ignore it.

Most things people learn through mistakes were brutally evident through the plentiful examples of other people’s mistakes.

This is what people do. If you’ve ever been a parent, you know this to be true. You can tell your kids everything they need to know, but do they listen? Of course not. Just like we did not listen to our parents.

So maybe the only valuable advice to a younger self would be, “Learn from other people’s mistakes.” But I’m pretty sure I heard that one a bajillion times in my life, too.

And did I listen?

2. The act of living has value

For some weird reason I haven’t yet figured out, we are obsessed with shortcuts. Maybe it’s capitalism. Maybe it’s a uniquely American thing. I don’t know.

We have developed this belief that the destination is the only thing that has value.

In the case of the “tell your younger self” question, the value of the entire journey you’ve been on needs to be neatly wrapped up in one shiny, glowing pearl of wisdom.

Give that pearl to your younger self, et voila! You now have a shortcut past all those mistakes and failures. Because the journey doesn’t matter. Only the destination matters.

Like driving to the top of a mountain when you could have hiked up.

I talk with people all the time who say they are anxious about the future and have trouble “being present.” It’s hard to be present and enjoy the journey when your attitude is “I wish I could get to the end without all this journeying.”

3. Your younger self needs different wisdom

A lot of the wisdom I hear older people talking about involves inner peace, perspective on life, fulfillment, accepting impermanence… the things people in a later season of life should be thinking about. (And a lot of the things I am thinking about for my own life.)

But not all of that is necessarily the right mindset advice for a younger person who is in a vigorous building season of life.

The balance someone wants to strike at one age may be very different from the balance they seek at a different age. If you were to change how you lived your youth, would you still feel as you do about life today?

If, for example, you spent your youth making a ton of money and now you feel like time is running out, would you advise your younger self to work less and pursue their passion? Then you might end up old and broke and wondering why you didn’t earn more and save better for your resting years.

I suppose where I’m going with this is that “advice to your younger self” feels to me mostly about finding things to regret and punish yourself about. I don’t see much point in that. It’s the opposite of living in a space of gratitude.

A turnaround

Maybe a better hypothetical question would be, “What is one thing your younger self would be proud of you for, if they could see you now?”

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