Someone lamented on Mi Yodeya:

I wasted my youth. I am 35 years old. I had a toxic relationship with my parents, especially my mother. My career never started, and I am still looking for a fresh start and finding it humiliating at my age.

What does the Torah says about wasting your youth? Is redemption possible?

My answer:

In addition to some other fine answers, here’s another thought.

In Pirqei Avos (4:1), Ben Zoma asks and answers:

איזה הוא עשיר? השמח בחלקו, שנאמר ״יְגִיעַ כַּפֶּיךָ כִּי תֹאכֵל אַשְׁרֶיךָ וְטוֹב לָךְ׃״

 

Who is wealthy? One who is happy with his lot. As it says, “When you eat the labor of your hands, you are enriched and it is good for you.” (Tehillim 128:2)

The plain meaning of his statement begs the question: While it is good to be happy with what you have, without care, it can become a recipe for complacency. If I am content with anything, what motivates striving?

I think the answer lies in Ben Zoma’s proof-text. Specifically when you eat “the labor of your hands” are you “enriched and it is good for you.” True wealth is associated with labor and earning, not complacency or passivity.

I think the key term to understanding Ben Zoma’s intent is “chelqo— his portion.” What is a person’s portion? Well, we are told, “All of Israel has a cheileq le’Olam Haba, a portion toward the World to Come.” (Sanhedrin 11:1) Our portion is toward — not what we have now or did in the past, but route to a goal; in this case a life’s ultimate goal. A person’s cheileq is not what they have in a moment; it describes the full path a life takes. In other words, Ben Zoma is not advising that true wealth is to stop striving for something beyond what we have, but to find happiness in the journey of trying to accomplish.

(Source, to self-quote, Widen Your Tent, Mosaica Press 2019, pp 281-282.)

Your past motivates your future. I doubt you are honestly assessing your past; saying it was entirely wasted was more likely an exaggeration. But even if you really had nothing to show for your past but regret, that regret is a big part of your future trajectory in life.

Reish Laqish was a highway robber before becoming one of the more quoted figures in the Talmud. So, he knew something about “wasted youth” and getting one’s life on track. He teaches (Yuma 76b) that teshuvah, a return to Hashem and the right path, that is performed out of love turns even sins that are intentional acts of rebellion into merits.

For just this reason — because those sins plus the regret of harming the Cause you now love, points you in the right direction. The path of your life, as a whole, can be enriched, a thing of beauty.