If I could speak to my younger self (who I can still envision sitting alone on the back steps of my yeshiva in a grey sweatshirt, broken hearted in a way very few seemed able to understand, hugging his knees and wondering endlessly) here are five things I’d tell him:

1. Beyond serving as your Father and King, Hashem wants to be your Best Friend in the world. Sharing His Oneness means sharing His Loneliness. Be alone with Him, and address Him naturally, as you would your Best Friend – in your own words!

2. Learning Gemara is not an end unto itself, but a primary means toward the end of fostering awareness of Hashem’s Presence in every detail of your life, achieving an expanded consciousness of spiritual maturity, and revealing His Presence in the physical realm. Irrelevant, boring, or convoluted as it may often seem, Gemara study is crucial (for a few deeply spiritual reasons we can discuss another time), but Torah is infinitely broader than the six to eight masechtos which modern-day Yeshivos traditionally study as well as the ways in which those very masechtos are traditionally learned. Sample the gamut of topics, areas, levels, approaches, and generations to identify your personal “headquarters”, and then work toward a synthesis, a healthy balance of the entire gamut; all with the realization that absorbing Hashem’s Mind within ours, Hashem’s Will within ours – accomplished by every kind of Torah study – affords the deepest possible intimacy with Him.

3. Mitzvos are not merely “commandments”, but “opportunities for connection.” (“tzavsa” – togetherness.) Hashem is not a slave driver Who demands that we do His restrictive bidding, or else. He is our loving Father whose sole Desire is to help us achieve our own sole desire – that which is objectively best for us, our true identity; the spark of Godliness within. Studying the spiritual depth of each mitzvah can help you to appreciate the nuance of these unique opportunities, making it so much easier to appreciate, and soon enjoy, relish, and delight in their fulfillment. In the same vein, tefillah is not about asking for stuff, as if Hashem is some sort of divine vending machine. It is an opportunity to pause, to reflect, to re-center, to reaffirm our reliance on Hashem. In this sense, regardless of whether the answer to our requests is “yes” or “no”, it is always “yes”. The prayer is itself the resolution.

4. Your “negative” passions and desires are holy energies in disguise. They are not to be squashed, castigated, or banished but appreciated, channeled, and elevated to holy pursuits. We live in an Olam Hafuch, an upside-down world. Oftentimes, the kids we refer to as “rebels” are truly the most devoted conformists – it’s just that instead of mindlessly conforming to a “system”, they are conforming to the authenticity of their own neshamos – with all the uncertainty and confusion this journey naturally entails. Your stormy soul holds a hurricane of holiness, and your tears are the life-giving rains that will sustain the seeds of your search. A relationship with God is not something you need to attain from without, but something you are able to reveal from within. Your searching, your seeking, your yearning, your struggling, your ups and downs on this roller coaster of spiritual striving, is the most precious thing in Hashem’s Eyes. He is with you – embracing, comforting, and beckoning – every step of the way.

5. Your Jewishness is not simply a cultural fact or technical label, just as avodas Hashem is not confined to overtly spiritual places or pursuits. Your Jewishness – and the mission it implies – is the very essence of who you are, and Hashem is therefore hiding in every arena of the human experience, waiting for us to find Him there, to recognize His Presence, and do whatever we can to amplify it. In addition to Torah, tefillah, and chessed, you can connect to Hashem through your normal teenaged interests and emotional states. Hang out with friends, play ball, work out, argue about politics, make music, eat too many potato chips, pursue hobbies, enjoy healthy entertainment! – but do so with Hashem (as-Best-Friend) and His Will (as-your-will/best interest) at the forefront of your mind, seeing everything you do, every person you encounter, and every circumstance you experience as a doorway to Him.


But that’s just me! What are some things you would tell your teenaged self? Let us know in the comments section below!

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R’ Yaakov Klein is the founder of the Lost Princess Initiative, an author, musician, and lecturer devoted to sharing the inner light of Torah through his books, music, and lectures.

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Sora Wolasky
2 years ago

I would tell my younger self that the struggle(s) you are going through now are the pathways of the wholeness and self confidence you will only fully realize later. It is a process and YOU with all of your self conceived flaws and inadequacies are just who you should be and the result will be just great. And, remember, you will always be a work in progress no matter what age and stage you are in. If you are able to learn and benefit from all you meet you will grow faster and be more whole.