One of the life-changing opportunities over the year in Israel is the chance to develop and source your Hashkafas HaChayim - your outlook on life. While you've heard many different things from parents and teachers until this point, it's unlikely that they were presented cohesively or in any structured, organized way. By learning different Sifrei Hashkafa, you'll start to formulate your understanding of how Hashem wants you to see the world, and the role you can play within that bigger picture. That's the most important aspect of any Hashkafa - it's not about your views, it's about Hashem's views. In fact, the overwhelming number of times the verb L'Hashkif is used in Tanach, it refers to someone looking down from above; in our case, that someone is Hashem.
Here are some of the questions a person's Hashkafa should help address:
These questions don’t have simple, pat answers. Even when you have an answer in theory, it is still very difficult to apply to the complex realities of life. Therefore, even when you have figured out the basics of your Hashkafa, it remains a process to apply it to the actual issues that you’re dealing with. A Rebbi who knows you well and subscribes to the same basic Hashkafa will be very helpful in navigating those questions as they come up. While you explore Sifrei Hashkafa, try to discuss these ideas with Rebbeim and role models and find someone who articulates ideas in ways that you connect to and identify with.
There's no one-size-fits-all Hashkafa in Judaism. Different people will connect to different perspectives, the same way they have different interests and enjoy different hobbies. Just like one person might connect deeply through a Kumzitz while his friend finds it a waste of time, one Hashkafa might be inspiring for one person while too theoretical or abstract for another. In fact, even individuals will connect to different perspectives at different points in their lives. While surprising, this makes sense. Part of it is based on circumstances. A teenager is wondering about and dealing with different questions than an adult is; his interests in learning will change as well. Mindset also changes with age; a teenager is more likely to be enthralled by inspiring ideals, while someone older will appreciate a more practical spin on things. There are many different legitimate positions within Judaism (Eilu V’Eilu Divrei Elokim Chayim; Shivim Panim L’Torah); as long as it’s based on real, recognized sources, there’s room for it within Orthodox Judaism.
Because of this, there's no single must-read Sefer of Hashkafa. There are a couple of sources which everyone draws on and are important to know, but the finished product will depend on what the reader will connect to and appreciate. First of all, the source of everything is Tanach. The name itself gives away the genre: The Torah is meant to be used as a Moreh, a guide as to how we should live our lives. The entire Sefer Breishis lays the groundwork for our understanding of Hashem's relationship with both mankind and Bnei Yisrael. The way specific Mitzvos are presented often add new dimensions that wouldn't necessarily be obvious if one was only looking at Halacha (for example, Ayin Tachas Ayin). Nevi'im Rishonim provide perspective on the connection between our people, our country, and our God, Nevi'im Achronim give Mussar on the mistakes we've made while sweetening it with hope for the future.
The Ramban is also accepted as an authoritative voice in Hashkafas HaTorah. Throughout his commentary on the Chumash, he addresses fundamental questions of faith raised by events in the Parshiyot. There's even a Kuntres that lists the "foundational" pieces in each Parsha. Throughout the Torah, he addresses ideas such as the relationship between the Avos and Bnei Yisrael, our perspective on nature vs miracles, the goal of the Mishkan and Korbanos, suggested reasons for a number of Mitzvos, and many more topics.
Another name worth mentioning is the Rambam. In addition to his famous Sefarim (Mishneh Torah, Moreh Nevuchim, and Peirush Mishnayos), he also has essays discussing topics like the formation and transmission of Torah SheBaal Peh and the fundamentals of Jewish belief. The Rambam’s 13 Principles of Faith are the closest we get to a “Psak” in the realm of Hashkafa/Machshava.
In addition to the basic Seforim mentioned above, there are a number of modern Sefarim which can be helpful for exploring questions of Hashkafa. Rav Samson Rephael Hirsch’s 19 Letters was by far the most impactful for me. The Sefer creates a framework to address many of the above questions, showing how all of the different pieces of the world and human history (Creation, mankind, Bnei Yisrael, Torah and Mitzvos, Eretz Yisrael) fit together to accomplish the goal Hashem set for mankind. Even better, many of the ideas in the 19 Letters are fleshed out across Rav Hirsch’s writings, including his Peirush on Chumash, Tehillim, the Siddur, and nine volumes of essays on many different topics. This was one of the most organized presentations of Judaism and Jewish thought I had ever seen, and it blew me away.
Another masterpiece is Rav Soloveitchik’s Halachik Man. The Rav presents his idea of the core of a Jewish Hashkafa as concretized by our fealty to the system of Halacha. Rather than trying to escape this world and enter a spiritual world disconnected from reality, Mitzvos and Halacha allow us to bring Hashem down into our world. The Rav’s perspective triggered a paradigm shift for me, leading me towards appreciating Mitzvos as so much more than just boxes to check or lines not to cross.
Another standout essay from the Rav is The Lonely Man of Faith. The essay opens with one of the Rav’s most famous ideas, the difference between two “types” of humans based on two Creation stories in beginning of Bereishis. Terming them Adam 1 and Adam 2, the Rav notes differences between them based on nuances in the different versions of how they were created and how Hashem interacts with each. From there, he extrapolates fundamental ideas regarding the human condition and applies them to a person navigating a modern life.
Finally, Rav Aharon Lichtenstein has a number of books with collected Sichot and essays. By His Light, Varieties of the Jewish Experience, and Leaves of Faith I and II are full of beautifully written pieces addressing many of the above questions. In keeping with his style in Iyun, he usually presents a wide range of options and opinions on a specific topic, before explaining which he is personally more drawn to. While he proudly sees himself within the Modern/Centrist Orthodox camp, he is also honest and critical about that camp’s shortcomings.
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