Man cannot rely on intellect alone to determine his spiritual work. A connection based on intellect alone is not long lasting. He can know intellectually… yet his heart and body remain far behind. He needs to bind his whole soul and life force (to Hashem) and penetrate his soul to elevate and awaken it, so it becomes passionate about all mitzvot, about Torah and tefilla, and find true spiritual delight and joy in them.
Hovot HaTalmidim—Piaseczno Rav
It hurts me so much to see how many Jewish kids from around the world are leaving their Jewish identities behind. Many come from non-observant homes where they were never really given any reason to “stay Jewish.” Many others grew up in observant homes, but something went wrong in their Jewish education, their social or family life—or the lure of the secular world was just too strong.
I speak to many kids who were brought up with a Judaism that was less than warm and inspiring, just being told by well-meaning teachers and parents to do things without really understanding the depth and meaning behind it. They often tell me they grew up with the idea that Hashem is an angry man in the sky, and we have to do what He says otherwise He gets angry. It's hard to build a close personal relationship with a God like that. Halakha can seem restrictive and davening impersonal. Some started questioning things as they got older and came into contact with secular ideas and science, and the adults they asked were not equipped with the knowledge, evidence, or understanding to answer their questions.
In fact, we are facing somewhat of a crisis as many more people are leaving religious observance than returning; there is an extremely high intermarriage rate; many religious Jews report that they are just going through the motions; some ba’alei teshuva run out of steam five years down the road; and many Jews don’t even identify as being Jewish anymore.
Looking into Judaism from the outside as I did for the first 29 years of my life, I wasn't too impressed either. On one hand, it was because of my own shortcomings. I realized that even though I had a strong Jewish identity, went to Hebrew School, had a bar mitzvah, Friday night dinners, celebrated the festivals, played on a Jewish football team, visited Israel, and had mostly Jewish friends, I was basically uneducated when it came to what the Torah actually teaches and why we believe that to be true. I had a superficial understanding of the beliefs and the rituals and was easily put off by things I saw in the Torah that went against my western secular moral value system.
I had never interacted with religious Jews, happy to just judge them unfavorably from afar. In short, I was uninformed and assumed things about the religion and its adherents without really challenging myself to look a little deeper.
On the other hand, I was disaffected because of some shortcomings I saw, and am still faced with in the Orthodox community today. It’s amazing how many conversations I have with highly conscious spiritually seeking Jews who come into Aish HaTorah and want to know why, if the Torah is true and enlightening, there is not more emphasis on things such as physical health, protecting the environment, universalism and an appreciation of art, music, and culture within the religious community.
The truth is that Judaism is a holistic path to perfecting ourselves and the world around us. The Rambam speaks of exercise and healthy eating as prerequisites for spiritual connection and the Torah, Talmud, and Midrash urge us to be environmentally conscious. As far as other nations are concerned, a Midrash tells us that there is great wisdom amongst them and Tanna D’Bei Eliyahu Rabbah teaches that the Holy Spirit rests on man, woman, Jew, and non-Jew, according to their deeds. So, when asked about this, I acknowledge their point and admit that religious Jews are just as human as everyone else, having their shortcomings, challenges, and areas they need to really work on. Being religious doesn't automatically make someone happy and perfect; we all have personal and societal struggles to overcome and have to prioritize what areas of growth to work on. There are also some times when people who are dressed as religious Jews can behave in ways that give the religion a bad name; but they aren’t representative of the religion at all, in fact it’s only when they are going against Torah that the negativity comes out.
However, I then feel compelled to point out that, as a whole, I have found that there is more goodwill, strength in community, welcoming of guests, giving of charity, sense of purpose, focus on growth, learning, and the development and teaching good values and character traits than in any other community I have ever come across anywhere in the world. The amount of charitable organizations, leadership, and growth initiatives and learning opportunities is truly remarkable.
Yet we do seem to be facing one real issue, one that Rav Joseph B. Soloveitchik expressed in his usual clear and insightful manner:
Contemporary Orthodoxy is well grounded intellectually. In spite of this, its followers lack passion and enthusiasm … from within the allegedly dry confines of Jewish law, there is an awesome, warm, enormous world—there is a definite transition from Halakha to Service of Hashem. 
Notwithstanding some issues of philosophy and practice, when one walks into a Buddhist Temple in Thailand you feel an aura of peace and serenity, removed from the hustle and bustle of everyday life. Step into a Hindu Temple in India, and you are met with a profound sense of the heightened spiritual energy pervading the atmosphere. Unfortunately, the same doesn't always seem to be the case when you walk into a synagogue, and it can feel like, as Rav Soleveitchik continued “many Jews don't want to pray, they want to have prayed.”
There are so many really nice, good, religiously observant people, who keep kosher and Shabbat and all the mitzvoth, whose kids go to yeshiva, who learn Torah and dress modestly. All this is crucial—it's who we are and what we need to do and it's keeping Judaism alive. Yet, sometimes, it seems like people lose the center and purpose of it all; a truly intimate, authentic, personal relationship with themselves and Hashem. Sometimes it feels like we have the body of Jewish practice, we're just lacking the heart. The Ramchal (Rabbi Moshe Hayyim Luzzato) laments in the introduction to Messilat Yesharim  that
There are those who have entered the realm of the sacred and are studying the Holy Torah … however few amongst them choose to devote thought and study to the total perfection of the Divine Service; Ahava, Yirah, Deveikut, and all other aspects of piety… which is the very essence of what Hashem is asking of us!
The truth is that just being technically correct, ticking the boxes and going through the motions is not the goal. Doing our religious obligations quickly so we can get back to work or entertainment, which we value more, is not the way it's meant to be. We were created with the express purpose of re-identifying ourselves as souls, feeling close to Hashem in a palpable way, and bringing God-consciousness into the world. The Torah and halakha are the guidelines, leading us toward an experience. It’s easy to get caught up in the laws and lose sight of the destination.
Rabbi David Aaron compares it to just looking at a menu in a restaurant without actually tasting the food, or studying the maps without going on the beautiful hike. Or, as one of my first teachers said “It is like a finger pointing away to the moon. Don’t concentrate on that finger or you will miss all the heavenly glory.”
We could be learning Torah and davening all day, working on our character traits, and doing mitzvoth, yet be sadly missing what it is all for. Torah is a Guidebook leading us to an experience. Just studying the Guidebook without tasting the experience means we could miss the whole point.
A story is told of the Hiddushei HaRim who was walking with a student and told him that one day there will be a time when there will be a proliferation of yeshivas, study halls, Torah literature, Jewish organizations and shuls, tzedakah, and mitzvoth. Yet at that time there’ll be one thing missing; Hashem.
So what is it that we need to be implementing in our lives? The Talmud in Sanhedrin 106a teaches that the Compassionate One just wants the heart. He wants us to really mean what we do; to do things consciously and build a real deep, loving authentic relationship. The Shulhan Arukh teaches that less done with more intention is better than doing a lot without intention, and the Mishna Berura adds, quoting the Talmud, that “one can do a lot, or one could do a little, just as long as the heart is directed towards heaven.”
Messilat Yesharim teaches that “the master blessed be He is not satisfied with deeds alone in the performance of mitzvoth. Rather, what is most important to Him is that the heart be so pure that it direct itself to true service of the eternal." It all comes down to a question of whether our heart is truly in it, do we really mean and feel it. We say in Aleinu three times a day,
“We should know today and place it in our heart that Hashem is our God in the heavens above and on the earth below, there is nothing else.”
Just knowing, even an intimate knowing, is not enough. It needs to be settled into and make an impression on our heart. One day just before Shavuot I was saying this passage when I noticed it contains the words Daat (knowledge) and Yishuv (to settle). It is teaching us the need to “settle the knowledge” in our hearts. This called to mind a famous teaching in the Likutei Morahan where Rebbe Nachman teaches: The reason the world feels far from Hashem and is not coming close to Him, may He be blessed, is only because they have no Yishuv haDaat— settling/peace of mind.
Putting these two teachings together, it occurred to me that Yishuv haDaat on the one hand means to settle our minds and find some peace and clarity, and it is also expressing the real goal of this exercise which is to Yishuv the Daat, to settle the intimate knowledge into our hearts and live fully with it. Once our mind is calm and still, we clear up space to feel the innate connection we already have in our heart and soul. Pirkei Avot teaches,
Go and see which is the best trait for a person to acquire. Said Rabbi Eliezer: A good eye. Said Rabbi Joshua: A good friend. Said Rabbi Yossei: A good neighbor. Said Rabbi Shimon: To see what is born [out of ones actions]. Said Rabbi Elazar: A good heart. Said he (Rav Yohanan) to them: I prefer the words of Elazar the son of Arakh to yours, for his words include all of yours.
A true Enlightened Jewish Master is one who compliments a balanced, trained and healthy mind, with a pure, good, and open heart.
The most essential and powerful practice we need to bring our hearts into the picture is what the Talmud calls Avodah SheB’lev—the work of the heart. What is the service of the heart? It is tefillah, prayer.
Prayer itself should come from the heart, and we use it as a time to ask Hashem for help in purifying our hearts to be able to connect even more authentically; “God, create for me a pure heart, and renew the correct spirit within me; purify our hearts to serve you in truth.”
What this points to is that the most powerful way to build a real authentic, intimate relationship with Hashem is through speaking to Him honestly and openly from the heart. Jewish prayer isn't an attempt to connect to a separate Being, thanking and praising and requesting things from Him. Rather the word for prayer, lehitpallel, is reflexive, i.e., something we are doing to ourselves! Various interpretations teach that we are evaluating ourselves, connecting to ourselves, and envisioning the ultimate state of our lives and the world. To pray is the ultimate expression of our souls. Rav Moshe Weinberger teaches that our connection to our souls and Hashem can be on one of the four levels of life on this earth—mineral, vegetable, animal, and human. For some people it is domem, quiet and stagnant like a rock. Then there are those who are tsomeah—growing; beginning to be aroused to seek for more, more depth, more meaning, more connection. Above that there are those who are hai—truly living with this consciousness; getting up to pray, learning, doing mitzvoth, working on themselves. Yet there is a level even higher than this. He points out that the word for human is medaber—one who speaks. The highest level of connection to self, Torah and Hashem is to be in a constant conversation with Him; to open our hearts and speak directly to Him, like a best friend, twin, father, guide, even spouse.
 Tanna D’Bei Eliyahu Rabbah 9.
 Before Hashem You Will Be Purified: Rabbi Joseph B Soloveitchik on the Days of Awe. Summarized and Annotated by Arnold Lustiger.
 Introduction to Messilat Yesharim.
 Bruce Lee: Enter the Dragon.
 Daat implies an intimate knowledge.
 Lekutei Mohoran Tinyana 10.
 We also learn this from Rabbeinu Yonah who explains that when Shimon HaTzaddik taught that the world is based on three things: Torah, Avodah, and Gemillut Hassadim; the Avodah is referring to prayer.
 Rashi, Bereishith 30:8.
 Rashi, Bereishith; 48:11.
 Domem is related to the word demamah, silence.