The High Holidays take us on a journey to the deepest places. Here are some questions to ask along the way.

1. Who am I, and who is G‑d?

The Kotzker Rebbe once put his tallit over his shoulder, and prepared himself to begin the morning prayers. The minyan was deep into the service and he was still in the same position. When someone asked why, he explained, “This morning I said Modeh ani, ‘I gratefully thank You,’ and ever since I’ve been wondering, who am I, and who are You?”

2. Why is there a world? And what am I supposed to be doing in it?

Most of us forget that there doesn’t have to be a world at all! In fact, nothing at all has to be the way it is. Reality is dynamic. Which means, you’re not stuck. Now that we know the secret, let’s take stock in all the things that can be.

3. Am I still growing? Or, am I going through life imitating the person I used to be?

Most of us decide at a certain point that we’ve more or less gotten life right. We then spend the rest of our lives imitating the people we used to be. In other words, we stop growing. The moment we do this is the moment we become “old” – and it can happen at any age. If, on the other hand, we never stop growing, we remain young till our last breath.

4. Are the majority of my prayers for myself and money?

Have you ever heard someone say, “That person is worth five million dollars”? I always think, how do you know how much they’re worth? They could have five million dollars and be worth two cents. The true worth of a person is based on our values, not our incomes. If we make ourselves into loving, sensitive people, our true worth skyrockets, no matter how much is in our bank accounts.

5. When is the last time I had a heart-to-heart conversation with G‑d where I cried?

Do you know why crying to G‑d feels good? Because deep down, on a soul level, we know that we’re pouring our hearts out to the One who loves us the most. G‑d loves us. As Rebbe Nachman of Breslov teaches, talk to Him like you’d talk to your best friend.

6. Do I still believe that I can be the person I once wanted to be? And if not, what died inside of me?

Some goals have expiration dates, like becoming an Olympic athlete. Others don’t, like becoming holy. The great thing about being alive is that we can set new goals at any stage of our lives. And the wiser we are, the more we invest in those things that last forever. Is there anything more everlasting than G‑d, or the piece of eternity that He puts inside of us which is our soul? We never stop being players. So, don’t give up.

7. Is G‑d an idea inside my head? Or am I an idea inside G‑d’s head? (And by the way, G‑d doesn’t have a head.)

What’s the difference between someone who believes in one G‑d and someone who believes in many gods? Someone who believes in many gods says there is a god in the flowers, a god in the mountains, and god in the forest. But someone who believes in One G‑d says that not only is there one G‑d in everything in the entire universe, but at the same time the entire universe is inside G‑d.

So many of us think that we make G‑d exist by believing in Him. But the reality is, without G‑d there is no us.

8. What can I do for the world that nobody else can (even if it’s small)?

The Sages teach that there is no thing without its purpose, and no one without their time. That means that everyone is important, and that the world isn’t complete without each and every one of us. So ask yourself: Why can’t the world exist without me? And whatever the answer is—do more of that.

9. Should I continue to boycott G‑d until He gives me what I want?

When we feel like our prayers aren’t being answered, many of us use the following strategy: “I will have nothing more to do with You, G‑d, until You give me what I want.” That approach might work with a difficult employee–but with G‑d? Not so much. If we’re going to make a breakthrough, we need a new approach. And maybe that means not less of G‑d, but more of G‑d in our lives.

10. Do I believe that I have a soul that lives forever?

This is a giant question because if my soul is eternal (and it is) that means that after I die… I live on. Which means the overwhelming majority of my life will be spent outside my body. If that’s the case, then the choices I make in this world have everlasting importance. We tend to think that the mitzvahs we do are for G‑d. But from this perspective we see that the chief beneficiary of all the good I do is… me.

11. Does G‑d know better than me, or do I know better than G‑d?

One of the turning points in my spiritual journey was when I realized that the Sages know me better than I know myself. It was a humbling moment. We tend to think of ourselves as the constant exception to every rule. But I’ve come to realize that that’s just wishful thinking.

12. Would you ever worship a G‑d you completely understood?

The Kotzker Rebbe famously said, “I would never worship a G‑d I understood.” I think he meant that if you know everything that G‑d knows, then you’re also G‑d, so what do you need G‑d for? This leads to a surprising thought: G‑d ceases to be G‑d if He can be totally understood. Or, put another way, the very premise of G‑d is that He cannot be totally understood. For some reason, that makes me really happy.

13. Do I believe that G‑d believes in me?

Every morning the first thing we do is say Modeh ani, where we thank G‑d for giving us another day of life. It concludes with the words rabah emunatechah, “How great is Your faith.” The Alexander Rebbe explains that that means, how great is G‑d’s faith in us! This idea is so important that our Sages literally made sure that it was the first thing we say every day! We don’t just have dreams for G‑d—G‑d has dreams for us—and He has great faith in us that we’ll accomplish them.