Tishrei Is Teaching Me to Trust Myself Again
What if teshuva isn’t about becoming someone else, but returning to the person you already are?
We just concluded the Tishrei holiday season.
Every year, I find myself going through a process of reflection, growth, and discovery. But this year, a pattern became especially clear to me.
Tishrei is here to remind me to listen to my soul.
In Chassidus, Tishrei is associated with isarusa d’letata, an arousal from below to above. Nissan, the month of Pesach, represents isarusa d’le’eila, an arousal from above to below. Hence, it’s the month of miracles.
In simpler terms, Tishrei begins with us. We do the work. We awaken something within ourselves and reach upward.
And perhaps that’s exactly what I’ve been (re)learning to do.
Learning to Trust My Own Compass
I’ve always been someone who goes against the current.
Since I experienced injuries and practiced meditation, I learned that I have a voice, to trust myself, make my own decisions, and follow what felt true to me, even when it meant taking a path that others around me weren’t taking.
That willingness to follow my own compass led me on a healing journey and eventually to an Orthodox Chabad lifestyle. It brought me to yeshiva, to Chassidus, and to a life I never could have imagined for myself.
And yet, once I entered that world, I encountered a new challenge.
In a life devoted to Chassidus, there’s an emphasis on listening to your mashpia, your spiritual mentor, and following the guidance of those who help you understand what the Rebbe wants from you.
There’s tremendous value in that. I believe in learning from people who have more experience, wisdom, and perspective than I do. I even have a podcast interviewing others.
But I’ve also had experiences where not following someone’s advice was precisely what led to blessing in my life.
Times when something within me was calling me in a different direction. Times when following that inner voice felt like listening to the Rebbe, and ultimately to Hashem.
And I struggled with that.
How do I reconcile being told to listen to my mashpia with the feeling that the person advising me isn’t necessarily feeling what I’m feeling? They aren’t living inside my body. They aren’t experiencing my soul from the inside.
How do I know when to listen to someone else’s wisdom and when to trust my own?
Recently, someone shared a story with me that really resonated.
He had spent time in yeshiva deferring much of his decision-making to his mashpiim and to what he believed the Rebbe wanted from him. When he eventually left yeshiva, a friend told him something along these lines:
You came from a very secular background. You found Judaism, Chabad, and the Rebbe. Among the people and influences you grew up with, something in you recognized that this was right for you. That tells you something about your compass. Trust yourself a little bit.
That stayed with me.
What if the very ability that led us to Torah is something we need to continue cultivating within our Torah lives?
What if we don’t need to abandon our inner compass when we find a spiritual framework? What if we need to learn how to use it more wisely?
That’s what this Tishrei has been teaching me.
Rosh Hashana: What Happens When You Trust Your Heart?
My Rosh Hashana experience this year was unlike anything I expected.
The second day started out exactly how I didn’t want it to.
I woke up at 10 a.m. after staying up late hosting guests. Ten o’clock was precisely when the minyan started.
This was not the way I wanted to begin Rosh Hashana.
I like having a morning routine. I like having time to wake up, wash negel vasser, say my morning prayers, meditate a little, and prepare myself for the day.
Instead, I rolled out of bed already feeling behind.
I went through my morning routine as best I could and headed to the mikvah, which is an important part of my preparation for davenen.
Except the mikvah near my place was closed. So was the next nearby one. The mikveh is not just a creature comfort or luxury, it’s an essential preparation to prayer.
I was hoping someone would have mercy and open the first one for me. The first person I approached was already in the middle of davenen and chose not to help. But as I was walking away, another person saw me and called me over.
He pulled out a key and opened the mikvah for me.
I gave him a huge hug.
Suddenly, I felt this sense of peace and confidence. My morning wasn’t going according to plan, but I was being taken care of.
I still had a chance to make it to davenen at 770, the Rebbe’s shul in Crown Heights.
When I arrived at yeshiva to collect my tallis and siddur, though, I started having second thoughts.
I was already about an hour behind. And davenen at 770 on Rosh Hashana is an experience in itself. It’s incredibly crowded. You’re packed shoulder to shoulder with your fellow Jews, holding your siddur up in the air, trying to follow the prayers.
It’s one of the most uncomfortable, comfortable spiritual experiences I’ve ever had.
I began questioning myself and, upon pressure, asking for help.
Wouldn’t it be more sensible to stay at yeshiva? Wouldn’t it be better to find a minyan that was starting at the right time, where I could pray in order and without the pressure of trying to catch up? The latter someone even recommended.
All these thoughts came up, dressed in the language of holiness, dressed up as my mentor.
You should be doing things in the proper order.
You should go find a minyan to start with.
And yet, underneath all those thoughts, there was another feeling.
My heart wanted to be at 770 with the main minyan.
It was Rosh Hashana. I wanted to be there. I wanted to experience the day in that place, surrounded by my fellow Jews, even if it wasn’t going to be neat or comfortable.
So I listened.
I went to 770.
And I’m so glad I did.
Despite arriving late and squeezing my way through the crowd, I managed to pray well and catch up to the congregation. By the time the shofar was sounded, I was right where I needed to be. Later, I even found myself standing right next to where the shofar was blown.
The experience was better than I could have imagined. It’s a wonderful memory imprinted in my mind!
And I couldn’t help thinking about teshuva.
We often associate teshuva with correcting our mistakes, doing things properly, and getting back on track. But perhaps there’s another dimension to it.
Sometimes, teshuva is about recognizing that even when things don’t begin the way we wanted them to, we can still find our way.
We can stop punishing ourselves for how we started and start responding to where we are.
I could have spent Rosh Hashana beating myself up for waking up late. I could have convinced myself that because I hadn’t done everything correctly, I should abandon what my heart was calling me toward. I could have listened to mashpiim and found another minyan, managing with the situation.
Instead, I made a decision based on what felt meaningful to me.
And it turned out beautifully.
Sometimes, the mistake isn’t that we got off track. It’s that we judge the situation and we become so preoccupied with having gotten off track that we stop listening to where we’re being called.
Yom Kippur: Sometimes, It’s Not Okay
If Rosh Hashana was about listening to my heart, Yom Kippur challenged me to listen to something else, and to share my voice.
My frustration.
The whole day felt like nothing was moving.
I was fasting. I was physically uncomfortable. I felt tension in my upper chest and neck, and I had been dealing with that tension for a while.
I found myself waiting for Hashem to help me.
Just be patient. Keep going. Push through.
I felt like I had become trapped in holiness.
Everything around me seemed to be telling me to endure, to stay composed, to keep davenen, to accept what was happening.
But something inside me wanted to scream.
I wanted to let out the frustration. I wanted to move. I wanted to stop pretending that everything was okay.
And yet, I didn’t feel safe doing that in public. It wasn’t the place to let everything out in the way I wanted to.
So I kept holding it in.
Until Neilah.
Neilah is the closing prayer of Yom Kippur, the culmination of the day. At its end, we cry out together: Shema Yisrael, Baruch Shem Kevod Malchuso Le’olam Va’ed, and Hashem Hu HaElokim.
And something in me broke open.
I started crying.
It felt almost like a scene in which I had been taking hit after hit, holding everything together, until I finally found the strength to yell back.
I was finally allowing myself to express what had been building up inside me.
And in that moment, something released.
I felt some of the tension begin to let go.
It made me think about how easily we can confuse spiritual growth with enduring everything quietly.
Of course, there are times when we need patience. There are times when we need to accept what we cannot change.
But there are also times when our discomfort is telling us something.
Sometimes, the most honest prayer isn’t, “Hashem, help me accept this.”
Sometimes it’s, “Hashem, this hurts. I don’t know what to do with this. I need help.”
Other times it’s, “I’m not going to wait for You, Hashem, and let myself get beat up. This is not what You want!”
Honestly, sometimes that last one is what’s really listening to Hashem.
He wants us to make a move first.
We don’t have to turn every difficult feeling into a lesson before we’re allowed to feel it.
We can bring our frustration, our tension, our resistance, and our questions into our relationship with Hashem.
Perhaps that’s part of what it means to serve Him with our whole selves.
Not just the composed, patient, spiritually polished version of ourselves.
All of us.
Sukkos: The Holiness of Letting Go
Then came Sukkos.
Sukkos represents life in this world. It’s movement, joy, connection, and being present with other people.
And nowhere was that more apparent than at the Simchas Beis Hashoeva, where we dance late into the night.
I find something paradoxical about it.
In my pre-chabad life, staying up late at a music festival wouldn’t necessarily have been something I’d associate with clarity, rest, or personal growth.
And yet, here I am, living an Orthodox Chabad lifestyle, being encouraged to farbreng, dance, celebrate, and stay up late as a means of experiencing real joy and connection.
Something that might once have seemed like the opposite of spiritual wellness can, in the right context, become an expression of it.
Of course, this doesn’t mean that sleep, rest, or taking care of our bodies don’t matter.
But it challenges the assumption that growth, inner peace, emotional stillness, always look like discipline, quiet, control, or doing everything the way we think we’re supposed to.
Sometimes emotional stillness looks like dancing.
Sometimes it’s singing with people you’ve never met.
Sometimes it’s allowing yourself to get swept up in the joy of the moment without needing to analyze it, optimize it, or make it productive.
The sages say a few things about joy:
He who has not seen the rejoicing of the water-drawing ceremonies has never in his life seen joy.
There’s no joy like the resolution of doubt.
There’s something incredibly freeing about no longer being caught between what you feel and what you think you’re supposed to feel.
About allowing yourself to be present instead of constantly evaluating whether you’re doing it right, and asking a mashpia what you should be doing.
And maybe that’s part of what Sukkos offers us: an opportunity to experience what happens when we loosen our grip.
When we stop trying to control every aspect of our spiritual lives and allow ourselves to actually live them.
Hoshana Rabba: The Advice I Gave and Needed to Hear
By Hoshana Rabba, I was exhausted.
I had pushed myself through a full Tishrei, and at some point, I passed out from exhaustion unable to read the customs at midnight.
The next morning, I was sitting in the sukkah having coffee before davenen when a friend walked by.
I noticed he seemed anxious.
The mikvah was closed, and the minyan had already started. He was worried about getting there late and missing Barchu.
I recognized the feeling.
So I shared some of my own experiences with him.
I told him there was another mikvah nearby. He could still go, take the time he needed, and arrive at davenen when he could. He might miss Barchu, but on that day, he would hear it during the Torah reading anyway.
There was no need to panic.
I encouraged him to go to the mikvah since it would help him daven, and to trust that Hashem was guiding his footsteps.
He went on his way.
After davenen, he came up to me and thanked me.
He explained that my words had relieved some of the pressure he felt around davenen and the need to make it look a certain way.
He said it was unusual to receive that kind of advice in a situation like this. Especially since, in my case, Rabbis’ answers are like: you lost, don’t let it happen, go find another minyan.
That conversation stayed with me.
Because I realized that I had given him the very permission I had been learning to give myself throughout Tishrei.
Permission to breathe.
Permission to be imperfect and to make “mistakes.”
Permission to make a decision without panicking.
Permission to trust that his relationship with Hashem wasn’t going to fall apart because his morning hadn’t gone according to plan.
And I wondered: Isn’t that what we’re trying to cultivate?
Isn’t the point to bring more light and joy into the world?
To build a relationship with Hashem that makes us more alive, more present, and more connected?
Not one that leaves us constantly afraid of making the wrong move nor limited my our own constructs.
Hashem Wants Your Heart
Chassidus teaches us something profound about the purpose of our lives.
The Torah tells us:
Ve’asu li mikdash veshachanti betocham.
“And they shall make Me a sanctuary, that I may dwell among them.” (Exodus 25:8)
The verse doesn’t simply say that Hashem wants to dwell in a sanctuary. Chassidus teaches that the ultimate intention is for Hashem to dwell within each and every one of us.
Within them.
Within you.
Within me.
That leaves me with a question.
How can we make a dwelling place for Hashem within ourselves if we aren’t encouraged to listen to ourselves, make mistakes, and grow?!
How can we develop an authentic relationship with Hashem if we’re constantly trying to become the person we think someone else wants us to be? And if the advice from our “mentors” doesn’t foster listening to ourselves but to rigid rules?
I’m not suggesting that we don’t need teachers, mentors, rabbis, or mashpiim. I believe we do. I believe that Torah provides us with a framework that is greater than our individual preferences, and that sometimes the guidance we need is precisely the guidance we don’t want to hear.
Even the prophet Jeremiah 31:33 states: “No longer shall one teach his neighbor or [shall] one [teach] his brother, saying, ‘Know the L-rd,’ for they shall all know Me, from their smallest to their greatest.
Listening to ourselves doesn’t mean that every impulse is wise, that every feeling is a command, or that we should dismiss the people who challenge us.
It means learning to distinguish between the voice of fear and the voice of our soul.
It means developing the discernment to know when we need guidance, when we need patience, when we need to change course, and when we need the courage to trust what we know deep down.
Our teachers can help us get there. They can offer perspective, challenge our assumptions, and help us see what we might otherwise miss.
But they cannot live our lives for us - especially when they try to.
They cannot feel everything we feel or experience our relationship with Hashem from the inside.
And at some point, we have to learn to stand on our own two feet.
To take responsibility for our choices.
To trust ourselves enough to act, and to remain humble enough to learn when we get it off-mark.
This has been an ongoing challenge for me. It’s a personal struggle that I continue to work through, and it’s also something I feel called to help others with.
Because I know what it’s like to spend so much time trying to get things right that you lose touch with the very person you’re trying to bring closer to Hashem.
Teshuva Is Returning to Yourself
Perhaps this is one of the deeper messages of Tishrei.
Teshuva is often translated as repentance, but its true meaning is return.
To return to Hashem.
To return to your soul.
To return to the person you are beneath all the layers of fear, expectation, conditioning, and pressure.
Not to become someone else.
Not to construct a perfect version of yourself.
But to reconnect with the part of you that knows how to seek truth, recognize goodness, love, and grow.
And sometimes, the path back requires us to question the very assumptions we’ve made about what it means to be a good person, a good Jew, or a good servant of Hashem.
Sometimes, we need to stop asking, “What am I supposed to do?” long enough to ask, “What is actually happening inside me?”
What am I feeling?
What am I afraid of?
What is my soul calling me toward?
And when I do ask someone for guidance, I’ve begun to realize something about myself.
When I’m caught in a moment of tension or uncertainty and ask someone, “What do I do?” I don’t always want them to make the decision for me.
Sometimes, what I’m really hoping to hear is:
You’ve got this.
Trust yourself.
There isn’t always one perfect way to do this.
Don’t be so afraid of making a mistake.
Just shoot.
As a former basketball player, I understand that last one.
You can spend so much time thinking about the perfect shot, analyzing the defense, and worrying about what happens if you miss that you never actually release the ball.
At some point, you have to trust your training, trust your instincts, and shoot.
You might miss.
You might learn something.
You might surprise yourself.
But you won’t find out what happens by standing there forever, waiting for someone to tell you that you’re allowed to take the shot.
And maybe that’s what I’ve been learning throughout this Tishrei.
To listen.
To feel.
To trust.
To express my voice.
To make mistakes without turning them into a verdict on who I am.
To allow my relationship with Hashem to be something I experience, rather than something I constantly measure myself against.
And to remember that the same inner compass that helped lead me toward Torah is something I still need to nurture within my life of Torah.
Tishrei begins with us reaching upward and inwards. But perhaps part of that journey is learning to recognize the G-d is already present within us.
The soul we’re trying to connect with.
The heart we’re trying to open.
The person Hashem wants us to become, not by erasing ourselves, but by bringing our truest selves into our relationship with Him.
As we enter the rest of the new year, with the new month of Cheshvan this Sunday, my hope for you is that you carry this with you.
Listen to your teachers. Learn from the people who help you grow. Stay open to being challenged.
But don’t lose yourself in the process.
Give yourself permission to feel, to question, to make mistakes, and to find your own way forward.
Hashem wants your heart.
And the world needs the unique light that only you can bring into it.
May this be continue to be a year in which we learn to trust that a little more.
A year of less fear, more joy, less pressure, more presence.
A year of returning, not to who we think we’re supposed to be or who others want us to be, but to who we truly are.
A year of teshuva.
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