“I Want to Be Where the People Are” Rabbi Oberstein’s Erev Rosh Hashanah 5786 Sermon

Rabbi Andrew Oberstein
Erev Rosh Hashanah, September 22, 2025 
Riverway Project | Temple Israel of Boston 

I want to share something with you that my younger self would be mortified to hear me say out loud.

I was not a popular child.

I know it’s hard to imagine that I,

the chubby, 

unathletic kid, 

obsessed with showtunes, 

who spent his recess time reading in the library wasn’t the big man on the elementary school campus.

But it’s true.

I can’t imagine why, 

but the other boys in my cabin at Jewish sleepaway camp were simply more interested in the latest issue of Sports Illustrated than in my latest copy of the Sondheim Review.

And as much as I loved the teachers, 

mentors, 

and adult role models in my life, 

my early years were marked by a very present sense of disconnection and marginalization among my peers.

I was a kid who heard a lot of affirmations rooted in the idea that it doesn’t actually matter what other people think –

It only matters what you think about yourself. 

 

*****

It’s a nice idea but, 

from my experience, 

it doesn’t always hold water. 

Our external relationships actually matter a great deal, 

and anyone who has ever felt both a sense of isolation and then a sense of belonging will tell you that there’s no comparison.

It wasn’t until I joined an after-school theater program that I understood what it really means to feel a sense of belonging, 

to find my people, 

to feel seen and known and loved for exactly who I am. 

And there’s nothing like that feeling.

 

*****

 

Even now, 

as a 38 year old man, 

I find that lonely little boy still alive within me. 

Thankfully, 

As I’ve gotten older, 

his presence in my life has shifted. 

I no longer see him when I look in the mirror, 

but instead he serves as the inspiration behind my strongest personal and professional goal in this world: 

to deepen people’s sense of belonging, 

to foster an environment of radical inclusivity, 

to ensure that there will always be a space – 

particularly a Jewish space – 

where people of all walks of life can feel known, 

feel seen, 

and feel loved.

 

*****

 

Over the past year, 

so many of you have shared with me your struggles to feel this sense of belonging.

You’ve shared stories with me about being in other faith communities that ostensibly seemed welcoming on the surface, 

but were unable to walk the walk and embrace you for the totality of who you are.

You’ve shared stories with me about being in secular spaces that ostensibly seemed welcoming on the surface, 

but were unable to provide the same embrace of your Jewishness that they might extend to other parts of identity.

Not to mention this post-pandemic reality where connecting to community – 

even imperfect community – 

is more elusive than ever.

 

*****

It’s not just you: 

statistics show that we are more and more isolated,

particularly in this Riverway demographic,

and despite social media allowing us to connect to anyone in the world with the touch of a fingertip, 

collectively we have never felt less secure in belonging.

 

And yet we know that Judaism is not neutral on this matter. 

 

******

I’ve mentioned before that there are only two instances of the phrase “lo tov” or “not good” appearing in the Torah. 

 

We find the phrase in Exodus, 

when Moses’s father-in-law, 

Yitro, 

tells him that it is “lo tov” or “not good” to take on the burden of leadership alone, without delegating and sharing responsibilities. 

 

But the first instance of the phrase appears right at the beginning of the Torah, 

in Genesis Chapter 2. 

 

At this point in our sacred story, 

God has created the first human being, 

Adam, 

but then shortly realizes that creating just one person simply won’t suffice. 

 

And the reason given is not the obvious one – 

which is, 

of course, 

that humanity cannot procreate if there’s only one human being on earth. 

 

Rather the reason given is just: 

“לֹא־ט֛וֹב הֱי֥וֹת הָֽאָדָ֖ם לְבַדּ֑וֹ” – 

because, 

inherently, 

it’s simply “not good” for the human being to be alone. 

 

Notably and importantly, 

when God goes on to create Eve to be Adam’s partner, 

the text doesn’t say, 

“it’s not good for the human being to be without a spouse.” 

 

The value here is not just about romantic partnership, 

it’s about avoiding solitude in any form. 

 

It’s the imperative expanded upon in our most famous work of ethical wisdom, Pirkei Avot: 

“אַל תִּפְרֹשׁ מִן הַצִּבּוּר” – 

do not separate yourself from the community. 

 

Isolating ourselves – 

choosing to “go it alone” –  

is dangerous for our souls and we’re seeing the effects of this isolation in deeply significant ways today.

 

*****

 

Many of you are familiar with the idea that certain Jewish prayers are traditionally not offered unless a minyan is present, 

a quorum of 10 Jewish adults. 

 

The most famous prayer that fits into this category is the Mourner’s Kaddish. 

 

Why, 

you might ask, 

would God even care if there are ten people present when a mourner wishes to offer this prayer? 

 

Personally, 

I can’t imagine a God who would oppose any individual offering kaddish in their moment of grief. 

 

The Talmud, 

in Masechet Berakhot, 

reminds us: עֲשָׂרָה שֶׁמִּתְפַּלְּלִין שֶׁשְּׁכִינָה עִמָּהֶם, 

when 10 people pray together, 

the Shechina, 

the dwelling presence of God, 

is with them. 

 

But, 

I actually believe the law requiring a minyan doesn’t serve as much of a theological need as a communal one. 

It means we’re not allowed to be alone in the times when we really need to be in community. 

It’s a built-in mechanism to make sure we are embraced when the temptation could be to isolate.

 

******

 

We’re all here tonight as individuals – 

I can’t presume to know what you personally need to leave behind from this year that ends tonight. 

 

I can’t presume to know what you need to get out of this year that is just beginning. 

 

You can’t possibly know what fear is consuming the person to your right or left,

what regret, 

what longing. 

 

You can’t possibly know what prayers resonate with the person in front of you, 

or behind you, 

or what prayers might trigger them. 

 

For those joining online, 

I can’t possibly know what fills you with nostalgia, 

or what might inspire you to change some aspect of your life in the year to come.

 

We actually don’t need to know.

 

But for all of us, 

onsite or online, 

we find ourselves right now in a moment that, 

like kaddish, 

demands a minyan. 

 

Simply put: 

I believe we are not living in times that are survivable on our own.

 

*****

 

It would be perfectly understandable for anyone here tonight to feel as though you are living in a world that seems to be crying out “you don’t belong.”

 

In a world dominated by social media, 

with carefully curated personae leading to incessant and unstoppable comparison, how can we not feel invisible?

 

In a political climate rooted in such deep polarization, 

the fear of speaking our minds and saying the “wrong thing” has created spaces where it becomes much easier to withdraw or stay silent, 

rather than risk becoming a pariah.

 

We know belonging isn’t always easy. 

 

In Jewish spaces today, 

disagreements—

especially about Israel and Gaza—

can certainly make us feel unsafe or unwelcome. 

 

On Kol Nidre, 

I’ll be speaking more explicitly about Israel and Gaza and the ways this phenomenon has uniquely manifested in the Jewish community.

 

Belonging doesn’t mean pretending those differences don’t exist. 

 

It means staying at the table anyway.

 

****

And it’s not only our politics or our religious affiliations that are making us feel lonely, 

disconnected, 

and isolated. 

 

It can sometimes feel like our society has been engineered to make us feel this way. 

 

It can feel like, 

no matter how old we get, 

there’s a part of us that is back in the middle school cafeteria, 

tray in hand, 

self-conscious, 

uncertain where to sit, 

longing for someone to wave us over and say, 

“This seat is for you.”

 

Maybe you even felt this way walking in here tonight.

 

*****

 

I want to propose a Jewish answer to the question of belonging – 

one that is ancient and yet countercultural today. 

 

As a rabbi currently focused primarily on engaging people in their 20s/30s, 

I hear from some segments of the Jewish world that synagogues are dead. 

 

It’s become a hot thing to say in innovative Jewish spaces that we are in a post-synagogue world, 

that we need to abandon this dinosaur notion of institutional affiliation and give the people what they want – 

a DIY, 

a-la-carte, 

niche focused series of one-off experiences, 

no strings attached. 

 

And I do understand why people feel this way.

 

There are beautiful Jewish spaces outside of synagogues—

independent minyanim, 

pop-up programs, 

online communities. 

 

They’re doing holy work and have touched countless lives. 

 

My point tonight isn’t that those are wrong, 

but that they need to be complemented by something enduring, 

a home base that can hold us through every season of our lives.

 

A synagogue is a space intentionally designed to be your home base, 

a constant presence that never goes away. 

 

Every Shabbat, 

every holiday, 

every significant moment in the year, 

we have a place for you to show up and be welcomed, 

be recognized, 

and belong. 

 

Even though we have initiatives like Riverway to connect similarly aged people, the synagogue itself is one of the few places left in society where people of all ages, 

with diverse opinions, 

spanning wildly varied lived experiences and perspectives, 

can come together to engage in discovery, 

dynamic spirituality, 

and righteous impact.

 

*****

 

Being a member of a synagogue was at one point a given for many Jewish people. Those days are over and now it’s actually somewhat countercultural to call someplace your spiritual home. 

 

But membership in a synagogue is not transactional like membership at the gym. Instead, 

it’s a declaration saying, 

“I am part of this community. 

I belong here. 

My presence matters here. 

These are my people and these are my rabbis.” 

 

Even if you haven’t experienced this yet, 

it’s an invitation to try.

 

I love being a synagogue rabbi because I get to be with people of all ages and hold them at their happiest moments and their most tragic. 

 

You may mostly see me here on the bimah, 

but I also get to stand with our members under the chuppah, 

and then name your babies and, 

if I stick around long enough, 

officiate those babies’ Bat Mitzvahs. 

 

I have the privilege of burying your loved ones and comforting the mourners in your living rooms. 

 

I sit by your hospital beds and cry with you in my office. 

 

I get to meet your families and your partners and walk with you through whatever life throws your way. 

 

And because we’re part of a broader synagogue, 

when you age out of Riverway, 

I still get to be your rabbi, 

and help you move into the next chapter of your life. 

 

This is what belonging looks like in action.

 

*****

Whether you’re just exploring Jewish community or have been tangentially connected, 

this may be the year to go deeper – 

consider joining and putting down some roots,

even somewhere else if it’s a better fit for you.

 

If you’re already a member, 

maybe this is the year to step into leadership or to expand your involvement in areas that may have been calling to you for a while.

 

This day of Rosh Hashanah is an invitation to reflect: 

Who do I want to be this year? 

Where do I want to place myself?

 

In a world of isolation, 

you have the opportunity this year to choose a community where you are seen, known, 

and valued.

 

Let this be the year where you show up. 

Let this be the year when we stop being afraid of affiliating –

it’s not a life sentence, 

it’s an invitation to go deeper.

 

*****

 

Belonging matters, 

it’s a Jewish value, 

and it’s active. 

 

In a world that sends us both subtle and overt messages that we do not belong, claim your place in a community where you do. 

 

Find your home in a community that loves you for however you do or do not practice Judaism, 

that celebrates queer identity and interfaith partnership, 

and yes, 

a place where the person sitting next to you may not see the world in the same way as you, 

but is willing to turn their discomfort into inquiry and engage nonetheless, 

a place where you can form friendships with your peers, 

but also intergenerational connections that simply don’t happen in most other spaces. 

You might find your people through our small group TI Circles, 

other people who want to read poetry, 

or cook Jewish food, 

or go on nature walks, 

or play Mah Jongg.

 

If you’ve ever felt outside – 

in a cafeteria, 

on a playground, 

in the Jewish world – 

know that here, 

you belong.

 

Rosh Hashanah calls us back – 

not just to God but to one another. 

 

A blessing in the machzor during tomorrow morning’s Shofar service reads:

 

“Blessed are we who hear, in these blasts of sound, the voice of community. 

Happy are we who know its embrace, 

its season of celebration, 

its quest for connection and purpose. 

 

Holy is this gift of community, 

blessed the act of belonging.”

 

*****

 

I don’t know what this year will bring. 

 

That part is out of our control. 

 

But whatever it throws our way, 

I can assure you it will be easier to navigate together.

 

May this Rosh Hashanah herald in a year of entering spaces where we are welcomed, 

recognized, 

and known. 

 

May we never lose our commitment to sustaining this sacred community as a place where everyone can belong.

 

Shana tova and welcome home.