Going Thru It

In this special episode of Going Thru It, Jill and Holly connect across coasts on September 11th—two years since losing their brother Adam to colorectal cancer. It’s also their first time recording together since Jill became a mom to her son, Luca Adam, lovingly named in his honor.

From solo late-night feedings on one coast to quiet moments of reflection on the other, they share what it feels like to grieve apart, navigate new motherhood, and mark this anniversary without being in the same place as a family—something they had last year.

With honesty, heart, and their usual banter, Jill and Holly explore how distance, grief, and new beginnings intersect, and how love for their brother continues to anchor them no matter where they are.

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What happens when you sit down with your oldest friend...the one who knows your childhood stories as well as you do? In this episode, Holly is joined by Aliza Krivisky, her childhood best friend who grew up Reform Jewish and later found her path in Chabad Lubavitch Judaism. With Jill on baby duty, Aliza was the perfect person to have a meaningful conversation and kibbitz with. Together, they reflect on faith, spirituality, grief and tradition, and why the oldest friendships may be the most grounding and meaningful connections we have. 

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MiYaD: Your Jewish Home, Away From Home 

MiYaD Hebrew School Info 

In this week's episode of Going Thru It, we sit down with our first mother/daughter duo. Rev. Naomi Tutu and her daughter, author and activist Mungi Ngomane. Together, they are a mother and daughter carrying not just their own stories, but the legacy of one of the most influential leaders of our time, Archbishop Desmond Tutu. We talk about what it means to grieve someone who didn’t just belong to you, the South African traditions that shaped how they honor loss, and the wisdom that moves between generations when a family is navigating both public and private grief. This conversation is part legacy, part love letter, and part reminder that across cultures, continents, and generations, grief connects us in the most human way possible. And a very happy belated birthday to Rev. Naomi! Of course you were born on the special day of 8/8....the Lion's Portal! 

Everyday Ubuntu by Mungi Ngomane 

Everyday Ubuntu on Audible

More about Rev. Nontombi Naomi Tutu

More about Mungi Ngomane

The Tutu Foundation 

Two years ago, we were preparing for one of life's hardest moments, the loss of our brother Adam. Now, same time of year, same sort of emotions but this time, we're waiting for a baby to arrive. In this episode we talk about the strange timing of life, how grief and joy keep showing up together and what it's like to be back in a season of anticipation, just for something completely different. Holly's in LA for a quick trip, Jill's very pregnant and very ready, and the family has rallied while her husband's working across the world. There's mahjongg, there are memories, and in true Shakoor fashion there's a full blown betting pool for the baby's gender and arrival date. Winner may not get much beyond the satisfaction of being right, but honestly speaking, isn't that what really matters? 

Want in on the betting action? Email us your best guess for baby gender and arrival date at [email protected] 

Play Mahjongg with us!  P.S.We're not very good 

Our new fav show (whose name Holly can never remember) Overcompensating on Prime Video 

Summer is here! But the vibes are.... complicated. Holly’s out on the North Fork while Jill’s in LA counting down the final weeks of her pregnancy and things aren’t exactly picture-perfect. Like the wise T Swift once said, “I Can Do It With a Broken Heart,” we talk about how often we find ourselves doing hard things in the middle of emotional chaos… and still managing to show up, smile, and get through it.

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BONUS DROP! Father’s Day may be over, but we’re not done celebrating our dad — and what better way to honor him than by reading his legendary Yelp reviews out loud? Jack S. has written over 200 passionate, misspelled, and wildly entertaining reviews of just about every place he visits. Whether he’s coining phrases like OTFC (Off The Freakin’ Charts) or signing off with “another one bites the dust,” his commentary is pure gold. It’s pure entertainment, and it’s a little glimpse into the man who raised us — one review at a time.

Jack S on YELP 

We’re kicking off our Sibling Series with a powerful and heartfelt conversation with sisters Caroline and Natalie DeJean. You might remember Caroline from a past episode (celebrity stylist, cool girl, song-of-summer expert), and today she’s joined by her younger sister Natalie as they open up about the loss of their mom, Miss Liz, seven years ago.

This episode dives into all the complexities surrounding grief. How siblings can experience the same loss in totally different ways, and how layered family dynamics, including divorce and emotional distance, can shape the grieving process. Caroline and Natalie reflect on where their relationship stood with their mom at the time of her passing, and how they’ve each made peace with that in their own way.

We also get into some classic sibling rivalry, the evolving bond between sisters, and — of course — our annual Song of Summer debate. It’s messy, moving, and filled with moments that’ll make you laugh, nod along, and maybe even call your sibling afterward.

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Song of Summer (according to Spotify) 

One of us may be growing a baby but both of us are still figuring out how to grow around grief. In this episode, we catch up on Jill's third trimester—including her very on-brand babymoon in Hawaii—and talk about what it’s like preparing for new life while still carrying the absence of our brother Adam, something Holly didn’t have to navigate during her own pregnancy.

We also touch on the Knicks’ brief but incredibly long overdue playoff run (recorded in the blissful window before they lost), how siblings shape your whole identity, and why joy and grief seem to be on a shared custody schedule. Come for the baby updates, stay for the real talk.

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Peter Bretter trying to Forget Sarah Marshall 

In case you missed it, Mike White on Survivor: Season 37

Drop your buffs—it’s time for an episode decades in the making. This week, we’re joined by Bianca Maria Asumpte Immaculate Roses (yes, that’s her full legal name, and no, it did not fit on her high school diploma). She’s Jill’s best friend of nearly 30 years, a major PR pro, and now… a freshly torched contestant from Season 48 of Survivor. In this week's episode, we talk all things Fiji, sleep deprivation, and what it's like to have to leave the island while the game is still being played. Whether you're a fan of the premiere reality series or not, this conversation has it all. Beyond the game, this episode is a celebration of chosen family, shared Survivor obsessions, and the Roses-Shakoor bond—one that Adam cherished deeply. The tribe may have spoken… but now it’s Bianca’s turn.

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Catch up on CBS' Survivor 

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We were lucky enough to connect with someone who has truly shaped the grief space: Rebecca Soffer, author, community builder, and cofounder of Modern Loss. In this episode, we talk about how Rebecca turned her personal tragedy of losing both of her parents in her early 30s into a movement that normalizes grief in all its messy, complicated glory.

From her days producing The Colbert Report to creating one of Substack’s top newsletters on mental health, Rebecca has been using her voice to remind us that grief isn’t something to “get over”—it’s something we live with, grow through, and even connect around. We get into resilience (the real kind, not the Pinterest-quote kind), the myths we wish people would stop repeating (“everything happens for a reason” can take a seat), and how to hold space for both the pain and the absurdity of loss.

Whether you’re deep in it or supporting someone who is, this one’s for you.

Going Thru it 

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Modern Loss 

Subscribe to Modern Loss on Substack 

Modern Loss Handbook