Two Things Can Be True at Once: How Jennifer Newberg Turned Loss Into a Lifeline for Widows
A little over two years ago, Jennifer Newberg’s husband, Jack, passed away. She was suddenly a young widow, facing not just the emotional weight of grief but a mountain of what she calls “widow chores” — the estate questions, the finances, the logistics of a life that had to keep moving even when hers felt like it had stopped. She went looking for other women who understood. She found pieces of what she needed here and there, but nothing that brought it all together. So she built it herself. That community is called It’s Lifey, and it has grown into one of the most personal, hands-on nonprofits supporting widows today.
Jennifer already knew the power of community before she needed it for herself. She is in recovery, and the group therapy and peer support that shaped that part of her life became the blueprint for what widows deserved too — a place where they could count on each other, be honest with each other, and trust each other through one of the hardest transitions a person can face. It’s Lifey now offers support groups and Hope Hub, an online platform, but the heart of the organization has become its in-person Widow Wellness Retreats. In the last ten months alone, Jennifer has hosted four of them. Women arrive as strangers and leave, three days later, as close friends who keep in daily contact long after they’ve gone home.
The Gap No One Else Was Filling
Ask Jennifer what a widow actually needs, and she doesn’t give you one answer — she gives you three. There’s the professional side: estate planners, financial planners, banks, life insurance agents, real estate agents, all of the decisions a person suddenly has to make about a home, an estate, a family’s future. There’s the emotional and physical side: therapists, grief coaches, lifestyle coaches, and — something Jennifer didn’t expect to embrace — practitioners like Reiki and hypnotherapy. “I thought that was a little woo woo for me,” she admits, “but I’ve learned that grief doesn’t just live in the mind. It really lives in the body.” And then there’s a third piece people rarely talk about: joy. Cards, spa days, a new outfit that makes you feel like yourself again. Jennifer even did a boudoir photo shoot a year after losing Jack, because it was freeing at a moment when she’d lost her sense of identity. Widows, she says, need all three kinds of support — not just one.
Going Narrow to Grow Wide
When Jennifer first envisioned It’s Lifey, she pictured something much bigger: a community for anyone navigating any kind of life transition. Her social media manager asked her a simple question on their first call — “who’s your target audience?” — and when Jennifer answered “everyone,” she was gently told that wasn’t going to work. It was advice she heard from more than one person before it finally landed: go narrow, and broaden out later, rather than starting broad and trying to narrow in. Today, It’s Lifey is laser-focused on widows. Down the road, Jennifer hopes to widen the circle to other transitions: career change, retirement, raising a child with special needs, and more. But she’s learned the hard way not to boil the ocean before the water’s even hot.
That focus has also shaped how she talks about grief itself. One of the biggest misconceptions she runs into is the idea that grief has an endpoint — that at some point, “you’re good again.” It doesn’t work that way, she says. Grief transforms, but it never fully goes away. Nor are widows the withdrawn, one-note figures people sometimes imagine. Many of the women in her retreats are navigating the worst thing that’s ever happened to them while also actively pursuing joy. “Two things can be true at once,” Jennifer says — it’s a phrase that comes up again and again in how she describes her work, and maybe the closest thing It’s Lifey has to a motto.
What Community Actually Looks Like
Jennifer is candid about what helps a grieving widow and what doesn’t. Flowers and casseroles, she jokes, are a hard pass. What actually makes a difference is far more specific: a friend who shows up to clean out a cluttered garage, or — in one memorable case — offers to pick up dog waste in the backyard. A GrubHub or Instacart gift card so a widow doesn’t have to think about cooking. A gift card for a manicure, or an insistence on going to dinner even when she says she doesn’t have the energy. “Sometimes forced joy and self-care is a huge step,” she says. The common thread is that these gestures require noticing what a person actually needs rather than defaulting to “let me know if you need anything” — because, as Jennifer points out, a woman whose head is swirling with a hundred decisions often doesn’t know what she needs until someone offers it.
That’s part of why peer community matters so much. Jennifer cites a striking number: there are an estimated 11.2 million widows under the age of 65 in the U.S. alone. Finding each other — even just having someone to text on a hard day — makes an enormous difference. Two of her retreat groups still have active text threads that light up daily, months after the events ended, filled with everything from hard days to insurance questions to simple “I miss you guys.” That ongoing bond, she says, is the real proof of concept for what It’s Lifey set out to build.
Building a Business She Never Trained For
Jennifer’s background is in marketing, partnerships, and nonprofit work — not entrepreneurship. She’ll be the first to say she had no idea how to run a business when she started, and she’s still learning. What entrepreneurship has taught her most, she says, is that she tends to bite off more than she can chew, and that everything has to be broken into smaller pieces and given time to work out — a hard lesson in a world that expects everything to happen immediately.
About a year in, she hit a wall. She was burned out and ready to walk away, and had to step back, take a hard look at what was actually working, and refocus around it. For Jennifer, that turned out to be the in-person gatherings — the retreats — over everything else she’d tried. She also credits her support system for keeping her going: three trusted people (she resists calling them “vendors”) who each hold a specific role, plus a virtual assistant she says has been genuinely life-changing. Her advice to other founders building something purpose-driven: make it personal, put yourself and your story at the center, and be specific about who you’re serving before you try to serve everyone.
She’s also learned to protect her own balance, not just her business. Jennifer describes five pillars in her life — work, parenting, recovery, self-care, and social connection — that she thinks of almost like a bar graph. When one gets too high at the expense of the others, she says, something eventually crashes. She’s lived that crash once already, taking a three-month break for an outpatient mental health program to reset before she could keep building. It’s a piece of the founder story she shares openly, because it’s part of the same message she brings to the widows she serves: taking care of yourself isn’t optional when your work is about taking care of others.
Pace Yourself
If there’s one thing Jennifer hopes every woman reading this takes away, it’s this: pace yourself, and give yourself grace. Not everything works on the first try, and it takes real trial and error to find what does. But when something clicks — when you feel it in your gut — trust it. Chances are, if it’s resonating with you, it’s resonating with other people too.
This November, that philosophy is showing up in Jennifer’s next chapter for It’s Lifey: a condensed, one-day version of her wellness retreats designed to reach widows who can’t always take time off work or afford a multi-day getaway. She’s currently building out the resources and partners who’ll be part of it, and she sees real opportunity for the WBL community here — the same range of professional and wellness services widows need every day, from estate and financial planning to therapy to beauty and self-care, are exactly the kind of businesses whose expertise could support the room. If your work touches any of those spaces and you’re curious about being part of it, it’s worth reaching out to Jennifer directly through It’s Lifey.
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