This blog post contains the transcription of a free virtual Lunch & Learn we hosted in September 2025 titled, “Turning Pain into a Passionate Business Idea.” You can view all of our upcoming webinars here.

We recently partnered with Jen Newberg of It’s Lifey to deliver a powerful webinar on Turning Pain into a Passionate Business Idea, which is exactly what she did. Keep reading for the tips and advice she shared with our attendees.

When Life Gets “Lifey”: Turning Personal Pain into a Community-Driven Business

Life rarely moves in a straight line. For many of us in Massachusetts—whether you’re on the Cape, in MetroWest, or anywhere across the Commonwealth—change arrives in waves: loss, divorce, blended families, recovery, and the everyday curveballs that upend routines. That’s the reality that inspired Natick resident Jen Newberg to create It’s Lifey, a growing community for people navigating major life transitions, starting with widowhood.

This is the story of how one woman transformed unimaginable grief into a practical, people-first venture—and the simple, replicable steps any purpose-led founder can borrow to build something that truly helps.

The Moment Everything Changed

After two decades in PR and marketing and several years with Boys & Girls Clubs of America in corporate partnerships, Jen’s life split into a before and after. During a long-planned trip to Greece with her husband, he suffered a sudden medical event and died within minutes. The logistics of being abroad were overwhelming; the grief was all-consuming.

Like many high-achieving New Englanders, her instinct was to get back to work. A few days at the desk proved it wasn’t sustainable. Instead, she stepped away, joined a retreat, and—somewhere between airports and quiet time—started sketching ideas for connection-focused gatherings. What began as one retreat concept evolved into a broader mission: create spaces where people facing similar life transitions can talk, listen, and feel less alone.

A Seed from Recovery, Watered by Community

Long before widowhood, Jen had entered recovery from addiction and discovered something powerful: community heals. That experience planted the seed for It’s Lifey. When grief hit, that seed sprouted. The throughline across her journey is simple and timeless: healing accelerates when we sit with others who “get it.”

From Too Many Ideas to the Right First Steps

If you’re an entrepreneur, this part will sound familiar. Early on, Jen generated a deck full of ideas—dozens of them. There was even a vision for a matchmaking-style app to connect people by life transition and for corporate affinity groups inside major employers (think ERGs for widowhood, divorce, step-parenting, or caring for family with mental health challenges).

Smart mentors helped her focus. The advice: start with what’s already in motion. That meant launching a local support group and continuing with the retreat she’d begun planning. The rest could wait in the “someday” file.

That focus delivered traction: intimate, well-run support groups; a retreat model that blends healing modalities with shared meals and unhurried conversation; and a network effect that grows naturally as participants invite others.

What It’s Lifey Offers (and Why It Works)

Support groups with guided discussion. Topics span the practical (paperwork, financial to-dos, navigating utilities and probate) and the emotional (the year-one rollercoaster, coping with anniversaries and holidays). Participation is at your pace—sharing is welcome, silence is respected.

Retreats designed around connection. Yes, there’s yoga, meditation, sound healing, walks, and journaling. But the heart of each weekend is community: sitting together at meals, finding a hiking buddy, and having the time and privacy to talk about what’s really hard.

Flexible formats. While in-person circles in places like MetroWest and the North Shore are cherished, virtual groups ensure people across Massachusetts (and beyond) can access support—especially during high-tide seasons like the holidays.

A curated resource network. It’s Lifey collaborates with therapists, social workers, holistic practitioners, and trusted service providers—financial advisors, attorneys, realtors—who understand the needs of widows and others in transition. The goal is not to replace professional care but to knit the “people piece” together with the practical.

How the Community Grew So Quickly

There’s no secret funnel here—just consistent, human outreach.

Lots of one-to-one conversations. Jen scheduled dozens of calls in the first two months, then kept going. If someone wanted to talk, she made time.

Showing up in the right rooms. From local women’s conferences to chamber events and mission-aligned gatherings, she leaned into Massachusetts’ dense ecosystem of business networks without trying to be everywhere.

Vulnerability as a strategy. Authenticity is overused as a buzzword, but in grief work it’s table stakes. Sharing her story—on good days and hard ones—built trust faster than polished marketing ever could.

Holding Space While Still Healing

Facilitating grief groups while grieving yourself can be draining. It can also be profoundly healing. The key has been boundaries and support: maintaining her own therapy and peer circles, honoring rest, and remembering that “a problem shared is a problem halved.” The work is emotional, but with the right structure, it replenishes rather than depletes.

A Note for Service Providers

Massachusetts is full of professionals whose clients are navigating loss—financial planners, estate attorneys, realtors, therapists, and more. It’s Lifey gives you a trusted, community-based resource to share when clients need connection alongside your services. Many advisors already find that a significant portion of their book includes widowed or divorced women; referring them to a compassionate peer network can make everything else you do more effective.

If You’re Newly Widowed and Don’t Know Where to Start

Give yourself time. You’re in a fog. Do only what truly can’t wait. If you take notes with a lawyer or banker and remember none of it later, that’s normal; revisit when you’re ready.

Ask for help, even if it feels awkward. In recovery and in grief, the first step is often raising your hand. A friend can make the intro; a facilitator can take the first call.

Try one small thing. Join a single session. Meet one person for coffee. Attend part of a retreat. You can always step back. Most people who “aren’t group people” discover that sitting with others who understand is the first deep breath they’ve taken in months.

Remember the health stakes. Loneliness isn’t just sad; it’s harmful. Choosing connection is an act of care for your mind and body.

Meeting People Exactly Where They Are

There’s no “right timeline” for grief. It’s Lifey welcomes people months, years, or many years after loss. In fact, mixed-timelines work beautifully: those further along reflect back practical tips and hope; those newer to loss remind the group what early days feel like and why gentleness matters.

Experiences differ, too. Some spouses died suddenly; others after long illness. The details vary, but the need for companionship, understanding, and steady encouragement is universal.

The Bigger Vision

Beyond widowhood, It’s Lifey will expand into other transitions, starting with divorce. The long-term dream is to nurture a network of “Lifers”—trained community builders embedded in towns across Massachusetts and eventually nationwide—each running circles, weekends, and pop-up gatherings that make it easy to find your people when life gets lifey.

There’s even room, down the road, for those “someday” ideas: corporate affinity groups for life transitions, and technology that bridges online introductions with offline friendships. But the core will remain the same: real humans, in real conversation, sharing what helps.

Getting Involved with It’s Lifey

Could you use some support that It’s Lifey provides? Check out their Widow Retreat and Circles of Support. If you’re interested in partnering, check out that as well here!