Navigating grief as a business owner might be one of the hardest things you’ll ever have to do. As entrepreneurs, we’re taught to “keep going,” to deliver results, show up for clients, and remain “on” even when life is falling apart behind the scenes. But what happens when something so massive—like the loss of a parent—brings everything to a halt?

That’s exactly what Leah Weinberg, attorney, former wedding planner, and founder of Weinberg Legal, had to navigate. In our latest episode of The Dream Biz Podcast, Leah joined me for a vulnerable and powerful conversation about grief, business, and how she learned to ask for help. Here’s her story and what all of us can learn from it.

Grieving While No One Knows

Leah’s story began years before she chose to publicly share it. In 2019, Leah’s father began experiencing health problems that led to a diagnosis of non-alcoholic fatty liver disease. As the pandemic took hold in 2020, his condition worsened. By 2022, Leah was witnessing the slow decline of her father’s cognition and personality, which was something she wasn’t prepared for and hadn’t been warned about by doctors.

At the same time, she was working in the high-pressure world of wedding planning. She had already decided to transition out of the industry after 2022, but still had multiple weddings on the books—and clients who expected her to deliver on their “most important day.” All the while, her dad’s health deteriorated. In June of 2022, he was officially denied a liver transplant. There was nothing else that could be done.

“I was planning weddings while watching my dad die,” Leah said.

When Work Feels Impossible

Leah reached a breaking point during a conversation with a friend who had also experienced significant loss. That friend’s asked her an important question: “If someone could support you, what would they do?” Leah answered honestly: they’d take the work off her plate.

So that’s what she did. Leah backed out of speaking engagements. She transferred three weddings to a trusted friend. For the first time in her professional life, she stepped away from her business to grieve, even though she didn’t tell most people what was really going on.

The Hidden Struggles of Entrepreneurship

After publicly sharing her story, Leah was flooded with messages from fellow business owners who were quietly dealing with similar grief. Parents with cancer. Loved ones battling Alzheimer’s. Entrepreneurs doing their best to keep up appearances while privately falling apart.

“There are so many of us silently suffering,” she said.

And yet, it’s the reality for many business owners. We power through because we think we have to. Because we fear losing clients, income, or momentum. But the truth is, as Leah’s story shows us: there’s power in pressing pause.

Creating Space to Heal

After her father passed away in May 2023, Leah gave herself the time and space to heal. She didn’t rush back to work. She didn’t force herself to “move on.” Instead, she embraced a deeply introspective, unconventional journey of healing. From therapy and antidepressants to energy work, human design, breathwork, astrology, and even a medium session, Leah followed her curiosity and leaned into what brought her comfort and connection.

She also learned to honor her grief through joyful rituals, like a confetti photo shoot and a celebratory trip to Disney with her mom.

“I wanted to find a way to celebrate his life. He loved Disney, and this felt like a joyful way to remember him,” she shared.

What Changed in Her Business

Leah’s experience didn’t just shift her personal life. It reshaped how she shows up professionally. Now, as a business attorney, she’s passionate about helping other business owners prepare for the unexpected.

She works with clients to build flexibility and humanity into their contracts—so that if something happens, they have the legal and emotional support to step away and take care of themselves without guilt.

“I was a lawyer, and I had to breach my own contracts because there was nothing in them that allowed for this,” she explained.

Today, she also talks to clients about emergency planning, business succession, and having contingency plans for when life gets hard.

Leah’s Advice for Entrepreneurs Navigating Grief

If you’re currently in a season of grief or hardship, Leah offers this advice:

1. Let people in. You don’t have to tell the whole internet, but let someone know what you’re going through. You might be surprised by who shows up.

2. Ask for help. Even if it’s uncomfortable. Even if it feels unnatural. Let others support you.

3. Don’t rush the process. Grief doesn’t operate on a timeline. It’s okay to still be healing a year—or many years—later.

4. Make space for joy. Healing doesn’t always have to look like sadness. Celebrating the life of someone you’ve lost, or honoring your own growth, can be incredibly powerful.

5. Build a business that allows room for being human. Whether it’s through flexible contracts or aligned systems, make sure your business supports you, not the other way around.

You’re Not Alone

There’s no guidebook for navigating grief as a business owner. But conversations like this one help us feel a little less alone.

Whether you’re currently grieving or simply want to create a more human-first business, Leah’s story reminds us that it’s okay to pause. It’s okay to choose your wellbeing over your workload. And it’s okay to ask for help.

If you’re ready to build a business that makes space for your full humanity: joy, grief, and everything in between—let this be your invitation.

You’re not alone.

Want to connect with Leah?
Visit Weinberg Legal for legal support designed for entrepreneurs who want their business to work for them—not the other way around. You can also find her on Instagram @theleahweinberg and @weinberglegal

If this blog resonated with you, feel free to share it with a fellow business owner who might be silently struggling. Let’s create space for more honest conversations in entrepreneurship.