On grief and ambition

Note: This article explores loss and grief, including references to illness, suicide, and other traumatic events. We encourage readers to engage at their own pace and comfort level.

Grief, eventually, strikes everyone — whether from death, divorce, illness, job loss, or one of life’s other great tragedies. The entrepreneur mindset is uniquely positioned for ambition, but grief can turn that on its head, requiring founders, CEOs, and workers in the world to reckon with what achievement means to them in the context of their grief, and if and how they can face ambition head on from a different perspective.

Shaken ambition in the wake of great trauma is a common theme among people and, more specifically, entrepreneurs, though what emerges from the sludge looks different for everyone.

I, for one, just took a roast chicken out of the oven at 10:30 in the morning while supposedly working the day away as a freelance journalist. A few months out from my brother’s suicide — which he completed after a years-long struggle with schizophrenia — the ephemeral productivity seems to be perpetually just out of reach. (I am, of course, “too hard on myself,” according to just about everyone.)

Amina Moreau, CEO of workspace rental platform Radious and competitive tennis player, is what she’d call a “chronic entrepreneur” because, “You have to be a little touched in the head to choose this lifestyle over and over and over again.” When Moreau was 14 years old, her mother completed suicide after several attempts. In her teen mind, anger was the best medicine — and for a long time, it worked. 

“I felt like anger was going to be a stronger defense mechanism for me, because anger is more motivating than being depressed,” said Moreau. “It took a long time, years, decades even, for that anger to dissipate. And that was my grieving process. It was letting anger dissolve.”

Over the years, Moreau started and sold companies, pursued professional relevance and maintained an ambition instilled in her through family and tennis. But when her dad died from heart failure in 2024, the coping mechanism she was most comfortable with didn’t work.

“The first few months, I was non-functional,” said Moreau.

Christine Droney, a licensed clinical social worker in Pennsylvania specializing in grief and palliative care, explains that “the process of grieving is very taxing on our brains and on our bodies.” It follows, then, that motivation is frequently impacted by it, in some way or another: “It can be a lack of motivation, or it can propel you forward, or it can do both.”

Chemically, too, grief impacts us. The burgeoning field of bereavement science goes beyond the “broken-heart syndrome” (death of a family member increases rates of heart failure in the short term) to find real changes in the immune system, inflammation, hormones, and brain function during grief. 

Sage Ke’alohilani Quiamno, founder turned strategic advisor and angel investor for tech and social impact companies, knows this firsthand. “I actually was diagnosed with rheumatoid arthritis at an early age because of all of the stress, and I don’t even genetically have that in my family,” she said.

In 2019, minutes before she was set to take the stage at a South By Southwest speaking event during a national roadshow to get her startup into new markets, Quiamno received a devastating text: Her grandfather had died.

But Quiamno was equipped with a survivor mentality. “Entrepreneurship is very lonely, and as a co-founder you have to compartmentalize, because you have to run a team,” she said. Moreover, she added, “If you‘re a woman of color and you’re a daughter from a working class family, there‘s a survival mechanism.”

Quiamno did go on stage that day, and she finished her talk with grace. But with the loss of her grandfather — a stern and wise man from the countryside of Oahu, Hawaii — at the midpoint of her startup journey, she was forced to reflect on what her grandfather sacrificed for his family. “He purposely moved away to be in cities so we [could] have a better education and have access to opportunities. And I’m living out that dream of his,” she said. “Hawaiian culture is about the collective and not about the self. But sometimes that boundary can lose itself as we’re continuing to work because we’re living under capitalist American Western society, where it’s take, take, take or give, give, give.”

While death is at the root of the grief most of us readily recognize, it’s not the only thing we grieve. “We need to understand that grief is not just death,” said Groney. We can grieve phases of our lives, relationships, and our “old selves” — the latter something that might feel acute after a serious illness like cancer or a transformative injury.

Dan Simons is the creator and co-owner of Farmers Restaurant Group (which includes seven Founding Farmers restaurants across a range of eastern states) along with the Founding Spirits distillery. “Restaurants are the only business I know,” he said. But after a wakeboarding accident left him with a severe concussion in 2019 — resulting in years of symptoms like headaches, confusion, fatigue, irritability, anxiety, depression, and more — the hustle of restaurant culture was setting his recovery back.

“In the beginning [after the accident], I couldn’t drive. I couldn’t read my emails, because it would just make the headache spike. I had a teammate that would read emails to me, and I’d dictate responses back,” said Simons. “I thought, what if I never get better? I was worried about letting my partner down, letting the team down. And I was thinking, who am I going to be without being in our restaurants?”

Simons and his business partner’s earlier plans of expansion were put on hold indefinitely, both because of the brain injury and the pandemic. It took years for him to find his footing in an industry that tends to be unforgiving to the ones making hospitality happen. For Simons, the people take precedence over the metrics.

Vanessa Rissetto, registered dietitian and founder of one-on-one clinical nutrition care startup Culina Health, was diagnosed with breast cancer while simultaneously trying to impress her company’s backers.

“I went to my oncologist, and was like, ‘I know that I have to do chemo, but you don’t understand. I cannot be bald and sick, because first of all, I’m vain, but also, this is not going to give confidence to anyone,’” Rissetto said.

As a woman of color, Rissetto felt even more pressure to succeed. “If I don’t return to my investors, am I out of the VC game?” she wondered. “If I was a white dude and I fucked up, it’s like, ‘oh, well, he tried.’ These people say they believe in me and I believe that. But let’s see what happens in this pressure situation.”

Because of her connections in the medical field, Rissetto was able to get surgery in just weeks, successfully avoiding chemotherapy and getting back on her feet. But the road ahead did not look exactly the same as before.

Grief, Droney said, is a teacher. Still in what my therapist calls acute grief, I can’t help but feel it’s an asshole of a teacher. Survival takes precedence, and growth is often put on the backburner. Yet I get glimpses of what it might teach me in the long run. “It can really open our eyes to what’s important to us,” said Droney, who herself credits her meaningful career of helping the grieving and the dying to her own history fleeing to the U.S. from Northern Ireland with her family after their house was bombed during The Troubles. “We can pivot, shift our sails into something new or something more meaningful.”

“When I was younger, and my family and I talked about ambition, we didn‘t necessarily explicitly talk about adding value and making a positive impact, but it's something that I learned through osmosis,” said Moreau. Her dad was a professor who thrived on conducting research as a way to contribute important discoveries and helping students become stronger selves. As a result of this upbringing and her grief, she’s become increasingly ambitious in her pursuit of adding good things into the world. Her workplace rental company, she knows, strengthens communities, builds neighbor relationships, and cuts down on commutes and fossil fuels. “That’s what gets me out of bed on the hardest mornings,” she said.

What’s changed, most, though, is her examination of work-life balance. Moreau said, “Yes, adding good to the world makes me feel fulfilled, but so does rest.”

And despite her history as a “chronic entrepreneur,” she hasn’t decided if she’d put herself through that rigor again. “Would I do another startup post-Radious? I‘m asking myself these questions. I’m not necessarily changing my behaviors yet, but life is short and so special — we only get one — and I’m in such an incredibly privileged position to have options. How can I not explore what those are?”

A year after losing her grandfather, Quiamno’s startup was successfully acquired. After a long hiatus from work, she went in-house at Amazon Prime before ultimately moving on. “You get the job, you get the money, and then you have all these responsibilities, which leads you to no time and more stress,” she said.

Quiamno’s late grandfather, Charles Waihinano Wright, was a construction worker who organized the first construction labor movement in Hawaii. Her work has always had a social impact tilt, but it bears more meaning now. “Because of my social impact work, and even my community grassroots work, I’m living through his work as well, being a community organizer, being able to create equity at any organization,” she said. “But it has made me look at ambition as intentionally asking yourself, ‘What is the purpose of this, and is this serving just me, or is it serving others too?’”

With that, naturally, comes the question of boundaries. Quiamno now asks herself, “What is the boundary that you need to have to ensure that you’re okay too?”

For his part, Simons found balance in work and care thanks largely to his supportive wife, sons, and business partner. He eventually found elite concussion specialists who could help him get rid of his one lingering symptom: daily headaches, which he suffered from for four years. “At that point I had almost given up. Like, whatever, I’ll just have a headache every day for the rest of my life, which meant, for me, very little laughter,” he said.

Today, rather than expanding his business, Simons is more focused on deepening the quality of his work. And while he’s always been a people-centric leader in the workplace, focusing on keeping teams healthy in mind and body (because, as he said, “Shouldn’t you just notice that you’re talking and working with whole human beings?”), he cares more about spreading the message beyond the restaurant’s walls.

“I’ll get an email from someone who lives somewhere else around the country, and they read my blog or heard me on a podcast talking about concussion recovery, and shared that with their relative or friend who’s dealing with brain injury recovery and it made a big difference,” he said. “I’ll sleep better that night. And I think, ‘You know what? This matters.’ And it just matters more [to me] than having a huge company.”

Empathy, said Simons, is a hard thing to conjure up out of thin air, but going through something difficult (and sometimes traumatizing) is a chance to use that empathy. “When you taste something bitter yourself [...] you want to help someone else not taste that bitterness,” he said.

Despite being cancer-free today, Rissetto still wakes up with the fear of dying or not being able to see her kids grow up. “Then you start to realize, control is just an illusion,” she said. “I just realized, what’s most important is that my kids are fully functioning humans, they’re kind people, and I am not leaving them with any debt. And if I were to die tomorrow, I don’t have any regrets. So I just made a couple of changes in my life, all for the better.”

Those changes included getting divorced and cutting down on her people-pleasing tendencies. Having lost a close cousin a number of years ago, she’s been on some version of a grief journey for a while now. “It is super traumatic to lose someone, get told you have cancer, and even though you’re better, and you’re living your life, this leaves something in your brain,” Rissetto said.

But through all the difficulties, Rissetto said people don’t have to wear their strength as a badge. “You can just say how you feel, and say that you’re having a hard time, maybe hide under the covers for the day, and that’s okay,” she said.

Droney talked about meaning making, where people who are grieving might ask themselves, “Is this really what I want to do with my life’s work?” That introspection and curiosity — and any action that comes from it — might be limited to a few years as they work through the grief or it might be permanent. This notion is deeply ingrained in her practice. A decorative bowl that sits on a coffee table in her office reads the famed Mary Oliver quote: “Tell me, what is it you plan to do with your one wild and precious life?”

And while her degrees, certifications, and achievements line the wall across from her, she knows it’s tangential to what’s really important. “Don‘t let your wall be more important than your relationships, because you can have this extremely broad resume and career that is so important,” said Droney. “It helps us find purpose, it helps us feed our families, it helps us do all kinds of things. It can be our identity. But at the end of the day, it’s the relationships that are most important.”

Through this story, I am starting to understand that my ambition right now might just be that my brother’s suffering and death, and all the pain that has rippled out from it, will not be in vain. Well, eventually. I still wake up every morning with the intention of just getting through the day, minimizing any suffering I can control and forgiving myself when I fall short.  

In that journey, Rissetto’s questions to keep herself on track hit home: “Am I showing up for the people in my life? Am I being truthful? Am I being of service anywhere that I can that is not to anyone’s detriment? How can I keep moving forward and not paralyze myself?”

If ambition once meant striving without end, perhaps grief’s hardest gift is the reminder that our lives’ work is not just to achieve, but to honor the fragile, fleeting time we are given, and the ups and downs along the way. Grief may slow us, soften us, or even undo us — but it can also teach us to move forward with a strength measured in meaning, and perhaps a strength that feels a little different than before.

^{If you or someone you know is struggling or in crisis, you can reach the Suicide & Crisis Lifeline at 988 for support.}