How a criminal defense lawyer became a world-class chocolatier

This article is part of the Places to Work feature in St. Louis Magazine‘s January 2018 issue.

At age 12, Shawn Askinosie watched his father in the courtroom, slamming home arguments that persuaded the jury.

At 13, Shawn was tapping the wasted flesh of his father’s leg, trying to find enough flesh to inject more Demerol.

The diagnosis, lung cancer, was terminal.

The following year, after the funeral, an Episcopal priest took Shawn aside and described the last day of his father’s life, on retreat at a Trappist monastery in Ava, Missouri. “He told me he’d been visited by three angels,” the priest said gently, “and they said he was going to die, he’d be OK, and his family would be protected.”

Instead of feeling comforted, Shawn was annoyed. He wanted his dad back, not some story about angels. He swallowed his tears and pushed to become the man his father would have wanted him to be. Waited eagerly to fit into his dad’s clothes and shoes, then walked where they led, becoming a criminal-defense lawyer.

He never lost a trial, and his cross-examination once persuaded a judge to take a death penalty case back from the jury and give the defendant, a victim of domestic abuse, probation. But after two decades, Askinosie was drained dry, stressed out and exhausted, brain in a fog, experiencing mild panic attacks, popping Lexapro. He could no longer wall off the pain and suffering he saw in his work—and he couldn’t suppress his own early grief any longer, either. Searching with his usual aggression for an answer, he even tried typing “What should I do with my life?” into a Google search bar.

He also bought a Mercedes convertible and, embarrassed at himself, sold it four months later. Finally, he started volunteering a few hours a week at a hospice.

When someone’s dying, you’re present. Focused wholly on them, praying for whatever peace or comfort they ask. Dropping his guard, Askinosie let himself feel the deep sorrow of the patients and their families. He expected only the bleak despair he’d always feared.

Instead, he glimpsed a kind of light and joy that, until he experienced it, would have smacked of cliché. He stopped being afraid to feel. And he stepped into the heart of a mystery he’d never before fathomed.

Now, he says that if he ever decides to have something inked on his flesh, it will be the Kahlil Gibran quote, “Our greatest joy is sorrow unmasked.”

“The connection with people in the hospice program threaded all the way back to the sorrow in me,” he says, “and pulled that thread forward and turned it into joy.”

“I don’t want to mislead you into thinking all of a sudden I was a different person,” he adds quickly. “Sometimes I’d feel that joy for only a few minutes. But once you recognize it, you want it again and again.”

Askinosie now had his first clue to the rest of his life: It had to involve service of some kind. The second clue? He couldn’t stay tough.

“We live in this society that values independence and almost a hardness as the thing that will get us through,” he says. “We’ve built this up over decades, maybe even centuries. Especially for me—softness and weakness were not in my wheelhouse. But it’s when we are able to peel off the mask of how we want to be perceived—everything perfect, everything in order”—that we get to something true.

As he volunteered with hospice, Askinosie realized why law had drained him: “I believe in the job that I did as a defense lawyer. I didn’t quit because I became jaded, not at all. But—in Buddhism, there is a principle of right work. I think some of the things that drain us are tasks in which we are pulled away from opportunities to express love, or we don’t have the chance to see love in the work we do. When you’re defending a murder case, there are very few expressions of love, no matter whose side you’re on. These jobs can suck the life out of you. And if your days are out of balance, with fewer and fewer opportunities to restore yourself, it begins to wear on you in a way that can be really harmful.”

That’s where he was when he heard a photographer who covered his court cases mention doing a shoot for the L.A. Times at Assumption Abbey.

Where his father spent the last days of his life.

Askinosie decided to go and see the place for himself. Still a hard-charging Type A, he showed up with a heavy sack of books, a little scared of keeping silent for a week with nothing to do. He’d always used free time to prepare for the courtroom.

Now he prepared to encounter—and cross-examine—his father’s angels.

It took several days of silence for Askinosie’s mind, hyperalert and thrumming with energy, to calm itself. Then the peace of the place seeped into him, and he realized that in 20 years of law and five years of searching, he’d been cluttering his thoughts with research, each new bit of information leading to another question, none of it yielding any real guidance. What he’d needed was “space, clarity, and peace.”

Once his mind was settled, serendipity took over. He’d been making a lot of chocolate desserts, and he thought, “Why not make the chocolate from scratch?” So he started a small-batch chocolate factory—just as American craft chocolate was about to boom.

Forbes has since named Askinosie Chocolate one of the 25 Best Small Companies in America. Askinosie flies to Ecuador, Tanzania, and the Philippines, working directly with farmers. He brings them the award-winning chocolate made from their cocoa beans; he tours the farms, checks on the health of the cacao trees, suggests postharvest and fermentation techniques. Together, they roast freshly harvested beans, nibble, savor, critique. Not only does Askinosie share profits with the farmers, but he collaborates on community development projects in their villages. Then, after meeting with retailers around the globe, he goes home to Springfield, Missouri, where 16 people make and package the bars.

He’s all about reverse scale, “the art of not getting bigger, but getting better at staying small.

“It’s tough to see your true self when you’re distanced from others,” he says. “I’m not trying to just make more and more and more. Young people respond to this idea; they’ve grown up in this culture of big, and they see the possibility of this countertrend.”

Capitalism’s in a worldwide crisis, he points out: It’s still the best system, but it needs to be reinvented in a form that’s sustainable, not predicated on impossible growth and runaway consumerism.

“We see the cumulative effects of that when someone gets killed in a Walmart stampede. I would challenge the notion that we must have this dizzying pace of consumption in order to have a healthy economy.”

Askinosie’s own product, chocolate, is “an affordable luxury that would not be possible without the hard work of farmers handling the beans very carefully, for which I pay them a premium.” He wants to narrow the gap between what the farmers are doing and what his customers enjoy. It’s too easy for companies to exploit and then try to hide that fact, “separating a luxury product from the people who made it or grew the ingredients for it.”

A 2011 issue of O: The Oprah Winfrey Magazine named Askinosie one of “15 Guys Who Are Saving the World.”

Now, with his daughter, Lawren Askinosie, he’s written a book titled Meaningful Work: A Quest to Do Great Business, Find Your Calling, and Feed Your Soul, published this November by Penguin. In it he warns against typing “What should I do with my life?” into the search bar. He also refuses to tell people, “Follow your dream,” words he finds trite, vague, and just not that helpful. “It’s stating the conclusion,” he says, not guiding people through the angst and strife of figuring out what that dream is. “It’s really, really hard for people to find their passion, and to translate that into what they do in their daily lives is just massively complex.”

You don’t just skip into the sunset, trailing your dream. You steel yourself, dig out the sorrows you’ve buried, and explore them. You make a pile of every glowing little thing that makes you proud. You identify what you’re passionate about and methodically cross-reference it with what the world needs at this moment. You serve without expecting any return. And you find a place of peace—internally and externally—where you can reflect, every step of the way.

When Askinosie asked middle-schoolers in Tanzania their vision of their life three years from now, he didn’t settle for “My dream is…” He made them write out the specifics. When he asked farmers for their vision 10 years out, one man said, “I woke up this morning, and my bed was a mattress. I looked up, and we had a ceiling in the house. My wife went to the market in our car, and bought the food we need.” He’d never let himself look into the future so hopefully before, and by the time he stopped talking, tears were coursing down his face.

In that moment, Askinosie had a hard time choking back his own emotions.

Then he remembered that he didn’t have to.

In two years, Askinosie will take permanent vows as a lay “family brother” at the monastery. Its monks were caught in a crisis of their own—too old and few to be allowed novices, but desperate to stay at their beloved monastery until they die. So they’ve decided to give their gorgeous Ozark grounds to Cistercian monks from Vietnam. Askinosie smiles, watching the elderly American monks learn Vietnamese and the Vietnamese monks learn to make fruitcake.

He knows his own journey isn’t over, either: “I love my job, but I harbored no illusion when I started chocolate that it was the solution to my woes. I counsel people that, when they feel as though they’ve found the right path, take it with their eyes wide open, understanding that there’s never a final solution. Otherwise, we spend our days thinking, ‘Well, I thought this was it, and it’s not.’ A lot of people have in some way given up on seeking: They thought they were going to arrive at an answer and never did, so they’ve resigned themselves to a rut.”

Today there’s even more pressure, he adds, “especially on young people, because all their friends are watching, and everybody’s waiting to see what major they pick, what job they get. It’s a lot of pressure for things to just snap into place.”

And life rarely works that way.

Here’s the crazy part: As a kid, Askinosie wasn’t even wild about chocolate. His mom was, though. Now he and his wife pop chocolate-covered malt balls into their mouths after dinner, and at work, he’s often tasting three or four products, swishing a palate cleanser of sparkling water in between. Then it’s work—but it’s still fun. “Even after 11 years, there are times I will taste something we’ve just made and be completely blown away.”

Last December, for example, an Ecuador bar he grabbed off the production line was the best he’d ever had. “I spent the next month trying to figure out what we did! One factor was the amount of cocoa butter, so we were able to replicate that, but the truth is, it’s kind of illusory. Ultimately, these are crops that are going to change from year to year.” Too many variables. That’s one reason he loves what he does: He knew he’d never master it.

Askinosie Chocolate is sold in St. Louis at Whole Foods, the Smokehouse Market in Chesterfield, Straub’s in Clayton, Parker’s Table, and Kakao. And Askinosie gives a good bit of it away—to the kids at Lost & Found, for example, a grief center he founded for children who’d lost someone they loved. “When that happens, especially to a teenager, it’s almost a fork in the road,” he observes. “You can choose destructive things, acting out in school, getting in trouble, drugs, alcohol, or you can choose overachieving, doing to distraction so there’s no time to be sad. And that path can have its own destructive outcomes.”

At least until you find the middle way.