How a Cookie Entrepreneur Spends Her Sundays

Janie Deegan said she was 25 and homeless when she got sober. Soon after, she discovered baking.

“I was stuck in an overwhelming darkness with no hope or glimpse of the future,” said Ms. Deegan, now 35, who is the founder of Janie’s Life-Changing Baked Goods, which she started out of her home almost eight years ago. “Baking became this controlled artistic, meditative act of self-care,” she said.

In 2021, she opened her first shop on Manhattan’s Upper West Side. Last fall, she opened a second location in East Harlem. For both stores, she has “an open-door hiring policy for people recently out of prison or a shelter who want to work,” she said. Janie’s, which specializes in pie crust cookies, or mini pies with fruit fillings, produces about 1,500 cookies per day.

Ms. Deegan lives on the Upper West Side with her boyfriend Josh Raff, 37, who co-owns Five4Five Films, which teaches media skills to high school students.

ALL ABOUT COFFEE Sunday is the one day I don’t set an alarm. I know people are at the bakery at 7 a.m., so from 7 to 9 I check my phone to make sure there aren’t any issues while trying to fall back to sleep. I’ve transferred my alcoholism to workaholism and coffee. I have several different contraptions in my house, including a Nespresso and a drip, but Josh is an early riser, and on Sundays he brings me this amazing coffee from Peaky Barista. I’m usually a traditional coffee drinker, but he gets us a dirty chai latte or pumpkin spice latte.

Ms. Deegan shown above with her boyfriend, Josh Raff, likes to play Wordle and Spelling Bee.Credit…Anna Watts for The New York Times

QUEEN BEE I do Wordle and Spelling Bee. There’s simplicity in this; it’s like meditation. It focuses me, and it’s gratifying if I get Queen Bee or solve Wordle in three words. These work well because I can’t play another until the next day. When it’s done, it’s done.

MILEAGE For the past five years, I’ve been training for the New York City Marathon. I’ve done two so far. If I’m not training, I’ll run four to six miles. I enter Central Park at 106th Street. I cheat a little, which helps me avoid Harlem Hill, which is extremely steep, and start at the top and run down and do the northern loop, down the east side, and end on 77th Street.

TREASURE HUNT I hit the Grand Bazaar on Columbus and do a quick walk-through, looking for cobalt-blue glass, which my grandmother loved. I inherited her collection, and I’ve expanded it to other colors. I look for glassware, pitchers, vases and medicine bottles from the 1800s. My father is a set designer and created these built-in shelves that go around the window, so now there are more than 100 pieces of glass displayed in a rainbow, which makes me sound like a grandma. I’m successful at finding them, but these can be really pricey, $400 or $500 for a four-inch medicine bottle, so I don’t make a lot of purchases.

A visit to the Grand Bazaar is a weekend tradition. Credit…Anna Watts for The New York Times
“I look for glassware, pitchers, vases and medicine bottles from the 1800s.” Credit…Anna Watts for The New York Times

BAKERY VISIT I get a second coffee with almond or coconut milk at our bakery on 80th Street. We have two people on Sunday, instead of 10 or 12, so this is an opportunity to check in with them, and then see what needs to be done while it’s calm. I still feel huge bursts of pride when I’m there.

STROLL, EAT I walk my way uptown on Broadway to meet Josh at either Community, a restaurant that makes decadent biscuits and gravy, or Le Monde, which make great French omelets. Then I have a third coffee. If we want something to go, we hit Milano Market, a fancy Italian deli that has crazy low prices for salads and sandwiches and is a Columbia University institution.

ODDS, ENDS I mill around and check emails — we do a lot of e-commerce business now — and plan for the week ahead while Josh, who is a big phone person, makes calls or does the laundry. I might visit our other store to see how they’re doing.

Checking in at work. Credit…Anna Watts for The New York Times
One of Ms. Deegan’s pie crust cookies.Credit…Anna Watts for The New York Times

SAME LANGUAGE At 4 or 5 I meet with a sober friend and order an almond matcha tea latte or a fourth coffee at PlantShed or Starbucks. We might walk in the park if it’s nice. Maintenance is life for me. I wish I could put being sober on a résumé because it’s my biggest achievement, so I’m always connecting with others in the program. All week I’m with people who don’t speak my language, and this is my chance to have someone who does. It’s comforting and reminds me I’m not alone.

COMMUNITY I go to a Sunday meeting on the West Side from 7 to 8. I get there early to set up. It’s a community of people I wouldn’t necessarily meet in my day-to-day life. I spent years trying to get sober and couldn’t. I tried rehab, therapy, different treatments. People thought I’d die of alcoholism.

CHANGES I have a squad of six or so people from the program who have become my best friends. Covid did many different things to relationships, and to me. I was an Irish Catholic girl who thought stoicism was sexy and vulnerability wasn’t. Covid chipped away at that. I softened to a degree I didn’t think was possible. I canceled a wedding. I ended a relationship. I met someone new. But I held onto these friends and our relationships became more poignant.

Janie Deegan has dinner at Bodrum, on the Upper West Side of Manhattan, with a group of her friends after their A.A. meeting.Credit…Anna Watts for The New York Times

OUTING We eat at Bodrum, a Turkish Mediterranean place. I’m not a great planner, so if I didn’t make a reservation and they can’t seat our group, we go to City Diner. Once we’re seated, it’s a madness of us trying to catch up and everyone is talking over each other in a loving way. We want to know who is dating whom, and what are we doing this summer, and who is getting married next.

WATCHING Josh has already eaten by the time I’m home, which is sometime between 9:30 and 10. Usually we watch what’s on HBO. We just finished “The White Lotus,” so we’re at a loss and are looking for a new show. We also recently watched “Only Murders in the Building.”

WRITING Josh goes to bed at 11. I love my alone time, when I can sit on the couch working until 1 a.m. I have to write things down for them to exist. I journal, jot down ideas, I might come up with a new idea for a cookie. Sometimes it’s paperwork and emails I’ve put off. Then I crawl into bed.

Sunday Routine readers can follow Janie Deegan on Instagram @janiedbakes.

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