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How 9 months at sea taught a St. Pete couple to leave the 9-to-5 behind

Two women and a cat sailed from St. Petersburg to Massachusetts and back.
 
Vanessa Goodrum, left, and Sara O'Brien sailed from St. Petersburg to Massachusetts and back on the boat "Good Stories." This photo was taken in Johns Island, South Carolina.
Vanessa Goodrum, left, and Sara O'Brien sailed from St. Petersburg to Massachusetts and back on the boat "Good Stories." This photo was taken in Johns Island, South Carolina. [ Courtesy of 2 Women Sailing ]
Published Jan. 31, 2022|Updated Feb. 4, 2022
Sara O’Brien runs shirts through a dryer after screen printing at Wide Sky in Pinellas Park on Wednesday, Jan. 26, 2022.
Sara O’Brien runs shirts through a dryer after screen printing at Wide Sky in Pinellas Park on Wednesday, Jan. 26, 2022. [ IVY CEBALLO | Times ]

Sara O’Brien and Vanessa Goodrum used to hold 9 to 5 jobs in St. Petersburg. On nights and weekends, O’Brien worked on her passion project, a clothing company called Wide Sky. Since 2014, she’s made a side hustle out of designing and screen printing fun T-shirts with hyper-local slogans like “It’s my way or the Skyway” and “I survived Thrill Hill.

But after the first year of pandemic living, the couple started to reassess the way they were living life — or rather, going along with the grind.

“The only way we knew the workday was over was to stop and have a beer,” Goodrum said.

It was a common occurrence during those post-work drinks to dream big about the world and where they could go together. Goodrum owns a 38-foot sailboat, named Good Stories, and frequently found herself looking at charts and checking the weather.

“Do you think we could get away for a week? Do you think we could get away for a month? How can we do this work from the boat?” Goodrum would ask O’Brien.

Finally, O’Brien said, “Are we going to do it or what?’”

Goodrum was willing to step down from her full-time position at the Poynter Institute for Media Studies, which owns the Tampa Bay Times, and work part time as a contract employee. She set to work crunching numbers, estimating costs for groceries, marinas, entertainment and boat repairs. How much time and money would it take to reach Cape Cod by the summer?

O’Brien, who also worked at Poynter, left her job, too. She packed up her house (the couple didn’t live together then) and put the items she didn’t sell in storage. Before she paused Wide Sky’s operations, she cranked out hundreds of extra T-Shirts to keep businesses like Old Southeast Market, The St. Pete Store & Visitors Center and ZaZoo’d stocked.

They left March 28, 2021, from the St. Pete Municipal Marina. For the rest of the year, the couple — plus a cat named Whippoorwill — would share 300 square feet of living space.

It took five weeks just to get around Florida. They sailed down to the Keys, looped up and stopped for nine days in St. Augustine to visit friends. The couple also started to document their travels on YouTube and Instagram under the name 2 Women Sailing.

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Every day, they’d wake up with the sun and have coffee and breakfast. O’Brien worked on videos for the YouTube channel, read and exercised on deck. If it wasn’t a travel day, Goodrum did her remote work. The days would end with happy hour in the cockpit and dinner.

They saw beautiful sunsets in Georgia. Learned history in Charleston, S.C. Checked out a seaport museum in Mystic, Conn., and cruised by the Statue of Liberty in New York City.

It wasn’t always fun.

There was a violent thunderstorm in Chesapeake Bay and terrible fog in North Carolina and Boston. They blew a giant hole in the head sail, tore the main sail, had engine problems and discovered a pinched fuel line.

“There were so many miniature disasters that were trying to work against us,” Goodrum said. “But it all worked out.”

When they finally reached Massachusetts, dropping anchor at a quaint little island called Cuttyhunk, it was all worth it. Goodrum cried.

“Being in the middle of such beauty and surrounded by water, it was just really breathtaking,” O’Brien said.

They spent some time in Massachusetts, then headed back. After roughly 5,000 miles, the trip concluded at the end of December.

During the voyage, the couple started to consider what things would be like when they got back. They vowed not to get back to the daily grind.

“We really, really want to live a slower life,” Goodrum said. “It doesn’t mean we want to be lazy. It means that we want to be selective about what to say yes to and not stress about all of the things we have to do.”

“I don’t see myself going back to a 40-hour-a-week job and I also don’t see myself working for anybody else anytime soon,” O’Brien said. “It became clearer and clearer as time went on that I wanted to take Wide Sky full time.”

Sara O’Brien screen prints a t-shirt at Wide Sky in Pinellas Park on Thursday, Jan. 27, 2022.
Sara O’Brien screen prints a t-shirt at Wide Sky in Pinellas Park on Thursday, Jan. 27, 2022. [ IVY CEBALLO | Times ]

Instead of going back to screen printing in a friend’s cramped garage, she went all in and rented a 1,200-square foot space in Pinellas Park.

“If being out there gave me one thing, it was the headspace to be creative on a whim and not have other stuff filling up my mind,” she said.

O’Brien plans to keep producing apparel with local pride for retail shops around the region. She has enough ideas for a boat-themed line. Her first new design will debut at the Wide Sky table at Localtopia on Feb. 12. She’ll also resume print jobs for other local businesses.

“The more we traveled and got away from the real world, and after 2020 being such a bad year for everybody, it makes you rethink things,” O’Brien said. “It makes you rethink what you’re doing with your life, what really makes you happy.”

Sara O’Brien laughs while setting up to begin screen printing at Wide Sky in Pinellas Park on Wednesday, Jan. 26, 2022. O’Brien needed a step stool to adjust the knobs in the way the machine was positioned.
Sara O’Brien laughs while setting up to begin screen printing at Wide Sky in Pinellas Park on Wednesday, Jan. 26, 2022. O’Brien needed a step stool to adjust the knobs in the way the machine was positioned. [ IVY CEBALLO | Times ]