Why Bridesmaid-for-Hire Jen Glantz Lives in a New City Every 30 Days
Jen Glantz, the world’s first bridesmaid-for-hire (more on this intriguing career to follow) loved living in New York City, but she didn’t love the crazy expense, or how stuck in her ways she’d become. After she and her boyfriend Adam Kossoff both lost their jobs, they created a life in which they could work anywhere while traveling across the United States. A few months ago, they moved out of New York and started calling a new place home every 30 days.
On the Postcard Academy podcast, I talk to Jen and Adam about losing your job, conquering fear of change, building a location-independent life, their favorite city so far (Portland), and more. Subscribe to the Postcard Academy podcast to hear the whole story.
First up, what’s a bridesmaid-for-hire??
Do you remember that movie 27 Dresses? That’s Jen! She’s sweet, reliable, and the person who even long-lost friends call to be their bridesmaid. So, she decided to go pro. A poetry major who’d never started a business, Jen tested the appetite for her Bridesmaid for Hire idea on Craigslist – and her ad went viral.
“Publications all over the world picked up the weird ad that I wrote about being a bridesmaid-for-hire and spread it everywhere,” Jen says, “I didn’t have very much money to grow this business, and I thought that PR would be my greatest asset to get people to learn about the business and hire me.” Her story’s been covered by hundreds of press outlets, including the TODAY show, Good Morning America, The New York Times, Cosmo, and Glamour.
As part of Bridesmaid for Hire, Jen does everything from talking brides through freak-outs to walking down the aisle for them. She also has services to help maids of honor with speechwriting and other duties.
“Planning a wedding is really hard,” Jen says. “A lot of people are lucky; they have close friends and family members to hold their hand and be there for them. But not everybody has that, and some people have that but they feel bad burdening them with it, so they reach out to me, and I'm there for them from start to finish of their wedding.”
The side hustle becomes the hustle
For a few years, Jen worked full time while running Bridesmaid for Hire, which may have remained a side hustle had she not lost her copywriting job. “I was working two jobs at once and I loved it. I loved having so much to do, but all of that came to a halt when I got laid off,” Jen says.
“It was heartbreaking. I remember my mom told me, ‘your legs were hanging off a mountain and you needed someone to push you. Because if you didn’t get laid off, you might have worked a full-time career for somebody else for your whole life.’ I think you need somebody to tell you to go off and spread your wings, and that’s exactly what happened.’”
Becoming a digital nomad
Jen’s boyfriend, Adam, also lost his job when the tech startup he worked at ran out of funding. Together, they decided this was the ideal time to leave New York and explore the U.S., something they'd been wanting to do. They both love the city, but felt stuck in a rut in one of the most expensive places on earth.
“I love New York City but I don’t love the person I’ve become in New York City,” Jen blogged before beginning their nomadic lifestyle. “I’m a recluse. I see friends maybe once every two months. I’ve become really stuck in my ways. I’ll only walk down certain avenues, eat pizza at certain places, buy clothes from certain stores. I’ve lost the adventure inside of me that used to be 60% of me and it was about time I made a decision that was scary, didn’t make much sense, and kept me up at night with excitement and with doubt.”
At first the couple couldn’t decide where to go. Should they road trip? They’d given up their New York apartments and started to panic that they didn’t have a plan. Finally, they made peace with the idea that they didn’t need everything mapped out, and would try living in a new city every 30 days.
“I traveled a lot for work and had been to different cities for a few days at a time,” Adam says, “but I never really got to fully immerse myself in those cities. I think we really do get a chance to live like a local after hitting a 30-day mark.”
“We can blend in like locals,” Jen says. “And the most important thing for us was that we could still work. We still wanted to fully commit to our jobs while being on the road and the 30-day thing helped us do that.”
When not at weddings, Jen manages Bridesmaid for Hire remotely, and has another company Jen & Juice, that offers one-on-one coaching for people looking to switch careers, start a business, or make a major life change. And she speaks at events. And she flies around the country teaching for General Assembly, Gotham Writer's Workshop, Google, and other places.
Living like a local
For their first city, Jen and Adam chose Portland, a place they’d never been and where they wouldn’t need a car, one of their requirements. They sold or gave away garbage bags filled with belongings and stored the rest with Adam’s parents. Then they booked an AirBnB, and they were off!
“If you stay at an AirBnB for 30 days or more you do get a discount – quite a big discount,” Adam says, “whether it’s just saving on the city tax that you would normally incur if it was less than 30 days, or a discount that’s passed on through the hosts as they prefer to have someone there for 30 days or more.”
Another thing Jen and Adam do in every city is to explore different workout studios.
“We found one in Portland that did hot yoga and neither of us had really ever done that before, but we started to go quite frequently,” Jen says, “and we made friends with people in the classes. I think that’s important if you live anywhere for 30 days to have those connections, to have people smile at you and say hello and know your name because the last thing you want to feel like is a tourist.”
It didn’t take long for Jen to find some local favorites, including Powell’s bookstore, the world’s largest independent bookshop. “They have a beautiful cafe inside. It’s a great place on a rainy Portland day. I spent hours there reading entire books in one sitting.”
If you were in Portland with her and Adam, they’d likely take you to Anna Bananas for brunch and then hiking at Dog Mountain. “Which has a reputation for being the most brutal bike hike in Washington,” Jen says.
“It is extremely steep and scary when you reach the top of it. I think it took us a couple hours to get to the top and then get back down. Our legs were completely numb.” The beauty is worth it, she promises, and if you finish with them, “We will then take you for ice cream, and there’s a lot of really cool ice cream shops around Portland!”
To save money, evenings out usually involve finding the best happy hour. “We find the places that have the best happy hour food the best happy hour wine and beer, and Portland had quite a few of them.” Jen says.
House or dog sitting for people is another way they save money on their nomadic adventure. When their friends went on vacation, Adam and Jen spent December in Austin caring for their two pitbulls. “We’re professional dog sitters if anyone in a cool city would like to hire us,” Adam jokes.
Advice for people looking to make a move
“There will be moments when you question what the heck you’re doing,” Jen says, “but know that when you put yourself in a situation where you’re packing up and living somewhere new every 30 days, you learn so many crazy things about yourself that you will never ever learn living in the same place. If I end this adventure tomorrow, I feel like I’ve learned a good five things about myself that I ignored being in the same place for a very long time.”
If you found this article useful, please share it, and subscribe to the Postcard Academy podcast. Each week, expats and adventurers share their insider travel tips on the best food and cultural experiences in the most interesting places around the globe. I’m your host, Sarah Mikutel, an American who's spent the last 7 years living in, and traveling around, Europe.