“If you want to win, you can win”: Introducing Emerge Alumna Diana Singer

  • Jul 27, 2020
  • Halle Newman

Diana Singer, an Emerge 2019 Alumna, joined Emerge because of two women: her daughter and Hillary Clinton.

After her loss in 2016, Clinton sent out an email to supporters about Emerge, encouraging women to enroll in the program. Singer’s daughter saw the letter, and sent it to her mom.  

“I had no idea what Emerge was, and then my daughter got a letter from Hillary Clinton,” Singer said. “I’ve always worked for Democratic campaigns and I was always interested in running myself at some point…and that’s the reason why I applied to Emerge – because I  had no idea how to do it.”

In 2019, Singer won her race to be a member of Greenwich’s Representative Town Meeting. However, there is more to this alumna’s story than her win last year. From writing a book to running her own educational consulting business, Singer’s career is rife with achievements. 

Children’s issues have always been at the core of Singer’s life. After graduating from college, she created a nonprofit organization in New York City to help homeless children, called “Magic Wishes and Hope”. It wasn’t until later that Singer decided to switch career paths. 

“Once I had children, I looked at the state of education when my children were young and I would tell my husband… how disappointed I was,” Singer said. Her husband told her to do three things: get a Master’s Degree in Education , start a business, and write a book. Singer took on the three-stage challenge. 

Singer got her Masters Degree over a span of two years and three summers, all while caring for two young children and husband. After checking off the first box on her to-do list, she started her business.

“[Starting a business] wasn’t ever ever going to be something that I wanted to do,” Singer said. “And then [my husband] got sick again and never recovered, and I just continued with [my business] and loved it, and never went back.”

Singer provides enrichment and processing support,  school counseling, parent consulting, test preparation, and more to students from 4-18 years old. Her business serves clients from around the tri-state area and throughout the country.

Finally, Singer met the third challenge; she wrote a book titled “Raising the Independent, Empowered Child”.

“I started [the book] in 2007… I’d take notes and I’d write about clients and experiences with my own children,” Singer said. “And finally, during COVID… I had a lot of time to go through the book and finish it.”

While COVID gave Singer extra time to write, she has been plenty busy attending Zoom meetings for the Greenwich Representative Town Meeting, organizing a call center for the elderly, and more to meet the challenges of COVID as an elected official. 

If you want to win, you can win. You need to be open to discussion with a huge amount of people.

This past June, the Democratic Town Committee in Greenwich asked Singer to run for State Representative, but she decided to focus on the Representative Town Meeting, business, and her book for now. She explains:  “COVID has made us all realize how incredibly important local government is to implement measures that the federal government has ignored, such as using masks and social distancing.”

Singer describes running for office last year as “one of the best experiences” of her life. She attributes part of her success to her willingness to talk to all people, regardless of their political party.

“I went to everybody’s door and if they weren’t there I left a note and my phone number,” Singer said. She guesses that she talked with about 800 people. 

“They would bring up national issues to me- Trump supporters, non-Trump supporters- and it was just fascinating listening, and at that point understanding why some of these people actually voted for Trump,” Singer said. Much of her campaigning experience was “hanging out on people’s sofas, drinking iced tea.”

Singer advises that women who want to run for office should have a sense of openness. 

“Never underestimate the power of talking to somebody one-on-one,” Singer said. “Make the time starting in May or June to canvas every single home you can. If you want to win, you can win. You need to be open to discussion with a huge amount of people.”

Never underestimate the power of talking to somebody one-on-one.

Singer recently started The Porchuck Neighborhood Association, which has worked to control dangerous speeding traffic through Greenwich’s curvy, blind, country roads. By engaging with her community in this way, she continues to understand the challenges in her community and implement needed change. She emphasized the importance of organizing to improve communities as well as running for office.

Besides writing a book, working with clients online, and representing her community members as an elected official, Singer has spent her COVID lockdown reading books (a favorite being The Goldfinch by Donna Tartt), catching up with friends, and going on hikes with her Labradoodle puppy, Apple. 

She’d like to give a shoutout to May Flexer and the Emerge Class of 2019.

“[There were] so many interesting, empowered women and it was just an honor to go through my sessions with them,” Singer said. 

Emerge is so grateful to have Diana Singer as an alumna of our program. She is nothing short of a remarkable and inspiring leader, and we cannot wait to see what else she accomplishes.