Kelsey Flynn O'Connor, Co-Founder


Kelsey, Kooz, Sunshine Girl... whatever you call her, she's the reason we exist. She was always asking for more, of everything she loved, everywhere she went. She taught us the meaning, and value, of true inclusion. She and her family showed us what's possible when communities value diversity and make space for all people. We're so grateful for your inspiration and humbled by your legacy, Kelsey. 


Kelsey Flynn O'Connor


Kelsey was born on February 17, 1987 in Newport, the daughter of Jack and Chyleene O'Connor.  She was the middle of three girls.  Her sisters, Meghan and Cate, adored Kelsey and Kelsey can take some of the credit for what led them both to become incredible teachers (and humans!). Kelsey was a proud aunt to Addie and Jack and loved both her brothers-in-law, Jay and Andrew, very much. Kelsey's housemates -- Hope, AnnMarie, and Rayna -- quickly became part of her family and she built a wonderful home with them in Newport. Cousins, aunts, uncles, and friends filled Kelsey's days with love and all can count the ways Kelsey influenced their lives.

Kelsey lived her life boldly and bravely. All who knew her will lovingly remember her contagious laugh and bright smile. She enjoyed the simple things in life – good food, loud music, sunshine, and quiet time with a book. Her adventurous side, though, loved roller coasters, fast boats, and skiing. She was constantly trying to make people laugh with fake burps, headlock hugs, and a sarcastic sense of humor. Kelsey taught so many about the importance of inclusion and focusing on ability over disability. Her lessons and light will continue to shine for many years to come.

Kelsey was wonderfully supported by many amazing people throughout her life, including caring doctors and nurses, teachers and friends at Middletown Public Schools, and the incredible staff at Looking Upwards.


She's missed dearly by all who loved her.

All I Know I Learned From Kelsey

Written by Beth O'Connor

Ask for what you want or need,
and keep asking until you get it.

Cry when you are sad,

laugh when you are happy,

yell and stomp your feet

when you need to.

Live life in the moment.

Delight in the little things.

Curl up in the sunshine.

Enjoy the wind blowing in your hair.

Savor every meal.

Read your favorite books everyday.

Listen to the sounds of the music surrounding you.

Smile, smile, smile.


Kelsey was able to find housing in the community that she loved. It took her family years to make that possible. She lived with roommates in a home  where she was supported and happy. But, for too many individuals and families, that dream is never realized. It's time to change that.

Family Stories

Jack's Story, Kelsey's Dad 

As Dorothy says in The Wizard of Oz, there’s no place like home! I was extremely lucky to meet and marry my best friend Chyleene in 1983 and in the last 34 years we’ve lived in 7 houses. These houses varied in size from a small one bedroom apartment; living upstairs from four wonderful men while Chyleene helped them with their day to day activities (our daughter Meghan’s first house - her bedroom was a cedar closet - it smelled so good!); a wonderful 4 bedroom family home on a cul-de-sac; and now our downsized new home that we’ll spend the rest of our lives together in. While I didn’t mention all 7 houses we lived in, one thing that remained constant was the love that filled them. 

Over the years our family grew and Meghan became big sister to Kelsey and Cate and needless to say things got a little crazier in our house! Big gatherings with family and friends for birthday parties, holidays, cookouts and graduations became the norm and we wouldn’t have had it any other way. Naturally, not all times were fun and some epic family fights took place - how can we forget Cate throwing chicken at Meghan to the horror of Jay on his first visit to our house. Somehow it all worked out as Meghan and Jay celebrated their 10th wedding anniversary this summer! Chyleene and I talked many times about how lucky we’ve been and how we hoped our kids would be as lucky to have a house filled with as much love when they got older.

Meghan and Cate's journey to their own homes followed a more traditional path like ours - graduating from college, living with friends in small apartments and then venturing out with their best friends (for Cate that's Andrew - wedding in July 2018!). Kelsey’s path to her own home was a different one due to her significant developmental disabilities. No doubt that she wanted to be like her sister’s and get out of our house to live on her own. She got very bored with the quiet when her sisters left - she made this very clear to us by saying bye-bye as often as possible! After a long process of finding the best fit for Kelsey she moved into her own house filled with more love that you can imagine four years ago. Her three roommates and the staff that help them all have become part of our extended family and family gatherings just keep getting bigger! We know Kelsey is happy as she throws us a big kiss whenever we visit but gives an even bigger bye-bye when we leave!

No doubt that the hopes that Chyleene and I had for our girls have come true and we could’t be more proud of their own homes! We also couldn’t be prouder of Micaela Connery, Kelsey’s cousin, and the work she’s doing to help all people achieve their dreams of having their own home. 

Cate's Story, Kelsey's Sister

Moving away from home is a dream for so many young people. I'm the youngest of three girls. Like many young people, there came a time when my oldest sister Meghan and I headed off on our own.  My first apartment was a tiny one in Boston with my best friend Lauren. I slept without a boxspring for three years because it wouldn't fit up our stairwell. We broke lots of glasses and burned more than a few frozen pizzas. We spent many nights laughing about it while eating take-out on our fire escape. We had a lot of fun, and learned so much about ourselves in the process.

My sister Kelsey had the same dream. Things were a little different for my sister Kelsey, but the dream was the same. Even though she has disabilities, it was important for her to have her own home, away from our parents. It took lots of time and a bit of creativity, but our family eventually found the perfect spot. Four years ago, Kelsey moved into the cutest little yellow house with gardens out front, a big deck out back, and lots of love inside. Her roommates have become Kelsey's best friends and their staff have become part of our family. They encourage each other during the tough times and cheer for each other during the good ones. Kelsey still spends each Sunday at my parents' house, and without fail, around three o'clock, Kelsey starts to wave her hands and say "buh-bye!" — her signal to my parents that she is ready to go back to her home. They drop her off with a big smile on her face. Kelsey loves her new home.

For too many people, this dream never becomes a reality. My sister was fortunate to have parents who advocated tirelessly for her and a support system that guided her transition into her new community. But, for so many people with disabilities, finding their own home feels almost impossible. Many lack the resources to afford housing in the community, don't have options that meet their needs, and are faced with housing choices that limit their inclusion in the community.

The Kelsey is changing that. That's why I'm excited to serve on the board of The Kelsey, named for my sister. Not only are we working to make sure people with disabilities get access to housing, but we do so with inclusion at the core.

Meghan's Story, Kelsey's Sister

When I was seven, my parents built a brand new house for our family. They made it accessible so that my sister Kelsey would have everything she needed to be comfortable and safe. We grew up and made many wonderful memories in that house. Then I went to college, moved out, got married, and rented then bought my own house. My sister, Cate, also went to college and moved to her own apartment in Boston. That left Kelsey home alone with my parents. She had the same goals that Cate and I had and thankfully has amazing parents who made those dreams come true. She moved out and into a home with some ladies who became her best friends. Now, here comes the best part... Once Kelsey moved out and my parents didn't need their big, accessible house, my husband Jay and I bought it! I got to move back into my childhood home to raise my own kids! We have put some of our own touches on it, the biggest addition was the pool and pubshed in the backyard, but it still feels just as much home as it did when I was seven. 

This has been wonderful for so many reasons. But, the biggest is that now my son Jack has an accessible home with everything he needs to be comfortable and safe while he grows up, just like Kelsey had. And, we can start working on plans for his and Addie's future #MyOwnHome story (in 20 years or so!). His only requirement is that it has a pool!

  • Twitter - White Circle
  • LinkedIn - White Circle
  • Facebook - White Circle
  • Instagram - White Circle
  • Vimeo The Kelsey

© 2020 The Kelsey™ 

The Kelsey is a 501c3

EIN 84-2909645


San Jose + San Francisco