Inspiring Mom Eileen

After teaching in Chicago Public Schools for 10 years, Eileen O’Connor lost her job. She faced unemployment with four young children and instead of sulking in her woes, she shook off her sorrows and headed over to Second City. Though her life as a counselor in CPS ended without warning, her career as a comedy writer was merely beginning.

Now with over 5,500 followers, Eileen runs a blog on womanhood as an ‘unemployed, orphaned-wife-mother-woman.’ Through sarcasm, she addresses both simple and complex issues she faces and leaves readers laughing out loud. From stepping on Legos to raising two non-conforming gender children, Eileen invites the public into her world.

With her unapologetic love for wine and honest humor, she looks at life through rose-colored glasses.

“My dad taught me to laugh. Even in the worst of times. There is humor in everything…He used to go nuts if we spilled something and used too many paper towels to clean it up. He was constantly ripping paper towels in half. I still feel a pang of guilt each time I use paper towels. If only he had lived to see the select-a-size.”

When Eileen lost both her parents in her early twenties, she struggled with being an ‘adult orphan.’ Soon, she created a support group for her friends that also lost parents to grieve together. In true Eileen O’Connor fashion, she named it the Dead Parents Society (DPS).

“Since it started, almost everyone in our group has been orphaned. It’s been so hard to see my friends going through that because I know how awful it is. We usually meet at one of our houses because there is lots of crying, but one time we took it out in public and all dressed like one of our dead parents.”

DPS Parents Night Out

Though outsiders gave them confused looks, the girls in the group laughed and laughed. Death is hard to talk about and accept, yet with a friendship and support group this strong, they embraced mortality to honor their parents in a lighthearted, quirky way.

“Life is so freaking short. My husband and I both lost parents too young and we have a child with special needs. When our baby was being tested for all sorts of chromosomal abnormalities, all we prayed for was our baby to live. Our prayers were answered and nothing much else matters anymore.”

Despite being a mother to four children, Eileen did not intend to write about her kids on her blog. But then something happened.

My husband and I said, Oh my god. We need to make sure these kids are okay.”

Their family witnessed firsthand the ugliness of society’s double standards. Two of Eileen’s children are gender non-conforming; one daughter wants to dress like a boy, one son wants to dress like a girl.

“I was a total tomboy just like my daughter. But it’s such a double standard. Nobody questions our daughter wearing boy clothes. Everyone says, “She’s so cute! She’s a tomboy,” but then with our son everyone says, “Oh my god, what’s wrong with him?”

In her blog, Eileen is using her voice to shed light on the petty and ridiculous things that people fixate on.

“There are children with terminal illnesses and parents who have lost a child. We are not wasting one precious moment with our kids on nonsense.  When it comes to what clothes our kids are wearing, we don’t care. As long as they’re name brand and I paid full price for them. In the grand scheme of things, that’s all that really matters.”

With a touch of sarcasm, she puts life in perspective and is inspiring others to speak out.

“A woman once came up to my crying, telling me that her brother was gay and killed himself. I just couldn’t imagine not accepting your child. I know our generation is different than the last when it comes to things like this but it really struck me,” said Eileen. “People also send me messages that their adult siblings finally have transitioned and that gives me so much hope.”

For other parents going through a similar situation, Eileen offered a few words of advice, “No matter what you do, you cannot change who they are or who they want to be. We could all cry and make my son wear pants. But it’s not going to change who he is and what he wants to be. Same with my daughter. Just love them like you love your other kids.”

Thanks Eileen, for making us laugh and realize life can be short and beautiful and children should wear whatever clothes make their hearts sing.


To read Eileen’s open letter to Caitlyn Jenner or laugh at her comedic and unfiltered posts about life, check out her blog or Like her on Facebook.