Grace Winston


TWO.  Both are boys… and they are 14 years apart in age.  Cassidy just turned 18 (yes, I am now the parent of an adult). Ryan will be 4 at the end of October. God has a plan, and it is beautiful. Tiring, but beautiful.  



I am a Senior Account Executive for WTTW Channel 11 Television and 98.7 WFMT Classical Radio.  My job is to gain corporate support for our stations, and I also run three major community outreach programs with which we conduct 60+ live events every year.

Full time at work & full time at home; I am blessed to have both.


I suffer (but suffer is actually not the correct word…) from “Jack of all trades/Master of none” syndrome.  I feel like I’m not able to give 100% to anything and I am definitely an “all or nothing” kind of gal. It gives me anxiety if I know that I’m not giving something or someone 100% of me, especially if it is my late-life-bonus-baby Ryan.


Write it down. Almost every pair of pants/shorts/skirt/dress I own has pockets.  I need to keep a pen and post-its in my pocket at all times. If I write things down, my anxiety lessens.  I then know that I don’t have to take up valuable brain space (because that brain space is becoming more and more crowded every day) with trying to remember multiple things at all moments.  And I’ll let you know my true secret. If something is SUPER important, then the post-it note goes in my bra. I can’t tell you how many times I’ve been putting my pajamas on at night and a yellow post-it falls on the floor.  I then determine if I need to deal with that super important thing before I go to bed, or first thing in the morning.

The only down side of this method is when I have a work function in the evening and have been collecting “SUPER important” post-its all day.  If I hug someone to say hello that evening, I feel a crunch in my upper region and get jabbed by the corners of the paper. I am happy to report, though, that I haven’t yet received any paper cuts!

How do you deal with the working mom guilt?

I hug my kids a lot and tell them how much I love them every day.  It also REALLY helps to have a great husband. I have to give Chris- my hubbest with the mostest- a huge round of credit because he has allowed me to get more things done and relieve my “guilt” by spending valuable time with our boys when I can’t.  If he is at the park with Ryan and/or at Cassidy’s baseball game and I am held up or running late because of having to finish a project at work, it feels good to know that he is having the quality time with our kids if I cannot.


Yes, you can, and yes, I do.  The key, for me, is to constantly remind myself that I do.  I thank God every morning and every night for the people I have in my life, and the blessings I am surrounded by and with.  My commute to and from the office is 45 minutes, and that is my time to give back and give thanks. I deliberately notice the flowers and the trees.  I notice children at the park laughing and gaze at their parents gazing at them. I smile and yell “you’re awesome” to the group of developmentally disabled high-schoolers walking to class across the street from my office.  I roll the window down and give whatever change I have in the car to the homeless person with the cardboard sign BECAUSE that person could be me and I am so very lucky that it is not. My husband and I believe, and live by, the powerful notion that we are here on earth to help one another.  If I can portray that to my children, and help them understand that THAT is the true key to happiness if you put it into action, then I will feel that I have given my very best to them.