Fall: What I’ve Learned about Raising a Boy

Mother and Son photoshoot

It’s Wednesday! In little over a week, I will face what I know will be a very dark moment, all over again. My daughter in heaven will be one year old, and I will not be able to hold her to say Happy Birthday. But this is not the story I want to tell you today. I want to tell you about the boy I do get to hold and how that joy and deep love I have for him has driven light into my heart since his birth, and what it means to have raised him into the young man he has become.353_FAMILY_JessicaI’ve learned so much about raising a boy. I can say with certainty that the following lessons are likely those you will face when raising a boy of your own (in some form or another!). And while I don’t know what it means to raise a little girl, I can only assume that some of these lessons apply to them too.

Little boys adore their mothers. And their fathers too. Seeing us play together, cook together, eat together, or even sometimes cry together is so important to letting our little guy know that we are all in this together.

Boys like quiet time. My son does not appreciate chaos. He revels in some of the quieter moments of his day, and I know this best when I hear him start singing a tune or just creating an amazing tale with his toys. It really is sweet to hear him being creative and imaginative.


Boys should understand emotion and speak what they feel. One of the earliest pieces of advice I got from a baby book was to show as many expressive faces of babies to my own. I bought so many books of baby faces and showed them to my son often. As he has grown, I ask him questions like “How did that make you feel?”, or “How did you make someone else feel happy today?” The conversations are fascinating and lessons I know he (and I) will hold on to for a lifetime.

Play and make a mess of everything. People who know me, know that I am a perfectionist. I like order and it comforts me to keep things organized, and well, perfect. But being a kid (or an adult for that matter!) isn’t always perfect. I’ve made peace with the fact that playing without worry of a mess can be fun, and healthy! So I get my hands dirty, spill something without freaking out, and let him turn over that huge bin of Lego’s with abandon. As he always says, ” Mom, we can just clean it up. It’s not the end of the world.”



Show them how to care for themselves. This is a life lesson for any child, but there is something about raising my son to care about his well-being and home that gives me comfort in knowing he can thrive as an adult. He cares about his clothing, and his hair and his health. He wants to like vegetables and does his best to “try it until he doesn’t like it”.

Show them how to care for others. Many girls get dolls to take care of. Many boys get cars to race against each other; not exactly the way to learn to care for another human being (unless I’m saying “Were the passengers in that Hot Wheels car crash wearing seat belts?”) Isn’t that how many of us grew up? And while my son’s own interest is often in clocks and gears and working objects, I know he knows how to care for others. I see it in how he responds to kids who get hurt on the playground (“Mommy, can I go help him!”), how he wants to pick up litter off the ground (“Why do people make the Earth such a mess?” Big question, I know!), but most importantly how he cares about his sister who he does not get to see (Is she happy there?”).




One day my son may marry someone. I’d like to think that he will look for someone who has attributes like his Dad and me. I know that the way we show him how we love each other is the way he will grow to understand love. So we work hard everyday to love, and show him our hearts to help him grow his own.



It was so lovely to spend the day in Central Park to take these family photos with JJ from  JJ Ignotz Photography. She has been such a wonderful photographer to work with in some of my favorite photoshoots around New York City seen in some of my top posts here, here and here.

My Outfit: J.Crew vest (old, under $30 here and similar here) | Ann Taylor jeans | Loft sweater (on sale!) | Joie over the knee boots ( absolutely loving these! and these under $70) | Ralph Lauren satchel | Urbancode keychain (all colors  from Michael Kors here)

Boy’s Outfit: Crewcuts half-zip sweater and plaid lined jeans  (now 30% off!) | Crewcuts Plaid button down (perfect for holidays here!) | Timberland boots (similar here and great dress-up pair here) | Men’s Polo Ralph Lauren half-zip sweater | J.Crew Men’s plaid button down


Thank you for reading!

Jessica TSG Signature

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  1. November 24, 2015 / 9:25 pm

    You have a beautiful family doll! From the sound of your post, you are doing a great job of raising your son to be an amazing young man. Keep up the great work mama!
    xx | A

    • Jess
      November 25, 2015 / 9:22 pm

      Anastasia, Thank you so much for your kind words! I appreciate your thoughtful comment! Have a wonderful Thanksgiving! xoxo, Jessica

  2. November 19, 2015 / 8:31 pm

    Beautiful story Jess! I’ve got happy tears :)

    • Jess
      November 25, 2015 / 9:26 pm

      Ana, You are too sweet! Thank you! xoxo, Jessica