Mom! What Were You Thinking?

Being in Toronto and hanging out with family has made this trip really great. The one thing that it has reminded me of was all the fun times my family and I have gone through ever since I was a little boy. My relatives have always wondered what I do for a living and some times it was hard for them to understand. Until now!

One of my relatives told me of a contest they’ve entered to blackmail one of their kids in the future (see, evilness runs rampant in my family). Actually, this contest is just a regular photo upload contest that is hosted by It’s called "Mom! What were you thinking" and they’re basically trying to see which mom had the nerve to dress up their kids in the worst possible fashions! Normally, I wouldn’t enter these kind of contests but I couldn’t pass up the prizes up for grabs.

  • Macbook Pro
  • 16GB iPod Touch
  • Speaker with built in Dock
  • Printer/Scanner
  • Laptop Case

To spice this contest up a little bit, I want to challenge all bloggers to post their own messed up childhood pictures. I tried asking my mom for any pictures of myself as a younger boy so I can be a good sport and play along, but "unfortunately" my mom said she didn’t have any pictures that I could use. So, I’m putting up Greg Morgan’s baby picture to show you what you can use to participate.

The Rules Are Simple

Just post your messed up childhood picture on your blog or a messed up picture of your own kid. Then write a little blurb about what the hell your mom was thinking or what you were thinking.

Since forgot to add a very important item to their prize package – I will be giving away a new Flip Mino and 20" Monitor to the best/worst/funniest post I notice in my Google Alert.

The winner will be announced through an email blast to my newsletter subscribers, so if you want to know who wins this thing in September, you’ll want to subscribe to my newsletter. Sign up here:

By the way, if I find any pictures from bloggers that are just too great to pass up, I’ll do a recap post to highlight some of these great bloggers, while I keep looking for my own messed up picture!

41 thoughts on “Mom! What Were You Thinking?”

  1. Neat contest. I’ll dig through some show boxes and see what I can find.

    1. *Shoe that is. 😉

    2. I can’t wait to see some of these for some of the A listers, good stuff, let me grab that shoebox as well. 😆

    3. I gotta check my old photoes. I guess the most embarassing photoes will earn top recognition on John Chow and then all over the internet..
      That’s definitely a tough decision to make 🙂

  2. BlogSavvy says:

    John, I’ve got my picture entered. Blogsavvy.

  3. ms danielle says:

    lol poor greg. his pic isn’t messed up though. he looks exactly the same!

    1. Gary Lee says:

      I beg to differ … If you say he looks the same, then I still think it’s a messed up picture! ….. Hahaha …. Don’t kill me greg!

    2. Tyler Ingram says:

      Not much has changed huh? lol

  4. Stephen says:

    What if you were adorable no matter what you wore? 😆

  5. We would like to see your childhood photo John

  6. Jorge says:

    I understand you John. I am also a man without childhood photos. 🙄 The few ones I had got lost. 🙁

  7. Caroline says:

    I’m sorry, “BlogSavvy”, but the photo of you with the black eyes, uni-bruise, and crushed velour shirt is HILARIOUS!!

    1. BlogSavvy says:

      Thanks dude it was the life of a kid! DAmn that Starwars toy! If it wasn’t for that there would be no picture!

  8. This was actually kinda fun looking through my old pictures, I put my entry up.

  9. Gary says:

    LOL…how the heck did you get that picture of Greg? That’s not a baby photo, that was taken last week!! 😛

  10. TheMoneyac says:

    Really an interesting contest. Boy, I have so much pictures, but I’ll try not to embarrass my self with those. I just found my shoe box that has all the pictures in, and man, I can really ask – MOM !!!! WHAT WERE YOU THINKING ????

  11. TheMoneyac says:

    Sorry for the double post.

    John, I sent you an email about a week ago regarding one thing. I understand that you could be busy, but could you please take a look at it ?

  12. Gary says:

    Oh, just read the rules for this contest…it’s only for US RESIDENTS!!! 🙂

    3. ELIGIBILITY: To be eligible for this Contest, at the time of entering, the Contestant must be: [1] a natural person legally residing in, and physically located within, the 50 United States or the District of Columbia (collectively, “Territory”);

  13. Ed Lau says:

    That picture isn’t embarassing enough. I’m sure we’ve all worn worse than a striped long-sleeve polo.

  14. I think I’d have a good chance at this. I used to wear neon-colored clothes. I wouldn’t be caught dead in them now: Neon-colored shirts, with matching neon-coloured leggings, matching neon-colored sneakers & matching neon-colored scrunchies. The colors were yellow, green, magenta & turquoise.

  15. Rajan says:

    This is such a coincidence. I was just browsing through old photos last month. Not only was I wearing some weird looking red shirt with these flowers on it. Flowers on a 3 year old boy? But on top of that every damn picture I have I am rocking the good old bowl cut.

    Looks ridiculous.

  16. David S. says:

    Ugh, all of the pictures I’ve seen don’t look too bad. At least your childhood didn’t feature you in a dress(boys don’t wear dresses). The picture is hanging in my living room, been there forever. Maybe I’ll take it down to show you guys, maybe.

  17. BlogSavvy says:

    Sorry for all the ping backs and comments, Was having computer issues, and then i made changes to my post and forgot I had already pingged you. No harm no foul? Right?

  18. Debo Hobo says:

    Oh heck no, I looked like a tomboy when I was a kid. No way Jose!

    Good luck to the winner 🙂

  19. Gary Lee says:

    I’ll probably enter once I get home from SES 🙂

  20. Shaun Carter says:

    I’ve got my entry in at and just wrote a post on my blog. It was really fun to go through those old pictures, certainly brings back some great memories.

  21. Ganesh says:

    I’ve got a good messy photo of my childhood. I’ll upload it and let’s see if I win the prize. 😉

  22. Raul says:

    Hey John,

    Glad you had a good time with family. See you when I get back!

  23. That is the point with an online business, you can move to a new location even a new country and contuinue to do your busness. You’ll recieve recidual income and get time to meet your family and friends at the same time when you are making $$$, Could you possible ask for more? :mrgreen: !

  24. bz says:

    I made my son wear a helmet. To daycare.

    Pictures AND video:

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