Tomorrow is the start of a new era: it's your first day of Kindergarten. Over these past 5 years, 2 months, 3 weeks and handful of days (who's counting?!) you have been by my side more than any other being. I have spent most of my days multitasking life with you, and though it's been trying at times, it's been more rewarding then anything I've ever done- you made me a mom. You also helped me discover my creative side- documenting your growth is what fueled my desire to start a business focusing on helping other families capture this special, fleeting era of babyhood & childhood.

Selfishly, of course I'll miss you. Without you, last winter, I would have struggled, I know. With a cranky newborn and with your dad traveling a lot, you were what kept me on schedule, and for lack of a better word, kept me sane (yes, even with all the lego chatter). It felt good to say "hey, what do you want for dinner tonight?" and get an actual answer. And for the record, you didn't always get your first choice (but sometimes when you requested pancakes, I happily obliged).

At a mere 5 years old, you seem older than you are.

You are incredibly compassionate which isn't the most common trait in 5 year old boys- so much so that you often cry harder than your brother when you accidentally knock him down or love on him a little too hard. I love this about you... it makes me proud to raise boys. You are teaching me so much, and I thank you for being my first; for letting me learn alongside you. I will never claim to know everything, or to always do the right thing, but I will always work my hardest to be the best mom for you... and when I fail at times (because I have, and I will), thank you for being patient with me. Know that I am doing my best, and love you with every fiber of my body.

Of course it hasn't been all roses- life is never that way. This summer I made sure to give you plenty of unscheduled down time. Some of this time was so refreshing and sometimes I could hear the pleas in your voice - "Pleeeeeeease play legos with me" 9 thousand times a day, which equally drove me nuts and filled me with guilt ("should I be entertaining him? But I really need to work! He needs to learn to entertain himself...but he'll only be begging me to play with him for so long..."). Sometimes I gave in, and sometimes I stuck to my guns and I think all in all, we've hit a good routine. But it's all about to change. 'Routine' for us consisted of leisurely wake ups, hot breakfasts, pj's till 10 (because why rush when your little brother has to take his morning nap anyway?!) or a short stroll to preschool (luckily both in the city and in our new place in the 'burbs, we were able to walk/bike to school which I was/am so thankful for) or out for a walk to get coffee. The infinite down time, which sometimes made the days drag on, are no longer.

You are now expected to be up and out of the house early in the morning. You are going to take a BUS to school. You are so freaking excited about this and I'm flipping the F out about this! Bullies! Older kids! No seatbelt (wait is that a thing? are there still not seatbelt on school buses? Clearly we'll find out). I'm now going to pine for you to get home, to tell me about your day.

You will now have an entire new world and new life that I won't be a part of- and that scares the crap out of me.

Listen- I believe in you. I know you will do amazing. You are smart, you are kind, you are social. But you are also sensitive and I love that about you but I worry about what the big bad world has in store for you at times. I don't want school to 'harden you up' yet I know a bit of callus is needed in the world at times. Baby boy, I just want you to continue to be you. Be confident in who you are. Right now you are a lover of legos, your cat, ice cream, tomatoes and cheeseburgers. You just lost your first tooth and started riding a two-wheel bike (on your first go!) You like things done your way (which I think is fairly common for most 5 year olds) but you have your dad's (and grandfather's and great-grandfather's) engineering blood in you...you love to build and you like it done right (I'm worried this will be challenging for you with peers at times...). You make friend wherever you go and talk a LOT (you'll have some trouble I suspect getting that under control in the classroom, but you'll figure it out). So basically, I love you to pieces but I'm worried about ALL the things. Apparently that never goes away, says the experienced moms-of-bigger-children I've talked to.

It's bittersweet... this end of an era. The era of me and you together most of the time. I can't get my heart around the fact that you'll be without me for the majority of the hours 5 days a week. BUT. I also know, you are going to be ok... it may take some adjusting and you'll likely be exhausted (and therefore incredibly grumpy) those first few weeks while you adjust- but, you will be more than ok... you, my love, will be amazing. You are stepping into a wonderful part of childhood: Elementary School. Your new orange camo backpack is packed with pencils, which you meticulously sharpened. Your clothes are set out. Your lunch is packed (forget the part about tomorrow being an incredibly 'gradual' day and your first full day isn't till Thursday).