One of the best things about having a kid is experiencing and re-experiencing childhood wonder through their eyes. Last year, I passed on trick or treating with a 5 month old for his first Halloween knowing how obviously it would be a parent-driven candy hoarding event and how indifferent my son would be to the fanfare (even if I did have a really good idea to dress him up as a mozzarella stick in a bucket of marinara…). 

This year though, he can walk. He can grab. He can charm people into giving him things, and while hardly encouraged, he can eat a little candy. We trick or treated. He was a lion. It was adorable. That being said, I wasn’t super excited. I still thought he’d be pretty indifferent (he was), and I still thought it would be pretty obvious we were collecting all this candy for ourselves (we were), but this year it was, apparently, non-negotiable. 

So, if I’m going to do a thing, I’m going to do it right. We went to a Halloween store and ran around being scared and humored by mechanical spiders, we imagined future family costumes, and we picked out his little lion suit. I teased out the mane to get that “not just out of a plastic bag” look. We gave him some time (some of it unhappy) in his lion suit, so he would get used to the concept of a costume. And put a few different trick or treating options on our family calendar. Trick or treating in this neighborhood was this day, but if we wanted to do that neighborhood we’d have to pass on this one… etc.  

For his first trick or treating experiences, my little lion got a very true Midwest experience on the last Saturday in October (pretty distant from Halloween) from 5-8 pm on a drizzly, 40 degree evening in a suburban neighborhood in northern Milwaukee. He was interested in the very dramatic costumes he saw, enjoyed riding in the covered wagon of our friends’ with a glowstick, and was excited when we stopped for pizza to warm up on our way home.  

The next day, a perfect 65 degree afternoon, the sun out, the leaves changed and falling, we walked through one of the loveliest areas Milwaukee has to offer – the neighborhood right along the lake – big beautiful houses, small yards (read: houses are close together), lots of kids, lots of candy.  

What did I learn? 

• First, there’s always something to learn from a first. It was hardly my first time trick or treating but it was my first time as a parent and my child’s first time. There was so much delight, so much excitement, so much to notice about how I’d remember this day, and how he’d (maybe) remember it, too. We took lots of pictures, made memories, and it’ll always be special. Always be present for firsts – they’re the only ones you get.  
• Trick or treating as a parent is fun. Passing out candy as a parent is fun… if you make it that way. We encountered curmudgeons who didn’t want to be giving out candy at all, were joyless in the presence of a cute lion, and who didn’t realize they could easily just stay in their house, turn off their lights, and not be disturbed by us, but we also met people who were so excited to be a part of the experience – they even had “adult” treats in the form of beverages that they bought… in bulk… to hand out to any parents who wanted/needed it. What? I didn’t know this was a thing! What a glory it is to be a parent on Halloween, truly, if you’re willing to have fun with it.  
• Enough is enough. As it was when we were kids and we ate all the candy… there’s a limit to the fun to be had. There are too many houses, too distant of routes,  too many pieces of candy, especially with a toddler. Sure, we could probably have another “adult treat” (sounds much more sinister than it was), but the little ones had had enough. Know when to call it quits, end on a high note, and not make everybody involved sick to their stomachs.  

While this is a story about a Halloween experience, it also isn’t – it’s about any experience, any first experience, and how to make it the best experience it can be. Someone’s first day? Make it fun, make it memorable, and know when too much paperwork is too much. Professional development? The same. A holiday event at work? The same: be present, be pleasant, and know when to quit.