I didn’t think my last monarch caterpillar was going to make it.
If you’ve been here awhile, you know that I raise monarch caterpillars in the summer. (If you’re new here — thank you! I promise I’ll bring this around to boys.) You may also know that every fall, the final generation of monarch butterflies migrates to Mexico. They overwinter there before beginning their spring trek northward.
Which means…these critters are up against a deadline. A caterpillar that doesn’t transform into a butterfly with enough time/good weather to make it to Mexico will likely die. He (or she) won’t be able to find the food needed to fuel the full journey. Or, cold render will render him slow, an easy target for predators.
So when I noticed a tiny caterpillar on a milkweed leaf in my habitat on September 5, I was concerned. I was planning to throw that milkweed away because my “last” caterpillar had just transformed into a chrysalis. This little one must have hatched from an unseen egg on the milkweed. Time was not on his side.
Monarch caterpillars typically grow for 2-3 weeks before pupating — before creating their chrysalis — and then need another 2 weeks or so to transform into a butterfly. Longer, in cool weather. Do the math: this one might not be ready to fly until mid-October. Sometimes, we in Wisconsin have freezing weather by then.

I decided to give the little guy a chance. He grew, slowly, and it was hard to get him adequate food; most of the milkweed around here is yellowing and drying up.
Yesterday, I crossed the road to get him fresh milkweed. And in the process of adding said milkweed to his habitat, I managed to knock the now-almost-fully-grown caterpillar off his nearly-stripped-bare milkweed & onto the floor. He wriggled violently. I carefully attempted to scoop him onto a leaf, using another leaf, so I could transfer him on to the new plant. He did not like my attention. I got him on the leaf & put him on the new plant - and he just sat there, stunned. Still. Determined not to move, lest his movements attract anymore attention.
I went about my business. When I checked the habitat a few hours later, the caterpillar was on top, clinging to the ceiling instead of his plant. They do that sometimes — crawl about the habitat — so I wasn’t concerned. A few hours later, the caterpillar was still in the same location, & I realized that he was spinning the silk pad he’d need to hang in a “J” & pupate.
Usually, caterpillars crawl around a lot before they settle down to pupate. Not this guy. It’s as if he knew that he needed to move quickly if he’s to make it to Mexico.
When I woke up this morning, his chrysalis was complete. I now believe he’s got a good shot of making his migration.
HOW does this apply to boys?
How many times, already, have you worried that your son is “behind?” How many millions of hours have parents spent fretting about their teenage sons’ apathy & lack of maturity? And how many of those sons then suddenly (& often, for no apparent reason) took major steps forward?
I can’t guarantee that your son will suddenly jump into action one day, and I definitely can’t tell you when that will be. I can tell you that nagging and trying to rush him to action won’t work; if he’s not ready, he’s not ready, and no amount of talking, yelling, motivating, or pushing will change that. At least not in a positive way — if anything, your son might stubbornly dig in and pull back from connection.
Your best best is to do what I did for my caterpillar: Create a “habitat” that gives him access to what he needs to grow and thrive. I am NOT advocating for helicopter parenting here; I am not suggesting that you give and give and give, or do things for him that he could do for himself. I’m talking about the basics: protection and space, food, care, time.
Now, humans are obviously much more complex that caterpillars. Use your discernment. Facilitate your sons interests and passions, when and how you can. Allow him to experience the consequences of his actions. And if you see signs of depression, anxiety, substance use, an eating disorder, or any other condition that’s beyond your expertise and personal capacity, seek help. There is no shame in seeking or accepting help. Creating a healthy habitat for our boys includes pulling together a formal or informal team to support his development.
As I said earlier this summer, boys change when they’re ready - not when we are. And often, their internal clock and calendar is more finely honed than we think. Give them what they need, and, like my caterpillar, they have a good shot at “making it” to their destination.
Here’s to building boys!
Jen
P.S. My next Substack Live — a conversation with “boy mom” & author Rebekah Peeples — is this afternoon at 2 pm ET.
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