Heartbreak and the Young Entrepreneur
On letting our kids take risks, fall down, and get back up.
This Saturday is the 10th annual Listen To Your Mother Boulder show, and so today’s column features the piece I read last year. I was a cast member in LTYM Denver 2013, and I started producing LTYM Boulder in 2016. Producing this incredible show is one of my favorite parts of my career and it’s some of the most meaningful work I’ve ever done. If you haven’t heard of the show before, it is a live storytelling show featuring original compositions written by local authors about motherhood—having a mom, being a mom, not having/being a mom, the good, the bad, and the ugly. It was founded by the incomparable Ann Imig, and at one point, over 40 cities had shows around Mother’s Day.
Whether or not you are a mom, or even a woman, this show is such a memorable night out. It’s more a celebration of storytelling, community, and connection than anything else, and it’s such an honor to be a part of it, whether as a producer, cast member, or audience member. If you’re local, you should absolutely grab tickets here and join us at the Boulder Theater this Saturday, May 4th, at 7:00 pm!
No spoilers for this year, so here is my story from last year, which feels even more meaningful a year later. I wrote this over ten years ago, when my kids were five years old and nine months old, which seems incredible.
Heartbreak and the Young Entrepreneur
It was a Saturday afternoon in early May, and I was on my way home from a 90-minute massage, one of the few times I had left my baby and kindergartener to do something enjoyable just for myself. I was delighted, and yet haunted by that foreboding sense that everything was about to go to shit upon my return. Despite the foreign and disorienting aprés-massage relaxation, I drove home as fast as I possibly could, certain that my arrival would avert some crisis that would have snowballed had I pulled up 45 seconds later.
My family was sitting on the front lawn waiting to welcome me—although there was no actual "crisis,"on this occasion, the scene was problematic in its own way. Pulling into the driveway, I noticed that my five-and-a-half year old had set up some sort of makeshift table out of an old box. Ahh, a “stand” of some sort, I supposed, noting a construction paper sign and stack of papers weighted down by a rock.
“Mother’s Day cards, one dollar!” Izzy bellowed. I shot a dismayed look at my husband, who shrugged apologetically. I glanced around our deserted block, a quiet cul-de-sac; there may as well have been a soundtrack of chirping crickets and tumbleweed blowing by. Hmmm. Perhaps not the best market for our product. I rushed inside and dug 27 cents in change out of my purse. Fortunately, the kindergarten curriculum had not yet covered money skills. Enthusiastically, I selected a card (for myself) and forked over the change. Izzy looked temporarily pleased, and then went back to her job.
“Mother’s Day cards, one dollar!” she boomed to no one in particular. It took approximately a minute-and-a-half to shift from confident entrepreneur to irritated salesperson to despondent outcast. “Nobody wants to buy my cards,” she whined plaintively. “I’ll never sell any.” I feebly attempted to describe the current abandoned state of our neighborhood, skipping over altogether the common practice of purchasing one’s OWN cards for one’s mothers, assuring her it had nothing to do with her skills as an artist or stand-operator. Inconsolable, she began to destroy her handiwork, ripping up her cards and knocking down her stand.
“Nobody likes my ideas!” she wept. Consider me officially triggered. She may as well have told me that nobody came to her birthday party. Although mindful not to be a helicopter parent, I am unable to watch my child descend into perceived worthlessness without desperately trying to convince her of her excellence. I crooned and cajoled, but she was having none of it. I looked up in desperation and saw two teenage girls emerge from their house across the street.
“Look, Izzy!” I exclaimed a little too brightly. “Let’s go give those girls one of your cards!” At this point I thought it best to abandon any money-making efforts and just settle for validation. Of course the girls were delighted to receive their slightly ridiculous cards and were appropriately effusive towards Izzy, who smiled smugly. I, on the other hand, had just caught a glimpse of all the years ahead of rejection: low-profit lemonade stands, desperately peddling girl scout cookies to neighbors to make our minimum sell, failed admission into clubs of tiny mean girls, boys laughing at her requests to dance, juvenile delinquents breaking her heart. . .
On the 4th of July, her creative endeavors took on a different form. We were planning a holiday barbecue and had invited family and friends over. The evening before, she spent hours on the living room floor with my dad, handwriting invitations to a parade that would occur the next day. Each note read as follows: “Everyone. There will be a parade at 4:30.” She rolled them up like scrolls, banded with her brand new hair ties, and announced her intention to deposit them on the stoops of every house on our block just like newspapers. I didn’t pay much attention at this stage. Assessing the likelihood of her follow-through, I reflected back on the dozens of personalized invitations to her “ball / tea party / talent show / concert…” that never actually came to fruition and foolishly figured we were safe.
The next morning, she loaded up her invites in a shopping bag and announced it was time to deliver them. My heart sank. Of course I complied, put the baby in the stroller, and watched Izzy skipping gaily ahead of me, shopping bag swinging. I flashed back to my own five-year-old self, selling rocks painted with watercolors to my poor neighbors. Oh God, she’s me all over again, I thought, and not for the first time. These are truly cringe-worthy moments as parents, when we see all too clearly our most painful and vulnerable qualities reflected in our children.
After having delivered all of the scrolls, we had a long talk about what would happen if:
It rained.
The other children coming to our gathering didn’t want to participate.
Our neighbors were at other people’s houses, leaving us without an audience.
The parade, in general, did not go as we had planned.
Yes, we are Type A.
When 4:15 rolled around, we excitedly gathered our parade equipment. Izzy’s sweet uncle had graciously agreed to participate in the parade to stack the odds against failure, bringing along his childhood juggling sticks. We were at a loss as to what to do about the parade music, it being essential that John Phillip Sousa’s marches accompanied our festivities. In a stroke of genius, my enterprising brother pulled his car into the cul-de-sac, set his iPod on repeat, and blared “Stars and Stripes Forever” from the car stereo. The symphonic strains blasting unleashed a wave of giddiness in me, as I remembered all the years of our own dad-championed 4th of July parades.
Led by Papa the bandmaster waving his baton, we took off. Izzy and her pal rode in her electric jeep, waving patriotic pinwheels, Grammy pushed the terrified and bawling baby in her decorated stroller, Uncle Brian juggled his impressive diablo sticks, and extras waved flags and blew bubbles.We were a motley crew, but having one hell of a time—I hoped our efforts alone would be enough reward for my young entrepreneur.
Then I spotted them. One of our neighbors down the block was having a barbecue, and at least a dozen people stood out front to watch our homemade parade. My eyes pricked with tears, knowing what a success this would feel like to my brave and ambitious daughter. The kids and grownups clapped and cheered as we marched by, Izzy beaming.
As I thanked my brother later for his efforts in making Izzy’s dreams a reality, he shrewdly replied, “Well, we saved her from humiliation. There isn’t much in life more important than that.” I knew I had many years ahead of trying—and failing—to save my daughter from heartbreak. A decade later, I’ve learned exactly how much that hurts, and I’m grateful I had only a vague sense of how much higher and more painful the stakes would become as we grappled with the tiny tragedies and victories of our first homemade parade.
We have had ten parades since, although they have evolved considerably—last year’s parade read more like a protest for reproductive rights and now we wave pride flags in equal measure—and the miracle of Bluetooth has mercifully elevated our sound system. Every year that we don streamers and gather with loved ones, it feels like a tiny celebration of resilience, endurance, and maybe a little defiance—look what we can do, no matter what we have been through. We show up, we remember where we’ve been, and we march into the sun, flags waving.
This is dedicated to my oldest daughter, the strongest, bravest, most resilient person I know. I would have given anything to shield her from pain—then and now—and ultimately I know that every heartbreak she has endured has made it that much more powerful when she gets back up and throws another parade.
XOXO,
Steph
Grab LTYM Boulder tickets here, and we’ll see you Saturday for some not-to-be-missed stories from a courageous, generous cast of writers.