Chapter 8
Chapter Eight
Jess
The impromptu party in her Aunt Lily’s backyard had been fun, for Maisie at least. Jess couldn’t stop feeling awkward and as if everyone was judging her. Aunt Lily and Anna had both told her they didn’t think any less of her, but it was still something she couldn’t shake.
Jess knew that thoughts flitting around in her head were those of her insecurities.
She had failed at her startup, and her marriage, but it didn’t mean that she was a failure.
Most of the world’s highest achievers, the legendary athletes, musicians, and CEOs, failed a hundred times before they ever hit it big.
She was in the best club she could be in, but no matter how many times she told herself that, it didn’t help.
It also didn’t help that her well-meaning parents continued to make random, passive-aggressive comments to her about growing up and getting a real job.
It didn’t matter that Jess had been very successful before Clark had sucked her business dry and forced her to shut it down.
That would never register with her parents.
They were old school and felt that working a nine-to-five was the adult thing to do.
Jess knelt beside the SUV, brushing peach juice from Maisie’s cheeks with a half-dry baby wipe.
“Hold still, sweetie. You’re a sticky little swamp monster.”
Maisie giggled, her curls tangled with grass and a smear of frosting still on her nose.
“That was the BEST party EVER! I had three cupcakes, and I climbed the peach tree! And Blaze showed me a turtle he found, and I got to feed him a hot dog. Don’t tell Mommy,” she added in a loud whisper to Claudia, who stood nearby holding the bag of party favors.
“Your secret’s safe with me,” Claudia said with a wink. She tucked a loose strand of silver hair behind her ear, eyes flicking to Jess with quiet amusement. “It was nice seeing Lily with a little spark again. Don’t you think?”
Jess nodded as she buckled Maisie into the car seat. “Yeah. It was.” She didn’t say more, because her throat tightened at the thought. Aunt Lily’s spark had flickered out for a long while, and seeing it reignited, even briefly, made Jess ache in ways she couldn’t name.
She climbed into the backseat next to her daughter, and her father pulled out of the driveway.
Jess leaned her head against the cool glass of the passenger window, the blur of trees and salt-marred fences slipping past as they drove toward Oak Bluffs.
Maisie’s happy humming drifted up from the backseat, but Jess barely heard it.
Her mind had wandered, back to the harbor, back to the dock, back to Uncle David.
She could still feel the tight hug he’d given her the morning she, her now ex-husband, Clark, and Maisie had boarded that one-way flight to California, the woodsmoke from his flannel clinging to her clothes long after he’d let go.
“You’re brave, Jess,” he’d said, cupping the side of her face with his calloused hand. His eyes had crinkled, that ever-present twinkle there. “Don’t let anyone make you feel like you’re not. It takes guts to chase something that doesn’t already have a map.”
She’d blinked away tears, nervous and unsure and trying to act braver than she felt. “I just… I hope it works out. I don’t want to disappoint anyone.”
David had scoffed then, loud and familiar.
“Disappoint who? The people who never dared to try? Listen…” He pointed at her.
“I’ve been on a boat since I was fourteen because that’s what we did.
Fishermen. Sons of fishermen. Your dad chose to follow our mom’s path and become a teacher and then a principal, and God love him for that, but I used to dream about building things with my hands that didn’t smell like bait.
Tables, dressers… chairs people might pass down someday, you know?
But I never went all in, because it was expected of me to uphold the family name and continue the legacy of Hartman fisherman.
You? You’re diving headfirst, and I think that’s incredible. ”
She could still feel the lump that rose in her throat then, the tears she barely managed to hold in.
He had believed in her, loudly and without hesitation, something her father never quite managed.
Not that Henry didn’t love her. He just…
showed it in quieter ways. Showing up. Fixing her fence.
Picking her up from the airport without saying much at all.
Uncle David shouted his love from rooftops. And when he passed the year before, a hole had opened that no one else tried to fill.
What gutted her now was the sense that she’d failed him. She’d lost the business. She was back home. Back in the room she painted purple when she was twelve. She imagined his voice, still encouraging, still proud, but she couldn’t quite believe it.
Jess stared out the window. She understood how her Aunt Lily had seemed to have lost her light. Uncle David had been that for a lot of people. She missed her uncle; she couldn’t imagine what it would be like to miss her husband in this way.
Her dad, Henry, cleared his throat as he drove the SUV.
He was tall, broad-shouldered, and still carried himself with the discipline of someone who’d spent his life doing things the right way.
No fanfare, no mess, no shortcuts. “We should have left a little sooner, before that ferry traffic clogs the road.”
The drive through Vineyard Haven was quiet for a few minutes, broken only by Maisie’s occasional chatter from beside her.
“Can we go back next week? Please? I want to see the turtle again. Aunt Margot said she might let me help make jam if I wash my hands this time.”
Jess turned in her seat, smiling at her daughter. “We’ll see, peanut. But I’m glad you had fun.”
Maisie yawned and leaned her head against the side of her car seat, eyes fluttering. “It smelled like honey and sunshine there.”
Claudia chuckled softly. “Poetic little soul for a six-year-old, isn’t she?”
Jess gave a half-laugh, looking out the window at the way the light kissed the tops of the trees.
They passed quiet homes with climbing roses on fences, yards littered with bikes and water toys, and neat hedgerows that framed glimpses of the water beyond.
Spring was still hanging on, the wind becoming warmer and lazy through the slightly cracked window.
Then Henry spoke, his voice even and direct. “Have you found a job yet?”
The question landed like a stone in Jess’s gut. She turned her head slowly, catching his eyes in the rearview mirror. He wasn’t angry or judgmental. Just…asking. The same way he might ask if the mail had come or if the tires had been rotated.
“Not yet,” she said, trying to keep her voice light.
“You been looking?”
Jess nodded. “Yeah. Of course.”
Henry grunted softly, his eyes back on the road. The silence after that seemed longer than it really was.
She folded her arms across her chest, wishing she could disappear into the leather seat. Her cheeks burned. She knew he didn’t mean anything cruel by it. That was just how he was. But still, it stung.
“I’m trying,” she added. “It’s just… not easy.”
Claudia glanced over from the backseat, a gentler tone in her voice. “Of course it’s not. It’s not like they can check your references, since you are your references.”
Jess swallowed hard, internally sighing at her mother’s unintentional jab.
Jess had run her own business for years.
It was hard to pivot back to someone else’s structure.
She’d made her own money and been in control of it herself.
Clocking in and out for someone else wasn’t something she wanted to do.
“Yeah,” Jess said. “That’s exactly it. I’ve been applying. I even had a few interviews. But nothing that felt right. Or paid enough to justify putting Maisie in daycare full time.”
Henry nodded once, slowly. “Well. Keep at it.”
That was it. No lecture. No encouragement. Just an expectation.
Jess swallowed hard. It wasn’t that he didn’t care.
He did, in his way. But she’d spent her entire adult life feeling like he was waiting for her to give up her silly dreams and join the real world.
“Real job” had always been code for stable, traditional, and unimpressive.
Nine to five. Benefits. Retirement plan.
She’d had all that in her own business—except the validation. And now that it had failed, she felt like she’d proven him right.
The SUV rolled through Edgartown Road, winding past thick forests and glimpses of ocean between the trees. The sun had begun to dip lower, casting long shadows over the road. The air smelled faintly of salt and pine.
They passed the old general store, still bustling despite the hour, and the ice cream shack Jess used to visit with Anna when they were thirteen and obsessed with boys and matching anklets. Everything looked smaller now. Not because it had changed, but because she had.
Maisie was asleep by the time they reached the outskirts of Oak Bluffs.
Her little chest rose and fell softly, the edges of her curls fluttering in the breeze from the air vent.
Jess turned to look at her and felt a pang of guilt.
Maisie had been so excited about the move, about being close to Nana and Pop-Pop, about adventure.
But Jess wasn’t sure if she was giving her daughter an adventure or just dragging her through the aftermath of a collapsed life.
The streets of Oak Bluffs were quiet, the clapboard houses painted in pastel shades that glowed in the fading light.
Jess had always thought of the town as postcard-perfect, like something out of a children’s book.
Her parents’ house sat near the edge of town, tucked beneath tall oaks with a wide front porch and hydrangeas flanking the walkway.
Henry pulled into the driveway, tires crunching softly on the gravel. No one spoke for a moment.
Then Claudia stirred. “I’ll take Maisie up and get her into pajamas. You two unload.”
Jess nodded, getting out and walking around the SUV to lift Maisie out of her seat. She smelled of sunshine and sugar, even under the dirt. Jess kissed her forehead and passed her to her mother, watching as Claudia carried her up the steps and disappeared inside.
She turned back to the car, grabbing the bags and folding the stroller.
“I know it’s hard,” Henry said behind her.
Jess froze, then looked over her shoulder.
He stood with his hands in his pockets, eyes fixed on the porch. “Coming home. Feeling like you failed. It’s not easy.”
Jess said nothing, afraid that if she spoke, she might cry.
“But it’s not the end of the world either.”
She gave a small, sad smile. “Sure feels like it some days.”
Henry looked at her then, and there was something uncharacteristically soft in his expression. “Just keep going. You’re still her mother. That means something. Maybe you and Clark will work it out.”
Jess nodded, knowing that last part would never happen.
Her divorce was finalized, and she wanted nothing to do with her ex-husband.
He should be in prison, and his only saving grace was their daughter, but Jess kept that information to herself.
After a moment, she followed him up the steps.
The porch light flicked on as they reached the door, casting their shadows long and crooked behind them.
And though she didn’t say it, Jess felt something in her chest loosen, just a bit.