Page 89 of Trust Fund Baby

“Winn …” My voice softened. “There’s nothing ridiculous about it in my eyes. You don’t have to live their life. You don’t owe them that.”

“Easy for you to say,” he said, eyes on the TV screen as he continued to scroll. “You broke out. You’re thriving. You’ve got a new business that’s thriving with people interested in your work, recognizing you for it. You’re proving every day that you can stand on your own.”

“None of this proves that you can’t do the same,” I told him.

Winn huffed out a laugh, but it was short and brittle. “You make it sound so simple.”

“Maybe it is,” I countered, tugging the blanket tighter around me. “You act like there’s only one version of success, and it’s the one our family hammered into our skulls. But success doesn’t mean sacrificing your sanity. It doesn’t mean waking up every day dreading what you’re about to do. If your workshop is the only place you feel like yourself, then maybe that’s worth listening to.”

He gave me a side-eye, and I could see something else holding him back.

“What is it?” I asked, trying my best to pry the last bits from him. My brother called me stubborn, but he was likely far more stubborn than I was.

“I worry about Renee.”

My eyebrows shot up. “Renee? Your assistant? What about her?”

Winn nodded slowly, rubbing the back of his neck as if the words were stuck. “She’s … she’s been holding things together for me more than I want to admit. If I walked away, I’d be leaving her behind to deal with Dad and Grandpa on her own. She’s good, brilliant. But she doesn’t deserve to be chewed up by that machine.”

I tilted my head, studying him. “So, you’re telling me you’ve been contemplating an entire career change, but part of what’s holding you back is making sure your assistant is okay?”

He grimaced. “Don’t say it like that. She’s more than just an assistant. She’s the only person in the firm who doesn’t make me feel like I’m suffocating.”

Something softened in my chest at the way he said it, and I couldn’t stop the small smile tugging at my lips. “I knew it. You like her.”

Winn groaned, dropping his head into his hands. “God, don’t start this again.”

“Oh, I’m definitely starting,” I said, leaning forward. “Because the way you just talked about her sounded less like a boss talking about an assistant and more like a man talking about a woman who sees him for who he really is.”

He shot me a glare, but there was no heat behind it. “It’s not like that.”

“Sure,” I mused, tucking my knees under me on the couch. “You’re telling me this woman keeps you sane, supports you, probably covers your ass more times than you’d like to admit, and you feel nothing beyond professional appreciation?”

Winn hesitated, his shoulders bunching up near his ears, and that was all the confirmation I needed.

I grinned. “You totally like her.”

“Roxie,” he said like a warning.

“What?” I lifted my hands innocently. “I think it’s kind of sweet.”

He groaned again, sinking deeper into the couch like he wanted the cushions to swallow him whole. “Even if I felt something, it’s not like I can act on it. It’s …”

“Complicated?” I offered, raising a brow. “Funny, that’s exactly what you accused me of hiding behind five minutes ago.”

Winn cracked a small smile, shaking his head. “Fair enough.”

I nudged his shoulder. “Look, maybe you don’t have to figure it all out tonight. But don’t stay in a career that’s crushing you just because you fear leaving it behind. If she’s as smart and capable as you say, she’ll land on her feet. And maybe she’ll even choose to follow wherever you go next.”

“I’m not sure that being an assistant to a carpenter is a job she wants in her repertoire.”

“Life doesn’t always go as planned. I know that better than anyone.”

But instead of saying that I was right, Winn leaned back and moved to switch the topic.

“How was seeing Sebastian at the Christmas Eve party?” he asked. “I never got the chance to ask you about it.”

My stomach lurched at the mention of Sebastian’s name. I gripped the blanket tighter, wishing I could disappear under it like a kid hiding from monsters. “It was fine,” I said lightly, though even to my own ears, it rang false.