The Boss Who Built Me Back Up

How a woman named Sam helped me find my voice again

After getting fired from a toxic job at a big NYC ad agency—the kind of job that crushed my spirit, made me question my confidence, and slowly dimmed the version of me I used to love—I did what any deeply bruised 27-year-old would do: I got into my older boyfriend’s Audi and let him drive me up to his family’s house in Vermont for the weekend. I was heartbroken, embarrassed, totally unsure of what came next—and also, somehow, calm. Because I knew I already had a meeting lined up for the following week.

What most people didn’t know was that 13 months earlier, I had turned down another job offer in New York. It was from a woman named Sam—a former big ad agency PR boss who had left to start her own boutique PR firm. She was sharp, stylish, wildly smart, and the kind of woman who could quote both The Beatles and Tolstoy and somehow make it all relevant to the pitch deck. I had liked her instantly.

But her offer back then had scared me. It was less money than the big agency, and going to work for a startup when I was moving to a brand-new city? Too risky. So I’d politely declined, said “let’s keep in touch,” and took the shiny corporate job instead.

Eleven months later, I was unemployed—with a bruised ego and a solid resume—and decided to reach back out to Sam. She welcomed me with open arms and scheduled a coffee with her new president within days. While I was secretly hoping to work directly for her, not another middle-aged man in a blazer, I was also desperate and deeply grateful. And, as it turned out, that man ended up being one of the tougher—but most respectful—bosses I’ve ever had. He challenged me, but he didn’t diminish me. There’s a difference.

They offered me the role of account director. I got a small raise. I got a bigger title. And more than that, I got dignity. It was the ego boost I didn’t even know I needed.

I was terrified. I’d never worked in client service before. Suddenly I had five clients—C-level clients—and I had to show up like I knew what I was doing. Which I didn’t, at first. But I remembered what my parents used to tell me as a kid: fake it till you make it. I’d gone to acting camp, for god’s sake—I knew how to play a part. So I played the part of a confident account director until I actually became one.

And Sam? She took me under her wing in a way I’d never experienced. She coached me, mentored me, encouraged me, never made me feel small. She sent notes after meetings. She sat with me to review my emails, gave me thoughtful feedback, took me to lunch, invited me to riff. She let me riff. She made space for me to be exactly who I was—which, ironically, was the thing all my previous bosses had tried to mute.

(me and a random dog at my new office in NYC circa 2011 or 2012?)

The things I’d been told were “too much” about me—speaking up, having opinions, being direct—were now my strengths. Clients liked that I was take-charge. Team members wanted to work with me. I was starting to become a leader.

My life outside of work shifted too. I started waking up early to take barre at Exhale or hit the Equinox I could barely afford. But I did it anyway—because it made me feel like I was investing in myself. I was still going out with friends, still occasionally hitting a club, but I was starting to feel a new kind of focus. A deeper ambition. I wasn’t just collecting fun nights—I was building something.

My wardrobe upgraded too. Mini skirts, blazers, and boots. Weekly blowouts ($29 at the corner NYC salon). I was polished, professional, but never boring. I was still me, just… elevated. Eventually, I moved into a bigger apartment in Gramercy. Okay, yes, we had to put up a fake wall to make my bedroom, but I didn’t care. I had a direct view of the Empire State Building, and every night, I’d fall asleep looking at it, whispering silent thanks that I got to live in this city, at this moment, doing what I loved.

(One of the many blazers I bought at Zara in the early 2010s! Perfect for work-to-date night attire!)

And then there was Sam. My five-foot-tall, five-inch-heel-wearing boss who strutted through life in Pucci dresses and Tods bags and made me believe I belonged in rooms I never thought I’d enter. She WANTED me in those rooms. She saw it as additive. And the more she gave me those opportunities, the more confidence I gained. The better I got at my craft. The more empowered I felt. The better manager I became.

We went to Cannes together three times for the International Festival of Creativity. I still remember strolling down the Croisette with her, cracking up about how we were fetching coffee and crepes for one of the biggest CMOs in the world—and secretly loving every second of it. We were women in a niche, male-dominated industry, doing what we loved, together. I learned SO much from her. Just by watching, absorbing.

(above: Sam, our colleague Megan and me at the International Festival of Creativity in Cannes, France in 2013)

(above: Sam and I working our butts off in Cannes - we traveled for business A LOT together….it was always hard work, but always fun!)

Years passed. The raises came. The bonuses followed. I kept climbing. I was in a complicated relationship with my very own Mr. Big—because of course I was—but honestly, the most defining relationship of that time was the one I had with my work. With Sam. With myself.

(above: Bill and me around 2013)

Then, in 2014, Mr. Big finally proposed. A few months later, he got a completely unexpected job offer in Austin, Texas. At first, I panicked. Leave New York? Leave this life I’d built? But then his new company flew us down, hired a realtor, gave us the full tour, and something in my gut whispered: Why not? Take the leap.

I went to Sam, fully expecting a warm goodbye.

Instead, she shocked me.

“Why don’t you be our first remote employee?”

(above: Myself, our colleague ML and Sam in Austin during SXSW once I’d made the move)

So I was. And once again, Sam didn’t just give me a job—she gave me permission to evolve. To keep growing. To hold on to what I’d built, even as I stepped into something completely new.

But that’s a story for another day.

What I know now, looking back:

• The right boss can change everything. Sam didn’t just hire me—she saw me. She trusted me, mentored me, and helped me rebuild my confidence after a career low. If you’ve ever had someone like that, send them a thank-you text today. If you are someone like that, keep going. It matters.

• You don’t have to have it all figured out. I didn’t know what I wanted “the rest of my life” to look like. I just knew what I didn’t want anymore. That’s enough to take the next step.

• Sometimes the thing you said no to becomes the exact thing you need. I turned Sam down the first time. Timing is everything. Be open to second chances.

Next up, the Austin chapter—and how becoming a wife, a mom, and eventually, an artist, flipped everything I thought I knew. Thank you for being here in this new space of mine! XO