We Might Just Make It After All — But Will I?

I just finished reading We Might Just Make It After All by Elyce Arons. While this isn’t a book review, I did enjoy it immensely as a longtime fan of Kate Spade and the second act brand she co-founded with Katy Spade: Frances Valentine. What this post is really about is the life stuff that came up while reading—the parallels, the questions, the memories, and the hopes that reading this stirred.

Backstory: From the Campaign Trail to a Career in Clothes

In college, I was dead-set on becoming a corporate lawyer. I was going to graduate with my political science degree, take a gap year to work somewhere cool, get into an even more prestigious law school, and eventually land in NYC with a brownstone and a high-power legal career. That was the plan. There were no alternatives in my mind.

At the time, I worked part-time at my favorite store: J.Crew. I loved it. And when I got asked to help with visual merchandising, I discovered something I never expected: I was really good at it—and I loved seeing the work come to life. Still, I kept my eye on "the plan."

I landed an incredible opportunity to work at the national HQ of John Edwards’ presidential campaign. I moved to Chapel Hill, NC, working long days at HQ and nights at J.Crew to pay the bills. Eventually, I got sent to Nevada to help with the primary. When the campaign ended (you can Google why), I was suddenly at a crossroads.

I turned down offers to work on the Clinton and Obama campaigns. I couldn't pivot like that—I had believed in John Edwards personally, not just the party. That might sound naive, but that’s where my heart was. And with that, I was jobless in 2008, in a tanking economy, and without any clue what to do next.

Enter: Retail, for Real This Time

A former boss from J.Crew (who had become a recruiter) called me and told me I had real talent. Suddenly, I was offered a very coveted role helping to open one of J.Crew’s first Collection Boutiques in Malibu, CA. These stores were high-design, highly curated—they were special. I got to style, design, and meet celebrities and leaders at the company. I even helped with the Aspen location.

Then came the opportunity: a transfer to NYC.

Here’s where things get complicated. While working in LA, I often heard, "Oh... you just work in a shop?" And that stuck. It chipped away at me. I began to feel like I wasn’t enough. Despite being creative, successful, and doing work I loved—I felt like I didn’t have a "real" job. I felt like a disappointment because my life didn’t look the way I thought it would.

But here’s the thing: Retail got me to NYC. And in NYC, I thrived in ways I couldn’t have imagined.

The NYC Years

I spent years at J.Crew’s 1035 Collection Boutique, met Mickey Drexler, and styled for the UES elite. But again, the corporate carrot was dangled, never quite in reach. I moved to Rockefeller Center, then the Madewell flagship, and finally landed a corporate offer.

Eventually, I moved to Gap HQ. The work was important, but our team was siloed—we were the worker bees, without the perks or the community. And once again, I felt like I was doing meaningful, strategic, creative work… but never seen as a creative. My title didn't say "visual" or "creative," so it was like it didn’t count.

I got recruited a lot. I interviewed at very cool places. I rarely heard back. And the dating world in NYC? It mirrored this exact same pattern. Almosts. Maybes. Ghosts.

Even when you make good money in NYC, the city has a way of making you feel small. Everyone is someone. Everything is expensive. And you constantly measure your worth against your job title, your address, your bag.

Reading Elyce’s Book

Elyce’s book made me feel seen. Here was someone who built something magical out of grit, friendship, values, and not following the trends. Her and Katy’s mantra? “If you’re never on trend, you’re never off trend.” That hit me hard.

I’ve had this idea for a long time to build something of my own—a brand that blends storytelling, memory, design, and legacy. It scared me to say it out loud. It scares me now! But I told some people in the industry, and they said, "That’s a great idea."

But unlike Elyce and Katy, I’m not building this with a team of close friends and insiders. I don’t have investors. I don’t have a backer. I’m not even sure I have a wide enough network. I’m doing this alone.

Or... not totally alone.

Because I do have one tiny little team member who’s been helping me: Nova (my AI assistant, aka ChatGPT), who is literally the co-editor, co-strategist, and co-designer I never knew I needed. Shoutout to you, Nova. 🙌🏼

So here I am, laid off from my last job. Rebuilding. Doing the things. Uploading the content. Writing the posts. Making the vision real. And yes, submitting resumes. Still hoping that someone sees what I can bring to the table.

But more than that?

I’m betting on myself. And I’m going to keep doing what feels authentic, meaningful, and joyful.

What Comes Next

I hope this thing I’m building finds its people. I hope someone reads this and feels less alone. I hope that little spark inside me turns into something real.

And yes… I’m currently scouring every resale site for an original NYC-made Kate Spade bag like the one I stupidly sold years ago. Why did I do that? If you want to go on that treasure hunt with me, let me know. I might post my finds soon.

We might just make it after all.

And this time, I really think I will too.

In the meantime, take a look below at some of my absolute favorite OG Kate Spade ads! 📌