Episode 002: For When You Have to Reinvent Yourself

In this episode, Kat dives into her experience of rebuilding after the closure of her first business, Tacocat. She opens up about the challenges she faced when leaving Hawaii to return to New York City and start over. Kat reflects on the emotional and mental hurdles of pivoting from failure to finding a new direction, emphasizing how growth often comes from navigating discomfort and uncertainty.

Kat discusses the process of reinventing herself—from working part-time jobs and interning at 30 to learning how to manage the ups and downs of building a business from scratch.

She shares stories about the moments that made her realize the value of her skills in branding and strategy, including collaborating with top photographers and securing her first big contract. These experiences helped her develop a clear vision for what would eventually become Afternoon Culture.

If you’re navigating your own reinvention or looking for inspiration on how to push through the tough moments, this episode is packed with lessons from someone who’s lived through it.

Kat emphasizes that the real work lies in staying focused on your purpose and continuing to move forward, no matter the setbacks. Her story offers valuable insights for anyone facing uncertainty or trying to recalibrate their own path in business.

Full Transcript

Last time, I shared a bit about my experiences as a first-gen Dominican-American who grew up in NYC with entrepreneurial immigrant parents.

I talked about how I moved to Hawaii just five days after finishing undergrad at Johns Hopkins, and how that experience ultimately led me to start a business in my mid-twenties, after leaving my first job after college.

The response to the first episode—the DMs, texts, or LinkedIn messages—has been incredibly encouraging, and I’m so grateful that my story has inspired so many of you.

This week, I want to explore what happens after failure, and what it looks like when it’s time to reinvent yourself. 

As trailblazers, imagining a new future and changing course is often how we level up and grow, but the truth is, being in transition can feel incredibly vulnerable and disorienting.

For me, the space between Tacocat and Afternoon Culture was one of the hardest, most transformative periods of my life.

If you're in the middle of a transformation right now, and you're feeling uncertain, or stuck between one version of yourself and the next, this episode is for you.

Let’s get into it.

After being in Honolulu for 7 years, I started to feel island fever. Because I was trying to get a business off the ground, I hadn’t been home to NYC  for years.

Around my 30th birthday, I was reflecting on my time on the island. I had come to Hawaii at 23, without a driver’s license, no work experience, and a big vision that I could barely articulate. 

Over the years, I evolved into a powerhouse who chased that vision, even when it felt impossible.

The week after I shut down Tacocat, I met my friend Matt for gelato. Matt had always been someone who championed my creativity and encouraged me to  trust my instincts. During that encounter, Matt helped me process why Tacocat had failed and said something that changed the my perspective on the experience: 

 “One thing I learned about you as I was watching you build is that you're a natural at building a brand. I think you should really double down on that.” 

I already knew I wanted to step in branding and storytelling but that moment was incredibly affirming. 

A month later, I announced that I was offering branding and marketing consulting with a new website. I recently revisited that site, and it made me chuckle because it was so basic. But within weeks, I had a handful of clients. 

After a few months, though, I wasn’t generating enough income to sustain myself, especially since I was still bouncing back from Tacocat. So, I also started a managing a bistro part-time at not far from where I lived." 

I did my best to balance consulting, my part-time job, and liquidating my failed business, but I felt heavy and defeated. Living in Hawaii had always felt like a dream, but now it felt like I was climbing an endless hill. When the business failed, I felt like I had dropped all the pieces of my life, and no matter how hard I tried, I couldn’t get them back together.

Looking back, it’s pretty crazy that I made changes that quickly. I was living my life in hard mode and did not give myself enough credit. 

It was a big change, but I was making it happen. One thing I found especially difficult was that people still had so many questions about Tacocat. I’ll never forget being at a bar with a friend when a stranger came up to me and said, 'You’re Kat from Tacocat! I miss you guys so much! What happened?'

Even though I was only associated with that brand for a year, it had made an impact. I was able to generate buzz and get people excited about it. Now, as I was shifting to something completely different, once again,people didn’t see my vision or understand where I was coming from.

In some ways, being a multi-talented person was actually working against me. I was challenging expectations, and that made shifting to something that felt so natural to me much more challenging than launching the thing I had originally hesitated to start.

I pushed for an entire year, but nothing seemed to come together for me. Still, I focused on building my consulting business because so many people wanted me to do for them what I had done for Tacocat. It was encouraging to have people invest in me, but physically, emotionally, and mentally, I was completely drained

I did my best to support my new clients and ended up doing some of my favorite work of my career. I was hungry, creative, and just going for it. But I was juggling a lot, and the financial pressure was intense. I leaned on my friends, who were incredibly supportive and held so much space for me during this transition. 

Still, I couldn’t tap into the flow and momentum I needed while managing everything and processing what had happened just months before—trying to make the creative work a success, working part-time, and dealing with the aftermath of failure and liquidating a business.

By the time the November 2016 election came around, I was ready to leave the island. The results woke me up to some harsh realities, and I wanted to build something that was part of the conversation and could make an impact. 

People were surprised when I decided to leave, especially after staying in such a transient place like Hawaii for so long. But I knew I had a lot of work to do on myself, and that work would be ugly and painful. I also missed being around other Afro-Latinos and longed to be in a place where I felt truly connected and understood.

Then one evening, a friend said, 'I get the feeling that you need to go try what you’re doing here in NYC for a while, just to see how you feel.' It was one of those moments where I instantly started daydreaming of New York—its energy, its culture, its momentum, the familiarity. It felt exhilarating, but also a little intimidating.

 I hadn’t lived in New York for over a decade, and the thought of going back felt like giving up on everything I had built in Hawaii. I had invested so much into my life there, and I wasn’t ready to let it go.

It took everything I had in me. At times, it felt like I was clawing my way out of something, but in December 2016, I headed home.

Two days after I landed in NYC, I had my first job interview at Food52, an online platform by a former New York Times food critic. I wanted to take my friend’s advice and continue building brands—but I didn’t have a network in New York, which meant I was starting from scratch.

I had already been job hunting for a few weeks before the move, mostly looking for roles that sat at the intersection of food and marketing. I felt drawn to Food52 because they were a recipe-sharing community with an e-commerce marketplace with a big Instagram presence.

 I was curious to learn more about them so I  took a look at their team page—and was stunned to see not a single person of color, despite being based in Chelsea in Manhattan. After spending seven years in Hawaii, this felt super jarring.

I did something out of character for me: I tweeted, “Yikes. Was excited about a job at Food52 until I took a look at their team.”

What happened next was unexpected. The company’s COO replied and asked to meet. I was hesitant. If a company in Manhattan had 0% diversity, what did that say about their leadership and culture? Still, I agreed to an initial Zoom interview with their COO a few weeks after the election. She seemed open to continuing the conversation once I arrived in NYC.

I don’t know if she thought I wouldn’t actually make the move—but I did. And two days after my plane touched down, I was in her office.

She wore pearls and a crisp white button-down, radiating that classic Martha Stewart Connecticut vibe. She glanced over my résumé and asked about my experience, admiring my courage and hustle. But when I inquired about specific entry-level roles on their team, she hesitated. The meeting ended with her asking me to “audit” their website and send over my findings. For free.

At first, I considered going along with it. I had just landed in New York and was desperate to get things moving. This was the momentum I had come for! But the more I thought about it, the clearer it became: I would be the only Black woman on their team, and instead of hiring me into an entry-level position with some kind of trial—something I was more than qualified for—they wanted free labor as a test. I walked out of that office with a mix of emotions.

When I told my mom what happened, she immediately said, “I know you want to bounce back after Tacocat, but something about this feels off. I saw how hard you worked on Tacocat when I visited, and maybe you should slow down and get acclimated before jumping into the first thing that comes your way.” She was right. Dismantling Tacocat had broken my spirit. 

A day later I got knocked down by the flu and was forced to slow down. I decided I would take my mom’s advice and focus on easing in, continue with my client work and not pursue any opportunities with Food52.

A few weeks later, I noticed that an award-winning food photographer I really admired was looking for studio interns. At the time, I was already doing a lot of creative direction, photography, and content creation as part of launching brand campaigns, but I was a self-taught photographer with no studio experience.

So, I reached out to her—and jumped on the opportunity. This is how I found myself balancing the role of a creative director leading brand campaigns and an unpaid intern in a Brooklyn photography studio at the same time.

In the seven months that followed, I did everything I could to make money in NYC. I networked—both online and in person. I worked on sets for HBO, Sesame Street, Benihana, LVMH, Chipotle, Alexander Wang, and Pepsi. I worked private parties as a bartender while also shooting content for fashion influencers and wellness startups. I led a brand campaign for a growing Korean beauty brand. My photography was published in Forbes, and I was hired by The Washington Post to shoot for their food section.

I learned so much, and it was exciting, but eventually, I realized I was working hard but stuck in a feast or famine cycle with all these gigs. Most of the opportunities I took on involved assisting in the execution of ideas, but I wasn’t at the table when it came to ideating or strategizing. I was happy to put in the work, but deep down, I knew that to feel truly fulfilled, I needed to be part of both—the strategy and the execution.

Then one afternoon, I had an idea: I’d design a postcard that featured my work, print 150 of them on Vistaprint, and handwrite notes to every restaurant & wellness brick and mortar in Manhattan that looked exciting to me. 

One of those responses came from a restaurant group, and it turned into my first contract. We began with content creation and social media management, but as we built trust, the project grew into a full rebrand. Just 10 months after arriving in NYC, I landed my first $50,000 contract—a moment that confirmed my hustle and strategy were finally paying off.

The following year, I started dreaming of building something bigger than me that would help mission-driven brands build bold identities that amplify their impact. And in May of 2018, less than a year and a half after I first landed in NYC, Afternoon Culture was born.

Right before I decided to leave Hawaii for New York, my roommate at the time had a very strong opinion. He thought I’d be better off staying in Hawaii because it’s smaller, more manageable. He believed that starting over in New York would be insanely difficult—and honestly, he doubted whether I could even start a brand consultancy in the first place.

He wasn’t entirely wrong. Starting over in New York, reinventing myself, and carving out a new path was some of the hardest work I’ve ever done—not just on my business but on myself. The first year and a half were filled with doubt, obstacles, and a lot of personal growth.

But here’s the thing: moving to New York taught me one of the most important lessons I carry with me today—Trailblazing is not about where you are. It’s about your mindset.

When you are a growth-oriented, change-driven person it doesn’t matter where you start—whether it’s a small town or a big city. 

That mindset can carry you anywhere. It’s not the location that defines your success. It’s the way you show up, the work you put in, and the belief that you can push through challenges and create something meaningful no matter what. 

Reinventing yourself requires you to imagine something new, and that’s hard. And after you imagine it you have to create it and that’s even harder. 

Not having a network and having to intern at the age of 30 challenged me deeply. It didn’t look good when I told people what I was doing. I had to confront all my insecurities about feeling like I was behind. Now I know, I was actually feeling the discomfort of growth and pushing of the edges of who I was up until that point. 

Transformation isn’t pretty. In fact, it’s often really ugly and uncomfortable while it’s happening. But it invites you to evaluate all of who you are, release what no longer fits, and rebuild yourself with new parts that align with the person you’re becoming.

As high achievers, we are creatures of momentum, always eager to see quick results. But transformation doesn’t work that way.

Transformation calls us into stillness and contemplation because a new version of yourself can only emerge when you truly make space for it.