Episode 004: For When You Need to Play Up a Level

Ever had that moment when you realize your vision is expanding beyond your comfort zone?

In this episode, Kat explores what it feels like to hit that tipping point and make a bold decision to level up.

Leveling up isn’t just about business growth; it’s an identity shift. It’s about getting clearer on your vision and betting on yourself, even when it feels uncomfortable. Sometimes, the leap isn’t about where you land but about proving to yourself that you’re ready for what’s next.

Kat explores the uncomfortable truths and key lessons about stepping into that next chapter and trusting yourself in the process.

If you're in the process of committing to the next version of yourself, even when the people closest to you don’t quite get it, this episode is for you. 

Full Transcript

Something about Spring always gets me thinking about growth—maybe it’s the energy of renewal, but March, April, and May have consistently been my months of leveling up.

I have noticed a little pattern. In May 2010, I moved to Hawaii. In the Spring of 2013, I left my job and started my entrepreneurial journey. Afternoon Culture was born in the Spring of 2018, and in 2022, I made the leap to LA. I even launched this podcast last month right after Spring started. 

Spring isn’t just about new beginnings for me. It’s the season when I really start pushing for change, growth, and new levels of impact.

In this episode, I want to explore what happens when you feel that push to play up —that moment when you wake up and realize your vision is outgrowing your comfort zone. 

Let’s get into it. 

The winter before I moved into my first office, I felt restless, like something needed to change, though I couldn’t put my finger on what it was. I don’t if you ever have that feeling when things just feel stale and you know you can’t keep going the same way.

For me, my work life just felt different. I was in startup mode trying to get Afternoon Culture off the ground and that was chaotic. There was no structure and no real workflow. 

I’d been in NYC for a little over a year, had hired an assistant, and the projects I was working on had grown in scale and complexity. Most of my clients were brick-and-mortar businesses, so I was bouncing from client to client, working on strategy, creating content with my assistant, or meeting with my favorite print shop to explore samples/packaging options. No two days were the same.

I have always been big on delegating, and my assistant was great, but I was leading rebrands and brand launches that are typically handled by full teams, all on my own. Her support just wasn’t enough to keep up with the demands of my growing business. But I also didn’t have the system in place to bring other people into the work. 

By February, I realized my approach to work needed to shift. I couldn’t build structure or systems if I was constantly on the move, so I started looking for a dedicated workspace in Manhattan.

I toured a few spots near my apartment, but most either had no openings or just didn’t feel like the right fit. I knew I wanted to join a coworking space—not just for the space, but for the community. I had been building alone for a while, and without many friends who were also entrepreneurs, I was starting to feel a bit isolated.

Then in mid-March, I found something in Midtown that caught my eye. It wasn’t exactly the neighborhood I pictured myself working in, but the coworking space was launching a business incubator in May. For $600 a month, I’d have a dedicated desk in a large room with 100 other founders, plus access to programming geared toward new entrepreneurs.

The monthly rent felt a little steep for a desk, and there was an even bigger deposit, but I was desperate to create some order in my work life, so I jumped in without even touring the space.

A few weeks after moving in, I invited one of my most entrepreneurial friends to check out my new space. I had always admired her because she’d built a really successful online business while also working full-time. I was excited to show her my new space and share more about Afternoon Culture.

But from the moment she walked into the lobby, I could tell something was off. She seemed uncomfortable, and I couldn’t quite figure out why. We eventually sat down for coffee on a big comfy couch, and that’s when she said it: “Kat, why don’t you just get a job?”

I was stunned. I had been building my business, designing a new website, acclimating to my new space, and juggling all the projects we had going. As an entrepreneur who had been running her side business for five years, I couldn’t understand how she didn’t see the leap I was making. But I let her continue, listening as she gave me feedback on how I should approach my work life.

Her suggestions all pointed to me abandoning the path I was on and putting Afternoon Culture on hold to go work for someone else.

I thought this conversation would be encouraging since she had built a business herself, but instead, it felt like she was questioning my entire vision. She asked me how I planned to grow an agency and why I’d moved downtown.

Up until that point, all of my clients had been uptown, and she felt that moving downtown meant I was going to be part of the startup scene with less diversity. It felt like she was critiquing everything I was trying to build.

I left our meeting with so many mixed emotions. On one hand, I think she was giving me practical advice that was based on her own experience. On the other, I had reached the threshold for how much longer I wanted to keep building the way I had for the first year.

What I didn’t realize about moving into that space is that I was committing to Afternoon Culture in a deeper way. I was betting on myself, and going all in.

And it wasn’t just about being in a physical space. Joining that incubator was me stepping up in ways I hadn’t even anticipated. I now had access to a network of other founders, I was able to collaborate with other entrepreneurs, and access mentorship and guidance from people who had been through similar experiences.

My clients got bigger. I started delegating more work. Instead of being the person executing everything, I started delegating parts of the work to people more talented than me, and that made our work even better.

In hindsight, I see that signing that lease pushed me out of my comfort zone and forced me to reevaluate everything. I thought I was just looking for a place to work, but it turned out to be much more. 

It transformed how I worked and how I approached my business. It also invited me to develop systems that would actually allow me to scale.

With that move, I had an identity shift, I was moving beyond being a solopreneur, and my friend couldn’t see it. The truth is, I had taken a leap that was beyond the ones that she had taken for herself — she was building a business in a way that allowed her to not really take any major risks since she kept her full-time job. But that also meant that her business was only able to grow really slowly.

I didn’t realize it at the time, but I was playing on a different level. While we were both entrepreneurs, our visions were very different, and her feedback didn’t really apply to me anymore.

By the time I joined the incubator, I had been an entrepreneur for five years and was halfway through an MBA program. I had only been in NYC for 18 months. I'd already learned a lot from my first business, and I was strategic and practical in building Afternoon Culture. 

But the truth is, there’s no set roadmap for entrepreneurship. Even with experience, building something from the ground up always comes with a bit of chaos, and it’s not always easy for others to see your vision early on.

Taking your vision to the next level means getting clear on who you are now, who you want to become, and why the leap matters. 

With that clarity, you'll still face plenty of uncertainty along the way. In those moments, it can feel like your life is a construction site. The truth is, even the most luxurious buildings start out looking like a mess once construction begins.

Over the past decade of taking leaps, I’ve learned that growth always comes with friction, resistance, and discomfort. 

Feedback and advice aren’t always helpful in these moments. Leveling up means that you are becoming something new and feedback can keep you tethered to the old version of yourself. 

Leveling up isn’t about figuring out every step in advance. It’s about knowing that what brought you to this point isn’t enough to carry you to the next. It’s about releasing your grip on the familiar and letting yourself rise into the unknown.