Episode 011: For When It’s Time to Dream Again

Have you ever been so focused on doing that you forgot how to dream?

In this episode, Kat shares how a season of nonstop execution made her realize she had lost sight of imagination and possibility. She reflects on the moment that reminded her why dreaming is essential, even when you are working hard to move forward.

Kat explores how joy and creativity fuel resilience and momentum. She offers insights on balancing action with space for dreaming so your vision can grow and thrive.

If you find yourself always busy but missing the excitement of dreaming big, this episode is for you.

Full Transcript

We’ve made it to episode 11! We only have one more episode this season before I take a summer break until September.

Last week, I told you about the conversation that inspired me to make moves on my vision again after a period of transition and transformation.

After that moment, I spent October and November building a roadmap, revamping my website, and redefining how I wanted to show up in every way.

For the first time in a long while, I had direction and a real sense of urgency. My team and I made a lot happen in just a few weeks.

Around that same time, I shared my plans with one of my closest friends, Melissa. At one point in our conversation, she said, “I hope you know next year is going to be major for you.”

I remember pausing and asking, “Wait, what do you mean?” She started speaking life into the year ahead, and it felt so encouraging and energizing.

But after we hung up, I felt a hesitation. I couldn’t quite put my finger on it at first, but I kept thinking about it. And then it hit me: I had stopped dreaming.

In this episode, I want to talk about what it looks like to reconnect with the spark that started it all. As trailblazers, our ideas come to life when we move from dreaming to doing. But when we focus too much on execution, it becomes easy to lose the joy that fueled the vision in the first place.

Let’s get into it.

I have to start by telling you about Melissa.

Melissa and I have been friends for over a decade. We met back when I was living in Hawaii and teaching. At the time, I was feeling a creative block that I couldn’t quite name.

I’ve always known I was an artistic person, but I didn’t yet have a clear way to express it.

Melissa and I started meeting up for art sessions, and slowly, I began making things just for myself. That’s where our friendship really started…through creativity, curiosity, and care.

As I transitioned out of Teach for America and into entrepreneurship, Melissa and I ended up living in the same house for a while. Eventually, we both left Hawaii, and now most of our conversations happen over the phone or on Zoom. Even though our lives have taken different directions, she’s still very much a part of my personal board of advisors.

I think every founder or executive has that one friend who holds the vision with them. Melissa is mine.

After moving from New York to Los Angeles, I found myself leaning on her even more. We would talk through ideas, challenges, and what the next chapter might look like.

When I was feeling uncertain about the direction of Afternoon Culture, she was one of the first people I called. We had a lot of conversations about what I was trying to reconcile, what I was trying to build, and what I needed in order to feel aligned again.

I talked a bit about year five in Episode 6. The aftermath of burnout and the process of reimagining the business required a lot of stillness, alone time, and long conversations with the people who know me best.

And real talk: my head was all over the place for a while. Finding clarity was a lengthy and arduous process. I felt like I had knocked down my house and was sorting through the rubble for a long while.

After all that, September felt like a cold plunge inviting me to get things going. I jumped right into execution mode and started building roadmaps, refining all our marketing, our website, building relationships, and I hosted four events within 12 weeks. I felt like I had fallen behind and I wanted to channel all my energy into getting back on track.

I felt eager to shift the atmosphere around my work and started putting in as much effort as possible. I spent all of December restructuring systems, writing content, and updating our customer experience. I wanted to start the year with fresh energy, and the truth is, I wanted to change so much.

I know this is an experience many fellow trailblazing founders and creatives feel...the urge to get all the ducks you think you’ve been neglecting in a row.

It was not until my conversation with Melissa that I noticed what was missing. I was making plans and setting goals. I was doing all the things I thought I needed to do to get back on track. However, I was not dwelling in possibilities or allowing myself to daydream.

I was so focused on being strategic and keeping things moving forward that I lost touch with the part of me that imagines something bigger. The part that allows ideas to be expansive instead of just efficient.

But last year something had changed for me. Internally, I was regrouping as a rough few years. And externally, all of the political transitions and economic uncertainty was looming over me and I was allowing it to rob me of my joy and sparkle.

And the thing is I mostly work with other visionaries for a living. Whether we are helping a startup or a senior executive at a Fortune 500 make their vision a reality, Afternoon Culture is a place where dreamers are welcome.

I have been fortunate to do this work for 7 years. When I first started I had a fire ablaze that inspired me to show up and give everything my all. I was always seen as passionate and relentless.

One time, I had a client visit with her family NYC from LA and I took them to dinner in this delicious Thai restaurant in the Upper West Side and at one point she turned to her sister and said: See what I mean about Kat being a whole vibe, after I spent a few minutes encouraging her as she prepared to apply to a Masters program.

I am here to champion the dreamers and make people’s wildest visions come to life. But in the past 7 years, I have seen so many challenges and setbacks that I found myself in a sort of permanent problem-solver mode.

Every time I’ve faced an unexpected hurdle my stance has been the same: assess the problem, tackle it with solutions, keep it moving. But in doing that, my dream of building a consultancy that creates mission driven brands that make our world more beautiful started to feel messy and heavy. 

I know I was made for this. Still, there have been countless moments when I have asked myself if I can keep going, and whether I even want to.

A few weeks ago, I had an interaction that I keep thinking about. I was speaking with a very spiritual woman, someone I had just met.

A few minutes into our conversation, she paused and told me something unexpected. Without knowing anything about me, she said I have an ancestor who was a trailblazer.

She said this was a woman who was not able to fulfill her life’s purpose. And that I am here to trailblaze in ways she could not.

She used the word trailblazer three times. She did not know about this podcast. She had no idea that the word is part of our brand’s messaging. But she said it with such clarity and conviction that it gave me a little pause.

I’ve been so focused on building structure, solving problems, and getting things done that I almost forgot what joy and magic feel like.

As trailblazers, we are breaking new ground and creating paths that do not yet exist. We are climbing steep mountains and navigating uncharted territory. Our work demands persistence and vision. But that does not mean we have to abandon joy along the way.

Everything we are called to do is bigger than ourselves. As we pursue the impossible, joy fuels our resilience and longevity. It creates the space for creativity, dreaming, and expansive thinking.

Joy is also what creates space for divergent thinking and innovation. The research shows that leaders who cultivate joy foster more trust and psychological safety.

In a time like this, with all the political unrest and uncertainty, Joy is what will keep us going. 

I’ve decided to double down on building community, cultivating spaces where trailblazers like you can process what they’re feeling, connect offscreen, break bread, and make room for lightness and play.

Because if dreaming is what activates your vision, joy is what will keep it alive.