June 2026
Am I on the upswing?
If May was ebb and flow, June felt more like flow. Things are emerging that I’m really excited about, and I’m feeling hopeful as we head towards the heart of summer.
Coding
For a while, I’ve wanted to play Dungeons & Dragons, but I didn’t know anyone who wanted to play. Fortunately, my friend group takes turns hosting an activity, and this time it was my turn. Forced participation, hurray!
Thing is, I’ve never played, dungeon mastered, or had a storyline built. But then I realized… I have Claude!
For a week and a half, I locked in to create an entire D&D experience based on the show Severance. We spent many evenings watching it together as a group, and it felt like the perfect way in. I used ChatGPT to generate ID cards I printed out and glued onto nice paper. Gemini for scene backdrops. ElevenLabs for voices and sound effects. Claude Code for walking me through the whole process, creating the storyline, building, and acting as a live dungeon master. Oh, and putting together this sweet refinement cold open game.
I champion the potential of AI, and this is one of the instances where I’m like… “Holy shit, I did that?” There’s no world I would’ve been able to without spending an exorbitant amount of time and money. All it took for an unforgettable night was a Claude Max plan, some API keys, and a whole lotta care for the homies.
People talk a lot about AI for creating apps or workflows, but not experiences.
Connection
I made new connections with a few people, one of whom even lives a five-minute walk away from me! I’m not actively trying to add more people into my life, but when there’s reciprocity and it happens easefully, I’m all for it. I’m not going to chase anyone to be my friend.
Work
June kicked off with the reopening of an opportunity I’d previously applied for in April. When I first applied, he spent thirty minutes reading my Substack and watching my old videos, ones I’d linked, not expecting him to look at them. I hadn’t even done the same for him. Even though he said no, it left a lasting impression on me.
When the process reopened in June and I started learning more about him, I thought, “What the heck? He’s an incredible dude I want to work with and learn from.” He’s just a solid human being. It’s felt less like I’m interviewing for the org or the role and more like I’m interviewing to work with him. Work feels different. Mundane tasks like planning a hypothetical travel itinerary feel imbued with meaning. I feel more care and devotion, like I want to give more of myself. It feels really fricking good.
People over everything.
I may be in the midst of a holy fuck.
YouTube
For about as long as I’ve been job searching, YouTube has been on pause. I didn’t feel like doing it. I attributed it to taking a break, which is true. After two years of consistently showing up and posting, it felt really good to step back, the same way it felt good to step back from lifting. But I’d tell friends, “I want to get back into it soon,” and a month would pass, and still no video. Another month, still no video. It became clear it was something else.
Deep down, I was avoiding the fact that making videos stopped feeling enjoyable. When I try to record the way I have before, I feel the inauthenticity. Which makes me wonder, how did it feel then?
I recently watched a video by Nathaniel Drew, a creator I’ve always resonated with, who shared something similar.
I’m in a similar question of discovering how I want to be expressed for who I am now. What do I actually want to talk about? How would I enjoy doing that? It feels like a much longer-term question than “How do I reach a million people?”
I’m viewing life, YouTube included, as craft. With YouTube, I’m finding that aesthetic matters to me more than it ever did before. I want things to feel and look beautiful. Not for any other reason than I enjoy it, much like a piece of art. I also want to share in a way that feels effortless and natural, where picking up the camera isn’t this ‘big thing’ like it’s felt like before. Maybe that means shooting on my smaller DJI instead of my massive full-frame Sony camera. Or treating YouTube as a Google Drive of video journals other people just happen to have access to.
As the name of this Substack implies, I’m living the questions! Here’s to July. Hope to share more soon.
