6 months of building solo; Why I pivoted

For a while, I loved building on my own. I felt motivated. Every win was because of me. I could ship what I wanted, test what I wanted, work when I wanted, and pivot without a meeting. The independence felt like freedom.

But sometimes the work was too easy to put aside. Not because it wasn't important to me, but because no one was waiting on it. No one to text when I figured something out at 1 am. No one to celebrate with when I hit a new goal. I had friends cheering me on, but they were all in the stands. And I missed having people on the field with me.

Then, in February, I got my heart broken, and all of a sudden, I needed to shift my life. Some of my friends had gotten up and moved after a breakup, but I love San Francisco and had no desire to leave. So instead, I thought, maybe I should go back and get a "real" job. I built a Claude skill to apply to jobs for me, ran it for a week, and got a 19% interview invitation rate (Prompt here). To be honest, I didn't think I would accept anything and was pretty sure I didn't actually want a "real" job. But I needed to do something that felt like switching up my life, and applying felt like doing something.

Randomly, a friend I had been casually helping with his startup texted asking if I wanted to help with some GTM events. I've always loved hosting events and bringing people together, so I figured, why not? I met with the team on a Wednesday afternoon in early March to learn what they were doing and quickly realized there were several other areas where I could actually help. That night my friend came over to debrief and next thing I knew I had agreed to join Tanagram as Chief of Staff at 50% starting tomorrow.

For me, 50% was perfect. I got to join a team and switch things up without closing the door on building for myself. Tanagram is seven people, early, figuring it out as we go. Everyone does a little bit of everything. We recently killed our product and decided to start from scratch. It's fast-moving, slightly chaotic, and overwhelming in all the best ways. It fills exactly what I was missing when I was working alone. When something goes wrong, there are people to work through it with. When an idea is bad, someone says so before I've built the whole thing. When something works, there's an office to be excited in.

I've since moved up to 75%. Which, at an early startup, still means 40-50 hours a week. But it leaves just enough room to keep ShareVita.org alive.

Working on a team has its own learning curve, though. Recently, I spent time building the lore.tanagram.ai/substrate page while someone else on the team was quietly redesigning our brand colors and the entire main site. I merged my PR without a single merge conflict. But then my colleague opened it and asked why I hadn't used the new style guide. Neither of us knew we had both been working on design-related PRs at the same time. It wasn't anyone's fault, but I was annoyed at the situation. I wouldn't have spent time designing the page the way I did if I'd known someone was overhauling our entire visual identity at the same time. It wasn't catastrophic, but I hate wasted work. But maybe it wasn't wasted time since it led us to start building a new feature for our product, Lore, that lets teams see what everyone is working on in real time. Lore already allows builders to share their Claude and Codex sessions publicly. This takes it to the team level.

I'm still figuring out what I like more. The freedom of solo building, or sitting next to my teammates who are also my cheerleaders, every day.

If you've made a jump like this, solo to team or team to solo, I'd love to know what surprised you. What did you miss that you didn't expect?