The Monthly Self-Interview

Right before 2024 ended, I watched the eighth annual “Same Interview” that Billie Eilish does with Vanity Fair. The format is deliberately uninteresting: the same questions, asked again, year after year. What makes it compelling is the accumulation of answers. Over time, her confidence becomes expressive and legible, and we get to see her grow up.

Watching it made me think about my goals and ambitious plans for 2025. I’m not a pop star, but I could benefit from the same accountability and self-reflection. What if I set up monthly self-interviews as a way to notice patterns in my life? The same prompts recorded on video every thirty days. I decided to try it, and I finished the final recording a few days ago. This post is not wholly about what I had to say, though I will include some videos at the end. What I wanted to share instead is the system: why repeating the same questions matters, how video changes the signal, and why boring, low-effort videos ended up producing far more clarity than I expected.

The system has three parts: reminders to record, the questions themselves, and periodic review to identify trends. You might set yours up differently (notebook entries, different questions, quarterly reviews), but the core is this: a cue, the recording, and a feedback loop that makes it meaningful. I created a recurring Google Calendar event for the 1st of each month titled “Monthly Interview” with my questions in the description. I recorded via QuickTime at my desk around the same time for consistent lighting. Videos went into a “Monthly Interviews” folder on my Desktop. I know myself well enough to recognize that without multiple reminders to press “Record”, I’d forget. A day or two of lag wouldn’t be the end of the world, but it was the principle that mattered.

Confession: I missed one interview with myself on July 1. Instead of recording late, I opted for a more comprehensive interview in August. Missing July didn’t meaningfully weaken the project, but it clarified what the system actually depended on, which is continuity. The August recording carried the same signals of energy and self-judgment, just with a slightly wider aperture.

Each month, I would ask myself the following questions:

• What day is it today?
• What’s something you’re looking forward to this month?
• What went well last month?
• What didn’t go well last month?
• What did you create last month?
• How do you feel?
• What surprised you?
• What are you worried about?
• What’s a song that you’re really into right now?

This list took a surprisingly high amount of effort to produce, despite the simplicity of the questions. They all target different aspects of my life that would benefit from an informational-temporal smear. I knew it would feel rewarding to observe myself speaking about events that I was excited for as someone who had already experienced them. I wanted to notice if worries were sustained across multiple months, or if they weren’t worth the fear in the first place. For example, I was occasionally worried about interactions that I had with close friends, or physical health issues that I was experiencing. With each passing month, I saw that these worries were temporary and would eventually pass. By asking myself what went well and what didn’t, I was confronted with the criteria that I generate in the moment for what constitutes a “good” or “bad” stretch of time. It was always different, but was usually broken up into achievement and disappointment, respectively.

I was also surprised by the variation in my appearance month over month. In Billie’s interviews, we’re looking at her life in cross sections whose width is a whole year. Of course she would look different. For myself, I noticed that I really liked to experiment with my hair length this year, and I could feel my energy levels through the screen just by the way my eyes looked at the camera or the way my voice modulated. In this way, video turned out to be essential. It captured tone, pace, posture, hesitation, and other signals I wasn’t consciously producing but couldn’t suppress. I didn’t transcribe or score anything. I just watched them in sequence, sometimes back-to-back, sometimes skipping around, looking for what repeated and what drifted. Video preserved the parts of myself that written reflection edits out, and repetition made those parts impossible to ignore.

See for yourself: take a look at the videos below to see glimpses of myself throughout 2025.

---

What are you looking forward to this month?

This was my favorite question to answer, I loved reminding myself about everything that I was excited for. And this year, there was a lot! I ran my first half marathon, traveled all over the country to visit friends, changed jobs, had concerts and events and new friends to meet each month, and more. It was a great year. Even if there wasn’t anything concrete that I could think of, this question made me search for the good in the moment, like the changing of the seasons or my health.

What didn’t go well last month?

This was a tough question to answer, but I was able to find some good in the moments that I was unhappy in. Similar to the “What are you nervous about?” question, it was comforting to realize that even though things didn’t go my way in the moment, life would eventually turn around. Ailments and disappointments were always temporary. Most of the answers you see here are on the lighter side; all things considered, 2025 was kind to me.

How do you feel?

Answering how I felt was a brutally honest reflection of my mood, energy levels, and overall well-being. It’s funny that during holidays like New Years’ Day, I was immediately kinder with myself and more optimistic about the future, and during the more mundane months I felt critical about my situation. There were some days this year where I just couldn’t bring myself to tell the camera that I was feeling good. Confronting that, instead of lying to the camera and myself, felt necessary. Instead of reading it in a notebook, hearing it from my own voice made it feel more real.

---

This project revealed that most worries dissolved on their own, the things I got excited about were usually worth it, and what I considered a “good” or “bad” month kept changing. Keeping the systemic harness constant made the small changes impossible to miss. The accountability worked because I had to show up honestly every thirty days, regardless of whether I was hitting my goals or not. I learned that the honest version of myself is an optimist who has a deep appreciation for his friends and family. He is remarkably open to new experiences, and surprisingly resilient. He also really likes to look to the left when he’s thinking about something.

I’m keeping the same setup for 2026. Same questions, same time each month, same desk (in a new apartment with more sunlight!). But now I know what it feels like to have a year of these behind me. If Billie can do eight years, I can probably manage a second one. If you’re thinking about trying this: pick your questions and just hit record on February 1st. It’s worth the brief awkwardness of talking to a camera. The insights build in ways you won’t see coming until you’re a few months deep.