In January, I ran into a parked Tesla outside of a store that sold overpriced cookies in Fishtown. Not a big deal (it was just a fender bender), but I felt terrible.

I called the owner to tell her.

She picked up the phone:

“This is not how I wanted to start the year.”

You’re telling me.

By any objective measure, it was a rough start to 2026. There was The Tesla Incident. Our fridge broke. We found water leaking through the stucco on the back of our house, which means we need to replace the entire exterior. We lost Deefer, our dog, in January.

So yeah. Rough quarter.

Underneath all of that, a lot happened.

What happened in Q1

Good Morning Philly newsletter

The biggest thing I built was Good Morning Philly, a free weekly newsletter covering the River Wards (Fishtown, Northern Liberties, Kensington, Port Richmond) that ships every Monday at 6 AM.

I’d been wanting to do this for almost a year but kept putting it off. In February, I just started. I got the landing page up on a Monday. Hit the first 100 subscribers by Wednesday through personal texts and posting in neighborhood groups. I published the first issue on February 23.

After six issues, we were at 450+ subscribers with an open rate of 66%.

The growth got interesting in mid-March when I used an AI tool called Perplexity Computer to set up Facebook ads.

I’d been putting off paid acquisition for months because it felt freaking daunting: creating a Meta Business account, adding a pixel, designing creative… On a whim, I asked Perplexity Computer to do it. On Tuesday it set up the infrastructure. By Wednesday, it placed the ad. And on Thursday morning, I had my first two paid subscribers.

(It felt like my very own hungry caterpillar. But instead of eating fruit, it ate to-do lists.)

Soon, I was spending around $25 and getting 30 new subscribers per day.

Perplexity computer also helped me build a summer camp finder with 130 camps searchable by age, budget, and neighborhood. And helped me write a 67-spot River Wards Insider Guide.

Putting RLOS in maintenance mode

For two years, I built Remote Life OS, a newsletter and coaching business for people looking for remote and flexible work. I grew the list to 8,000+ subscribers. I launched coaching cohorts, then pivoted to 1-on-1 coaching, then built a service called Land The Interview, where I analyze resumes and LinkedIn profiles.

The top of the funnel worked. People signed up. People opened the emails. But the revenue model never clicked. Land The Interview had interest but few conversions.

On March 23, I made the call to put it all on maintenance mode. The automated job posts keep running. The list stays warm. But I’m not writing new newsletter content and I’m not trying to force a business model that hasn’t shown signs of life after two years.

The one thing I kept: coaching. I still genuinely love the 1-on-1 sessions. Helping someone reframe their job search or rethink their career path is energizing in a way that writing another newsletter issue isn’t. So the coaching stays, even as the rest winds down.

How AI is changing how I work

At the start of this year, I was intimidated by Claude Code. I’d heard about it, I knew it was powerful, but I hadn’t actually used it. In January, I talked to my friends Jill and Akash about it and they pushed me to just start building with it.

Now I use it every single day.

I’ve built 15+ custom commands that handle my daily operations. Morning triage, email prioritization, newsletter research, note organization. I built start-of-day and end-of-day routines that review my notes, surface action items, and catch things that would otherwise slip, e.g. a reply I owe someone, a deadline coming up, or a connection between two projects I hadn’t noticed.

One of the biggest wins this quarter was using AI for tax prep. I have four business entities, and organizing the expenses, CSVs, and documentation for my CPA used to be a multi-weekend project. This year I did it in a few focused sessions with Claude Code pulling it all together.

Going from “I’ve heard of this but haven’t tried it” in January to “I can’t imagine working without it” by March has been one of the bigger shifts in how I operate.

How the family is doing

Some updates:

  • We hit our monthly hosting goal: a Chinese New Year dinner with 15 people, a karaoke session with our NJ family, and regular neighborhood dinners.

  • Madeline is adjusting beautifully, Theodore is the funniest person in the family, and Oliver and Annabel walk to school together with their friends.

  • We lost Deefer in January. He was on palliative care for months, and we knew it was coming, but it still hit hard.

What I’m focused on for Q2

  • Good Morning Philly: Get to 4,000 subscribers. Start monetizing with local sponsorships

  • Consulting: Keep doing good work for Clay and OpenAI.

  • Health and fitness: Training 3-4x per week and finding the afternoon slot that actually works for me.

  • Family: Navigate Amy going back to work in mid-April. Spring break activities. Nashville trip in April. Keep the monthly dinner hosting cadence. Take more photos.

  • RLOS: Cull the list. Keep the automated job posts running. Keep coaching.

One more thing

The biggest lesson from this quarter isn’t about newsletters or AI or training consistency. It’s about knowing what to stop.

I spent two years trying to make RLOS into a business. It’s a good newsletter with a real audience. 8,000 people who care about remote work. But the business model wasn’t working, and I was spending hours on something that generated a fraction of what consulting produced in a single day.

When I put it in maintenance mode, it felt like the right call; not giving up, but being honest about where my time should go.

There are only so many hours.


This is my fifth quarterly review. I’ve been doing these since 2022. Previous reviews: 2022 Q1, 2022 Q2, 2022 Q3, 2024 Q2. I publish them because accountability works better in public, and because someone usually replies saying they needed to hear the same thing I needed to write.

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