How We’re Building Sunday Planning (With a Little Help From AI)

Written By Laura Wong

By Ryan, Co-Founder of Sundays Online

Imagine this: it’s a lazy Sunday afternoon. You’re sipping coffee, daydreaming about your next big adventure. Maybe it’s Tokyo during cherry blossom season, or a cozy weekend in Lisbon. You’re not booking flights yet—you’re just dreaming. That’s the moment Sunday Planning was born, the first product from Sundays Online.

We’re building a travel planning app that helps you turn those dreamy Sunday thoughts into real, unforgettable trips. Not just logistics like flights and hotels—but the meals you’ll rave about, the hidden gems you’ll stumble into, and the memories you’ll actually want to frame.

But let me back up a bit.

From Problem Solver to Trip Dreamer

I’ve never been much of a planner. I live life problem to problem—solve what’s in front of me, move on. That’s how I used to travel too: book the flight, find a hotel, done. Once I landed, I’d wander around solving new problems—where to eat, what to do, how to not waste the day.

Spoiler: I ate a lot of average meals and missed out on the best experiences because I hadn’t booked ahead. I spent more time Googling than exploring.

Then I met Laura, co-founder of Sundays Online.

She planned our first trip together like it was her job. Blogs, videos, spreadsheets, Google Maps, MyMaps—you name it. I thought she was a little intense. But she loved it. It was her way of dreaming, visualizing, and curating the trip we really wanted.

And it worked. That trip was incredible. Not because every minute was scheduled, but because we had a plan for the things we cared about. We had backups. We had tickets. We had time to explore without scrambling. You can read more about how we plan trips today here.

Still, we were juggling too many tools. Sheets, Maps, saved links, screenshots. It was messy. The problem solver in me kicked in: there had to be a better way.

Why Sunday Planning Exists

We looked around. There are endless travel tools—but we felt the tools weren’t built for planning—they were built for storing. Google lets you save places, but doesn’t help you organize them by day, priority, or ticket status. AI “planners” spit out generic itineraries that feel like someone else’s vacation.

We wanted something better:

  • A place to save and organize the spots you care about

  • A way to plan your days with flexibility and structure

  • Smart reminders for reservations, tickets, and timing

  • A tool that anticipates your questions before you ask

  • A planning space that feels like a dream board, not a spreadsheet

If we could build this, our friends said they’d use it too. Maybe we could make travel planning joyful, not stressful. Accessible, not overwhelming. Where planning is part of the journey itself.

Can AI Build It?

At first, I thought: why not let AI build it?

I tried Cursor. Gave it a few paragraphs. It generated files, plans, code—some I asked for, some I didn’t but probably needed. Then I told it to run. It crashed. I asked it to fix the error. It couldn’t.

I hadn’t coded in 15 years. Debugging thousands of lines of AI-generated code? Not happening.

Next I tried Lovable and Base44. Started small: a trip planning screen with drag-and-drop. They built something! But not everything. I iterated. Things got worse. One step forward, two steps back. I didn’t understand what was happening under the hood.

Lesson learned: AI can’t replace engineers and designers. But it can supercharge them—if you know what you’re doing.

What AI Can Do (And Why It’s Our Secret Weapon)

Once I stopped trying to outsource the whole build, I realized AI is an incredible partner.

It’s like having a team of super interns who never sleep:

  • Research assistant: AI helped me analyze the market, understand traveler personas, and map out competitors.

  • Tech advisor: It answered questions like “What’s the difference between React and Vue?” and “Should I use Supabase or Firebase?”

  • Project manager: It suggested next steps, helped me break down features, and even nudged me when I got stuck.

  • Learning buddy: I’d watch a YouTube tutorial, pause, ask AI to explain a concept, and keep going. It was like having a mentor on call.

Eventually, I stopped asking AI to build the whole thing and started asking it to help me learn how to build it myself. That changed everything.

The Stack That Stuck

I’m new to modern web development. I knew the fundamentals, but the last time I coded was in the .NET era. At my last company, we used Node and React, but I didn’t fully understand them.

So I started from scratch. I wanted to learn just enough to use AI effectively—feature by feature, like writing user stories. I needed to understand the code, troubleshoot small issues, and avoid spaghetti messes.

After long chats with Copilot, I landed on:

  • React for the frontend: responsive UI, reusable components, JSX syntax

  • Next.js for full-stack capabilities

  • Supabase for backend: PostgreSQL database, authentication, file storage

This combo felt manageable and powerful. I built a markdown editor and a Trello clone to learn about auth, navigation, drag-and-drop, and component libraries like Tailwind and shadcn.

The UX rabbit hole

There are disjointed tools that service the planner today so Sunday Planning has to be different. It’s not just for the hyper-organized or the spreadsheet-obsessed—it’s for the planner-dreamer who wants to feel confident, the explorer who wants to be prepared, and the couple who wants to make every moment count. We’re designing for those that value flexibility, but also want to make the most of their time away.

That means the experience has to be joyful, intuitive, and quietly powerful.

I dove deep into design systems, UI kits, and Figma templates. I tried Lovable to generate mockups, explored Tailwind and shadcn component libraries, and watched hours of YouTube tutorials—just to see how people styled a button to match a vision.

It blew my mind how many layers CSS has. Typography, spacing, hover states, responsiveness—it’s what brings an app to life. And it’s what makes a product feel trustworthy.

I realized: good design isn’t just about aesthetics. It’s about confidence. When a user sees a clean, thoughtful interface, they feel like the product has their back. That’s what we’re aiming for.

Familiar, but Fresh

We’re not trying to reinvent the wheel—we’re trying to make it roll smoother. That means leaning into familiar patterns (cards, lists, calendars) but layering in intelligence and delight.

Think:

  • The flexibility of a spreadsheet, but with structure and automation

  • The joy of Pinterest boards, but with real-time planning power

  • The clarity of a checklist, but with context and recommendations

We want Sunday Planning to feel like a tool you didn’t know you needed—but now can’t imagine traveling without.

Building With Empathy

Every design decision is rooted in empathy. We’re asking:

  • What’s frustrating about planning today?

  • What do people wish they could track, but can’t?

  • How do we reduce decision fatigue without removing freedom?

We’re designing for the person who wants to plan better—not just faster. For the traveller who wants to feel prepared, not boxed in. For the couple who wants to spend less time Googling and more time exploring.

The AI Renaissance (And Why We’re All In)

Once I had a foundation, I dove deeper into how engineers use AI today.

Claude Code changed the game. I learned about token limits, memory, and agents—specialized AI workers with narrow scopes. Instead of one giant chat, you split tasks across agents with shared global context. Each agent focuses on design, testing, database, subscriptions—whatever you need.

This led to a wild question: could a two-person company move 10X faster than a 10-person team? What about 100X?

Turns out, AI-native companies are real. They’re not just chatbots—they’re businesses with AI in their DNA. Dev teams with 3 engineers and 10 agents each. AI checking in code, completing Jira tasks, flagging bugs, answering Slack questions.

Some early AI-native companies are seeing over $3M in revenue per employee. We’re just getting started, but embedding AI into our processes early is how we move fast.

Where We Are Now

If you’re still reading—thank you. You’re officially part of the journey.

We’re breaking ground this week. The main repo for Sunday Planning is live. We’re working with AI to define global context, brand guidelines, and writing style guides. We’re generating agents to work through the backlog.

I’ve been deep in system design and data modeling. With a solid schema in place, we’re ready to build features one by one.

Our goal: launch a beta in the next 60 days. Start the new year with a product we’re proud to share—with friends, family, and fellow travellers who want to plan their next great getaway.

If you’ve ever dreamed of a better way to plan travel, we’re building it. And we’d love to have you along for the ride.

Be part of our early community — sign up for updates and beta access to Sundays Online’s first release: Sunday Planning here.

Laura Wong