Designing The Next Five Years

Outline

I attempted to ship a new feature using Cursor, hoping to accelerate the build–test–iterate cycle with real users. I didn’t fully succeed — but I learned a lot about where LLMs shine (and where they don’t), and what it really takes for a designer to ship production-ready code. Here’s a behind-the-scenes look at the experiment and what I’d change next time.

Phase One: Designing for Business Impact

From the moment I chose to become a designer, I saw design as a tool for solving problems. Early in my career, I was obsessed with identifying the “core” of a problem — a universal principle I could use to guide every solution. But I quickly learned that problems are context-specific, and that clarity often comes not from abstraction, but from asking the right questions.

Working at startups taught me the most powerful question of all: “Why does this problem need to be solved now?”

This question grounded my approach in business impact. It helped me align design efforts with the startup’s most urgent needs — things like increasing retention, improving conversion, or reducing churn. I started measuring design outcomes not just through user experience, but through tangible business results.

This mindset naturally drew me to B2B SaaS startups. I found that in B2B, problems are often more specific, tied to clear stakeholder needs, and impact is easier to measure. This clarity made it easier to design with confidence and focus.

The Tipping Point: Validating with Real Users

One of the most important lessons I learned in this phase was that early product validation works best when you are close to real, paying customers, not just running abstract experiments.

At the time, many playbooks were emerging: pre-type testing, fake door, landing pages with waitlists. These were helpful, but I came to believe that true product-market fit is found through usage—by shipping something real, collecting feedback, and iterating quickly.

That’s also why I was immediately drawn to the potential of LLMs. When they first emerged, I did not just see them as a trend—I saw a tool to help validate MVPs faster and more meaningfully, by giving real users something to interact with and respond to.

Phase Two: Becoming a Designer who Ships

“Designers who ship have the power to serve users — not just ideas.”

— Soleio, Dive Club Ep. 78

This quote captures something that I deeply believe: when designers ship their ideas to the users directly, the product can become more user-centric.

Since early in my career, what I want to do is not just mock up ideas — I want to see them live in users’ hands and iterate based on user's feedback. Through this process, I was able to define and solve the actual problem of users, and I did not have to waste my time exploring a misguided solution. I think that this can make a designer shorten the distance between the user's expectation and a released product.

Shipping turns design from theory into service.

The Next Five Years: What I am Focused on

“Forget job titles. Work on the thing together.”

— Ryo Lu, Dive Club Ep. 37

Looking ahead, I want to go even deeper. My next chapter is about designing in the real world — with real users, real constraints, and real outcomes.

Here is what that looks like:

1. Work closely with customers — to deeply understand their needs and identify moments of real value

2. Design by shipping — stay involved in the implementation process, iterate quickly, and make smart trade-offs between scope and quality.

3. Prioritize real products over polished mockups — deliver functional value early and improve through real-world use.