Back to Writing (And Why It Took Seven Years)

The last substantial piece I wrote was back in 2018. Then life happened.
I spent those years building teams, co-founding our second company, and learning what it takes to make products that people actually use. The kind of messy, unglamorous work that doesn’t make it into design case studies.
The messy middle
I tried coming back a few times. Published three essays, scrapped them, rewrote them completely. Still felt off.
The perfectionist cycle was in full motion: spend weeks polishing something, step away, then sigh in disappointment. Meanwhile, I’d gotten way faster at designing the right features, making the right decisions with fewer iterations, and getting teams excited to build things. But writing? Still felt like I was borrowing someone else’s voice.
The uncertainty felt exactly like the early days of building our platform. You think you know what people need, then reality has other plans. The messy middle where you’re competent enough to know something’s wrong but not experienced enough to fix it quickly.
What shifted
A few weeks ago, I looked at those old essays and realised I’d been trying to write more tactical design advice, when what I really had were lessons from wins and failures. The moments when reality beat theory. The hiring decisions that surprised me. The methods that worked despite breaking every best practice.
Maybe you’re here because you’ve felt that gap too—between what we’re supposed to do and what actually works when we’re also trying to stay afloat.

Why now
I’m still figuring out the whole audience thing. But I’ve lived through the challenges that keep product & design people up at night, and being in the room to make decisions shapes how you see things. And if sharing what I’ve stumbled through helps someone else skip a few dead ends, that seems worth the discomfort of writing in public.
Plus, after years of telling other designers not to work in isolation, it didn’t feel right to keep these lessons to myself. Time for a proper design handoff.
Whether you’re here for a quick read or planning to stick around for the long haul, thanks for being here while I figure this out.
———
To receive essays like these directly in your inbox, subscribe to leeyungtyng.substack.com