5 Years of Building Products

2024

The uncomfortable truths

Good design can't fix a bad product. I've learned this the hard way. You can polish a terrible idea until it shines, but it's still a terrible idea. The best designers I've worked with spend more time questioning what to build than how to build it.

"What if we do nothing?" is a powerful question. Most features don't need to exist. The courage to ship less is underrated.

Titles don't mean as much as you think they do. Early in my career, I chased titles. Now I chase interesting problems and great people to solve them with.

What actually moves the needle

  • Be the most helpful person in the room. Not the smartest, not the loudest—the most helpful.
  • Act like a leader before you are one. Nobody promotes people who wait for permission.
  • Look for simple solutions to complex problems. Complexity is easy. Simplicity is hard.

On success and luck

Success is probability. Show up more often = more luck.

I used to think successful people had some secret. They don't. They just showed up more times than everyone else. They shipped more, failed more, learned more.

Questions that changed how I work

  • "Why?" Ask it more often. Questions create clarity.
  • "What's the tradeoff?" There is no "best" anything. It's all tradeoffs.
  • "Can I change the rules?" When you can't win the game, sometimes you need to play a different one.

The meta-skills

Writing is how to clarify your thinking. If you can't write it clearly, you don't understand it clearly.

Everything is a negotiation. Deadlines, scope, what you work on—all of it.

Fear kills trust. Lack of trust kills culture. I've seen teams implode not because of bad strategy, but because people were afraid to speak up.

What I wish I knew earlier

  • Side projects are a great way to learn new things quickly
  • Understand the business, not just the craft
  • Estimates are guesses, not promises
  • Find a mentor or a coach—don't struggle alone
  • Imposter syndrome never goes away; keep learning anyway
  • Be someone you'd want to work with

The career advice I actually follow

Be the go-to expert in something. Not everything. Something.

Establish design culture wherever you go:

  1. Growth: Regular 1:1s focused on development
  2. Community: Chapter meetings and group critiques
  3. Radiation: Be the ambassador across the organization

Five years in, I'm more certain about less. And somehow, that feels like progress.