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Apr 06 • 4 min read

your career has a leak


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Livestream with Chris


Read time: 1m 59s

Most designers treat their career like a lottery ticket.

Apply. Wait. Hope. Repeat.

This week I sat down with Ran Liu — product design leader, ex-Shopify, ex-Webflow, ex-Adobe, now building at AirOps — and she reframed the whole thing with one line.

"Your career is something you can deliberately design."

Obvious when you hear it, almost nobody actually does it.

Here's what we broke down 👇

1. Juniors: stop applying harder to a broken strategy

Ran applied to OpenAI five times. She's a growth specialist. Adobe, Shopify, AND Webflow on the resume.

Ghosted. Five times.

So it's not about working harder. It's about diagnosing what's broken.

  • Is your experience irrelevant?
  • Is your work not good enough?
  • Are you bad at selling yourself in interviews?

The move that works: informational interviews.

Not "can I get a job?" — genuine mentorship asks. Five outreach messages a week gets you one meeting. That one meeting tells you more than 500 application rejections ever will.

Oh, and with AI? Build something real. Ship it. Track the data. Show iteration. That's a case study nobody else has.


2. Mid-levels: nobody is keeping tabs on you

Ran got denied a promotion after years of solid work. She thought doing great work was enough.

It's not. It was never enough.

Your manager is running six or seven people. They're not watching you. And here's the uncomfortable truth — you are the only person responsible for your career progression.

The reframe that changed everything for Ran: stop thinking "look what I did" and start thinking "here's what I learned that could help the team."

Share experiment results. Surface user research clips. Celebrate team wins publicly. Same impact, completely different energy, it stops feeling like self-promotion and starts feeling like leadership.


3. Seniors: the project doesn't exist yet

Pre-senior is a straight line. Bigger projects, sharper craft, cleaner output.

Post-senior? All over the place. No playbook. No clear next step.

Here's why: the impactful projects at this level are invisible. Nobody put them on a roadmap because nobody's named them as problems yet.

Your job is to find them in the gaps: the friction between teams, the thing everyone complains about in Slack but nobody's owned.

Then you name it. Build a coalition. Get buy-in. Pitch for the resources.

One tactic Ran swears by: Just complain about the problem to your teammates.

Sounds counterintuitive, but product teams are wired to solve problems. The moment you surface one, people naturally start brainstorming with you.

Suddenly you have allies working towards your idea instead of pushing back on your pitch.


Ran said something that stuck with me:

"If you keep doing the thing that's not working really, really hard — you're not going to land a job."

Remember the job search is a funnel. Fix the leak before you pour more water in.

Ran's "Beat the Gloom" playlist is the most honest job-hunting resource I've seen. Every tactic she shared today, documented in full. Worth bookmarking whether you're actively searching or just want to stay sharp.

If you like it, give her a sub at: youtube.com/@rantalksdesign


Want to learn more?

We also went deep on the 90-day zero-experience playbook, Ran's exact freelance client strategy, and how much research you should show in a case study. Watch the full ask my anything ↓


P.S. Next livestream: How A Designer Becomes A Founder — AMA with Michael Wong (Mizko), April 15, 2026. Join us on LinkedIn or YouTube!


I help UX designers go from Fuzziness to Focused, 3 types of designers I help:

1. Entry-level designer? Transition into UX by crafting an unforgettable portfolio

2. Mid-level or Senior designer? Step up and become a design leader

3. Lead or Manager? Get private 1 on 1 coaching to maximise your impact

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