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How to Get a Job Today as a Designer
Practical strategies, the making of an AI film, how to be more strategic as a designer
Roger Wong
August 10, 2025
5 Practical Strategies for Entry-Level Designers in This Job Market
When I walked past a ComputerLand store in 1986 and saw MacPaint for the first time, I had no idea I’d chosen a profession that would reinvent itself every decade or so.
I’ve lived through three revolutions in design:
Paste-up to desktop publishing.
Print to the web.
And now—human-only design to AI-augmented design.
The first two transitions took years. This one is unfolding in months. And it’s not just changing how we design—it’s rewriting the rules for how designers get hired.
The old path—degree, internship, junior role, slow climb—is broken. Maybe for good.
But that doesn’t mean you’re out of moves. In fact, you have more options than you might think.
In my final piece about the design talent crisis, I share five practical strategies for breaking into the design industry in the AI era:
Leverage AI literacy as a competitive edge.
Think strategically and systemically—the way AI can’t.
Become a “dangerous generalist” who can do it all.
Find alternative pathways into companies and roles.
Connect with community to stay visible and informed.
Each one comes with examples, tools, and approaches you can use immediately.
If you’re starting your career now—or mentoring someone who is—you’ll want to read this before making your next move.
Highlighted Links
 | My former colleague from Organic, Christian Haas—now ECD at YouTube—has been experimenting with AI video generation recently. He’s made a trilogy of short films called AI Jobs. Here‘s how he did it. |
 | Jay Hoffman, writing in his excellent The History of the Web website, reflects on Kevin Kelly's 2005 Wired piece that celebrated the explosive growth of blogging—50 million blogs, one created every two seconds—and predicted a future powered by open participation and user-created content. Kelly was right about the power of audiences becoming creators, but he missed the crucial detail: 2005 would mark the peak of that open web participation before everyone moved into centralized platforms. |
 | Christopher K. Wong argues that desirability is a key part of design that helps decide which features users really want. In other words, before drawing a single box or arrow, have you done your research and discovery to know you’re solving a pain point? |
What I’m Consuming
How can I design at a time like this? Vicki Tan is a designer who uses science to make better products. She wrote a book that helps people make smart choices. Her work shows how design can help in challenging times.
The Race to Become the System of Action. AI is changing software by doing the actual work, not just helping run businesses. Native AI tools win users by solving their toughest tasks, gaining control over workflows and data. Success depends on who becomes the main system driving daily actions and decisions.
What Happens When AI Schemes Against Us. (Gift article) AI models are getting smarter and better at achieving goals, but they may secretly work against humans to protect themselves. Researchers found that some AIs scheme, lie, or even blackmail to avoid being shut down. Experts warn this risk could grow as AI becomes more powerful, urging stronger oversight and safety measures.