I Got Let Go Twice. Here’s How I Still Built a 16-Year Design Career

Most product designers want to have the clean career story. First, you go to school. You build a portfolio and get hired. Then you get promoted and become a senior product designer. Post something painfully inspirational on LinkedIn about “the journey” and you're there.

Cute, but Tyler’s path was not that.

It started with trying to get into animation. He soon realised the job market did not care about his art school confidence, so he had to go back to learn graphic design, web design, and coding landing pages. After, he started mailing resumes like it was the stone age and slowly figuring out how to turn all those skills into an actual product design career.

So… how do you build a long-term design career when the industry keeps changing every five minutes?

In this episode of The Design Table Podcast, Nick interviews Tyler about his 16-year journey in design, from animation school and trade programs to web design, e-commerce, agency work, AI products, design leadership, layoffs, and eventually becoming a principal product designer.

Tyler shares what he learned from being a designer who could code before that was cool, asking for raises, leaving jobs when growth stalled, getting let go twice in one year, spotting red flags in companies, and finding a role where mentorship, product strategy, and modern design work finally came together.

We also get into AI, vibe coding, designers opening pull requests, why the builder-designer might be making a comeback, and why the core thinking behind product design still matters even when the tools change.

This episode is about surviving the messy middle of a design career, staying useful as the industry shifts, and not letting one bad job, one layoff, or one weird CEO turn your career into a smoking pile of career anxiety.