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.

In this episode you’ll learn:
🔸 How Tyler accidentally moved from animation into web design
🔸 Why early career confidence can disappear fast in the real job market
🔸 How coding helped Tyler stand out as a designer
🔸 Why staying current matters more than clinging to one process
🔸 How to ask for raises when you can actually back it up
🔸 What layoffs taught Tyler about career risk
🔸 How to spot red flags before joining a company
🔸 Why AI and code are changing the product design role again

⏱ Chapters
00:00 Why the design industry feels unstable right now
02:00 Tyler’s accidental start in design
04:30 When art school confidence meets the job market
06:20 Learning graphic design, web design, and code
08:00 Why old skills still show up later in your career
10:11 Going into monk mode to get better
12:13 Landing the first internship
14:06 Applying for the first real design job
16:15 Negotiating salary before knowing what you’re worth
19:16 Struggling in the first job
21:14 Becoming the only designer
23:44 Designers who code and the builder-designer comeback
25:39 Leaving a job to keep growing
29:38 Taking a pay cut to learn something new
32:18 Spotting company red flags
34:38 Moving from web designer to UI/UX designer
36:23 Agency work, AI, and design leadership
40:30 Asking for a $15,000 raise
43:03 Fighting for user research
44:21 Becoming a solo product designer
47:00 Building trust with engineering
48:30 Getting let go after four years
51:54 Updating the portfolio after a layoff
54:04 Joining a sinking ship
58:21 Getting let go twice in one year
59:19 Finding green flags in the next role
01:01:05 Why designers may need to touch code again
01:03:59 What designers should do to stay relevant
01:06:23 Why your only real competition is your past self

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More about Tyler and Nick
Tyler: https://www.designtablepodcast.com/hosts/tyler-white
Nick: https://www.designtablepodcast.com/hosts/nick-groeneveld