Think all you need is a polished portfolio and a perfect case study to land your next job? Trevor Alexander says otherwise. In this episode, we challenge the traditional career advice designers are given and talk about what actually leads to long-term success, resilience, and trust. |
What if everything you’ve been told about how to build a successful design career was wrong?
A few years ago I came across a successful designer who had never applied for a job.
They never put together a portfolio.
They didn’t have pixel-perfect case studies.
🤯🤯🤯
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Sounds crazy that a designer with over 20 years of experience would never need these things, right?
All Trevor Alexander needed to land a role was his reputation, and he wrote a book called “An Ugly Design Career” to teach you all about it.
Now, am I suggesting you go and delete your portfolio today?
No way. Definitely don’t do that.
But this week, Trevor joins the show to talk about what makes a design career anti-fragile—one that doesn’t shatter when everything around you starts to fall apart.
We talk about:
⇢ Why tools are table stakes (and Figma won’t save your job)
⇢ How soft skills like storytelling and improv make you more valuable
⇢ The compounding power of trust and showing up
⇢ Lifestyle creep and learning to define “better” for yourself
⇢ How to stay relevant, even when you’re unemployed
No fluff. No hustle culture. Just an honest look at what it takes to stay in this industry when the titles disappear, the tools change, and the job market gets weird.
If you’ve ever asked yourself, “How do I keep going?” this one’s for you.
🎯 Here are some key takeaways from our chat |
1️⃣ Your portfolio is not your product. You are: Trevor built a nearly 20-year career without ever applying for a job or maintaining a portfolio. Why? Because people trusted him. They brought him along. The lesson: your reputation, your relationships, and how you make others feel often carry more weight than your case study layout.
2️⃣ Focus less on mastering tools and more on delivering value: Figma isn’t your career. It’s just a tool—and one that may be replaced tomorrow. Instead of becoming a tool specialist, use those tools to deliver value to your team and company efficiently. The real differentiator isn’t how well you know Auto Layout—it’s how well you solve problems, build trust, and help your team move faster and smarter.
3️⃣ Grit can get you further than talent alone: Trevor says it best: “You might be more talented than me, but you won’t outwork me.” In a field full of talented people, it’s your tenacity—your ability to push through ambiguity, failure, and missed opportunities—that can set you apart. Grit is a muscle. Build it.
4️⃣ Redefine what “better” means for you: More money. A bigger title. A fancier company name. These aren’t always signs of progress. Trevor shares a powerful exercise: write out your perfect day in vivid detail. It helps you define your version of success—and shows you what to optimize for. Sometimes “better” means less money and more meaning. Or fewer benefits and more flexibility.
5️⃣ Sometimes free work is the smartest move: Networking doesn’t always look like schmoozing at conferences. Sometimes it looks like helping a friend, designing a logo for your aunt’s cupcake shop, or building a tiny tool with a scrappy founder. Do it on your terms, but don’t underestimate the long tail of generosity.
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You iterated, pivoted, circle-backed, and made it out of Q2 (barely).
You’ve earned a Merit-ish Badge!
Choose from three sets: • Soft Skills, Sharp Tongue • Cult of Figma Initiation • Pixel Pusher Survivor Kit
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They don't teach this stuff in school
Learn the things they left off the syllabus.
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