Ep 134 Career: Tough Love for Your Portfolio: Stand Out or Stay Stuck

Show notes

What’s going on, everybody? Welcome to the 134th episode of The Crazy One Podcast. As always, I’m your host, Stephen Gates, and this is the show where we talk about creativity, design, leadership, and all the things that matter to creative people.

Before we dive in, do me a favor—subscribe to the show, leave a comment, share it with a friend. You’ve heard me say it 133 times before, but it really helps.

Why This Episode Matters

There are still so many people out there trying to find a job—whether they’ve been laid off or are just unhappy in their current role. And a lot of those job searches just aren’t yielding results. As I’ve been doing mentoring and coaching—over 80 sessions at this point—the same topic keeps coming up: portfolios. What’s working, what’s not, and why so many people are struggling.

We’ve touched on this before, especially in episodes about red flags, but I want to approach it differently this time. I want to give you the hiring manager’s perspective—what we’re looking for, how we evaluate portfolios, and why you might not be getting the results you want.

Why Feedback Is Rare and the Process Feels Broken

Let’s start with the reality: the job hunt process is broken. You send out resumes, go through interviews, and then—crickets. No feedback. No closure. It’s maddening. I’ve seen companies miss out on incredible talent simply because the candidate had a bad experience and warned others away. The system lacks empathy, transparency, and basic humanity.

Your Portfolio Is More Than Just Work Samples

If you’re a creative, your portfolio isn’t just a collection of work—it’s your resume, your narrative, and your credibility all in one. And the biggest mistake I see? Too many portfolios are either:

• Too sparse: just screenshots with no context, no story, and no personality.

• Too overloaded: every project since kindergarten in agonizing detail.

You need to find the balance. Show enough to spark interest, but not so much it overwhelms. Treat your portfolio like advertising. Give people a reason to care.

The Harsh Truth About How Portfolios Are Reviewed

Let’s be honest: someone’s going to judge years of your work in 10 minutes or less. That’s not fair—but it’s the reality. We’re looking at 50, sometimes 100 portfolios. You have to stand out.

What we’re really doing is reading between the lines. If there are typos, broken links, poor formatting—that signals lack of attention to detail. If you use nonsense like skill sliders (“I’m 90% in Figma!”), we think you follow trends blindly without critical thinking.

We’re not just judging your design skills—we’re assessing how you think.

What We Want to See

We’re looking for:

• Process: not just outcomes, but how you got there.

• Self-awareness: can you articulate your role and what you learned?

• Focus: don’t try to be everything to everyone.

• Narrative: tell me who you are and what makes you different.

• Craft: even if your past jobs didn’t allow great work, show me you put care into your portfolio.

• Reflection: show wins and failures—what worked, what didn’t, and what you learned.

Think of your portfolio like a design project. Do the research. Benchmark against others in your space. Understand the competition. Design for the reviewer’s experience.

Be Direct. Be Human. Be Strategic.

If you’re presenting your work, ask what the team wants to see. Too many people try to guess and get it wrong. Ask: do they want a deep dive into one project? A high-level overview? A focus on strategy? Tailor your presentation accordingly.

And ask for feedback. Most candidates don’t, but when someone says, “What could I have done better?” it changes the conversation. Even if they didn’t get the job, they leave a lasting impression.

Don’t Be Generic. Be You.

The temptation during a job search is to appeal to everyone. Don’t. Generic portfolios appeal to no one. Show your passion. Prioritize your strengths. Focus your message.

And if you’re worried your book doesn’t reflect who you really are—start there. Be honest about your identity as a creative. Make your work a reflection of your values, process, and ambition.

And to Hiring Managers—Do Better

To those of us doing the hiring: we need to take more responsibility. Give feedback. Be human. Stop treating people like resources. If we don’t, we’ll keep wondering why teams lack talent or loyalty.

Final Thoughts

Your career is yours—and the effort you put into your portfolio reflects how much you care. The people who do the work get results. Those who don’t, won’t. It’s that simple.

Success is a choice. Take control. Own the process. Treat yourself like a client. Create something you’re proud of.

If you want feedback, I do three sessions a week on ADPList. Or reach out on social media—I’d love to help.

Until next time—stay crazy.

Tagged as:
career growth creative careers creative ind creative job search creative leadership design portfolio design work job interview tips job search strategy personal brand portfolio feedback portfolio mistakes portfolio presentation self-promotion