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Designer's Roadmap

A weekly email on portfolios, job search strategy, confidence, and career growth. From a designer with 25+ years in the industry helping 500+ designers level up. Read past issues below. Get the next one in your inbox every Tuesday.

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Featured Post

The guide I wish I had as a mid-level designer

Instead of my usual Tuesday tip I want to share something I've been building for the past few months.Early in my career I had real experience. I had the work. I had put in the hours...a lot of hours.But what I didn't have was anyone telling me that the way I was presenting my work was working against me. I had to figure it out myself. Through rejections I didn't understand, feedback that came too late, and lessons that took me years to learn when they should have taken weeks.That's the guide...

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Over the last couple of weeks we talked about building visibility, getting on people’s radars, and finding design roles beyond standard job boards.Now, let’s talk about what happens when it all works.You got the recruiter email. You passed the phone screen and now you’re sitting in the portfolio review loop, walking the team through your best case study.Your work is strong. But mid-interview something happens. The panel smiles, nods, thanks you for your time and then two days later you get...

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I’ve worked with so many talented designers who were uncomfortable talking about their work.They could solve difficult design problems, help teammates, and take on challenging projects. But ask them what they’re good at, and they struggle to answer.I understand that feeling. I've been there.But after 25+ years in design, here’s what I’ve learned:People need to understand what you bring to the table before they can think of you for the right opportunities.And that takes a little...

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One of the best jobs I've had in my career wasn’t posted anywhere.I had reconnected with a former colleague I had worked with at AOL. During that conversation they mentioned a friend’s company was looking for someone to lead design.I asked for an introduction.That intro became a conversation, then an interview, then a job offer. Boom, just like that.It wasn’t a clever networking strategy on my part. I was talking with someone who knew my work and they knew someone who needed it.When I think...

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Recently, I was working with a designer on his case studies.The work was solid and the case studies were structured well. But the outcomes section for an education platform was empty.I asked: “What happened after this launched?” He said: “It’s been adopted by over 1,000 educators globally.”He hadn’t included it because he didn’t think it counted.More than a thousand educators were using a platform he had helped design and that information was missing from his portfolio.I see this more times...

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If you’re in a job search right now and your portfolio isn’t where you want it to be, this email is for you.The version of you who needs something that works now, with what you have, before the next opportunity appears.I’ve worked with designers in this position: a layoff that came without warning, or a role that hit a ceiling.Strong, talented designers who got caught without something ready to show.What I have learned from watching designers face this is that the goal is not a perfect...

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There was a point in my career, when I was a mid-level designer when things started to feel very still.I was doing solid work. I was leading projects. I was trusted by my team. I wasn’t struggling by any visible measure.But that excitement of growth and rapid promotion that had marked my earlier years was somehow gone.I found myself in this odd space between “doing well” and “what’s next?”Productive. Skilled. Recognized. And yet I was somehow stuck.I hear this from designers often. And I have...

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A designer I worked with got a job offer this summer. He did it in 2026. In this market. And I want to share what helped him get there. Where he started We started working together at the beginning of his job search. Over two months, he had three interviews but none had converted into an offer. He was applying, showing up, and doing the work. And throughout the search we kept refining things. But something wasn't landing. When we looked at his portfolio and resume together it became clear....

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I see the same thing in almost every coaching session I have.A talented, experienced designer with real work and plenty of experience behind them who's convinced they're not good enough.They're not falling apart. They're showing up, applying, doing the work.But underneath it all there's this steady hum of doubt. A sense that everyone else has something figured out that they haven't. That the designers getting hired, getting promoted, getting recognized are somehow more ready than they are.I...

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I've coached a lot of designers who came to design from somewhere else.Teachers. Therapists. Accountants. Flight attendants. Hospitality professionals. Project managers.And, they all worried about the same thing:"Is my past going to hold me back?"My answer has always been:No. Your past may be one of the things that makes you valuable.That's even more true in today's design market. Your past experience is not a detour Design is about understanding people, solving problems, making decisions,...

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I've been paying close attention to what's happening in the design job market this summer.Not just in the headlines, but with the designers I'm coaching, the hiring conversations I'm hearing about and the patterns I'm seeing in who's getting traction and who isn't.Here's the honest picture:The market is competitive.Design teams are leaner. Companies are asking more from individual designers. And there are still more designers looking for work than there are open roles.If you've been feeling...