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Hey Reader
This week is about building confidence as a designer when you’re stretched across a million responsibilities. Where you can reframe your experience, sharpen your positioning, and make smarter career moves in 2026.
In today's email:
- Sharpening product polish: Griddy Icons for a solid, consistent icon set, Interface Craft for going beyond "functional and forgettable," plus Inflight + Becoming a Confident Facilitator for cleaner feedback loops and smoother collaboration.
- Designing for the AI era: AI Design Field Guide for grounded perspectives on what AI design work actually looks like, plus Gemini AI Visual Design for a behind-the-scenes look at how gradient and shapes built trust and clarity.
- When doing everything feels like doing nothing: The generalist designer paradox and why this experience is more valuable than you think, how to get external benchmarks, and what to do if you're feeling stuck or spread too thin.
Design gems of the week
- Griddy Icons: Created by Filip Gres and developed by Zuzana Benova, Griddy Icons is a free, open-source library with 1,350 icons now available. If you want solid, consistent icon set, this is a great one to bookmark. The set is still expanding.
- AI Design Field Guide: Want grounded perspectives on emerging roles like the "Model Designer" and what AI design work actually looks like in practice? Check out this guide for how design is changing alongside AI, built around insights from designers from OpenAI, Anthropic, Figma, and more.
- Becoming a Confident Facilitator: A practical guide for running smoother collaborative sessions: how to prepare, setting the tone, guiding the room, and landing real outcomes. Great for any role that requires collaboration.
- Interface Craft: Created by John Puckett (Wealthfront, DropBox), this is a working library for those who want to go beyond "functional but forgettable" – with articles, videos, and examples on designing with uncommon care.
- Inflight: A design feedback tool for product teams that keeps your video walkthroughs, prototypes, and feedback all in one place (no meetings required). Now out of alpha and in beta, so anyone can sign up.
- Gemini AI Visual Design: A behind the scenes look at how Google designers use gradients, motions, and shapes to make an AI assistant feel trustworthy and intuitive (especially as features keep evolving).
Open design roles worth a look
It's a new year and there are a lot of open design roles! Check out these exciting opportunities below.
When doing everything feels like doing nothing
Last week, I talked to Stefan—a designer who's been at the same company for nearly nine years. He's the most senior designer on his team, has shipped multiple products from concept to launch, and currently finds himself spending months writing knowledge base articles while also doing UX work, QA testing, and whatever else needs doing.
"I feel like I'm lacking some external benchmarks – what I've been struggling with is trying to evaluate whether my experience is actually valuable" he told me. If you've ever felt this way— in a role where you're stretched across many responsibilities for a long time, wondering if your broad experience is actually making you less marketable—this is for you.
The paradox of the generalist designer
There's a strange tension that happens when you're the person who does everything on your team. On paper, you have tremendous impact and autonomy. But day-to-day, it can feel like you're scattered, unfocused, and building expertise in nothing.
This feeling shows up in three common scenarios:
The long-tenured designer has built their entire career at one company. They're starting to worry: Am I pigeonholed? Does the market want someone with my kind of experience?
The startup generalist is wearing all the hats on a small team. One week it's product design, the next it's writing help documentation or fixing the website. They wonder: Am I actually getting better at design, or just good at juggling?
The senior IC without leadership support is the most experienced designer on their team, but has no one to learn from. They lack benchmarks for what "good" looks like and feel pressure to step into leadership before they're ready.
Why this experience is actually valuable
When Stefan described his situation, I could hear the doubt in his voice. But here's what I told him:
Companies are looking for self-starters. They want people who don't necessarily have all the answers but are hungry to find them. Navigating ambiguity, solving problems without a playbook, advocating for resources? That's not a gap—that's evidence of exactly the mindset companies want.
0-to-1 experience is rare. Taking a product from concept to launch, even if it's messy, teaches you things you cannot learn anywhere else. You understand the full lifecycle. You know what it's like to ship something that's good enough, not perfect.
Your advocacy skills matter. Maybe you haven't gotten the research budget you wanted, or you're still trying to convince leadership to invest in design systems. The fact that you're trying to solve these problems—that you even recognize they need solving—is itself valuable experience.
You understand how businesses actually work. When you've worked with limited resources and competing priorities, you develop systems thinking that many designers don't have. You know how to make tradeoffs and speak to stakeholders in their language.
The market has shifted toward builders—especially in startups and AI companies. There's less emphasis on pixel-perfect portfolios and more focus on people who can navigate ambiguity and problem solve as they go.
What you can actually do about it
1. Test the market (without committing)
Update your portfolio and resume. Put out some feelers. See what kind of response you get.
The goal isn't to leave—it's to gather data. What do recruiters respond to? Where do you feel confident in interviews? You can always say no to offers, but the information you gather is incredibly valuable.
2. Advocate internally for what you need
- Request external mentorship or coaching (many companies provide this for senior ICs)
- Propose focusing on work that builds skills you want to develop (more research, earlier strategy involvement)
- Shape the design culture if leadership opportunities emerge—define the role on your terms
- Ask for conference budgets, training, or external speakers to expose yourself to how other companies solve similar problems
3. Find external perspective
Join design communities where you can compare notes. Attend conferences. Seek out mentors who can give you honest feedback. Connect with designers at other companies and ask them what their day-to-day looks like.
This isn't just about learning new techniques—it's about calibrating your own experience. You need to know: Is this normal? Am I actually behind, or does it just feel that way?
4. Reframe how you talk about your experience
Don't hide the generalist work—position it strategically:
- Frame around business problems you solved and outcomes you drove
- Highlight constraints you worked within and decisions you made
- Show how you advocated for change, even if you didn't always get it
- Emphasize your ability to navigate ambiguity and make smart tradeoffs
The narrative isn't "I did everything because I had to"—it's "I built products from the ground up in resource-constrained environments and learned how to prioritize ruthlessly, advocate strategically, and ship meaningful work under real business pressure."
5. Be intentional about leadership
If you're being nudged toward a leadership role, don't let it happen by default.
Have the conversation now: What would you be responsible for? What would you need to be successful? What would you have to give up in hands-on work?
Define it on your terms rather than inheriting whatever structure your company happens to have. And if leadership isn't what you want right now? That's okay too. But be clear about it.
The permission slip you didn't know you needed
Here's what I want you to take away:
- Long tenure isn't bad. It's better than job-hopping every year and never seeing your work through to its full impact.
- Generalist experience is increasingly valuable, especially as companies look for people who can wear multiple hats and build things from scratch.
- Not having all the answers is normal. You've learned how to figure things out scrappily, and that's its own superpower.
- You can explore options without committing. Testing the market gives you information and helps you make decisions from confidence, not fear.
- The messy work has value. Companies who are actually building things will recognize that.
If you're feeling stuck or spread too thin: you're not falling behind. You're building a different kind of expertise. And with some intentional reframing and strategic moves, you can turn that into the career you actually want.
Looking for more? Here's how I can help:
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