I recently talked with Dean about what makes design teams succeed or fail. His perspective flipped my understanding of leadership upside down and made me question how I've been approaching design problems all along.

Breaking Boundaries from Day One

Dean's path to design began in high school when a substitute teacher—who happened to be the design teacher—caught him doodling instead of paying attention in class. "You should think about doing design as a subject when you get to choose your subject," the teacher suggested. That simple nudge opened a door Dean hadn't considered before.

What followed was an exploration of illustration, character design, and manga art. By 15, Dean had landed his first paid gig creating comic book work. "I was terrible looking back at it," he admits with a laugh, "but at the time, you know, you're like, 'Oh, I'll do that.'"

As he transitioned to college, Dean encountered his first real creative obstacle. While studying advertising, he realized the institution was stuck in the past—focused entirely on billboards, TV ads, and magazines while the digital world was rapidly evolving. The prescribed career path felt limiting: study, complete an internship, and hope someone would hire you.

"I thought it was quite an expensive path to get a job," Dean explains. "So I figured I'd do something else."

That "something else" became a pattern of creative rebellion. When assignments called for print deliverables, Dean submitted digital versions instead. His lecturer pushed back: "You're doing something very different from what I asked for." But Dean persisted, choosing to solve the core problems rather than checking arbitrary boxes.

This boundary-breaking approach led him to Formula D Interactive, a design agency doing pioneering work with interactive installations and digital experiences. After seeing their innovative holographic touchscreen technology online—essentially a pane of glass with a special film that created touch-responsive projections—Dean was captivated.

"This is minority report. It lives, it's real. I want to do that thing," he remembers thinking. So he did something most students wouldn't: he found their email address and reached out directly, asking if he could simply observe how they created such technology.

To his surprise, they not only welcomed him but offered to pay him. When I asked what gave him such confidence to make that leap, Dean's response was illuminating: "I don't really see some boundaries that I think other people do."

From Rule-Breaker to Leader

Dean's willingness to ignore conventional boundaries served him well as he progressed through his career. He moved from agency work to product design, eventually landing in the banking sector where his approach to problem-solving would evolve significantly.

By this point, Dean was leading a team of over 150 designers spread across multiple countries, handling everything from branch experiences to corporate investment banking. The scale and complexity of the work forced him to look beyond design methodologies to understand why some teams thrived while others struggled.

"Nine times out of ten, when a system's not working, it has nothing to do with what you drew on a slide," he explained to me. The actual problem? People not talking to each other effectively. Design issues almost always masked deeper communication challenges.

This insight became a turning point. One of his design directors made an observation that would change Dean's approach forever: "You're not designing experiences or products. You're designing humans."

The Birth of Designing Humans

That powerful insight led Dean to found Designing Humans in 2018, a consultancy focused on helping companies build effective design teams. The name directly reflected his philosophy that the people creating the products matter more than the processes they follow.

"My key skill really is people," Dean explained. Through expanding his network and conversations with other leaders, he discovered a common struggle: companies simply couldn't get their design teams working effectively.

Designing Humans aimed to solve two key problems: first, how to widen the talent pool without lowering standards, and second, how to organize teams so businesses get value while designers do work they're proud of.

"I'd rather make the entire pool bigger, which increases the catchment zone for talent," Dean says. This meant focusing on career development and team structure simultaneously—bringing more people into design while ensuring they could thrive once there.

Think about what this means for how we approach UX. All those tools and frameworks we obsess over? Secondary. What truly matters is understanding ourselves and how we relate to others.

"You cannot be in any relationship that works without knowing yourself really well," Dean explains. "And if you want to build products people actually love, you've got to know what is creating that product."

How to Spot When You're Stuck

Through his work with designers at various career stages, Dean developed a keen eye for identifying when someone is stuck—often before they realize it themselves.

"They seem like they're held together with elastic bands," he says, describing the visible anxiety and rigidity that appears when designers hit a wall. The physical manifestation of being stuck is unmistakable: tense body language, circular thinking, and a growing frustration that compounds the problem.

Dean shared a story that perfectly captures both the problem and his unconventional approach to solving it. Early in his current role, he noticed a designer struggling with the same problem for hours. Dean observed him from a distance, left for meetings, and returned to find the designer still in the exact same spot, wrestling with the same issue.

After watching this continue, Dean walked over, picked up a pen, and wrote two words on the designer's notebook: "Try harder."

"He looked at me and said, 'This is so rude. This is exactly what I'm doing,'" Dean recalls. The designer was understandably frustrated—he was clearly putting in effort.

Dean's response cut to the heart of being stuck: "You're getting no different result, so we should do something different. You are trying hard. But you're not pivoting."

That's the crucial insight: Being stuck rarely comes from lack of effort. It comes from continuing to apply the same approach even when it's not working. The inability to pivot—to try a fundamentally different angle—is what keeps talented designers trapped in unproductive cycles.

Embracing the Power of Mistakes

Dean's approach to mistakes runs counter to design culture's perfectionism. In an industry often obsessed with flawless execution, his perspective feels revolutionary.

"Until you see a zombie, it's not the end of the world," he tells his team to put things in perspective. "It's not a Slack message. It's not a design review. It's not your prototype."

Dean operates with the assumption that mistakes are inevitable. He doesn't know what they'll be, but he knows they're coming—and that mindset allows him to start moving instead of being paralyzed by the fear of getting things wrong.

When facing a tight deadline before the year-end break, he told his team: "Just get stuck in. There's no time for perfection. There's only time for effectiveness. Even if you break something but learn something, that's better than being perfect."

He frames mistakes as cognitive fitness training. We readily accept that physical workouts are uncomfortable but make us stronger. Yet somehow, we expect our thinking work to be painless and perfect on the first try.

"For some reason, cognitively we're like, 'Oh my gosh, it's all death and destruction if I get something wrong,'" Dean explains. "That for me is just a fitness issue."

This reframing helps his team push boundaries without the paralyzing fear of failure. It's not about being reckless—it's about recognizing that mistakes are often the fastest path to learning.

How to Unstick Your Team (And Yourself)

Dean's approach to helping stuck designers isn't about providing answers—it's about creating situations that force new perspectives.

One of his design leads captured this perfectly: "I just gotta remember we're all guinea pigs to Dean. He's just poking us to see where we'll go next."

Rather than being offended, Dean embraced the description. "I provide situations that help people reflect in a safe environment. If I can stretch you, you become more marketable. My team gets stronger."

Through his coaching work, Dean has identified three types of designers who typically get stuck:

1. The anxiety-driven ones who seem "held together with elastic bands"—where anxiety is visibly holding them back

2. Those explicitly asking for help—the "I wish somebody would help me" type who recognize they're stuck

3. Motivated people who simply don't know where to start—eager but lacking direction

For each type, Dean tailors his approach while following a common principle: use their current work as the teaching tool. He creates what he calls "teachable moments" by drawing unexpected analogies to help designers see their problems differently.

These analogies range widely—from comparing team dynamics to plant growth patterns, to using car mechanics as a metaphor for design systems, to a particularly vivid comparison about perspective that uses the Titanic.

"I used one of the Titanic the other day," Dean explains, "which had to do with perspective of being in the engine room versus on the deck just after the iceberg hit. Some people are running around screaming and others are drinking champagne."

The analogy highlights how different roles in an organization can have completely different perspectives on the same crisis—a crucial insight for designers trying to navigate complex organizational dynamics.

His underlying philosophy ties back to his self-described nature: "I am long-term lazy. I'll work hard now so I don't have to later. I invest in people until they don't need me anymore."

The Humility Factor: You're Just a Participant

The most striking perspective Dean shared was his view on how designers should think about their relationship with users.

"We ask permission to participate in the lives of our customers," he says. "They're not thinking about us. And that's okay."

This perspective is refreshingly humble in an industry where designers often believe their work is central to users' lives. The reality? We're not the main characters in our users' stories—we're just visitors who need permission to be there at all.

Dean observed this misconception particularly in advertising and then later in tech: the belief that users are constantly thinking about our products, brands, or experiences. The truth is far more humbling—we're competing for brief moments of attention in lives that are full of more important priorities.

"The more self-aware you are, the more you realize it's not about you," he explains. "You shouldn't force your full design process on everything just because you can. Remember who you're actually trying to help."

This perspective shift fundamentally changes how we approach problems. Instead of imposing our process or preferences, we begin with the humble recognition that we're guests in our users' lives—and that shapes everything from research to final delivery.

Start With Self-Awareness

If there's one actionable practice you can adopt after reading about Dean's approach, it's developing better self-awareness—both for yourself and your team.

Dean suggests a simple weekly reflection ritual: spend 30 minutes every Friday afternoon contemplating what frustrated you, excited you, and made you happy that week. The simple act of writing it down helps you externalize these thoughts and look at them objectively.

"Just the act of doing that is already getting it out of your brain. And then you're looking at it as if somebody else wrote it, in a way," he explains.

Then comes the crucial step: share these reflections with two specific people—someone you trust completely and someone you don't get along with. "The truth is somewhere between their perspectives," Dean says.

This structured approach to self-reflection isn't just personal development—it directly impacts your design work. Understanding yourself better helps you collaborate more effectively, recognize your biases, and create products that genuinely serve users rather than feeding your ego.

The practice also helps you identify when you're stuck in your own patterns, giving you the awareness to pivot before investing too much time in unproductive directions.

As Dean puts it, summing up his philosophy: "If you know yourself best, you're also at your most valuable."

Want more insights from Dean Broadley? Listen to our full conversation where we dig deeper into his journey, leadership approach, and practical advice for designers at every career stage.​​​​​​​​​​​​​​​​

In this article, you’ll learn how to shape case studies around real problems, constraints, and human-centered outcomes. By the end, you’ll know how to craft a portfolio that resonates with hiring managers and design leads—and how to position yourself for design’s next evolution.

Early Influences: A Nontraditional Path to Design

Stefan’s path into design wasn’t conventional. With a degree in communications and a curiosity for early web projects, he landed a role at a B2B speaker company—far from the sleek world of digital product design. But that experience became an unexpected advantage.

Working within those constraints forced him to think beyond aesthetics. He had to prioritize problem-solving, efficiency, and business realities—skills that later became invaluable at Google, where he spent eight years not only refining his craft but also shaping the company’s design job ladder.

By the time he moved on to lead design for HubSpot’s AI platform, he’d seen firsthand how the best portfolios weren’t just a collection of visuals. The most compelling ones told clear, constraint-driven stories—demonstrating how designers tackled real challenges, adapted to limitations, and created tangible impact.

Why Constraints and Clarity Beat Overstuffed Work

From agency projects to Google initiatives, Stefan has reviewed countless portfolios. Most designers try too hard to prove breadth, listing every wireframe or logo redesign, hoping to showcase versatility. But he warns:

He learned this lesson firsthand at Google when seeking a principal-level promotion. After two rejections, he trimmed his portfolio to three case studies that showcased his unique strengths—and was promoted immediately. It wasn’t the volume of work but the depth of narrative and constraints he overcame that made the difference.

Highlighting the Constraints

Portfolios that gloss over time pressure, stakeholder conflicts, or limited resources miss what Stefan calls the “real world of design.” He believes highlighting constraints demonstrates real skill:

Actionable Insight: Turn Constraints into a Narrative Hook

If you had to complete user research in two weeks instead of a month, highlight that constraint. Show how you maximized resources or made tough trade-offs. This proves you can ship under pressure—precisely what recruiters and design leads want to see.

Constraint-based storytelling is one piece of the puzzle. Equally important is demonstrating judgment, especially in an era when AI handles more routine design work.

The Role of AI: Extending (but Not Replacing) Human Judgment

Stefan focuses on designing AI-driven tools for marketing and sales teams at HubSpot. He’s adamant that while AI will automate routine tasks—like generating layout variants or filling in brand guidelines—it won’t replace the need for critical thinking.

For Stefan, the best designers will:

• Use AI to accelerate iterative tasks.

• Show why they refined or rejected AI-generated elements.

• Document trade-offs made along the way.

When telling the story of a product in your portfolio, a short section on how you used AI (or any tool) to handle repetitive tasks—then layering in your unique perspective—can highlight adaptability. That’s precisely the narrative hiring managers want.

Actionable Insight: Showcase Your AI-Enhanced Process

If you used ChatGPT or another tool to generate an initial copy, include the prompt and raw output in your case study. Then, please explain how you critiqued and improved it. This step-by-step approach showcases critical thinking and technical fluency.

AI tools may evolve, but Stefan insists that a portfolio’s real power is demonstrating sound design judgment. That’s what separates good designers from great ones.

Cultivating “Design Judgment” in Your Portfolio

“Design judgment is understanding which rules to follow, which to break, and why,” Stefan explains. It’s not about perfection—it’s about critical thinking. At Google, he co-authored the internal design job ladder to encourage designers to highlight the trade-offs they faced:

• Did you have to cut research time?

• Did a stakeholder insist on a specific feature?

• Did engineers face database constraints?

By naming these factors, you show you can navigate real-world complexity rather than ignore it. That’s what hiring managers seek: someone who thrives under pressure and balances conflicting needs.

Pottery Lesson for Designers

Stefan likens design to a pottery class where students split into two groups—one focused on quality, the other on quantity. Surprisingly, the quantity group produces higher-quality work because they make more mistakes and learn faster. The same applies to designers: the more projects you tackle, the sharper your judgment.

Actionable Insight: Document Your Trade-Offs Clearly

In each portfolio case study, include a brief bullet list of 2–3 major decisions you made—plus the pros, cons, and outcomes. This shifts your case study from a passive ‘here’s what I made’ to an active ‘here’s how I decided what to make.’

With so many threads—constraints, AI, design judgment—how do you package your portfolio into a cohesive, compelling narrative?

Tying It All Together: Weaving a Consistent Narrative

Because designers juggle multiple roles or interests, portfolios often resemble scattered highlight reels. Stefan recommends a consistent narrative thread:

1. Open with Context: Define the project’s audience or problem space.

2. Frame the Constraints: Time, budget, technical limitations, or stakeholder demands.

3. Reveal Your Process: Show sketches, iterations, or AI-generated mockups—and how you refined them.

4. Explain Key Decisions: Why did you choose one user flow over another? How did constraints shape outcomes?

5. Show Impact: Metrics, user feedback, or next steps you’d take with more time.

This structure ensures each case study reads like a compelling story—engaging, logical, and relevant.

Wrap-Up

Stefan Klocek’s journey—from a B2B speaker manufacturer to shaping Google’s design standards and leading HubSpot’s AI initiatives—reinforces a key truth: A portfolio isn’t just a collection of pretty designs. It’s a narrative of navigating constraints, applying critical thinking, and delivering real user impact. Whether you integrate AI or rely on classic user research, your most significant differentiator is showing why you made specific decisions in messy, real-world contexts.

Questions for You:

• What challenge or constraint in your recent project can you feature to showcase your design judgment?

• How might you incorporate AI-assisted tasks to demonstrate adaptability?

Listen to the Full Interview

If Stefan’s insights resonated, check out our entire conversation on the podcast. You’ll gain deeper insights into developing a resilient mindset, balancing speed with quality, and positioning yourself for the future of UX—where clarity and constraint-driven thinking will always matter, no matter the tools.

The Power of Context: Grounding Your Work in Real Stories

Before jumping into color palettes and layouts, it’s crucial to highlight why you’re building something in the first place. Facts and figures can show a workflow is inefficient, but a human story—like the struggles of someone juggling multiple tasks while wrestling with a clumsy interface—makes your stakeholders care.

I’ve seen designers pour endless hours into wireframes only for stakeholders to nod politely and move on without grasping the real significance. Then one day, I mentored a designer who faced a similar situation. She was on a team revamping an internal support tool and had data proving her design improvements were needed. But once she wrapped her findings around a story about a support rep scrambling to resolve a complicated ticket—missing details, flipping between tabs—everyone in the room perked up. That anecdote clarified how her redesign made someone’s job easier. It wasn’t a “nice-to-have” anymore; it became an essential solution to a frustrating routine.

Try This: Showcase the Human Element

• Begin your design presentation with a user-focused story—one spotlighting their frustrations or goals.

• Include direct quotes from interviews or user feedback. Even a brief line like, “I waste 10 minutes every time I file a request,” humanizes the issue.

• Refer back to this story whenever you explain specific features or layout choices.

By setting the context early, you create a framework for deeper discussions. But how do you keep your audience hooked from start to finish? Let’s look at a tactic that holds attention from the get-go.

Flipping the Script: Front-Loading Your Solution

A standard method of presenting designs is to save the final reveal for last—walking through a mountain of data before unveiling your mockups. However, people have limited attention spans. If they don’t know where you’re headed, you can lose them before you reach the good part.

While mentoring a designer at a large tech company, I watched her thoroughly outline the problem space—charts, user flows, diagrams—but the audience checked out halfway through. Finally, she showed the new design, and everyone’s heads snapped up. Later, we talked about leading with that solution, so they’d have a clear vision of the “prize” from the start. The next time she presented, she revealed the refined interface and benefits in the first two minutes, then walked the team through user feedback and the iterative journey. The jump in engagement was striking.

Try This: Grab Attention with the Destination

1. Begin with your final design or concept. Let everyone see what you’ve built right off the bat.

2. Emphasize the main impact. Instead of hiding your best stats or user quotes in the middle, lead with how it addresses the problem you introduced.

3. Walk through the path behind it. After they see the outcome, unpack your research, tests, and user input.

Front-loading your solution anchors the audience in why each detail matters. But to make it stick, you also need an emotional pull.

Emotional Resonance: Let Feelings Drive Action

In design, data provides clarity, but emotions prompt people to act. A 50% drop-off in a crucial workflow might raise eyebrows, but pairing it with a quote like, “I’m so confused I dread opening this tool every morning,” paints a richer picture. Now it’s no longer just a statistic; it’s a real person’s stress. And that can sink morale, sap productivity, and waste resources if left unresolved.

One designer I mentored saw her team ignore a minor usability tweak. The metrics weren’t alarming, but when she played a user interview clip capturing the user’s exasperation, stakeholders immediately pushed to fix the issue. That emotional evidence turned a “low-priority” item into a pressing concern the entire team rallied around.

Try This: Elevate Data with Empathy

• Combine metrics (like task completion rates) with user voices (quotes, video clips) to reveal both the scope of a problem and its human cost.

• Keep a “story bank” of short, authentic anecdotes you can reference in design presentations.

• Whenever possible, let users speak for themselves—whether through recorded videos or direct quotes in your slide deck.

Once you’ve shaped a story with context, highlighted your solution early, and woven in emotional resonance, you’re on track. But remember: a powerful story isn’t a single shot; it grows along with your design.

Keeping Your Story Alive Through Iteration

A solid narrative unifies your project, but it doesn’t need to stay frozen in time. As you gain insights—maybe from usability testing or new internal feedback—refresh the story to reflect what you’ve learned.

Many teams treat storytelling as a one-time event: present, secure buy-in, then move on. But if you’re designing a product that keeps evolving (and these days, which one doesn’t?), your story must evolve too. Suppose your initial narrative centered on reducing clicks in a workflow. After shipping the new features, you find that while clicks are down, people now complain about slow load times. Add that twist to your broader story. By continuously adjusting the narrative, you ensure everyone stays aligned on the real target: a better user experience.

Try This: Develop a Living Narrative

• Hold regular check-ins where the team revisits the original user story and updates it with fresh insights.

• Note any surprises—like clever user workarounds or unexpected usage patterns—and incorporate them into your design presentations.

• Use a shared online space (Confluence, Miro, Notion) so everyone stays connected to the evolving story and can offer real-time input.

When you weave storytelling into your daily design process, you tap into a powerful method for fostering empathy, clarity, and unity. Context helps stakeholders see the real world behind the specs, front-loading your solution holds their attention, and emotional touchpoints convert half-hearted agreement into genuine excitement. Most important, by treating your narrative as a living, breathing element, you keep each new iteration of your product focused on the people who use it.

Ready to explore more? Check out my upcoming course on storytelling for designers, where I’ll share frameworks you can apply at every stage of your workflow. Whether you’re orchestrating a major redesign or refining a single feature, storytelling will help your work resonate—and make a lasting impression in your organization.

We kick off soon! If you’re ready to craft compelling product visions and cut through the noise, I’d love to see you in class. I am offering all my subscribers a very special discount to my course. 👉 Use code PIXELATEDPATH for 25% off.

VIEW THE COURSE SYLLABUS

Which tip speaks to you the most? Have you tried flipping your design presentations to start with the solution? Or maybe you’re eager to add emotional snapshots in your next meeting? I’d love to hear your thoughts—drop a comment below or get in touch any time!

The Early Spark: A Love for Research

Jessica’s curiosity about human behavior developed long before the corporate world entered the picture. In high school, an animated debate—“What is truth?”—ignited a passion to guide her later work. Growing up with an archaeologist father taught her that unearthing buried stories blends emotion with data. At the University of Rochester, she majored in anthropology and statistics. This unusual combination lets her weave together narrative and numbers.

She recalls a turning point: “I realized numbers only tell part of the story—you need real human context to interpret them.” That mindset formed the basis of her career, fueling a habit of questioning old assumptions.

With this investigative spirit, Jessica approached each professional pivot with a thoughtful, open mind.

Try This: Keep a “Passion Journal”

Write down sparks of interest—during a chat with friends, while listening to a podcast, or even in a random moment of inspiration.

Look back at those notes every few weeks. Patterns often emerge, revealing themes or hidden pursuits you might want to follow.

Riding the Ups and Downs of Layoffs and Career Shifts

Jessica’s tech journey was anything but straightforward. Early roles let her shape human-focused research practices in hectic workplaces. At one point, she helped build a research function at Bill.com but soon faced a corporate restructuring that cost her her job—something most people dread.

Despite the shock, Jessica felt an odd sense of relief. “I remember thinking, ‘I’ve outgrown this role anyway—maybe this gives me permission to try something else.’” Although the layoff hurt, it gave her a pause to explore what she truly valued. Rather than obsess over a lost position, she treated it like a deliberate break—time to rethink her direction and chase roles that felt more in sync with her core beliefs.

Her ability to turn a painful moment into a fresh start reveals how her inner grounding shapes her career moves.

Try This: Turn Setbacks into Space for Rethinking

If your budget and life situation allows, take a focused week to map out your top strengths, interests, and preferred work culture.

If that’s impossible, carve out time on weekends or evenings. Look at these notes for clues about the path you want next.

Finding Calm in the Tech World

The nonstop pace of tech can wear people down. Jessica found ways to weave mindfulness and self-care into her daily rhythm. She opens team meetings with a brief check-in or short meditation, uses light scents to set a calm tone, and encourages folks to toss Franklin balls during discussions—anything to stay physically active and clear-headed.

This approach isn’t just “nice to have”—it’s a defense against burnout. “If we don’t pause for a quick self-scan,” she says, “we can miss the stress creeping up on us.” Research backs this up: small, mindful breaks can significantly reduce on-the-job anxiety.

By valuing mental well-being, Jessica created a healthier environment for herself and her team—a mindset that prepared her for more significant personal milestones.

Try This: Schedule Short Recharge Times

Block off a half-hour on your calendar for a walk, a short meditation, or a few minutes of journaling.

If a half-hour isn’t realistic, sprinkle in several 5-minute breaks. Step away from the screen, stand up, and breathe deeply.

Redefining Success: From Pregnancy to Inclusive Workplaces

As her career grew, Jessica faced a major personal milestone: leading a tech team while pregnant during the pandemic. A colleague’s offhand question about whether she needed “permission” to have a baby underscored lingering biases in the workplace.

Rather than let that comment rattle her, Jessica started advocating for inclusive policies and safer work cultures. She sparked honest discussions about mental health, flexible schedules, and working parents' juggling acts. Her leadership opened the door for conversations about childcare, caring for older relatives, and other life roles.

“Success isn’t limited to promotions and product rollouts,” she says. “It’s also about creating an environment where people feel safe bringing their whole selves to work.” Jessica challenges the conventional idea that work and life must remain separate by promoting empathy and openness.

Try This: Build a Real Support Network

Seek mentors and peers who respect and understand life’s varied demands—at home and on the job.

Host informal get-togethers or group chats where people can be candid about work-life hurdles, mental health, and career crossroads.

Collaborate on ways to make the work environment more inclusive for everyone managing multiple roles.

A Final Note

Jessica Sommer’s story shows how resilience, mindfulness, and honest reflection can reshape a career. From questioning truths in her teens to navigating layoffs and confronting workplace bias, she’s refused to accept that adversity has to derail us. A setback can be a nudge toward reevaluating goals and forging a more fulfilling path.

Catch our entire conversation on Pixelated Path for deeper insights. Meanwhile, think about moments in your journey—losing a job, grappling with a health issue, or stepping up to new family responsibilities—that spurred you to rethink your priorities. Which tip from Jessica resonates with you most?

Feel free to leave a comment or reach out directly. I’d love to know how you plan to thrive during life’s inevitable twists and turns.

Yet this shift isn’t just a hunch or a rumor. I’ve seen it across the board through my experience leading design teams at Google and mentoring designers who are desperate to stand out. I also run an investment syndicate where I regularly evaluate startups, and their hiring patterns confirm that specialization and referrals drive many decisions.

Below, we’ll explore how to adapt to this new reality, using data from a comprehensive TrueUp report on the global UX market. You’ll see where design roles are most abundant, which companies and industries are hiring, and how to position yourself so you’re not lost in a sea of applicants.

The Brutal New Reality of UX Jobs

A few years ago, recruiters reached out to designers on LinkedIn, eager to fill newly created UX roles. Now, even highly experienced designers send out dozens—sometimes hundreds—of applications before getting a phone screen.

Why is this happening?

1. Crowded Talent Pool. Growth in design boot camps, the increased visibility of UX as a career path, and (maybe most importantly) large layoff rounds from big tech companies have brought an influx of skilled designers into the market. This intense competition makes each open role that much more challenging to land.

2. Hyper-Specific Hiring Requirements. Companies need to see a precise match between your background and their needs. If they build enterprise analytics dashboards, they want someone who can handle dense data and complex user flows from day one. If they build a social network for dentists, they want someone who’s designed for dentists (kind of kidding, but not really).

3. Referral-Heavy Culture. With hundreds of applications rolling in for each opening, recruiters look for ways to trim the list. Inside connections and employee referrals often become a shortcut for shortlisting candidates.

TrueUp Data: The Global Landscape

Recent data from TrueUp paints a detailed picture:

The San Francisco Bay Area still leads , followed by New York City. However, other global hubs—Bengaluru, London, Tel Aviv, and Singapore—are on the rise.

Even in a slowdown, tech giants still hire and expect top-notch portfolios.

Public tech companies advertise the most roles, but early-stage startups offer 568 openings, which can be prime opportunities if you align with their niche.

Add up these numbers and you’ll see a vibrant market—if you can play by its rules.

Why a Generic Portfolio Won’t Cut It

The Importance of Branding Yourself

When recruiters wade through hundreds of resumes, they look for evidence that you’re exactly what their team needs. Generic “UX/UI Designer” labels no longer impress. Vague claims like “I’m passionate about users” or “I’ve designed across all platforms” fade into the background.

Here’s a real-world example:

I’ve been working with a designer with a solid track record but he lacked a defined focus in his portfolio. Companies saw him as “one more mid-level designer” until we dug into his strongest work—an ambitious redesign for a performance management platform that required deep research into manager and employee workflows. His application response rate shot up by elevating how we talked about his work. His story went from talking about how he designed a new feature, to how he used user research, his knowledge of HR processes, and critical thinking, to identify a gap in the company’s product strategy.

Lesson: Hiring managers want to see an immediate fit. Convincing them you’re a perfect match involves anchoring your portfolio and professional story in a specific domain or skill.

What Companies Expect to See

1. Domain Relevance. If you’re applying to a fintech startup, show fintech case studies. If it’s game tech, highlight your experience (or side projects) related to game design or game mechanics in business products.

2. Tangible Outcomes. Demonstrate real impact—did you reduce sign-up friction, boost revenue, or shorten the onboarding process? Data helps hiring managers see you as a proven problem-solver.

3. Depth and Process. Make it clear you can handle research, strategy, and stakeholder alignment. In short, show that you’re not just pushing pixels but delivering thoughtful design solutions at scale.

Carve Out a Niche That Sets You Apart

Specialization isn’t about limiting yourself. Instead, it’s about positioning yourself so hiring managers can immediately understand your value.

#1 Pick an Industry or Domain

Look at where the jobs are. TrueUp says consumer products are the lead, but B2B SaaS and GameTech aren’t far behind. If you already have experience in any of these areas—even tangentially—position yourself as an expert. Be explicit:

• “FinTech UX Consultant with a flair for data visualization.”

• “Enterprise SaaS Designer with deep knowledge of cloud infrastructure products”

• “Conversation Designer for AI-driven chatbots and voice interfaces”

Companies want specialists who can hit the ground running with minimal onboarding. Adopting a more precise label allows you to stand out in a sea of generalists.

#2 Brand Yourself Around a Superpower

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This post highlights the pivotal moments that shaped Jason’s path—from sketching car posters in Kingston to developing radiology software at Kodak to orchestrating a major Google redesign and culminating in a rebound after a tech layoff. By weaving in his anecdotes, hard-won lessons, and step-by-step tips, I hope you’ll see how to find opportunity in chaos and build lasting resilience. Let’s dive in.

Jamaican Roots—Learning to Embrace the Unknown

Jason’s passion for design started on the walls of his childhood home in Jamaica—literally. “I remember my mom yelling at me for covering the living room with crayons,” he laughed. “But when she stopped to look at my drawings, she saw promise.” Even at age six, Jason sketched cars with a three-dimensional flair that distinguished him from his classmates.

That encouragement clashed with a tough economy. As Jason entered his teens, he noticed Jamaica’s limited creative arts market. The local economy made it hard for artists to earn a comfortable wage, let alone thrive. “If you were a painter or sculptor, you had to rely on commissions,” Jason explained. It was a grind, no matter how good you were.”

Still, he immersed himself in his craft. In high school, Jason meticulously hand-lettered labels and posters, measuring every letter and perfecting the kerning. This detail-oriented process taught him a lesson he carried to every future role: deep craft always shines.

Actionable Insight: “Pinpoint Your Core Skill”

Reflect on your early passions—whether drawing, storytelling, or problem-solving—and note how they appear in your work today. Lean on those core skills when you feel stuck. They form the backbone for your next leap, just as Jason’s early drawing discipline shaped his approach to design.

Jason’s commitment to detail carried him across the ocean to the Rochester Institute of Technology. However, culture shock soon ranked low among his challenges.

Surviving Kodak Layoffs—Building Grit Through Constraints

When Jason finished graduate studies at RIT, he believed digital design was the future. “Print still had its place, but post-9/11, everything shifted,” he said. Kodak offered him a full-time role on the camera team. Yet on day one, he learned he’d design radiologist software—a stark contrast from splashy consumer interfaces. The assignment demanded a deeply user-centric process because he couldn’t guess how radiologists worked.

“We had calls with actual radiologists twice weekly,” Jason told me. “I had to listen intently and prototype quickly, testing each idea. I would've failed if I tried to rely on my instincts about medical workflows.”

This methodical approach gave him strong credibility. When Kodak shed entire teams during restructuring, Jason oversaw multiple product lines. “Fewer designers stayed,” he said, “but the projects kept coming.” He navigated hardware constraints, manufacturing budgets, and shipping schedules, aware each design decision sent ripples through procurement, engineering, and the bottom line.

This era served as his wake-up call on job security. “You can’t take your role for granted. I watched talented people laid off in waves,” he recalled. Yet for Jason, layoffs spurred more significant responsibilities and more profound resilience. “Being there taught me not to fear complexity. Whenever things got complicated, I dove in deeper.”

Actionable Insight: “Run Toward the Hard Stuff”

Watch for projects beyond your current skill or comfort zone and volunteer. Document every obstacle—and how you resolve it. Looking back, those “impossible” assignments often become your most significant growth engines, just as Kodak’s complexities prepared Jason for a global stage.

Those experiences—championing user needs while balancing business realities—formed the skills that landed Jason at Google, an exhilarating and daunting leap.

Shaping Google’s Homepage—The Power of Trust and Diplomacy

After facing rejections from other tech giants, Jason secured a role on Google’s Ads team. It might sound like a dream job, but Google’s fast-paced, experimental culture tested his adaptability yet again. Then, a once-in-a-lifetime project emerged: redesigning Google’s main search results page, including the homepage.

It wasn’t a simple assignment by any stretch. It demanded meeting three distinct goals:

1. Revenue/Ads: Preserve and grow ad revenue.

2. Search UX: Maintain a clean, user-friendly interface that billions rely on daily.

3. Commerce Features: Integrate specialized experiences for shopping, travel, and more.

“This wasn’t about moving a button,” Jason said. “It was a puzzle where each piece—ads, user experience, commerce—needed a champion. So I borrowed designers from each group and formed a federated team.” That approach balanced everyone’s agendas but required constant communication and deep trust across organizational boundaries.

The amount of detail in Jason’s sketches and prototypes was mind-blowing. However, those details kept him grounded as he avoided getting overwhelmed by billions of potential users. “You learn to focus on how you’ll measure success. We constantly tested changes with real users, letting data and design instincts guide iteration.”

Actionable Insight: “Translate Conflicting Goals into One Vision”

Create a shared project charter. On one page, outline each stakeholder’s top priorities and success metrics. Then, identify a unifying theme (e.g., “Promote clarity and speed”). Present every design choice through that lens to transform friction into collaboration.

Though every pixel matters, Jason's biggest hurdle wasn’t color or type—it was navigating departmental politics. That stakeholder diplomacy skill proved vital again when major economic shifts blindsided Jason.

A Layoff After 13 Years—Turning Setbacks into a Springboard

Then came the email every tech professional feared: Jason was laid off. After 13 years at Google—where his designs reached billions—he felt stunned. Yet, in hindsight, he saw the signals: his team’s scope had shifted, new leaders reorganized priorities, and the company cut costs in a public wave of layoffs.

“My heart sank,” he admitted. “I’d poured everything into Google. But I also recalled how Kodak’s layoffs once propelled me forward.” This time, Jason had perspective and a plan. He took a few days to process the blow, then shared the news on LinkedIn, showing pride in his Google run and readiness for a new chapter.

The months after, he concentrated on family, health, and reactivating his network. That same willingness to tackle complexity took him to consulting roles with smaller startups, where he contributed design insights while weighing his next full-time move. “If I’ve learned anything,” Jason said, “it’s that every pivot can be your best move—if you choose to see it that way.”

Actionable Insight: “Build Your ‘Escape Velocity’ Fund”

Even if you feel secure, save three to six months of living expenses. This buffer prevents panic during layoffs or sudden transitions, letting you explore new paths on your terms—just as Jason did.

This theme—choosing to see turbulence as an opportunity—threads through Jason’s anecdotes. It’s a perspective anyone can adopt, no matter their career stage.

Wrap-Up

Jason Blythe’s journey—from sketching cars in Jamaica to refining radiology interfaces at Kodak to orchestrating a Google.com redesign and finally weathering a layoff—shows one truth: resilience grows from challenges we choose to tackle.

Maybe you’re eyeing a significant career move or reeling from upheaval. Or you feel stuck, unsure which skill sets you apart. Wherever you stand, Jason’s story highlights how leaps of faith—anchored by craft, humility, and learning—often lead to profound results. Sometimes, the worst setback becomes a stepping stone to your best work.

If Jason’s experiences resonate, listen to our full interview on the podcast. He dives deeper into staying calm under pressure at Kodak and Google, how cultural identity shapes his design approach, and his steps after Google.

I want to hear from you:

• When have you faced a career crossroads, and how did you push through?

• Which of Jason’s lessons on relationship-building, user-centric design, or honest self-assessment hit home?

Drop a comment below or connect on social. For more creative resilience stories, subscribe—our upcoming episodes continue this conversation.

That’s precisely where Dr. Claire Snell-Rood found herself: wrestling with the rigid structures of academia despite her passion for community-focused, hands-on work. She’d witnessed families in rural Appalachia struggle with mental health care. She collaborated with local partners in India to tackle entrenched social issues—yet found too many of her insights locked behind grant approvals and academic silos. Eager to see ideas come to life more quickly, Claire took the leap into UX and product research.

When I sat down with Claire, I expected to hear a story about career transition. What I didn’t expect was how deeply her story would resonate with my own struggles in navigating change.

In this article, you’ll discover key insights from our conversation—whether you're considering a career pivot yourself or simply curious about how research can shape product strategy, her journey offers a powerful roadmap for making meaningful shifts without losing sight of your core values.

Early Influences: When Curiosity Outgrew the Classroom

Claire’s interest in human complexity took root long before academia. In high school, she stumbled upon an anthropology book exploring why certain impoverished communities in Brazil exhibited seemingly “unattached” parenting. Rather than judging these mothers, the anthropologist questioned the social conditions fueling their reactions. This fresh way of viewing society deeply resonated with Claire. It was never just about labeling behavior; it was about understanding the context that creates it.

By the time she entered college, she was fully invested in anthropology’s power to uncover the “why” behind human actions. From hair salons to rural villages, she saw every environment as a microcosm of more significant social forces. Yet as her fieldwork expanded—encompassing global public health challenges, mental health policy, and university-level teaching—Claire encountered a persistent hurdle: limited avenues to turn her insights into tangible change. Despite collaborating with nonprofits and community stakeholders, the tight constraints of academic research often prevented her findings from becoming widespread, impactful solutions.

Actionable Insight: Welcome the Unexpected “Spark”

Next time something sparks your curiosity—a book, a conversation, an unexpected compliment—write it down in a “Pivot Journal.” After a month, review your notes and look for patterns. What topics keep showing up? Those might be pointing you toward your next career move.

The Great Pivot: Trading Grant Proposals for Product Prototypes

Despite her love for fieldwork, Claire found academia increasingly stifling. Writing grant after grant to keep her projects afloat, she felt a gnawing sense that her research—though valuable—was not shaping real-world outcomes quickly enough. Eventually, she decided to explore a new frontier: technology.

Her gateway turned out to be a design and research agency called Forge. A friend introduced her to a co-founder who was buried in client projects but was short on researchers. Claire jumped in, bringing her excellent skills in qualitative interviews and ethnographic observation—yet also realizing she’d need to reframe her approach for corporate timelines and deliverables. One of her first adjustments was learning to communicate findings visually and succinctly, a contrast from the lengthy academic papers she was used to.

For Claire, the agency environment was both exhilarating and daunting. She worked with diverse clients—from contractor platforms to government programs—exposing her to the broad spectrum of “real-world problems” tech teams strive to solve. Each day felt like a crash course in product lifecycles and design priorities. The experience also highlighted cultural gaps; in academia, a robust literature review might precede any formal conclusions, but in industry, stakeholders often want key insights yesterday.

Actionable Insight: Adapt Your Deep Expertise to Fast-Moving Milestones

Academia values depth; industry values speed. If you’re used to long-form analysis, practice distilling your insights into formats that decision-makers can act on quickly. Take a recent report or research project and turn it into a one-page summary, a five-slide deck, or even a single sharp takeaway. The more effortlessly you can translate complex ideas into clear, actionable insights, the more impact you’ll have around time-strapped stakeholders.

Finding a Long-Term Home: Joining Rippling and Going In-House

This is something I’ve heard from so many professionals making the jump into tech—at first, you crave variety, but eventually, you want to go deeper. Claire felt the same pull, which led her to Rippling, an HR and IT platform known for rapid innovation. Moving in-house forced her to think far beyond discrete projects. Now, she had to grasp how various modules—payroll, employee management, reporting—fit together under one corporate umbrella. Each product decision impacted multiple user types, from C-suite executives to frontline managers.

Navigating this new environment felt akin to studying a “field site.” Claire mapped out who influenced decisions, how teams interacted, and where her research would yield maximum impact. Going in-house required even sharper organizational awareness. Technical jargon abounded, release cycles moved fast, and cross-functional alignment could feel like a marathon. But the payoff was tangible: instead of handing research off and hoping for the best, she watched her insights shape internal roadmaps and steer product design over time.

Actionable Insight: Cultivate a “Company as Field Site” Mindset

Think of your first month in a new role as fieldwork. Pay attention to who actually makes decisions—not just by title, but by influence. Notice which teams hold the most valuable insights and who people turn to for unofficial advice. Watch how ideas move through the company—who needs to sign off, who gets things done quietly, and where the real momentum happens. The faster you decode these hidden dynamics, the more effectively you can navigate and contribute.

Tech Culture Through an Anthropologist’s Lens

At one point in our conversation, Claire laughed and said, “It’s funny—engineers assume everyone sits at a desk all day. But what if you’re a retail worker? What if you’re on a factory floor?”

That’s when it hit me: The biggest blind spots in tech don’t come from bad intentions—they come from bad assumptions.

Well-educated, computer-savvy employees tend to assume all users work in a similar environment, constantly tethered to their laptops. Yet Rippling’s software is also used by employees in retail, manufacturing, and other sectors who don’t share Silicon Valley’s daily rhythms. Claire highlights the danger: a solution that looks perfect in a product demo might fail spectacularly on a busy factory floor.

In her view, this disconnect isn’t simply a “technical” oversight—it’s a social phenomenon. It reflects whose voices are present in design meetings and which assumptions get baked into the product. By employing anthropological techniques like open-ended questioning and observational studies, Claire helps teams see past their biases. Sometimes, this means gently challenging engineers with “dumb questions” like, “Why do we assume they can even open a laptop during working hours?” Instead of a weakness, these clarifying questions often spark breakthroughs.

Actionable Insight: Challenge Groupthink with Open-Ended Questions

If something seems off, ask. The simplest “Why do we do it this way?” can expose valuable assumptions and steer a product toward real user needs.

The “Platform” Adventure: Finding People in the Weeds of Data

Platform roles might seem dry—often, they’re about building backend systems, setting up data structures, or integrating permissions. Yet Claire sees it differently. “Platform” is essentially the skeleton supporting every other feature in a product suite, and that skeleton touches a broad range of human concerns. For instance, setting up user permissions is not just a technical detail; it’s about trust, accountability, and the consequences of getting it wrong. If an HR manager can’t guarantee data privacy, someone’s job could be on the line.

In this sense, the “platform” is as human as a front-end feature. Claire’s research unearths hidden patterns in how teams use data. She observes how finance departments define “sensitive” information differently than HR or operations might. She notices which metrics matter most to different roles, revealing unspoken hierarchies within a single organization. By framing these details as social puzzles rather than purely technical ones, Claire amplifies the relevance and urgency of platform decisions, encouraging her colleagues to address real-world stakes—like job security, legal compliance, and interpersonal trust.

Actionable Insight: Look for the Human Angle in Technical Spaces

Even if you’re working on back-end or data-heavy features, ask what’s genuinely at stake for people. Identifying emotional or career-related risks helps build empathy into the product design.

Bridging Research & Design: Lessons for Early-Career Professionals

When she first arrived at Forge, Claire admits she could have engaged more deeply with designers—understanding how they draft user flows, iterate on wireframes, and weigh aesthetic decisions against usability. She describes her initial hesitation as a “fear of looking ignorant.” Over time, however, she realized that immersing herself in design critiques and team brainstorming sessions sharpened her approach. By viewing design as a structured methodology, she discovered more ways to add value as a researcher.

For those early in their careers, Claire’s experiences underscore the importance of absorbing adjacent disciplines. Whether you’re a junior researcher figuring out how to analyze data for a product roadmap or a new designer learning to interpret user interviews, an empathetic blend of skill sets can accelerate outcomes and help you stand out in a competitive field.

Actionable Insight: Immerse Yourself in Cross-Functional Collaboration

Great work doesn’t happen in silos. If you’re a researcher, spend time in design critiques to see how insights shape user flows. If you’re a designer, shadow a researcher during interviews to understand how real user needs emerge. The more you embed yourself in other disciplines—learning their language, tools, and thought processes—the faster ideas turn into impactful decisions.

Overcoming Self-Doubt: Facing the “Imposter” Voice

No major pivot is free of self-doubt. Coming from academia, Claire grappled with imposter syndrome—wondering if her scholarly background truly fit the cut-and-thrust of tech. She found solutions in straightforward yet powerful strategies. First, she kept a “mental check-in” list, jotting down each moment of anxiety or indecision, then revisiting those notes when she felt clearer. Second, she relied on an “accountability buddy,” someone who understood her aspirations and could affirm the incremental milestones she was achieving.

By openly acknowledging the fear of “not measuring up,” Claire freed herself to focus on learning. Over time, her broad experience in anthropological research, community partnerships, and academic writing proved invaluable. Product teams needed a professional who could rapidly uncover user motivations, highlight deeper cultural context, and present those insights concisely and persuasively—and that was Claire’s specialty.

Actionable Insight: Turn Self-Doubt into a Growth Tool

Self-doubt isn’t a stop sign—it’s a signal. Pay attention to when it shows up and why. Is it a lack of experience? A missing skill? Instead of letting it hold you back, treat it like a personal growth audit. Keep a simple list of moments when you felt unsure, then look for patterns. Where do you need more practice, mentoring, or exposure? What once felt like a weakness can quickly become your next strength.

Conclusion: Merging Intellect and Impact

Claire’s story proves that a specialized academic path can evolve into a dynamic industry career where intellectual rigor meets fast-paced product strategy. Her drive to ask “why?” and her willingness to step into uncharted territory have allowed her to shape technology that resonates with genuinely diverse user realities. Whether clarifying permission structures or championing front-line workers’ needs, Claire applies her anthropological lens to keep tech solutions grounded in everyday life.

If you found Dr. Claire Snell-Rood’s journey insightful, I invite you to explore our entire conversation. You’ll discover more practical tips on networking, translating research for executive audiences, and navigating the emotional complexities of career change.

So here’s a question: Have you ever made a career pivot—big or small? What was the moment that made you realize you had to change? Hit reply and tell me—I read every response! If her experiences with forging a new career identity inspire you, consider sharing your thoughts or next steps in the comments—or reach out with your own stories of pivoting from one discipline to another.

Until next time,

Chris ✌️

If you’ve ever questioned whether you “belong” in design or felt unsure about how to build a lasting career, Matt’s journey will inspire you to look beyond formal paths. From his self-taught beginnings to navigating high-pressure rebrands, Matt shows that a blend of humility, curiosity, and personal authenticity can bring success—even in the face of imposter syndrome and industry upheavals.

An Unlikely Start: Computers, Forums, and a Flash of Inspiration

A Taste of Tech

Matt was just four years old when his family got their first computer—an ancient DOS machine that sparked a fascination with technology. By high school, he was lugging bulky gaming PCs into school to play Unreal Tournament with friends and tinkering with web design for small local projects.

Yet Matt didn’t see design as a legitimate career path. Instead, he viewed it as a handy hobby—a way to help his school community or create fun online graphics. “I had no idea I could do this for a living,” he recalls. That all changed when he and a friend started a small web design business, tackling everything from a teacher’s local shop website to the high school’s homepage.

Actionable Insight #1: Recognize Hobbies as Hidden Clues

If you find yourself spending hours perfecting layouts or color palettes “just for fun,” you might be onto a bigger opportunity. Ask yourself: Could this be more than a hobby?

From Support Tickets to Surprising Design Gigs

The Dropbox Detour

Not long after college, Matt landed at Dropbox—which, at the time, was still considered a “scrappy” startup with around 90 employees. He wore multiple hats, dabbling in everything from customer support to data science. “I didn’t realize design was even an option,” he admits, explaining that he initially saw himself as a project manager or operations specialist.

As Dropbox ballooned into a company of over 2,000 employees, Matt faced the chaos of hyper-growth: late nights, tight deadlines, and a fast-paced environment in which job titles often felt irrelevant. Though intense, Matt credits that period for teaching him to be flexible and adapt—skills that would soon become crucial.

Finding a Design Role at Zendesk

It wasn’t until he moved to Zendesk that Matt’s creative streak took center stage. Tasked with marketing responsibilities for gaming clients, he designed and coded the company’s booth, posters, and website for the Game Developers Conference (GDC)—simply because no one else was available. His work turned heads. “The design you did for GDC was pretty good,” a program manager told him. “Do you want to do this full-time?”

That seemingly casual offer transformed Matt’s career overnight. He joined the Zendesk design team, eventually working on the company’s broader rebrand and developing its design system, Garden. Looking back, he jokes, “I just got bored over Christmas one year and ended up redesigning all of Zendesk.” Still, there’s no doubt the experience cemented his confidence as a professional designer.

Actionable Insight: Step Up When No One Else Will

If your organization lacks a design resource, volunteer your skills. Even if it’s outside your formal role, you’ll sharpen your abilities and prove your readiness to grow.

Scaling New Heights and Grappling with Self-Doubt

The Call of the Big Leagues

With brand-building accolades under his belt at Zendesk, Matt eventually found his way back to Dropbox and later jumped to Eventbrite, Square, and Meta in varied design capacities. He often focused on design systems, rebrands, and bridging product and marketing teams.

To outside observers, it seemed like a meteoric rise. But behind the scenes, imposter syndrome loomed large. Despite his achievements, Matt questioned whether he truly “belonged” in design. “It’s ironic,” he notes. “I’ve worked on big projects and managed teams, yet I still wonder if I’m good enough.”

Therapy and Genuine Conversations

Eventually, the stress of hyper-growth and constant pivots took a toll. Matt realized that simply powering through wasn’t sustainable. He sought therapy—a move he encourages for anyone in high-stakes fields. “You shouldn’t have to wait until you’re near a breaking point to talk to someone,” he emphasizes.

Through professional help and candid conversations with peers, he learned to compartmentalize his emotions, set boundaries, and stand firm despite shifting priorities. According to Matt, “Vulnerability isn’t a weakness. It’s a tool for authentic leadership that helps you and your team navigate change without resorting to sugarcoating or panic.”

Actionable Insight: Normalize Mental Health Check-Ins

Whether it’s therapy, peer-to-peer chats, or mentorship, find outlets for stress before burnout strikes. Regularly reflect on your feelings about work and ask yourself if you’re still enjoying the journey.

Embracing Collaboration: The Power of “Jam Sessions”

Why Jam Sessions Matter

As Matt’s responsibilities shifted from individual contributor to leading design teams, he discovered the magic of “jam sessions”—casual, co-working times dedicated to tackling a single design problem. By pairing up with team members in Figma, they could brainstorm off-the-wall ideas and question whether the tried-and-true approach was always best.

This environment sparked more innovative solutions and made it easier for newer designers to voice their ideas without fear. “When you’re free to prototype wild concepts, you realize there’s more than one ‘right way’ to do something,” Matt explains.

Creating a Culture of Exploration

While rebrands and product overhauls often come with tight timelines, Matt urges leaders to reserve some buffer room for experimentation. “Otherwise, you end up just repeating the same patterns everyone else has already done,” he warns. For a designer who once taught himself by building forum graphics, exploration remains the heart of creativity.

Actionable Insight: Encourage Low-Stakes Brainstorming

Set aside an hour weekly for your team to co-create solutions—even if they’re initially far-fetched. Breaking out of routine patterns leads to fresh perspectives that can elevate the final product.

Navigating an Uncertain Industry: Advice for Aspiring Designers

The Tough Reality of “Junior” Roles

Matt doesn’t sugarcoat the difficulty of entering design right now. “Companies hire fewer entry-level designers,” he says, pointing out that internships or long chains of contract gigs are increasingly the norm. Yet he believes the industry should champion up-and-coming talent. “It’s on us as senior folks to push for these junior roles—everyone wins when you have fresh perspectives on your team.”

Building Skill and Visibility

Still, self-driven practice can set you apart. Whether posting concept work on Behance or Dribbble, contributing to an open-source project, or seeking design meetups, Matt encourages aspiring designers to show up and share. “Your next opportunity might start with a direct message or casual introduction,” he notes. After all, a spontaneous conversation with Zendesk coworkers catapulted him into design full-time.

Actionable Insight: Create and Connect Consistently

Even if you lack “official” design tasks, build mock-ups, redesigns, or passion projects. Then, share them publicly. Real-world feedback is the fastest way to refine your craft and attract potential employers.

Conclusion: Your Next Step on the Path

Matt Armstrong’s journey—from high school web gigs and gaming forums to designing for some of tech’s biggest names—offers a refreshing blueprint for forging a career in unexpected ways. You don’t have to start sure of your path or hold a fancy design degree. Authenticity, a hunger for exploration, and a willingness to jump into the unknown can carry you far.

If you found Matt’s story insightful, I invite you to dive deeper into our full podcast conversation. He shares more about juggling brand and product constraints, learning to say “I don’t know” when stakes are high, and leaning on therapy to stay grounded in an ever-shifting industry.

Which piece of Matt’s journey resonates with you the most? I’d love to hear your thoughts. Reach out and let me know. Until next time, keep experimenting, keep learning, and remember that the spark you accidentally discover might be your greatest asset.

Ready for more real-world design lessons and candid career advice? Listen to the full interview with Matt Armstrong here.

Feel free to share your thoughts or tag us on social media with your takeaways.

From Childhood Blueprints to a New Canvas

Have you ever set your sights on a future career at the age of eight? For Beril, that moment came when she wandered into a family friend’s architectural studio and fell in love with a sprawling set of building plans. Architecture seemed like the perfect blend of art and problem-solving—something she would chase through college and even graduate school in New York.

Yet fate had other ideas. As a student at Columbia University’s architecture program, Beril discovered the lure of technology. She worked with cutting-edge software and even helped classmates embrace the digital tools shaping modern design. This newfound fascination would soon eclipse her original plans.

Open Question: What happens when the very field you’ve trained for gives way to a passion you never expected?

A Leap into the Tech Unknown

When the dot-com era dawned, Beril took a bold turn. Forget the lengthy timelines and rigid codes of architecture—she was drawn to the dynamism of technology. She joined a startup at the height of the boom, diving into UX at a time when formal training in the discipline was rare.

But the ride was bumpy. As the dot-com bubble burst, Beril experienced her first layoff. Suddenly, her carefully laid plans evaporated. She faced immigration hurdles and the daunting pressure of finding a new job quickly in a collapsing market.

Reflective Moment: How do you hold onto your sense of worth in challenging times? Beril’s story shows that setbacks aren’t verdicts on your talent—they’re moments that can spark reinvention.

Resilience Through Reinvention

Beril fought back tears, updated her résumé, and applied everywhere. Against the odds, she found a way through. She rejoined her previous company within a short time, dodging a bullet as other firms folded around her.

This early test shaped her approach to design and career growth. She learned to adapt, seek help from mentors, and leverage every experience—both good and bad—to strengthen her foundation. Over time, Beril honed the skills to navigate challenging conversations with product managers, negotiate constraints with engineers, and deliver meaningful user experiences.

Open Question: Could the roadblocks that impede your path forge a more resilient, resourceful version of you?

From B2B Rigor to Consumer Curiosity

At Salesforce, Beril climbed from individual contributor to design leader, overseeing cross-functional teams and aligning complex initiatives. She loved the craft but soon craved variety. After years of crafting enterprise tools, Beril stepped into uncharted territory again—this time at Rodan + Fields, a skincare company undergoing digital transformation.

Switching industries wasn’t easy. She had no direct consumer-tech experience but knew how to highlight her strengths and promised to learn what she didn’t know. The gamble paid off, proving that staying open to new verticals can spark professional growth and deepen your skill set.

Takeaway: When you dare to break out of your comfort zone, you gain perspective, transferable skills, and the ability to thrive in unfamiliar terrain.

Scaling Up at Google: A New Chapter

Eventually, Google came calling. As a senior manager and then a director, Beril faced a familiar truth: leadership in large organizations isn’t about having all the answers—it’s about building alliances, understanding the business’s needs, and championing your team’s growth.

She learned to balance empathy with candor, invest time in high performers and those who struggled, and align design outcomes with larger business goals. Her experience taught her that no title—senior manager, director, or beyond—exempts you from building relationships and influencing stakeholders. The difference lies in the scale and complexity of the challenges you face.

Reflective Moment: How do you retain your passion for mentoring and supporting others as responsibilities grow? For Beril, it meant evolving from hands-on guidance to fostering ecosystems where design talent thrives.

Weathering Layoffs and Embracing Change—Again

Even after reaching a prestigious role at Google, Beril faced another layoff when the tech giant downsized. Despite her established career, it stung. She questioned her worth and wrestled with self-doubt. But Beril’s earlier experiences had forged a resolute spirit. She reminded herself that these upheavals are rarely about one’s abilities but about shifting company priorities and market forces beyond any individual’s control.

Instead of despair, Beril leaned on her support network, connected with peers navigating the same uncertainties, and reflected on her achievements. She knew each challenge could be a catalyst for reinvention and every disappointment an invitation to explore new opportunities.

Open Question: After unexpected setbacks, can you refocus on your strengths, rediscovering the value you bring to any role you choose next?

Advice for the Uncertain Times

For those feeling the weight of an uncertain market or facing the reality of layoffs, Beril’s journey offers guidance:

• Own Your Narrative: Highlight your unique contributions and results at past jobs. Customize your résumé and portfolio to resonate with potential employers.

• Stay Curious and Agile: Don’t box yourself into one industry. Embrace the opportunity to learn new domains.

• Seek Mentors and Allies: Ask for help, share your struggles, and learn from others. A strong support network can lift you when self-doubt creeps in.

• Resilience Over Perfection: Accept that not every role will be your dream job, and not every project will go smoothly. These experiences build resilience and adaptability.

• Redefine Setbacks as Opportunities: Layoffs and rejection letters aren’t the end of your story—just chapters that can lead you to reinvent, redirect, and rise stronger.

Looking Ahead

Beril’s path is a testament to the power of resilience, adaptability, and the willingness to explore unfamiliar territories. From studying architecture in Turkey to shaping enterprise software at Salesforce, from pioneering new directions at Rodan + Fields to guiding teams at Google, her story reminds us that success in UX—or any field—often involves embracing the unexpected.

Are you prepared to turn setbacks into stepping stones and harness the lessons hidden in each career twist?

If you’re as inspired by Beril’s journey as I am, I invite you to watch the full interview. Her insights into career pivots, negotiation, leadership, and resilience hold lessons for anyone navigating an uncertain market.

👉 Watch the full interview with Beril Maples here

As always, I’d love to hear your thoughts. Which part of Beril’s story resonated most with you? Feel free to reach out and share your reflections.

Until next time,

Chris ✌️

The Leap from Art to Design

Scott’s foray into design wasn’t a straight path. Initially enamored with painting and the pure expression of fine arts, he resisted the idea of commercial design. It wasn’t until a candid conversation with his college design professor that he considered graphic design as a viable path.

“I saw it as such a meaningful form of communication,” Scott shared. He realized that design could be a conduit for creativity and expression, not just a commercial endeavor. This shift in perspective is a valuable lesson: sometimes, stepping outside our comfort zone can unlock new dimensions in our careers.

Actionable Tip: Be open to advice from mentors and professors. They often see potential paths that we might overlook. Don’t dismiss opportunities because they don’t fit your initial plan.

From Boutique Studios to Corporate Giants

Moving from a small design boutique to a behemoth like IBM is no small feat. Friends and colleagues questioned Scott’s decision, thinking he had “sold his soul.” Yet, this move was transformative.

Scott was thrust into roles at IBM that challenged him beyond his experience level. His executive creative director had more confidence in him than he had in himself. She placed him in situations where he had to sink or swim, accelerating his growth exponentially.

Actionable Tip: Seek leaders who believe in you and will challenge you. Embrace opportunities that stretch your abilities—they’re the crucibles where growth happens.

The Power of Empathy in Leadership

One of our conversation's standout themes was empathy's role in leadership. Scott emphasized that empathy isn’t just about understanding users and creating a safe space for team members to express themselves.

However, he also pointed out a nuanced perspective: sometimes, as leaders, we need to dial down empathy just enough to make tough decisions. This doesn’t mean becoming insensitive; instead, it’s about balancing compassion with the needs of the business.

Actionable Tip: Cultivate empathy and develop the ability to make difficult decisions when necessary. Leadership isn’t just about being liked; it’s about guiding your team through good and challenging times.

Navigating Layoffs and Career Uncertainty

Scott’s insights on layoffs are particularly resonant in today's volatile job market. Having been on both sides of the table, he understands the emotional toll. His advice? Recognize that layoffs often aren’t about individual performance but larger economic factors.

He also shared how being laid off early in his career changed his perspective on employment. It taught him to focus on making the most of his time with a company, building meaningful relationships, and not overworking to the point of burnout.

Actionable Tip: Don’t let a layoff define you. Use it as an opportunity to reassess and realign your career goals. Remember, your worth isn’t tied to a single job or company.

Embracing Cross-Industry Experiences

Scott has worked across diverse industries—from mining to retail to finance. This breadth of experience has honed his problem-solving skills and made him a more versatile designer.

“There’s so much more commonality across industries than we give credit for,” he noted. By exposing ourselves to different fields, we expand our skill set and uncover new passions.

Actionable Tip: Don’t box yourself into a single industry. Seek opportunities that challenge you in new ways. The skills you gain are transferable and enrich your perspective.

The Convergence of Design and Product Management

We also dug into the increasingly blurred lines between design and product management. Scott sees a future where these disciplines overlap more significantly, enhancing collaboration and product outcomes.

Gaining experience in both areas can be incredibly beneficial for those early in their careers. It makes you more versatile and enhances your understanding of the product development lifecycle.

Actionable Tip: If you’re a designer, consider learning more about product management—and vice versa. This interdisciplinary knowledge can set you apart and open up new career avenues.

Final Thoughts: Charting Your Own Path

Scott’s journey is a testament to the power of embracing change and following your instincts. He encourages designers to be organic in their career planning, seize unexpected opportunities, and not be afraid of making shifts—even if they seem daunting.

“You own your career,” he reminded us. “No company can control you. You have the insight you need to make your own decisions.”

If Scott’s story resonated with you as much as it did with me, I highly recommend watching our full interview. We dig deeper into these topics and explore even more actionable advice for navigating a fulfilling career in UX.

Watch the full interview here, and let’s continue the conversation.

A Cinematic Spark Ignites a Passion

Imagine being a high school student, already immersed in every art class available, from drawing to painting. One evening, Jenna is seated in a theater, popcorn in hand, ready to watch the thriller Seven. As the film begins, something extraordinary happens—not on the screen, but in the opening credits.

"I was completely blown away," Jenna recalls, her eyes lighting up. "It was this incredible expression of art and design through motion graphics and typography. I didn't even care what the rest of the movie was about. I was obsessed with the credits!"

At that moment, Jenna knew she wanted to become a title designer. The fusion of art, motion, and typography resonated with her in a way nothing else had. But this was 1995, and the world of digital design was still in its infancy. Undeterred, she set out to turn her newfound passion into a career.

From Art School to the Intersection of Humanity and Technology

Jenna enrolled in art school with a clear mission: to master the craft of title design. Yet, as she dove deeper into her studies, she discovered a world far more expansive than she had imagined. A pivotal course called Net Cultures caught her attention.

"We studied how the internet was changing human behavior," she explains. "I became fascinated by how technology and humanity influence each other."

This fascination led her to Georgia Tech's Information Design and Technology program. Here, Jenna immersed herself in semiotics and the psychology of design. She explored how media and technology could alter our memories, even undertaking projects examining how millions of people taking similar photos at iconic landmarks create shared experiences.

"I realized that as a UX designer, you could manipulate that thin membrane between the human and the technology," she says. "That felt really powerful."

The Cold Reality of the Tech World

Armed with academic accolades and a head full of ideas, Jenna stepped into the professional world, only to be met with a stark contrast between theory and practice.

"I got a cold shower when I entered the workforce," she admits with a wry smile. "Everything I had been taught in school felt like a lie. I had to break down my entire belief system and rebuild it."

The constraints of real-world projects, the limitations of technology, and the demands of clients forced her to merge her idealism with practicality. It was a challenging period, but one that would ultimately make her a more versatile and resilient designer.

Ascending the Ranks at Google

Jenna's career took a monumental turn when she landed a role at Google. But her early days were anything but smooth.

"On my third day, I was in a meeting where I had no idea what anyone was talking about," she recalls. "I called my mom that evening, weeping. I thought I'd wrecked my life."

Yet, in true Jenna fashion, she didn't let this setback define her. Surrounded by some of the brightest minds tackling problems at an unimaginable scale, she found herself absorbing knowledge like a sponge.

"The education I got there was transformative," she reflects. "Working at Google made me nearly invincible to any design problem thrown my way in the future."

From Gmail to YouTube, she contributed to products that impacted millions, if not billions, of users worldwide. The complexity and scale of these projects honed her skills and expanded her understanding of what's possible when ambition meets resources.

Breaking the Pixel Glass Ceiling

Despite her success, Jenna noticed a recurring theme in the design world: an overemphasis on pixels and screens.

"Focusing on the pixel is the designer's glass ceiling," she asserts passionately. "To truly scale your impact, you need to design the rules of the system, not just the screens."

She shifted her focus from crafting individual interfaces to developing frameworks and logic systems that could adapt and grow, making her work more scalable and enduring.

"Designing the logic layer frees you from the endless cycle of redesigning the same elements over and over," she explains. "It allows you to create something that lasts, something that has a real impact."

Venturing into Entrepreneurship

Fueled by a desire to be multifaceted and to have a broader impact, Jenna co-founded her own company. This venture allowed her to wear multiple hats, blending her design expertise with product management and business strategy.

"I wanted to stretch myself in new ways," she says. "Starting my own company gave me the freedom to learn about finance, forecasting, and all the aspects of running a business."

This move wasn't without its challenges, but it epitomized Jenna's fearless approach to her career: constantly evolving, always pushing boundaries.

The Art of Framework Design

Today, Jenna is channeling her wealth of experience into a new endeavor: writing a book on framework design. She believes this approach is the key to breaking through many designers' limitations.

"Once you start abstracting concepts away from their pixel representation, a lot of things free up," she shares. "You begin to create systems that are scalable, adaptable, and far less brittle."

She encourages designers to map out their systems' "nouns and verbs"—the objects and their interactions—to build a solid logic layer that transcends individual screens or features.

Navigating Between Product and Design

Jenna has fluidly moved between design and product management roles throughout her journey. Her secret? Being true to herself and intentional in her choices.

"I always show up the same way, whether my title is designer or product manager," she says. "It's about leveraging user experience and product thinking to drive customer value and business outcomes."

Her advice to others grappling with similar crossroads is straightforward:

1. Be Intentional: Don't let your career just happen to you. Make conscious decisions about your path.

2. Embrace Change: If something isn't working, don't be afraid to pivot. Flexibility is a strength, not a setback.

3. Understand the Culture: Your impact often depends on an organization's culture and how it values your role.

A Legacy of Innovation and Empowerment

Jenna's story is a testament to the power of resilience, adaptability, and visionary thinking. She has navigated the complexities of a rapidly evolving industry and consistently pushed it forward.

"I don't change who I am based on my title," she emphasizes. "I bring the same passion and curiosity to every role, always aiming to create something that matters."

If Jenna's journey resonates with you as much as it does with me, I invite you to dive deeper. Her insights into breaking through career limitations, embracing the logic behind design, and navigating complex professional landscapes are invaluable for anyone looking to make a lasting impact.

👉 Watch the full interview with Jenna Bilotta here

As always, I'd love to hear your thoughts. What part of Jenna's story inspired you the most? Feel free to reach out and share your reflections.

Until next time,

Chris ✌️

From Anthropology to UX Design

Peter’s journey is anything but traditional. Starting off as an anthropology major, he didn’t set out to become a design leader. But his innate curiosity about human behavior led him to discover books like Information Anxiety by Richard Saul Wurman and The Design of Everyday Things by Don Norman. These works sparked his interest in how design impacts people’s interactions with the world around them.

The Birth of Adaptive Path

We dove deep into the early days of Adaptive Path, the design firm Peter co-founded that played a pivotal role in defining user experience as we know it today. What’s fascinating is how a group of like-minded individuals came together with a mission to advance the field of UX. They weren’t just building a company; they were shaping a movement.

Scaling Design Teams Globally

Peter shared valuable insights on what it means to lead and scale design teams in today’s global landscape. He talked about the challenges of maintaining a human-centered focus while managing teams that have grown to unprecedented sizes. His experiences offer a roadmap for anyone looking to navigate the complexities of modern design leadership.

Advice for Early-Career Designers

If you’re an early-career designer feeling stuck in a tactical role, Peter has some heartfelt advice for you. We discussed how to break out of the box and make a more significant impact within your organization. It’s all about showing up as your authentic self and finding environments that value your unique contributions.

Navigating the Hiring Process

We also touched on hiring practices in the design industry. Peter emphasized the importance of understanding a company’s design maturity and how it can affect your experience as a candidate. He offered tips on how to assess potential employers and position yourself for success.

I could go on about all the nuggets of wisdom Peter shared, but I think you’d get the most out of hearing it directly from him. His story is both inspiring and practical, especially if you’re interested in building a career that bridges creativity, technology, and leadership.

As always, I’d love to hear your thoughts.

Until next time,

Chris ✌️

I recently had the pleasure of sitting down with Angel Steger, a design leader whose journey from the structured world of architecture to the dynamic realm of tech is nothing short of inspiring. Angel didn’t follow the traditional path into tech. Still, her unique background has given her powerful tools for success in UX design.

In our latest episode of Pixelated Path, Angel shares how her architectural training gave her a competitive edge in the tech industry. We also explore how the rigorous methodologies and problem-solving skills inherent in architecture translate seamlessly into designing digital experiences.

Discovering Architecture at RISD

Angel started her journey at the Rhode Island School of Design (RISD), initially drawn to performance art. However, she found herself captivated by the complexity and creativity of architecture. She was intrigued by how architecture isn’t just about buildings; it’s about designing experiences at multiple scales—from the layout of a city to the flow of people through a space.

She loved that architecture challenged her to think abstractly, question everything from first principles, and balance many factors, such as physics, aesthetics, and human interaction. These skills would later become invaluable in her tech career.

The Reality of an Architecture Career

Despite her passion, Angel realized that the traditional path in architecture wasn’t for her. The long hours and lifestyle didn’t align with her desire for a more balanced and creative life. She was concerned about becoming solely defined by her work and missing out on other aspects of life.

Transitioning from Architecture to Tech

Angel’s pivot into tech happened somewhat by accident. Friends who had transitioned from architecture to tech invited her to try her hand at digital design. The idea of working on a product used by millions was exhilarating. She was fascinated by how people “live” in digital spaces, much like in physical ones.

Her first foray into tech was with a startup integrated into MySpace, the social media giant of the time. She quickly realized that many of the skills she honed in architecture—like managing complexity and thinking at different scales—were directly applicable to designing digital products.

Lessons in Leadership and Team Dynamics

At a subsequent startup, Angel learned invaluable lessons in leadership and team dynamics. The company prioritized investing in people—not just professionally but also in health and well-being. From providing healthy meals to group coaching sessions, the leadership understood that nurturing their team holistically led to better collaboration and creativity.

Angel emphasized the importance of being a colleague others can count on and the value of building genuine relationships. She believes in the power of diverse experiences and backgrounds, stating that they enrich the problem-solving process and lead to more innovative solutions.

Navigating Career Transitions and Building a Strong Portfolio

For those looking to pivot into UX design from a different field, Angel offers insightful advice:

• Leverage Your Unique Background: Whatever your previous experience, you have valuable skills that can transfer to design. Identify them and highlight how they make you a stronger candidate.

• Network Authentically: Build relationships based on mutual respect and shared interests. Don’t just focus on what others can do for you; consider how you can add value to others.

• Craft a Compelling Portfolio: Showcasing your work is crucial. Even if your experience isn’t directly in UX design, create case studies or projects demonstrating your skills and thought process. Focus on solving real problems and telling a story that resonates.

Embracing Diverse Backgrounds in Design

Angel is a strong advocate for embracing diverse backgrounds in the design field. She believes that unconventional paths can lead to unique insights and innovations, and your education and life experiences can differentiate you in the industry.

Ready to Dive Deeper?

Angel’s journey is a testament to the power of transferable skills and the importance of following your passion—even if it leads you off the beaten path. Suppose you’re interested in career pivots, problem-solving, or unlocking new potential in your own work. In that case, you won’t want to miss this conversation.

Watch the Full Episode

Tune in to the full interview on Pixelated Path to hear more about Angel’s experiences, insights, and advice for designers at all stages of their careers.

I hope you find Angel’s story as inspiring as I did. Don’t forget to subscribe to Pixelated Path so you never miss an episode filled with inspiring stories like this one.

Thanks for reading. As always, I’d love to hear your thoughts!

Best,

Chris ✌️

In the latest episode of Pixelated Path, I enjoyed chatting with Michelle Morrison, a seasoned design operations leader whose unconventional path took her from almost becoming a dentist to leading design ops at companies like Square, Twitter, and now Google.

Early Aspirations and a Life-Changing Redirection

Michelle’s story begins with a surprising twist. As a teenager, she was set on becoming a dentist. In fact, she was so committed that she took a job at her family dentist’s office to get a feel for the profession. But after a few months, her dentist sat her down and said, “This is as fun as it’s ever going to get. You definitely should not become a dentist.” Instead, he encouraged her to pursue art and design—a suggestion that would change the course of her life.

This unexpected redirection led Michelle to study industrial design, fueled by her love for creating physical products and her fascination with how things are made.

Navigating the Impact of the 2008 Recession

While attending San Francisco State University, Michelle’s plans took another unexpected turn. The 2008 recession hit, and her industrial design program was cut due to funding issues. Faced with this setback, she doubled down on her job at the Apple Store, managing inventory control.

But this wasn’t just any retail job. Apple taught her about supply chain management, operations, and how a tech giant functions. These experiences laid the groundwork for her future in tech operations.

Joining Square and Building a Foundation in Design Ops

Michelle’s transition into tech was facilitated by a former Apple colleague who recommended her for a role at Square, a tiny startup of about 100 people. Starting in general business operations, she quickly became immersed in the dynamic world of a hyper-growth company.

Michelle honed her skills in scaling operations and managing complex projects under the mentorship of leaders like Keith Rabois, Square’s COO at the time, and Jude, the VP of People. After a year as Jude’s chief of staff, she was allowed to move into any role she wanted. She chose to join the design team, becoming one of Square’s first design producers and design operations leads.

Scaling Challenges and Growth at Square

During her time at Square, Michelle played a pivotal role in scaling the company from 100 to 4,000 employees, seeing it through from Series C funding to its IPO. She shared insights about the challenges of launching products globally, dealing with technical complexities, and fostering a culture of transparency and learning.

One of her key takeaways? “Literally anything is possible,” she says, emphasizing the power of teamwork, adaptability, and a willingness to learn from successes and failures.

Design Operations Across Different Companies

Michelle’s career didn’t stop at Square. She went on to lead design operations at Facebook, Dropbox, and Twitter, each role offering new challenges and learning opportunities.

At Dropbox, she was tasked with rebuilding the design team after significant turnover post-IPO. She implemented creative strategies for talent acquisition, focusing on building internal culture and community. Initiatives like hosting dinner parties for designers and launching the Dropbox Design website helped attract top talent and revitalize the team’s spirit.

Navigating High-Stakes Roles and Joining Google

Her tenure at Twitter coincided with a tumultuous time as the company navigated Elon Musk’s acquisition. Despite the uncertainty, Michelle and her team remained focused, launching significant features like the long-awaited edit button.

Ultimately, she decided to join Google, overcoming her insecurities about not having a degree. At Google, she’s leading design operations for the AI portfolio and Search, continuing her journey of growth and learning.

Overcoming Insecurities and Embracing Lifelong Learning

One of the most inspiring aspects of Michelle’s story is her openness about not having a college degree. She shares how she overcame insecurities about her educational background by focusing on building confidence through her work and continuous learning.

Her advice to others? Understand how you like to learn and don’t be afraid to take non-traditional paths. Whether through hands-on experience, mentorship, or even teaching others, there are multiple ways to build a fulfilling career in tech.

Balancing Mental Health and Creative Work

Michelle also emphasizes the importance of mental health, especially in high-pressure environments. She discusses her strategies for staying balanced, such as setting boundaries, taking regular breaks, and maintaining a solid support network.

Amplifying Marginalized Voices in Design

Beyond her professional roles, Michelle is passionate about amplifying marginalized voices in the design community. She has co-founded conferences like Vectors and hosted events that bring together diverse perspectives in design. Her work in this area underscores the importance of inclusivity and representation in shaping the future of tech.

Ready to Dive Deeper?

Michelle Morrison’s journey is a testament to the power of embracing the unexpected and forging your own path. Her experiences offer valuable lessons for anyone interested in non-traditional careers in tech, design operations, or simply navigating change with resilience and creativity.

Watch the Full Episode

To hear more about Michelle’s insights on building teams, navigating high-stakes roles, and her advice for aspiring design operations professionals, tune in to the full interview on Pixelated Path.

I hope you find Michelle’s story as inspiring as I did. I’d love to hear your thoughts and continue the conversation.

Don’t forget to subscribe to Pixelated Path so you never miss an episode packed with inspiring stories and career insights.

Thanks for reading!

Best,

Chris ✌️

I recently had the pleasure of speaking with Kai, whose journey from studying anthropology to becoming a leading force in UX design is nothing short of inspiring. In our latest episode of Pixelated Path, we explore how her curiosity and resilience propelled her through multiple transitions—from agency work to in-house leadership—and how she continuously finds new ways to challenge herself and grow.

Early Roots in Creativity

Kai’s story begins in Oakland, where she attended an arts magnet school that fostered her love for the creative arts from an early age. She was exposed to various artistic disciplines, including etching, printmaking, and setting type, which laid the foundation for her future in design.

Despite this solid creative background, Kai initially studied math and anthropology in college. She found herself drawn to the analytical aspects of these fields but eventually realized that her true passion lay in the intersection of creativity and problem-solving.

Exploring Diverse Creative Disciplines

Kai didn’t limit herself to one field; she explored architecture and industrial design and ultimately found her calling in UX design. She was fascinated by the design processes inherent in these disciplines, particularly the participant observation component that allowed her to understand how people interact with spaces and objects. This approach would later become a cornerstone of her work in UX design.

Her ability to move across different creative fields was driven by deep curiosity and an openness to learning new things. She embraced challenges as opportunities to grow, whether transitioning from working at Yahoo to returning to school for a master’s degree or jumping into the complex world of cryptocurrency at Coinbase.

Starting Her Own Agency

Early in her career, Kai decided to start her own design agency. She wore many hats—handling business development, design operations, client management, and even teaching herself to code to build websites. The agency specialized in full-service branding and communications, working primarily with startups in Silicon Valley.

While the experience was invaluable, Kai later reflected on the benefits of working under seasoned professionals before venturing independently. She advises young designers to consider gaining experience and learning from others before starting their own businesses.

Transitioning to In-House Roles

Kai eventually moved into in-house roles, first at Charles Schwab and then at Yahoo. Working in-house allowed her to focus more on creative problem-solving without the additional responsibilities of running a business. She also appreciated the opportunity to see projects through from conception to execution.

Returning to School and the Value of Continuous Learning

Feeling the need to challenge herself further, Kai returned to school to earn a master’s degree in design from California College of the Arts. She sought to build a more structured creative practice and deepen her understanding of design principles and methodologies.

Kai emphasizes that the impact of such an education becomes more apparent five to ten years later. For her, it wasn’t about climbing the corporate ladder but enriching her design approach and expanding her network.

Pioneering Design Sprints at Google

At Google, Kai was pivotal in shaping and disseminating the design sprint methodology. She participated in the early stages of developing design sprints and helped create the Sprint Leadership Academy. Recognizing their effectiveness, she advocated for sharing this methodology within Google and with the broader design community.

Kai organized the first Sprint Conference and developed external resources to help others implement design sprints in various contexts. Her work has significantly impacted how teams approach problem-solving and collaboration.

Embracing New Challenges and Continuous Growth

Kai has consistently sought new challenges and learning opportunities throughout her career. Whether it’s exploring health tech or diving into the rapidly evolving field of AI, she remains committed to expanding her horizons.

She advises others to stay curious, continue building their network, and keep feeding their creative engines. In times of uncertainty, she encourages designers to engage in projects that inspire them and maintain community connections.

Ready to Dive Deeper?

Kai Haley’s journey is a testament to the power of curiosity and the willingness to embrace new challenges. Her story offers valuable insights for anyone interested in the intersection of creativity and strategy or those looking to thrive in a fast-evolving field like UX design.

Watch the Full Episode

Tune in to the full interview on Pixelated Path to hear more about Kai’s experiences, insights, and advice.

I hope you find Kai’s story as inspiring as I did. I’d love to hear your thoughts and continue the conversation.

Don’t forget to subscribe to Pixelated Path so you never miss an episode packed with inspiring stories and career insights.

Thanks for reading!

Best,

Chris ✌️

Breaking into HCI: The Early Days

Jess’s foray into HCI began during an internship at a startup in Eugene, Oregon. Tasked with designing a webpage to sell ads—with no prior coding experience—he dove in headfirst. Armed with a copy of Dreamweaver, he learned by trial and error, commenting out code to see what changed.

This hands-on experience led him back to his grad school advisor. “I’m interested in psychology, technology, and art,” he told him. The advisor’s response? “You should go into HCI.” That simple suggestion set Jess on a path that would define his career.

The Role of Art and Emotional Design

Art wasn’t new to Jess; his mother was a painter, and he grew up with an appreciation for creativity. However, it was during the iPod era that he noticed people's emotional reactions to technology. This intersection of emotion and design pulled him deeper into HCI.

Navigating Rejection and Early Career Challenges

Despite earning a PhD, Jess faced significant hurdles entering the job market. He applied to 50 jobs and received 49 rejections before landing a contractor role at Microsoft. “It felt terrible,” he admitted. The experience taught him resilience and the importance of self-motivation.

For those facing similar challenges today, Jess advises making the job search your full-time job while practicing self-care. “It’s hard not to take rejection personally,” he said, emphasizing the need to maintain balance during tough times.

The Value of a PhD in UX Research

Jess shared insights on pursuing a PhD, emphasizing that it should be driven by passion rather than career advancement. “You need to have an almost unhealthy obsession with the research topic,” he noted. While a PhD provides valuable tools and a deeper understanding of human-technology interactions, it’s not a guaranteed gateway to career success in UX Research.

Transitioning into Management

At Microsoft, Jess transitioned from an individual contributor to a management role. He emphasized the importance of transparency and respect when moving into leadership, especially when managing former peers or when others may have wanted the role. “I think that transparency helps,” he said, acknowledging that conversations can be awkward and crucial for building strong team dynamics.

Addressing Imposter Syndrome and Self-Awareness

Imposter syndrome is common in the tech industry, and Jess is no stranger to it. He stressed the importance of having an accurate self-assessment and being open to feedback. “The hardest thing is to have an accurate view of yourself,” he explained. He also warned about the dangers of overconfidence, which can be just as detrimental as self-doubt.

The Evolution of AI and Responsible Design

Jess’s career took a pivotal turn when he joined Google and later Meta, focusing on AI and responsible design. He recounted attending a presentation by Blaise Agüera y Arcas at Google, which ignited his passion for AI. Starting as a 20% project, his work in AI quickly became his full-time focus.

He emphasized the importance of building AI with values—fairness, safety, trust, and accountability. “If we believe this is going to be one of the most consequential technologies, then we better be sure that we build it responsibly,” he asserted.

Staying Sharp in a Rapidly Evolving Field

In a field as dynamic as AI, continuous learning is crucial. Jess shared his approach to staying updated: consuming a variety of newsletters and academic papers and actively using new products to understand design intentions. He also reads history and biographies to gain broader context, currently enjoying “Masters of Doom,” a book about the creators of the game Doom.

Advice for Aspiring AI and UX Professionals

For those early in their careers and interested in AI, Jess advises balancing technical awareness with practical application. “Assume AI will be woven in somehow,” he said, “but think about how it can provide the most value to people in a responsible way.” He encourages viewing AI as a design material—one of many tools at your disposal to create meaningful user experiences.

Final Thoughts

My conversation with Jess was both enlightening and motivating. His journey underscores the importance of resilience, continuous learning, and ethical considerations in technology. As AI continues to evolve, professionals like Jess remind us of the human element that must remain at the core of innovation.

Watch the Full Episode

Tune in to the full episode of Pixelated Path to learn more about Jess's experiences and insights.

I hope you found Jess’s story as inspiring as I did. I’d love to hear your thoughts and continue the conversation.

Don’t forget to subscribe to Pixelated Path so you never miss an episode packed with inspiring stories and career insights.

Thanks for reading!

Best,

Chris ✌️

Discovering Design Through Nonprofit Work

Jen’s entry into the world of design wasn’t traditional. While studying sociology at UCLA, she strongly desired to make a difference. She started a nonprofit focused on foster care children called “Fosterity and Beyond.” Lacking resources, she took it upon herself to learn design tools through LinkedIn Learning (formerly Lynda.com), creating logos and websites to support her cause.

“I was learning a bunch of skills because I couldn’t hire anyone and didn’t have the funds,” Jen recalls. This hands-on approach ignited her interest in design and user experience (UX).

The Importance of Authenticity

Growing up in various households, Jen often felt like a diluted version of herself. It wasn’t until she pursued her genuine interests that she began to thrive.

“When you’re yourself, you shine. People see it,” she emphasizes. Jen believes authenticity enhances personal happiness and allows others to genuinely connect with you.

Bold Career Moves and Entrepreneurship

Despite securing a coveted position at Dropbox, Jen felt unfulfilled. Her passion for nonprofit work and social entrepreneurship led her to make a daring decision: leaving Dropbox to pursue further education at UC Berkeley.

“I wanted to break my own status quo and enter into the world of entrepreneurship,” she explains. This move allowed her to engage in projects that truly resonated with her despite the uncertainty and financial instability that often comes with startups.

Managing Mental Health and Self-Validation

Jen candidly discussed her struggles with mental health, particularly anxiety and the challenges of high-pressure environments. She highlighted the importance of self-validation over seeking external approval.

“I realized I wasn’t validating myself. I was always seeking external validation,” she notes. She found a healthier balance in her professional life by maintaining a “work wins” diary and focusing on personal achievements.

Thriving as a Senior Designer at Netflix

At Netflix, Jen found an environment that satisfied her entrepreneurial spirit within a larger organization. She is surrounded by talented colleagues and continues to learn and grow in her role.

She emphasizes taking initiative, even on small projects. She encourages designers to dig deeper into problems rather than just doing what they’re told.

“You can make any tiny thing inspiring. It’s how you sell it and what you make of it,” she says.

Navigating ADHD in the Workplace

Jen also opened up about her experiences with ADHD and how it influences her work style. She thrives in fast-paced environments and uses strategies like setting personal deadlines and focusing on passion projects to stay engaged.

“I need to be strategic about filling that time with things I want to do,” she advises. Recognizing her needs has been crucial in managing her mental health and maintaining productivity.

Embracing AI and the Future of UX Design

When it comes to AI, Jen is optimistic. She frequently uses tools like ChatGPT and Copilot as soundboards. She believes AI can handle some execution work, allowing designers to focus more on strategic and creative tasks.

“Designers should be responsible for designing algorithms or GPT prompts,” she asserts. She encourages designers to adapt by learning prompt engineering and integrating AI into their workflows.

Advice for Aspiring Designers

For those entering the field, Jen emphasizes the importance of:

• Product Strategy: Develop a strong understanding of how design decisions impact the overall product and business goals. Jen advises designers to think beyond aesthetics by considering feasibility, prioritization, and collaborating closely with product managers and engineers.

• Self-Reflection: Regularly assess your own skills and mindset. Jen emphasizes moving away from a victim mentality and focusing on personal growth by identifying areas for improvement and actively working to address them.

• Building Skills: Enhance your design abilities by focusing on visual polish, storytelling, and practical skills. Jen suggests seeking constructive feedback to refine your work and continually learning to stay competitive.

• Networking: Build genuine connections rather than relying on generic outreach. Jen recommends personalizing your interactions to foster meaningful relationships that can support your professional journey.

“Think about what you can do to be a better designer,” she suggests. Designers can navigate the challenging job market more effectively by focusing on actionable steps and personal development.

Conclusion

Jen Wong’s journey is a compelling example of how authenticity, mental health awareness, and a willingness to take risks can lead to a fulfilling career. Her insights offer valuable lessons for designers at any stage of their careers.

Watch the Full Episode

Tune in to the full episode of Pixelated Path to learn more about Jen's experiences and insights.

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00:00 Introduction

02:12 The Early Days: How Josh and Billie Met

07:12 Entrepreneurial Beginnings

12:20 Josh's Leap into Schwadesign

22:51 Billie's Path to Synesthetics

32:22 First Professional Collaboration

35:36 The Role of AI in Design

36:50 The Importance of Buy-In and Culture Change

37:38 Teaching and Mentoring in Design

39:22 Navigating Workplace Politics

41:03 Building Sustainable and Scalable Products

42:49 Empowering Junior Designers

45:09 The Value of Fresh Perspectives

53:58 The Impact of the Pandemic on Careers

59:09 Launching a Group Coaching Club

01:11:15 Words of Wisdom for New Designers