Advice

Practical tips and insights on design thinking, product strategy, and personal growth.

  • WordPress Almost Didn’t Happen

    What if Matt had joined Google instead of starting WordPress?

    The internet might have felt a little less like ours.

    In his recent post, Matt mentioned “How the internet might have turned out differently if I had taken that job, as my mom wanted me to (because they offered free food).”

    Funny line. But also wild to think about. It’s incredible how much of the web traces back to one person deciding to build something open.

    I think about that sometimes. The tiny choices that ripple out for decades. Who’s choosing open now? And what will that mean twenty years from here?

  • Ridiculous Swings

    I used to kill ideas before they had a real chance.

    Every spark of curiosity met the same mental gate: Is this worth my time? What’s the opportunity cost? Can I even do this? The auditor in my head would run the numbers and most ideas would die right there.

    Then something shifted. Not because AI models got smarter, but because the marginal cost of curiosity drops close to zero.

    Building a prototype used to mean weeks of coding. Now it’s an afternoon conversation with Claude or v0. I explore weirder ideas. And I take ridiculous swings because ideas cost almost nothing.

    The math changed. When exploration is cheap, you stop rationing curiosity. When you can afford to explore bad ideas, you stumble onto good ones you’d never have planned. Instead of hoarding best guesses, splurge on exploration.

    For myself, this freedom to explore without commitment is quite liberating. What about you?

  • Be Wrong More Often

    The best product leaders are comfortable being wrong. They’ve figured out that waiting for certainty costs more than making mistakes. Every day you spend seeking perfect information is a day you fall behind.

    Strong opinions accelerate learning. Each one tests a hypothesis about users or the market. Some fail, and each wrong assumption teaches you something about your product or the people using it.

    Most breakthrough products started as ideas that seemed misguided. Early versions were rough, value propositions unproven. But the teams had focus and conviction when data was scarce and feedback was mixed. Waiting for all the answers is just fear dressed up as caution.

    Exceptional product leaders are more decisive than accurate. They push into territory where certainty doesn’t exist. Each wrong turn narrows the path, which is exactly what you want.

    Commit fully to your best hypothesis. Tentative implementations produce ambiguous results. When you build something with conviction, reality responds with clarity. That’s how you develop product intuition—confident action, honest assessment, repeat.

    Being right feels nice. Being confidently wrong feels like progress.

    So risk the stumble. It’s the only way forward.

  • Advice to My Younger Self

    A collection of principles that turn good work into exceptional work. These aren’t tips – they’re fundamental truths I wish I’d understood from the start. Each one still shapes my path from competence toward mastery.

    Choose worthy problems. The biggest wins come from picking the right problems to solve. The best opportunities often hide in plain sight, written off as unreasonable or impossible by others. Find something that matters to you, and trust your ability to figure it out.

    Develop taste. Learn to spot what’s exceptional in every field you touch. Good taste builds on itself – it guides your choices, attracts excellence, and raises your standards. Study the best work you can find, understand what makes it special, then demand that standard from yourself.

    Stay curious. Questions beat answers. Don’t just collect information – pursue understanding. Keep asking “why” until you hit bedrock. Push into what you don’t understand. Knowledge builds on itself faster than anything else.

    Master focus. Progress happens when you do the right things, not everything. Deep focus is your superpower in a distracted world. Protect your attention like your most valuable asset because it is. Your best work happens in the spaces you create by saying no to urgent but unimportant stuff.

    Be steady. Do what you love daily. Small actions, repeated with conviction, reshape your skills, your work, and your life. Consistency beats intensity every time. What you do every day matters more than what you do sometimes. Small improvements build into big changes over time.

    Care about your craft. The best craftsmen get pulled forward by the work itself. When you find work that excites you, protect and nurture that connection. This excitement is rare and precious – it’s what will carry you through the tough periods. Life’s too short to make things you don’t care about.

    Build with integrity. Do excellent work, especially where it’s hidden. The back of the fence says more about your work than the front. True craftsmanship shows in the details others won’t see – but you do. This hidden excellence can become your superpower.

    Embrace being wrong. Being wrong isn’t just okay – it’s expected. The faster you spot and admit mistakes, the faster you improve. Success comes from how quickly you learn from being wrong. Make it easy for others to tell you when you’re off track.

    Hold strong convictions, loosely. The best ideas come from believing in something while staying open to being wrong. Strong opinions should be earned through experience, defended hard, and dropped when wrong. This balance is tough but crucial – conviction gives you the strength to pursue bold ideas, while openness keeps you from getting trapped by them.

    Communicate simply. Clear writing reflects clear thinking. Use simple words for complex ideas. If you can’t explain something simply, you don’t understand it well enough yet.

  • The Physics of Focus

    Focus isn’t what you think it is.

    Most people treat it like a skill to master—using timers and productivity hacks to fend off distractions, forcing focus through willpower. But that misses the fundamental truth: focus isn’t about disciplining your mind—it’s about being so interested in one thing that everything else feels unimportant. 

    The best work comes from people who are obsessed. When someone builds a great company or makes a scientific discovery, it’s not because of good habits or time management skills. It’s because they lived the problem they were trying to solve. It consumed them. Like Einstein visualizing himself riding alongside a beam of light, or Marie Curie spending years processing tons of pitchblende to isolate radium—their focus wasn’t forced, it was inevitable.

    Focus compounds—when you align time, energy, and skill on one goal, progress accelerates. What starts as curiosity becomes understanding, then expertise, then breakthrough—yet most people confuse activity with progress. They push in ten directions at once, getting nowhere. 

    Being busy feels productive, but scattered effort does not compound. It dissipates like heat, while focused effort builds like potential energy.

    The physics of focus is unforgiving but simple: If you want to do something exceptional, be ruthless about what you focus on. Everything else is noise.

  • You don’t need a flashy redesign

    Your __________ doesn’t need a flashy redesign; it needs to work better.

    You might think that a new coat of paint will solve your problems. But if the core functionality is lackluster, users likely care about sleek interfaces.

    Instead of redesigning, focus on the core elements that matter to users. Fix the bugs that frustrate customers, then streamline flows for intuitive navigation and task completion. 

    Only then, consider adding genuinely useful features that address real user needs and pain points. These improvements, while less visually apparent than a redesign, result in higher satisfaction and retention.

    It’s always substance over style. A functional but plain product will outperform a pretty but broken one.

    Focus on solving real problems to drive growth, not trendy designs. You don’t need a flashy redesign, for now.

  • WordPress Contributors, Think Like a Designer

    Open source is beautiful. And open source is often messy.

    WordPress, with its global community of contributors, is no exception. We’re a passionate bunch, each bringing our ideas, skills, and perspectives to the table. It’s what makes WordPress different—a competitive advantage. But this freedom comes with a challenge: together, how do we build a cohesive, intuitive, and human-centric WordPress experience?

    More than ever, WordPress should be design led.

    That doesn’t mean a few designers make all the decisions. Actually, it’s the opposite; every contributor—developer, writer, marketer, or designer—thinks more like a designer.

    To think like a designer means looking beyond the immediate task and considering the bigger picture. It requires understanding how every change impacts the user experience and approaching decisions with empathy, ensuring every interaction feels purposeful and seamless.

    This approach challenges us to avoid arbitrary decisions and lean on holistic solutions that prioritize user experience. Because at the end of the day, it doesn’t matter how beautiful, extensible, or accessible WordPress is. If WordPress is not usable, it can’t democratize publishing.

    “It doesn’t matter how beautiful, extensible, or accessible WordPress is. If WordPress is not usable, it can’t democratize publishing.”

    Rich Tabor

    I’m not saying WordPress isn’t usable today (although there’s room for improvement), but that open source isn’t an excuse for sloppiness; it’s a call for excellence—especially with a project that matters, like WordPress. 

    As contributors, we have the opportunity to create a more thoughtful, human-centric experience that empowers people to publish, if we all think more like a designer.

  • Good taste: the currency of the future

    This interview with David Lee, the CCO of Squarespace, poses an interesting question: Will AI make human creativity a luxury?

    Creativity is not just about technical skill or craft; it’s about identifying what resonates with people and captures the human experience. That is, taste.

    In today’s world, where AI is increasingly capable of creating art, music, and literature, taste matters more than ever. I agree with David here—taste is the currency of this inevitable future, which perhaps is already here.

    Good taste helps creatives produce resonate work that reflects personal style and originality. It involves a level of vulnerability, exposure to diverse influences, trusting instincts, and knowing when to follow or diverge from trends.

  • Practical contentment

    I recently discovered Muji’s ethos, where the company champion against a world obsessed with perfection:

    “We do not make objects to entice responses of strong affinity, like, “This is what I really want” or, “I must have this.” MUJI’s goal is to give customers a rational satisfaction, expressed not with, “This is what I really want” but with “This will do.”

    “This is what I really want” expresses both faint egoism and discord, while “This will do” expresses conciliatory reasoning. In fact, it may even incorporate resignation and a little dissatisfaction.

    MUJI’s goal is to sweep away that slight dissatisfaction, and raise the level of the response, “This will do” to one filled with clarity and confidence.”

    In product and software development, balancing perfection and completeness is incredibly difficult.

    I appreciate this mindset because it’s not about compromising quality, but appreciating sufficiency. It’s a shift from chasing perfection to finding contentment in what meets our needs.

  • On contributing to open source

    The best part of WordPress is that we get to work together making something we appreciate better. 

    Contributing to open source is all about caring deeply for something and following up that passion with progress. Working together with others. 

    It’s like embarking on a side quest in your favorite massive multiplayer gamer, where success hinges on assembling a party of adventurers. Each party member (or contributor) brings their unique skills to the table, driven by a shared commitment to progress. 

    I know it can be difficult to find the intersection of what’s important to a project and what’s interesting to you as a contributor. My advice here is to connect with other contributors and make your interests known. 

    Blog about your curiosities, your explorations, what drives you as a person. And when you do form that party of adventurers interested in the same areas of work around you, that’s when you will start picking up real momentum.

    This dynamic interplay of passion, collaboration, and community underscores the art of contributing to open source. A reminder that at the heart of open source lies a vibrant community of people, each playing a role in shaping its future.

    That’s why I build, and publish, with WordPress.  

  • WordPress & Iteration

    Iteration is all about relentless improvement; not merely fixing what’s broken. It involves striking the right balance between innovation and problem-solving, one that fosters sustainable forward-moving progress.

    Is software anything but constant iteration?

    The fundamental objective of iteration is not deciding whether to iterate, but rather prioritizing the most impactful ideas—whether new features, enhancements, or bug fixes. The challenge lies in prioritizing the big wins and minimizing those distractions that divert focus from those wins.

  • Your corner of the internet

    A blog is more than just a collection of posts. It’s about the power of written words, an ongoing conversation that shapes how we see things, opens our minds, and helps us connect with others.

    Each post adds to the rich mix of human stories. Whether you’re sharing experiences, teaching something new, or just capturing everyday thoughts, a blog gives you an independent space to express yourself.

    Blogging offers an escape from the algorithm-driven world (a place where you can simply write). It reminds us of when sharing thoughts wasn’t about chasing likes or trends, but about real digital connection.

    Your blog belongs to you. It reflects who you are.

    It’s your corner of the internet.

    Make it yours, and let it show your personality in this huge digital world.

    Thanks, WordPress.

  • Tiny details

    Like the nuanced brushstrokes of a painting or the delicate notes of a melody, tiny details often go unnoticed, yet they play a key role in profoundly shaping creative outcomes.

    In the realm of design and product, these tiny details are essential catalysts for curating thoughtful experiences.

    Subtle animations, uniform copy, cohesive design metrics, and harmonious micro-interactions all come together seamlessly to level-up an application into a delightful user experience.

    You might not see tiny details, but you certainly feel them.

    Tiny details are not just embellishments; they are the cornerstone of design. And it’s in these seemingly insignificant tiny details that we transform mediocrity into excellence.

    Such attentiveness to detail is absolutely vital, as the antithesis of tiny details is carelessness—which leads to outcomes that feel unfinished and unintuitive.

    So, sweat the tiny details; they matter more than you think.

  • Fail Fast

    Failure is a vital part of the iterative process. An invitation to introspection. An indispensable role in exploration and creativity. 

    To fail is to learn—provided one seeks to learn. When we fail, we face an opportunity to sharpen our focus, unearth solutions, and gradually inch closer to our goals. 

    Software development (i.e. problem solving) is centered on eliminating variables, i.e. failing. Failing as many times as it takes, until a solution in narrowed into view.

    That’s just how it works. That’s how most things work. Rather than a symbol of defeat, failure represents a testament to progress. 

    Don’t fear failure; invite it in. These are the moments where you—and your team—become better. 

    Fail often. Fail fast.

  • Build something that matters

    In creativity and innovation, there’s a tension between pursuing meaningful work and getting stuck on trivial tasks. These distractions disguise themselves as progress, creating fake productivity where small, unimportant details actually prevent us from making a real impact.

    Focus on true progress—the kind that comes from clear purpose—control distractions, and build something that matters, like WordPress.