I recently stumbled across The Oatmeal’s series on Creativity. While all of it is spot on, the part on erasers hit especially hard.

“There is a lot of shame associated with backpedaling; things like quitting your job, getting a divorce, or simply starting over are considered shameful.

But forward isn’t always progress.

And backward isn’t always regress.

Sometimes going down the wrong path isn’t a mistake — it’s a construction line.”

— Matthew Inman (The Oatmeal)

It was exactly what I needed to hear. You see, only a few days prior, Font Awesome and I had parted ways — the end of a short, but transformative chapter. I’m proud of what we built together, and grateful for what I learned along the way. But it was time to move on.

Jobs are a lot like relationships. They often start with infatuation — and end with the realization that you’re simply not compatible, and that’s no-one’s fault. Letting go always stings, even when it’s the right call. There’s always grief: when you’re not ready to move on, you grieve the bond; when you are, you grieve your expectations. But every ending leaves behind clarity — about who you are, and what makes you happy.

The pursuit of happiness

Today is my 39th birthday — and this summer marks 20 years since I first dipped my toes into this industry. Naturally, I’ve been doing a lot of reflection.

As is typical for ADHDers, I have done a ton of different things, and built a diverse skillset as a result. But what made me happiest? The list of highs went a bit like this:

Entrepreneurship: Co-founding a startup and driving it to become a household name (in Greece — this was 2008!)
Consulting: Being a full-time consultant, speaker, and author, traveling the world and jumping from one exciting gig to another
Academia:^[1] Pushing the boundaries of Human-Computer Interaction at MIT and teaching MIT CS students to care about people.

All had three things in common: autonomy, breadth, and impact.

These three things have been the biggest predictors of happiness for me — far more than income ^[2] or work-life balance, which are the usual suspects.

I used to aspire to work-life balance in the same way I aspired to frequent exercise — because it was good for me, not because it gave me joy. Eventually I realized that what makes me happy isn’t working less, it’s loving what I do, and feeling it matters. Working less cannot transform how your work makes you feel; it can only dampen the effects. But dilution doesn’t turn misery into joy — at best it just makes it tolerable. Don’t get me wrong, poor WLB can absolutely make you miserable; when long hours are an externally imposed expectation, not an internal drive fueled by passion. As with many things in life, it’s enthusiastic consent that makes all the difference.

Then there’s breadth. Most jobs try to box you in: PM or engineer? Scientist or practitioner? UX Researcher or designer? DevRel or standards? And I’m like…

Aurora is my spirit animal 🫶🏼 Source

It’s silly that people are forced to choose, and present themselves as less than to seem more attractive to hiring managers. To use myself as an example:

Web architecture: I have designed several web technologies that have shipped across all browsers. I’ve spent 4 years in the TAG, reviewing new web technologies across the web platform, and eventually leading the Web Platform Design Principles effort.
Product/usability/HCI: Prior to working as Product Lead at Font Awesome, I’ve earned a PhD at MIT in Human-Computer Interaction with a minor in Entrepreneurship & Innovation. I published peer reviewed papers in top-tier HCI conferences, and co-created/taught a course on usability & web technologies that is now a permanent subject. I have run user research for scientific and industry projects. I have started several open source projects, some used by millions. In the more distant past, I co-founded a (then) well-known social startup in my home country, Greece and ran product, engineering, and design for three years (six if you count pre-incorporation).
DevRel: I’ve given over 100 conference talks, published a bestselling book on CSS, and was the first devrel hire at W3C back in 2012. I have built dozens of apps and polyfills that stimulated developer interest in new Web features and drove browser adoption.

Should I present myself as a web architecture expert, a usability/product person, an HCI researcher, or a Developer Advocate?

What a pointless dilemma if I ever saw one!

Combining skills across different areas is a strength to be celebrated, not a weakness to be swept under the rug. The crossover between skills is where the magic happens. Off the top of my head:

Understanding usability principles has made me a far better web standards designer.
Web standards work is product design on hard mode. After the impossibly hard constraints and tradeoffs you deal with when designing APIs for the Web platform, regular product problems seem like a cakewalk (we have versions? And we can actually change things?? And we have reliable metrics?!? And the stakeholders all work at the same company?!? 🤯).
They often feed into each other: DevRel work made me a better communicator in everything I do. Usability made me a better speaker and educator^[3], so a better developer advocate too.
Leading the Web Platform Design Principles convinced me that explicit design principles are immensely useful for all product work.
Web standards taught me that contrary to popular belief, you do not need a benevolent dictator to ship. But then you do need a good process. Consensus does not magically grow on trees, building consensus is its own art.

Lastly, impact does not have to be about solving world hunger or curing cancer. Making people’s lives a little better is meaningful impact too. It all boils down to:

Impact=Individual Impact×Reach

You can achieve the same total impact by improving the lives of a few people a lot, or the lives of many people a little. For example, my work on web standards has been some of the most fulfilling work I’ve ever done. Its Individual Impact is small, but the Reach is millions, since all front-end developers out there use the same web platform.

What’s next?

Since consulting and entrepreneurship have been my happiness peaks, I figured I’d try them again. Yes, both at once, because after all, we’ve already established that WLB is a foreign concept 🤣

My apprentice Dmitry and I have been in high gear building some exciting things, which I hope to be able to share soon, and I feel more exhilarated than I have in years. I had missed drawing my own lines.

In parallel, I’m taking on select consulting work, so if you need help with certain challenges, or to level up your team around web architecture, CSS, or usability, get in touch.

Don’t get me wrong, I’m not closing the door to full-time roles. I know there are roles out there that value passion and offer the kind of autonomy, breadth, and impact that would let me thrive. It’s the ROI of digging through rubble to find them that gives me pause — as a product person at heart, I/E tradeoffs are top of mind. But if you have such a unicorn, I’m all ears.

I also finally took a few small steps to make my pro bono work financially sustainable, a long overdue todo item. Both pages still need work, but you can now support my writing via ko-fi^[4], and my open source work via GitHub Sponsors. I made separate pages for my two most popular projects, Prism (nearing 1.8 billion total npm installs! 🤯) and Color.js. This is as much about prioritization as it is about sustainability: money is an excellent signal about what truly matters to people.

It should go without saying that if you’re a for-profit company depending on open source work, you are expected to fund it. This is not a legal expectation, mainly because enforcement is a headache, but it absolutely is an ethical one. It is also in your best interest — funding the open source software you use ensures that it continues to be maintained. Don’t be the reason we can’t have nice things.

I don’t have a polished “next” to announce yet.
But I’m exactly where I need to be.

Sometimes the clearest lines are the ones drawn after you erase.

Many things wrong with academia, but the intellectual freedom is unparalleled, and it makes up for a lot. ↩︎
See also Alan Watts’ “What if money was no object?” — a classic, but still relevant. ↩︎
Teaching is absolutely a form of UI design — a UI that exposes your knowledge to students — the users. There are many similarities between how good educators design their material and how good UI designers design interfaces. ↩︎
Thanks Dan Abramov for the wording inspiration (with permission). These things are so hard. ↩︎