Your career portfolio; self-publishing lessons; Cloudflare saves the Web: Newsletter 3 September 2025

Newsletter 109. Building your career portfolio one fascinating project at a time. Plus, no more Lego custom orders, the problems with the federal design studio, three people to follow, three books to read, and one last chance to tell us about how much you love or hate AI.

Making growth your portfolio objective

You should be building something with every project you do.

I don’t mean for the external audience. I mean for you. Your own skillset and collection of experiences stays with you until you die. Even failures, as seen from the external perspective, become valuable knowledge you can build on. A failure you learn from may ultimately be more valuable than a success that’s just a duplicate of something you built before.

This is the philosophy of building a portfolio for your own growth. If you’re freelance, you do this by selecting the projects you work on. If you work for a company, you do it by positioning yourself for the work that seems most likely to enable your growth.

What kind of projects should be in your portfolio?

• Work you can master and deliver profitably with quality and on time. This should be up to half of your portfolio, to keep the risks manageable and the revenue stream predictable.
• Projects you can do completely on your own — to demonstrate mastery and enable rapid experimentation.
• Projects you create as part of a team, to expose yourself to others’ skills and competencies and improve your teamwork and communication.
• Work that is repeatable, because that’s easy to sell and requires a predictable level of effort.
• Work at the experimental edge of your skill set, to stretch your knowledge.
• Projects with a big risk and a big potential payoff, because they might lead you in an exciting and lucrative new direction.
• Pro-bono or pro-social projects you can feel good about working on.
• Huge projects that require months or years of effort, because they’ll develop a broad collection of skills and experiences — and a lot of satisfaction when you complete them.
• Quickies, even if they don’t pay much, because you can slot them into small openings in your workflow and get the quick dopamine hit of finishing them.
• Something completely different from what you normally do, just for the experience. (But don’t let this derail you from your main set of goals.)
• Work with diverse new kinds of people — people with a variety of experiences, personalities, industries, races, nationalities, and roles. You’ll learn a lot from people who are different from you and the people you normally work with.
• Work that demands travel to places you’ve never been.
• Work that pays a lot — but don’t let this distract you from all the other portfolio elements.
• Work that requires intense effort.
• Work that allows you to dream and be creative without limits.

You only get so much time to experience life, and work is such a big part of it. Stop doing the same thing again and again, which only drives you deeper into a rut. Diversify your portfolio. Because in the long run, that’s how you’ll discover what new directions for your future will be most rewarding, exciting, and enlightening.

News for writers and others who think

Who’s getting rich off of AI? One surprising example is Anguilla, a Caribbean nation half the size of Washington, DC, which is on track to generate one-fourth of its government revenue from the .ai top-level-domain that it controls.

Fred Vogelstein interviews Matthew Prince, CEO of Cloudflare, on his quest to establish a new legal and technical framework for AI and rescue the business model of the internet.

Ethan Marcotte critiques the government initiative to create a national federal design studio. Is centralizing the design of government sites really going to improve our experience?

So, you’re creating something with Lego and want to order that one missing piece that will complete your vision? You used to be able to do that with Lego’s “Pick a Brick” service. But with the end of the de minimus tariff exemption, Lego has stopped shipping products from Denmark to consumers. Tariffs are abstract. This is as concrete and upsetting as stepping on a Lego brick barefoot in the dark.

Wired cofounder and author Kevin Kelly shares everything he knows about book publishing in a long essay. While he completely ignores hybrid publishing, his extended discussion of a variety of self-publishing options is fascinating.

Three people to follow

Emily Riley, founder of the Women in the One Percent, a groundbreaking initiative to get talented, impressive women paid what they’re worth

Justin Wolfers, economics professor who explains essential macroeconomic news so clearly that anyone can grasp it

Fatemeh Khatibloo (she/her), ethical and responsible AI expert

Three books to read

If Anyone Builds It, Everyone Dies: Why Superhuman AI Would Kill Us All by Eliezer Yudkowsky and Nate Soares (Little, Brown, 2025). As jeremiads go, perhaps overstated , but decide for yourself.

Freemium: How Zoom, Hubspot, Atlassian, and Other Top Companies Use Product-Led Growth for Low-Cost Customer Acquisition and Expansion by Dave Boyce (Stanford Business, 2025). How to build products so great they sell themselves.

Move. Think. Rest.: Redefining Productivity & Our Relationship with Time by Natalie Nixon, PhD (Balance, 2025). Harnessing creativity at work with a purposeful relationship to time.

Last call to make yourself heard on AI and writing

You know you mean to take our survey. If you already did, thanks. If not, take it today or tomorrow — the survey closes on Thursday September 4. Take 15 minutes to join the 1200 other writers who told us how they felt.