2026-02-19 18:03:00
When phone cameras got good enough, portrait photographers scolded people who took their own headshots.
And when the Mac got pretty good at typesetting, professional designers pointed out that people who can’t tell a font from a typeface and don’t care about kerning should avoid it.
Professional translators bring humanity and insight to transforming writing from one language to another, but many people continue to use Google Translate…
Here’s the thing: the translators take their own headshots. Web designers often use translation software. And life coaches build their own websites with Squarespace and put their own selfies on Linkedin. We all make our own decisions, and most of the time, we use tech to do it ourselves.
This began with the Model T. Before that, people with enough money to buy a car also had a driver.
It’s not easy to find clients, particularly when technology makes it straightforward for many people to do the mechanical part of what you do for them on their own. It’s more convenient, faster and cheaper. It might not be as good by your standards, but if the client wants faster and cheaper, you’re unlikely to win that argument.
When was the last time you hired a studio photographer instead of using a stock photo of a piece of fruit? Or paid for a stock photo instead of using a cc or ai image? You might not cut your own hair (I’m not an expert) but you probably pump your own gas and cook your own meals.
The opportunity isn’t to race to the bottom, or to try to persuade someone that it’s worth upgrading. Instead, we can celebrate the fact that more people are discovering the power of photos, of type, of coaching and of cooking… and we can upgrade what we offer.
The goal is to be the first choice for people who couldn’t imagine doing it themselves, simply because their work is too important or your work is too good for them to ignore.
The best way to upgrade a freelance career is to get better clients. They challenge you, pay you more and talk about you more. And you don’t get better clients by working hard for lousy clients. You get better clients by becoming the kind of freelancer that better clients want to hire.
2026-02-18 18:03:00
An AI like Claude is actually a pretty good fortune cookie. You can ask a simple question and get a simple answer, sometimes a profound one.
But this is a waste of the tool’s potential.
The AI is patient. It’s capable of remembering things over time. And it will persist if you let it.
Several of my friends have shared that they’re at a crossroads with their work, and I suggested an AI coach might unlock something. Here’s a chance to spin up an AI coach who will stick with you for hours or weeks as you explore a new skill or grapple with a hard decision.
The first one:
You are my thinking partner and life design coach. I’m not looking for a quick answer. I’m looking for a smart, patient collaborator who will help me explore what’s next—over weeks and months, not in a single conversation. Ask more than you tell, at least at first.
About me: I’m 63. I’m retiring with full pay from a successful career as an educator in Chicago. I’m not burned out—I’m ready. I’ve spent decades being good at something that matters, and I want to find the next thing that deserves that same energy.
What I’m not looking for: A list of “top ten encore careers.” A personality quiz. Pressure to monetize immediately. I don’t need to replace my income—I need to replace my sense of purpose and craft.
What I am looking for:
Start by asking me five or six good questions. Not surface-level ones. The kind a wise friend would ask over a long dinner.
And the next:
You are my AI filmmaking coach and tutor. Your job is to help me build, step by step, the skills and workflow to create a short film using AI tools. I learn best by doing—give me exercises, not just explanations. Be honest when something isn’t ready for what I need.
About me: I’m a filmmaker and author. I’ve written and directed five critically acclaimed independent films. I’m an experienced screenwriter. I’m new to AI creative tools but I’m a fast, motivated learner.
The project: I want to make a short film about …. I want to lean into what AI does well stylistically and avoid the uncanny valley entirely.
Tools I’m aware of: I’ve seen Midjourney produce still images that match the mood and visual style I’m after. I’ve seen tools like Runway, Kling, and Sora that generate short video clips from prompts. I don’t yet know how to connect these into a production workflow.
What I need from you:
Enjoy the journey.
2026-02-17 18:03:00
Industrialism brought us the idea of optimization. Incremental improvements combined with measurement to gradually improve results.
We can optimize for precision. A car made in 2026 is orders of magnitude more reliable because the parts fit together so well.
We can optimize for customer satisfaction. By reviewing every element of a user’s experience, we can remove the annoyances and increase delight.
We can optimize a horror movie to make it scarier, and we can optimize a workout to make it more effective.
Lately, though, the fad is to optimize for short-term profit.
This will probably get you a bonus. It means degrading the experience of customers, suppliers and employees in exchange for maximizing quarterly returns.
Make a list of every well-known organizational failure (from big firms like Yahoo to Enron to Sears all the way to the little pizza place down the block) and you’ll see the short-term optimizer’s fingerprints.
You can’t profit maximize your way to greatness.
2026-02-16 18:03:00
A watched pot will boil.
As it heats up, there’s no way to predict where the cavitation will start and which bubble will arrive first. But with enough time and enough heat, it’s going to boil.
That tree down the street is going to lose its leaves this winter. We don’t know which leaf will go last, but we can be pretty sure they’ll go sooner or later.
Complex systems can be predictable even when any individual node in the system seems unknowable.
One of the traps that marketing measurement presents is our unwillingness to consider populations instead of individuals.
2026-02-15 18:03:00
“There, it’s done.”
This is the production mindset and the rule of school. Pencils down. Hand it in.
The alternative is, “Sign me up for a commitment to better.”
Ship an update every day. Learn from what works, relentlessly improve what doesn’t.
The hard part about this path is persisting. Never done projects pile up pretty quickly.
That’s precisely why they’re a competitive advantage.
2026-02-14 17:02:00
Often aren’t.
In fact, they might be the safest way forward.
