I’d spent the morning going down some rabbit hole, reading about random AI topics. I was doing work that felt very interesting to me, but didn’t fit the traditional productivity mold. I felt great in the process, but later I was feeling guilty and anxious about a slow work day. The employee schedule I’d internalized from years in tech had come to bite me in entrepreneur life.

I’ve been on the entrepreneurship path for a while, building my own ideas like Bookling. But it’s only now I’m realizing that despite working for myself, I was measuring my work in the wrong ways. I was trying to force myself to be on an employee’s schedule, instead of being on an entrepreneur’s schedule.

Paul Graham wrote about the maker’s schedule versus the manager’s schedule more than a decade ago. In it he brings up key points like, how programmers need long blocks of uninterrupted time while managers work in hourly slots. More people now are neither employees nor managers though – they’re entrepreneurs working for themselves. And AI-driven layoffs are only going to increase the number of people hopping on this train.

By entrepreneur I mean people who’re actually independent. Who have complete control over where they spend their energy. Whose calendars only fill up when they want them to. Their exact title is irrelevant. I know many “founders” who’re entrepreneurs on paper, but in practice have no control over their time and energy. I also know many people who work for a company, but because of their skill/seniority/role, they have full freedom. The key things are: 1) mostly no one is telling you what to do, and 2) you’re in the driver’s seat for your time, calendar, energy.

Let me tell you about a real entrepreneur, with a capital E.

One of my big inspirations in life is my uncle, who unfortunately passed away a decade ago. At the age of 40, he started a CPG foods business from scratch, and made it a success exactly as he envisioned – complete control over quality, manufacturing, packaging, and distribution – selling products only in company-owned branded stores.

He never took a dollar of outside investment. “If I take their money,” he’d say, “it’s their business, not mine.” Even though the business became a big success – multiple stores, large manufacturing facility, made him wealthy – “growth as a goal” was never even a thing. He never invested his money into other people’s businesses either. “Why would I put my money into a business I don’t run? Why not put that money into things I can execute?”

He worked hard, but didn’t believe in “always work hard.” He took vacations and time off, but didn’t believe in taking time off to “recharge.” Some days he’d be at the factory earlier than usual working like crazy. Other days he’d be at home reading newspapers until noon. When we kids would visit his factory, he’d switch off his business side entirely and get playful with us. He was deeply passionate about every aspect of the business. He could talk for hours about why a certain machine needs to work in a certain way, to cut biscuits just right. He often even designed the machines himself.

He had the real entrepreneur’s schedule. So let’s talk about what that actually means:

On employee’s schedule you treat busyness as a badge of honor. Packed calendar, always in meetings.
On entrepreneur’s schedule you treat an empty calendar as the goal. The point isn’t to fill time, it’s to free it.

On employee’s schedule you often fight the natural rhythm. Guilt on slow days, pressure to “catch up,” anxiety about inconsistent output.
On entrepreneur’s schedule you accept the rhythm. Some days you’re loading your RAM. Some days you’re executing. Some days your contribution graph looks like shit. It’s all part of the game.

On employee’s schedule you optimize for visible output. Steady commits, consistent velocity, full activity logs.
On entrepreneur’s schedule you optimize for leverage. A week’s worth of work done in three focused hours beats five days of steady grinding.

On employee’s schedule you measure value in hours worked, commits made, or conversations had.
On entrepreneur’s schedule you measure value in new insights gained. One key realization can be worth more than a month of busy work.

On employee’s schedule you see wandering as procrastination. Reading papers, digging in Discord or Slack communities, exploring rabbit holes feels like wasted time.
On entrepreneur’s schedule you know wandering is how your brain makes connections. The meandering is part of the work.

On employee’s schedule you seek certainty and external validation. The boss, the performance review, the contribution graph.
On entrepreneur’s schedule you trust internal signals. Does this feel right? Where does my energy want to go today? You can’t ask permission when you’re the one responsible.

The epiphany isn’t that I should work less. It’s that forcing consistent output is actually less productive than accepting the natural rhythm. When you’re an entrepreneur, you get to make a little universe where you control the laws. A big part of that is working when and how you work best, not forcing a schedule that doesn’t fit. After 14 years, I finally know how to work.

• Improve spacing and typography consistency across the site

• Improve inline link styling and color consistency

• Reorganize Photos section to full-width layout

• Improve mobile layout density and readability

• Fix frontend test quality and eliminate anti-patterns

• Refactor endpoint_form_controller to follow Stimulus best practices

Looks productive, right? Except I spent hours making barely visible changes to my blog and projects while avoiding the actual work I needed to do. Welcome to generative procrastination: where AI helps you avoid real work at superhuman speed.

Traditional procrastination had natural limits. Want to reorganize your desk instead of writing that PRD? Fine, but how long can you really spend arranging stuff? Want to refactor that old code instead of tackling the gnarly bug? Sure, but eventually you’d hit the tedium wall and give up.

AI has destroyed those limits.

Now I can generate infinite busywork that looks, feels, and commits like real work. I can refactor entire areas of a codebase in an afternoon. I can build elaborate CLI tools to solve problems I sparingly have. And it all happens at lightning speed, leaving a trail of commits that would make anyone feel very good.

It’s a perfect dopamine loop. Every prompt answered, every file updated, every test passing. You’re not scrolling Twitter, you’re shipping! You’re not playing video games, you’re building! Your brain can’t tell the difference between motion and progress anymore.

When you browse Reddit for three hours, you know you’ve wasted time. The guilt of traditional procrastination is immediate and useful. But when you’ve spent those same three hours pair-programming with Claude to build a comprehensive Tailwind component library for your side project? That’s different. You’ve got tangible, deployable output. But was it useful? Or was it just generative procrastination?

The most dangerous part is how it hijacks our identity as builders. We’re the people who bias toward action. AI tools let us maintain that identity while completely avoiding the hard, important work.

I’ve watched myself do this for a while now. For example, I have a customer waiting for their children’s storybook to be updated with suggested edits. It means learning how to upscale all the illustrations, recreate some illustrations, redoing the book layout, and communicating to the customer. But here I am, redesigning and refactoring my projects super fast. It’s just so easy to pair with Claude and quickly knock things out that used to take a long time!

The output is often very good. That refactored code? Actually cleaner. That documentation? Actually helpful. We’re not making garbage; we’re making high-quality irrelevance at high speed.

AI tools are powerful, but they make it even more important for us to be super honest about what’s actually nedle-moving. The strategic thinking, the ambiguous problems, the human conversations still feel like work because AI can’t instantly solve them.

Ask yourself: “Am I using AI for the well-defined, fun stuff instead of the messy, important stuff? Would I prioritize this task if I had to code it manually?” Sometimes the answer will be “I’m just enjoying building this temp side thing,” and that’s fine. We all need our outlets. Like this article itself is for me. But it isn’t work still, just new kind of recreation.

The real thinking still happens with a pen and paper, far away from AI. But good luck explaining that to your contribution graph. Anyway, I should stop writing about generative procrastination and tackle that user feedback I got for Bookling. Right after I fix this blog’s typography one more time?

It’s the same job-title churn we’ve seen for a decade. You’re not looking for a new type of person. You’re looking for a Product Engineer who’s mastered new tools.

I get it – hype cycles demand new jargon, your VCs want buzzwords. “Product Engineer” sounds a little too plain. But while we’re busy inventing titles, we’re missing the actual problem: we still don’t know how to find and evaluate these people well.

Five years ago, a Product Engineer wired up React to Rails and deployed on Heroku. Today, that same person builds LLM workflows, writes evals more than unit tests, hooks up MCP tool calls, and spends more time context engineering than coding. Completely different stack, and yet the same instinct.

Great Product Engineers do not care for specific frameworks, languages, or techniques. And they certainly do not care for your new neon-decal title. They worship solving a problem well. They’ll use whatever gives them the most leverage to getting shit done.

How about, instead of trying to come up with a new persona, we focus our energies towards finding and interviewing this type of person well? How about we finally stop asking them to solve random coding puzzles? How about we give them real tickets to solve from our actual codebase, instead of made-up quizzes? How about we watch how they work with AI, instead of making them write an algorithm on a whiteboard?

The person who mastered full-stack web apps is the same person who now masters agentic workflows. Their talent isn’t knowing specific tech – it’s their drive to find the shortest path from problem to solution.

Anyway, if tomorrow I see something like “Holistic Prompt Stack Synergist,” on LinkedIn, I’m building a Chrome extension that replaces all these terms with two simple words: Product Engineer.

Quick hat tip: The exact origin of “Product Engineer” is murky. Facebook was one of the earliest to build its engineering culture around the idea. The term was also heavily championed by leaders like Jean-Michel Lemieux (JML) during his time at Atlassian and later Shopify.