Entrepreneur's Schedule vs Employee's Schedule
After 14 years, I finally know how to work
Yesterday I messaged my wife in the middle of the day saying, “I finally know how to work.” Which is a weird realization to have after working professionally for 14 years.
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.