I Achieved the Four-hour Workweek. So Why Did I Just Take a Job?

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In 2023, 12 years after reading The 4-Hour Work Week, I was making enough passive income from my Udemy course on prompt engineering to achieve the Tim Ferriss dream.

I didn’t need a job. Yet I decided to trade freedom for a monthly paycheck again when I joined Every in February full-time to lead tech consulting and write.

My friends are puzzled. Isn’t the course making more money than ever (despite what the prompt engineering haters say)? What will it be like having a boss after five years of self-employment and six years building a company before that? Don’t you remember vowing to never take another job?

My answer is that it’s the best time in history to join a company. AI has made it easier to build new products, but it hasn’t made it easier to find customers. Entrepreneurship has arguably gotten harder. Deploying AI within a company that’s already working beats building the fifth version of a product that nobody will use. Plus, you can learn things inside a company that never get shared on X.

Making money the hard way

On paper, I had it made. I had no boss, could work from anywhere, and made money while I slept. The reality is that solo is harder than it looks.

I make money from my online course because I spent many sleepless (and unpaid!) nights working with GPT-3 for years before ChatGPT was released and AI went mainstream. I gave up lucrative data science retainers to take on AI projects, slashed my day rates 75 percent, and even worked for free, because I was excited by the potential and wanted to learn.

I could have never predicted that any of this would pay off, and I also can’t predict when it will end. Sometimes I worked on the course every day, other times I went months without updating it, and nothing seems to make a difference to revenue. I’ve created two other AI courses— both flopped. Passive income may sound great, but it is a fickle beast.

It wasn’t just the course. Almost all the work I did as an entrepreneur started with months of unpaid work. I worked for two months without a paycheck when I started my marketing agency, and only started paying myself six figures when we scaled past 30 people. I worked for three months for free on a data science project as a learning exercise before turning that into a seven-figure consulting practice. I spent a year writing a prompt engineering book for O’Reilly before I saw my first royalty check.

Then there were the failures. The video editor and content repurposing tool that never got a single customer. The marketing book I wrote that only 200 people read. The product I spent months on and never got released after a cofounder falling-out. The list goes on.

Friends who run startups report similar low batting averages, and most successful entrepreneurs have many more failures than they do wins. The hardest thing to cope with, however, is the uncertainty.