I re-read the 4 hour work week recently

Actually read it for the first time - but it's just so much later now....

The 4 Hour Work Week (2008) is a self-help book by Tim Ferriss that according to Wikipedia →

repudiates the traditional "deferred" life plan in which people work grueling hours and take few vacations for decades and save money in order to relax after retirement.

Instead, the 4 hour work week describes different methods to reach your pivotal kind of lifestyle design.

I finally finished reading the book after starting it a few years ago. It feels a lot more prescient than before because of the Great Resignation and the Covid remote work shift.

But parts of the 4 Hour Work Week feels cliche because it talks about quitting your job, traveling the world, and building a drop-shipping business that “prints money while you sleep”. Then I realized it was only cliche because Ferriss was the one that originated that idea in the first place, which also eventually gave rise to many gurus selling their own expensive “print money while you sleep courses” while posting pictures of themselves usually renting Ferraris.

A couple useful nuggets still stood out from The 4 Hour Work Week.

The first were the ideas around the “New Rich” (a term that definitely did not catch on as much as his ideas). The New Rich are bathing in the luxury of free time, where life is built around your needs versus built around work.

This is the fundament idea behind FIRE (financial independence retire early). Once members from the FIRE community reach their “target number”, it grants them the ability to never have to work again if they stay within their lifestyle budget. Though many in the FIRE community seem to forget to enjoy life while on the journey to achieve it, Ferriss seems more enthusiastic around being more meticulous around lifestyle design from the very start.

A second great nugget was on automation. Again related to flexibility, the proposed concept asks to systematically understand which aspects of your business and life you could automate to free up more time for activities you enjoy. This sort of automation has almost no bounds from using no-code tools to automate your business to hiring virtual assistants to pay your bills and even gift flowers to your spouse. In my experience, outsourcing to virtual assistants does require a lot of upfront work, but it’s been easier and easier in the last few years with new tools like Loom and Slack for coordination.

Ferriss definitely took some parts of FIRE and flexibility to the extreme. He seems to be a bit of a polymath, taking two years after automating his business to learn new languages, participate in dance competitions, and become a kick-boxing champion. But it was also an effect from him being burned out from working at his business until he automated most it.

Noticeably in the last decade he’s been working as hard as the rest of us and has usually been putting in more than 4 hours a week. Which brings me back to the constant question of what’s the fine line between “free time” and “work” once you’ve started optimizing for flexibility.

For example, many times I find myself coding or writing late into the night after “work hours” during my “free time”. Which makes me wonder if by optimizing for flexibility, I instead just naturally gave myself the capacity to do more work because I enjoy working?

It’s hard to draw the line especially when it comes down to “lifestyle business”. You could take the argument, that a regular venture capital funded business has the necessity to take the most optimal path towards growth at the expense of everything else.

So if you’re instead branded as a lifestyle business, your pitch and slogan is → "well we didn't completely maximize our growth trajectory to the extent of our financial engineering capabilities, but we also didn't completely wreck our lives either." And usually that has to be shown off by having the founders travel to Hawaii and post on Instagram, and all that good stuff....

At the end of the day, the 4 Hour Work Week is a small Catch-22. Tim Ferriss figured out the exact processes and hacks that got him financial freedom and life flexibility, but likely can’t stop working because the journey to get him there was so addicting that he couldn’t stop.

And so it goes to say that most people don't really want to retire or work four hours a week, they just want the eventual choice of doing so. And that choice means everything even if no one actually does chooses the option.