Sometimes the scarce resource is not money, but free time and mental availability. "Randomly walking around" could increase his chances of bumping into a hidden opportunity. I say go for it.
I've never seen entrepreneurship as a means to escape a tedious, loathsome working life - it is a means to achieve my dreams, not a refuge from boredom. IMHO if you're striking out on your own solely because you hated your job, perhaps you worked for the wrong people, and your problem isn't with employment in general, but with your employer.
I dislike the author's tone on a few points:
> "A job is working on someone else’s dream."
Bull. I'm working on my dream right now (one of many, but I digress). It's high-impact, and can't be done on my own (even with funding) by sheer virtue of inertia and existing infrastructure. We fought for the idea, proved its worth, and now we get to work on something game-changing, making all the important calls along the way. It's freedom, working with smart people, on your dream, with deep pockets, and the support of an army of equally talented people.
> "A job is selling your time."
Since when? There are lots of jobs, particularly on this side of the country (um, the west) where your performance is judged by your work and not the time on the clock (if you're even clocked!). I have no "competing motivations" - perhaps an artifact of, oh, working on things I actually desire to complete.
I applaud the author for doing things his way - but I wish he didn't have to resort to denigrating the concept of employment to justify his own lifestyle.
I've found that most places expect at least an eight-hour day out of you, whether you're formally "clocked" or not. I think often that a salaried position is seen as an opportunity for exploitation by bosses. My last job was like that, and my co-workers just ate it up; the bosses demanded ten-hour days and other concessions and everyone just went along because since we were salaried it meant we had to do whatever they said (we were even taken to the boss's house one day to help move furniture) without any prospect of fair compensation, or something like that. I don't really get it.
There may be a bit more leniency with breaks and that kind of thing at a salary job, but if you're not there before 9 and you're not still there after 5, and this happens even rarely without prior approval, your bosses aren't going to be pleased.
I agree that a job can provide a way for an employee to work on "his dream", but such a situation is incredibly rare, and even rarer is the situation where, when this dream is realized through your work, you'll get due credit and compensation.
Working for the man is just an all-around bad deal if you're looking to control your own life or do something big. That's just my opinion. If you're OK with a work-a-day routine, OK with even the possibility of eventual bullying from the bosses, OK with getting paid 1/4 or less of the value you actually generate, then working for someone else permanently may not be so bad, but that's not how I am, and I presume that many of us on HN have similar aversions.
I say permanently because I think working for other people can be a good experience, and it's nice to get a significant amount of it under your belt; it helps you understand human dynamics and politics, can accelerate your skills and force you to learn new things, introduce you to cool people, etc., so a job isn't all bad, but I have a very hard time with the idea that I would be stuck working for someone else for the next fifty years.
I don't understand the people who let their bosses push them around and then complain about how much employment sucks. Anymore, at least - at my first job, I thought that way, and it was miserable. Then I left to found a startup, and then rejoined the working world after it failed.
The best thing the startup did was give me perspective. I realized that if I took a job and hated it, I could just do whatever I needed to do to make myself not hate it. And if my boss had a problem with that, the very worst thing he could do is fire me. Which would put me back in exactly the same position I was in before I took the job, except I'd be somewhat richer, more experienced, and would have accomplished more.
There's no such thing as "permanent" in this economy. I don't really understand this either/or dichotomy, where you're either a salaried employee or an entrepreneur. Most really good hackers I know have done both. Take the best opportunity open to you, regardless of whether it's your own company or someone else's.
People who enjoy working a rewarding job are "rationalizing their addiction"?
[edit] Specifically, I object to the false polarization of this topic: working a job means bowing to The Man, working on boring crap with stupid bosses, and other such nonsense. It does a disservice to both people who work at a job, and people who are in business for themselves by generating false expectations.
Entrepreneurship is not a silver bullet to your boredom, nor is it a guaranteed ticket to working only on things you love. Nor is employment a silver bullet solution to stability and consistency. This polarized portrayal of either side really just adds noise to the discussion.
tl;dr: Working at a job doesn't mean you don't work on things you are passionate about. Working for yourself doesn't mean you get to avoid all the tedium you used to deal with on the job.
I treat my employees like people, and valuable resources, and experts in their job. I defend them from outside distractions and criticism, taking all the crap on their behalf, and giving them ALL the glory. I don't get to make decisions, I HAVE TO make decision with the best intelligence at my disposal, which includes my Employees expert opinions. I'm paying them for that; I'd be a fool to ignore it.
The idea that you can work a regular job AND start your own thing is a common misconception. Nothing to do with whether your job is rewarding or not; either way it precludes striking out on your own. The hours in the day prevent it.
The addiction is to the soft life. Lots of ways to explain why you enjoy that - and I understand completely. But its not going to get you anywhere but where you are.
When somebody has this level of emotion, I like to ask: if you were going to die in a year, how would you spend that time? And then: what are you waiting for.
I have plenty of savings, and plenty of earning potential - if I really get stuck (I don't believe likely) I can always pick up another job. Money is a means, not an end.
I think this is the key. You have two years of runway to figure out what to do next (according to the blog). That money in the bank is a lot more security than any job can offer, by itself. Staying in your job for another two years might be the greater risk, when opportunity costs are taken into account.