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I like to think the same, and I did once have an independent contractor job where I wasn't sure how much money I'd make week-to-week so I know the feeling of that aspect, but that was back when I was younger, had a roommate, no mortgage, fewer bills etc...
On the other hand, I'm getting to the point where I've been with my current company for 7 years, and gotten a raise just once (despite having excellent reviews each year). I'm feeling more dead-ended each day.
Fueco, I think if you were successful in your own endeavor, whipped up a sharp website, wrote creative ad copy for listings etc, that's as good as any other experience in design should you opt for the indoor job life...proven success should get you a few hops up the ladder off the bat if you switched tracks.
When I mull it over, I always go back to corporate job benefits other than a salary & paycheck. Current job gives me 20 paid days off per year, paid sick time, reimbursement for internet, partial reimbursement for health insurance, 50% 401k matching, 1.5x pay for overtime and 2x pay for 12+ hour days, 100% work from home, sizable year-end bonus... Of course, it's not all about the money - you gotta be happy, as stress-free as possible, have time for friends & family, and have fun. I'd be OK making less $, if that meant less stress. But, making a lot less $ would lead to stress as well. Argh.
I'm in a rather unique situation. My wife works for a major Silicon Valley corporation, so my medical and dental are covered through her employer. The freedom that working for myself allows makes sense given our lifestyle (bike races, triathlons, travel, etc.). The one thing that I don't get is paid for days I don't work. But I'm okay with that. I'm also okay with the idea that once we have a child, I'll be free to care for him/her during the day. And yes, once that kid is old enough, she will know the difference between shell and calfskin.
I feel strongly that with the right motivation, you can make whatever you choose to do work well. I think of it in terms of Walter White saying, "I'm in the empire building business." It's not about making money, or being successful. It's about picking something and doing it as well as I possibly can. It's what I was missing when I was in my twenties. I had the thought of flipping for profit as far back as 2002, when I sold my first item on Ebay, but I lacked the motivation to do it right. Now, I have the motivation, the technical knowhow and the space and capital to give it a real go. I can easily see myself opening a brick and mortar shop at some point in the future, but the online stuff is going to have to skyrocket before that will happen.