"You have a bunch of stuff and still talk about simplicity, what's with that?"
Well, I have accumulated a few things in my life. I used to make a lot of money (relatively speaking). I bought the Mercedes, the toys, the stuff.
I have gotten rid of a lot, and am trying to learn to get rid of the rest. I want to keep only what I need, and maybe a few wants. It is hard. I grew up with little, so when I was making decent money, I wanted to buy the stuff I never had. Over time I have come to the realisation the stuff never made me happy. I found the doing is better than the having.
I have acquired many of the things I have by coincidence or luck. I am not afraid to dumpster-dive. I take my kids if I can, we make it a game. I have stopped on the side of the road to pick up something that someone else is tossing out. My wheelbarrow came from the dump, some guy was tossing it because "it's annoying", whatever that means.
I have traded a lot. Craigslist is my friend when it comes to trading.
Value is the governing factor with the things I possess. I was going to say own, but I don't think I own anything, I just possess it until it leaves my possession. I still have trouble letting go though, some things just have too much potential.
I feel qualified to share my experiences and tips with the world because I am actually doing every one of the steps on my list. I have been unemployed for 16 months (I did work for two months in the middle there). For ten of those months I collected no unemployment benefits. I now am collecting unemployment benefits (I felt that I shouldn't do it, but someone reminded me that it was my money). I am going to school on the Post-9/11 G.I. Bill, and making it work on the little money I get from these two sources. My wife is a nurse and can make good money, but we choose for her to work less so she can be home for the summer with the kids. During the rest of the year she works and we save, we have eliminated most of our bills to make this a possibility. I am now unemployed by choice because juggling school, work, and kids is too much for anyone person and my heart goes out to those that manage to do it. My wife was in that position when we met and I quickly convinced her to stop working and let me handle the money part so she could continue her schooling. I saw how hard it can be, and do not want to do that myself (she is definitely stronger than me).
I like stuff, it is programmed into me from my childhood, from TV, from the outside forces of the media and U.S. culture. I am trying to de-program myself.
Instead of working hard just so we can pay the credit card bills and loans for the stuff we don't need, we work what we need to, just so we can do the things that give us the one thing we truly own, memories.
I've recently started reading your blog after a connection from the Bike Trailer Blog. Your situations sound very similar to mine. I applaud you for continuing education even though it may be hard financially for your family. My wife supported me and worked while I finished my degree, though we didn't have our daughter until I graduated and got my first salary job. Now my wife doesn't work so she can stay home with the little one (18 months).
You also posted about getting rid of your car. This is something I did about 6 months ago. We have one car (Honda CRV) and I bike to work everyday though it's a short 10 blocks. I can say we are just now over the initial regret stage and are enjoying it. I have sacrificed a few things, but I have also gained a few things (non-material).
I have a book recommendation for you since you're talking about getting rid of stuff. "Put Your Life on a Diet". This is a short read by a guy who lives by himself in a small 140 Sq. Ft. trailer. He's not saying you should live in a trailer, but he does have lots of ideas about slimming down not only yourself but everything else in your life. I was very inspired by this and have recently rid my entire house of things that haven't been used in one year (to the tune of about $400). Like you I am also a Craigslist veteran.
I can't say I share your view on tools though. I feel it's less important to have a good set of tools and more important to have a neighbor who has a good set of tools (and a good relationship with such a neighbor). I've cleaned my gutters quarterly using my neighbor's 10 ft. step ladder.