I think Bob Dylan said it best, “A man is a success when he get’s up in the morning and goes to bed at night and in between, he does what he wants”. Or something like that!

Another area where I find the over-reaction manifests itself is the simplicity and frugality movements. There are so many reformed cluttery people who become “50-thing” people or previously debtor-types who have become super-frugal. I have often wondered why that is and whether they will swing back towards a happy medium over time.

I also think that such questions as “if you had enough money (or time) to do whatever you want, what would that be?” are largely academic until you actually do have the money or time. Most people need to feel their way into what they want from life, take in new information and adjust their lives accordingly and radical change is one way they do that I suppose. One thing that most of us don’t do is actually imagine what life would be like (in a practical way) if we go with that radical change – we have the escape fantasy of traveling the world etc., but don’t stop and think about what we’ll actually DO every day or the challenges we’ll face on a daily basis in that kind of scenario.

I retired 9 years ago when I was 34. Unfortunately, I only wanted freedom from work that I didn’t like. Once out of the rat race, I didn’t know what I wanted to do with my free life.

Over time, I’ve learned that I have gained the freedom to travel, learn languages, make interesting friends, help my family, become physically fit, and even work part-time as a teacher. Once I figured out what I wanted, retirement became the best experience of my life.

I get more intolerant and crabby as I get older, and now I have nearly enough money to not have to put up with the jerks I don’t plan to put up with them. I may still do engineering though, it interests me and I like the challenge.

As it turns out, I’m a programmer and I love it. I suspect when I get to be financially independent I will still program but I will also do some of my other loves like photography and woodwork.

Crowds are dangerous, so although my response is no more thoughtful, I tend to seek out and do precisely what crowds do not do. I attempt to fool myself into believing that my chances of success are improved in that way. ;-\

I’ve read Millionaire Mommy and am well aligned we her approaches financially (and admire her confidence and results), but I don’t read the blog regularly. Too retail/monetized for my taste. I like the smaller, contrarian productions. ;-\

For instance, when we first retired we anticipated traveling the country in an RV for a year, then adopting our daughter, then deciding whether to continue our vagabond lifestyle with her or settle back into a sticks and bricks home. But the current of life can take unexpected turns – like the need to care for a gravely ill family member – and you instead feel thankful that you have the freedom to be there and help.

So we rest, regroup and create new visions.

Jacob, I just found your blog (via Chad at his new Sentient Money blog). You sound like my kind of tribe! Looks like I have a couple additions to make to my blogroll. (BTW, I’m a fan of Retired Syd and Soultravelers3 – Cool to find you here!)

Several things came together where it became obvious that it was now or never when we “jumped”…& now we can see it was the best decision of our lives!

Yes, I have done a lot of travel in my life and even lived a year in Italy when I was young, but exploring the world together slowly as a family is even more enriching than we imagined.

We are almost 2 years into our travels and love our mobile lifestyle where we travel for 7 months and then settle into a beautiful village in a lovely ocean view rental home in southern Spain for a sunny, warm winter for 5 months.

We can both be workaholics so I wondered how we would do with an endless summer lifestyle, but we have thrived on our new existence and love living in the “now”, never needing to know what day or time it is.

We mostly got out of the dollar when it was high and sold our home at peak in 2005, so those things help us continue to live large on little even in Europe. The educational benefits for our daughter have been extraordinary and we even take classrooms of kids along with us virtually ( some from disadvantage areas who will never travel).

The internet and free skype webcams keep us close to family and friends as we roam at will.We worried about a lot of things before doing this, but now wish we would have done this sooner as this kind of freedom is the way to live!

Life is short, follow your dreams..it really is easier than most imagine. We were motivated to do this for our child, but it has been so rewarding for all of us on every level.

I have had friends say to me that they admire my ability to make decisions. I don’t agonize about decisions–I know what I want, and I go get it. It’s very easy for me. While my total dropout from a 22 year career in finance to retire may seem extreme– I have never been happier. But I knew exactly what I wanted, this was not an agonizing decision for me.

So, unfortunately, that makes me the worst person to give advice in this regard, since it’s not something that I learned how to do–it’s just me.