While I’m sure the “grass is greener” mentality is at work, as you say, I think the problem is much more basic. I think people generally don’t know themselves very well. We clutter up our lives with whatever career and other busy-ness and we don’t really get a chance to know what we really want for ourselves, because we don’t take the time to listen.

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.

I think it’s important to create a vision of what you’re moving towards, rather than the circumstances (like work) that you’re eager to move away from. And then it’s critical to stay flexible, move with the flow of life, rather than fight the current.

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!)

ERE, I’m still mentally hackeysacking your “idea that one must believe in something” line. I’ve heard that notion before, from incredulous souls who can only imagine motivation from their own FORs. “You gotta do this…”, “You have to be this way today…”, “You can’t live that way in these times…”, etc.

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 don’t believe in the concept of “the grass is always greener on the other side” since everyone is chasing something different. To me, the green will always be greener on my side, if not, I just add more seeds, water and watch it grow :))
About the whole religion thing, I was raised Catholic but I don’t believe in God in the traditional sense. I’m agnostic. I believe in a higher consciousness that can only be achieved through balance and harmony. I’m a nature person, I’m happiest alone in the midst of the woods or sailing the oceans 🙂
Basic science supports the concept of where we go after we die:matter cannot be created or destroyed only change it’s form. So in a sense we are all immortal 😉
I’m one of those creative type that need to be constantly engaged, and not necessarily by people. Books, ideas, crafts, finance etc keep me entertained.
I know exactly where my money is going, asidefeom some charities and my daughter, my love of creative people whose art I sometimes finance, music is very big 😉
Entrepreneurs may try to quit starting new
Business but I give them a month or two tops and they will be back at the computer creating something new because that’s hour the brain of an entrepreneur works. It’s addictive. You want to see how far you can take the nxt concept before you exit. Like running, its so addictive you spend months locked in your basement before you see daylight worming on your ideas. Powerfully tool, the mind on an entrepreneur

For me it is about control; I’m not that unhappy with what I am doing but I am pig-sick of incompetent jerks who I have no respect for telling me what to do, and stupid practices like performance management that offend my being.

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.

Re getting into the same problems in a new way – I wonder if it isn’t somewhat inevitable? There’s probably something within their previous field of work that a retired person really loves. Like meetings… as much as they whine about them, many people LOVE meetings (having some degree of extroversion probably helps for this), just not too many. I suppose the meetings get in the way of doing their work, just like working at a job can get in the way of a personal life.

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.

Meetings are great if properly run. The problem is, so few are. A good meeting has the following components:
1. A start time.
2. An end time-normally no longer than an hour but shorter if possible. In some cases somebody may have to make a long speech. This is OK if the rest of the rules are followed consistently.
3. An agenda that is followed
4. Specific attendees, a target audience. No mandatory attendance “just because” or to “pass information.” That’s what mass email is for.
5. Expected inputs communicated to specific attendees to bring to the meeting.
6. Expected meeting output(a): ideas, recommendations, decisions. This is the real litmus test of whether the meeting is worthwhile or not.
7. No one on one or even one on two conversations during the meeting. These are to be done “off line.”
8. A note taker

A properly conducted meeting has one final benefit: It sends the message that the participants’ time is at least as important as the manager’s.

Some engineers want to do advanced scientific experimenting research but don’t need nor want the required Ph.D. license process after reading all the textbooks (without needing an grade or tuition to “pass” or learn the subjects well); rather then apply the science for profits. Unconventional methods and processes for science discoveries are also achieved by the poor, though passionate achiever.

For some of us, the root issue is a problem-seeking personality. I am a prosecutor. I take the cases law enforcement brings me and try to hold the perpetrators of crime accountable. Much of the work is devoted to crafting tactics to get the evidence admitted at trial so that the jury has as truthful a version of the story as possible. The things I hate about the work are usually heaped on the failings of management, the actual work itself is often interesting and intellectually stimulating. Earlier in my life, I left a monastery where I was training to be a priest because dealing in relationships with others that focused on the mysteries of life (birth, love, death, hatred, sickness, pain) simply did not suit me. I need to see the beginning and the end of a project.

So, retirement allows one to leave the work place, with its leadership vacuum and its idiot bosses; but the problem-seeking solver of problems is going to want some to occupy his or her waking hours. And trivial problems or repetitive ones (i.e. same problem, different person) aren’t attractive. I almost wish for a crisis situation that places the problems of adaptation and survival truly at issue. That would brace the body and mind quite engagingly. Still, it seems a bit selfish and antisocial to wish for a crisis that would potentially harm some people just to make my life zesty.

Maybe I’ll just sleep a lot, like a lazy old dog on a sunny day.

For me it is not the greener gras or the reinventing what”s make me tick with new vigour.
Last three years I plunged in supporting a neighbour family of which the husband had severe brain(tumor) problems. Now he is stable, I walk with him every week. His personality has (slightly) changed and he prefers to be on his own.I get on with the two children and I have become a very close friend with their mother. Luckily she found another man to live with so my friendship with her did not grow to proportions which would spoil my own marriage. This is something I make now time for and which gave me a lot of satisfaction. It was complete new for me.
It has learned me and my wife to stay open for others, and let go (to quite a range) the idea that spouses are excluding others to be very close friends with.
I hope that my financial independence may help for more unexpected adventures.