This is always a tricky subject. I've seen people that have worked hard to have a stable financial future, never took time to really enjoy life, then died early. I've also seen others who never really had a good job because they were following their dreams and had to rely on others to support them in their old age.

 

While money can't buy happiness, the lack of money can quicky lead to misery.

 

That is a tricky one. Always planning on a future that never comes versus living-for-the-now but ending up broke at the end. What to do? We need crystal balls.

I like your statement about lack of money quickly leading to misery. So true.

Another factor would be whether one's work is meaningful. Will you be able to look back on your life and say that you did something meaningful with it? Some jobs seem so pointless that I wonder if I could do them even if it meant more money.

This is kind of tangential but I recently read an article about a man who retired in his 30s by learning how to live and support his family on a $2000 per month tight budget, income entirely from investments. The article made it sound like that was a good achievement but I saw it differently. What the hell would you do for the next 50 or 60 years if you lived that long? Could you look back at the end and say you lived a meaningful life? Or, would you look back and say that you didn't really contribute to society in any way, that you just coasted through it?

I've been trying to find the link. Hold please, I'll keep looking...

Interesting, but I don't want to live like that. That story would do nothing but encourage me to keep working.

What happens if his rental house ends up vacant for several months because the rental market gets saturated? If that happens when the stock market is trending down, he has NO INCOME. It's a pretty flimsy plan.

 

Those thoughts went through my mind too, but he's being presented as some sort of financial guru. Maybe I missed it in the article, but since he's self-employed (if you can call it that) does his family have health insurance? Are they not covered? If one of them needs surgery are they totally focked?

Another good question. He's not buying health insurance out of his $2000 per month income stream. Social assistance? I'm sure he would probably qualify.

My 6 yr old, in the midst of a tantrum this morning, said "I don't have to brush my teeth.  I don't have to do things I don't want to do".  DW of course went into the ole speech about all of us having to do things we don't like.  So I chimed in and said "ok that means I don't have to work anymore...but...that means we will have no house to live in, or much food to eat".  He's only 6 so I don't expect him to truly "get it" but it was true.  I would certainly rather be doing other things.  There has to be balance to working (in order to make money in order to live) and spending time with family.

And about the identity being what we do for a living: while I agree that shouldn't be our identity, it often is because we spend so much time doing it.  I literally spend just as much time (if not more) with coworkers than I do with my family.

About 38 yr ago (Jan 1975), I quit a reasonably good-paying job to go back to school and retrain in a different profession. I was in late 20s, no dependents, but also no alternate income-maker. This was back when jobs with big industry were usually stable. My parents freaked out since they grew up in the depression - you just didn't quit a job because you didn't like it.

I was in an office job with 2 wks off a year for the first 5 or so yr, iirc. Weekends were 6 hr drives either north or south to get to mountains, vacations were cross-country drives (east coast to Rockies), backpack for 10 days and back again. I wasn't sure how or why, but I couldn't see myself retiring from that company so decided to jump ship before I had much invested (about 5 yrs). I drove cross country in my Gremlin with most of my earthly belongings (read: hiking and backpacking gear) in early January to enroll in Colo State.

Spent 5.5 yr in school retraining as a vegetation ecologist, and stumbled upon a job announcement for a vegetation job in Alaska - a location that was beyond my wildest dreams. I got to hike and spend a lot of times outdoors - under many kinds of weather. I didn't start more structured running until I was close to retirement. (frustrations with one project drove me to running). There were rough years trying to get grants funded, but I could live on 50% of my yearly salary. But 90% of those grants and contracts were projects I enjoyed and felt I was contributing to knowledge up here.

I don't need a lot to live on and generally don't carry debt (except house, which was paid off early).

Retiring doesn't mean stopping doing productive work. It just means you start drawing funds from a retirement fund (your own or company's defined benefit) and volunteering your time. I really enjoy volunteering with trails - either building, maintaining, or working with a new foundation. The standing joke around here is that volunteers are more busy than when they worked.

Our local borough (county) is about the size of WV, has about 2000mi of trails, and a couple full time trails people and maybe 5-10 summer or half-time helpers. Volunteers are critical to our trail system up here.

Long-winded way of saying that, yes, I'd take a lower paying job to do something I enjoy.

MTA: The other part of the story is that I had been working for Bell Labs - before AT&T divestiture. Glad I jumped ship when I did, but I was too young and ignorant to foresee what divestiture might bring for employees, so that was definitely not the reason. (it actually brought a lot for the few shares of stocks I'd gotten there in 1974, a low point in stock market)

I think John M. spends a lot of time helping on trails - way more than many.