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What's the sorriest situation you've known of someone who couldn't retire?

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swampwiz:
What I mean here is that someone whose situation is that he can't possibly think about early retiring.

I'll start.  I knew a guy (early 30's at the time) who had 4 young children at the time, all from a fairly high-maintenance wife (stay-at-home at the time), who had just rolled all his savings into his McMansion in California's Imperial Valley (I think it was Moreno Valley) in early 2007, and still with about $50K of student debt (instead of paying that down, he had built up his savings to buy a $550K home in what had been "the hottest real estate market around".  He said that he absolutely could not lose his job (aerospace engineer), so he made sure to be the hardest working, boss-supplicating corporate peon at work - and totally miserable - so that he would be at the bottom of any layoff list.  He said that he could see 20 years in the future as when he could start to "sock away retirement cash".

wageslave23:
This is going to be the most depressing thread ever.  I don't know if I can think of a more depressing situation than a person who hates their job and has no way out.  The Million Dollar Baby of threads ;(

EconDiva:
Not sure why the person in your example couldn't find a way to retire...if that was 2007, it's 10 years later so any updates?  Did they change anything/start thinking about retirement?

Not sure if you want examples of people who claim they can't think of retiring early or people actually in situations where they cannot retire early (i.e., 68 years old with no savings, tons of debt, no pension, high recurring monthly bills, no job, no education and no spouse or family to help out would be the kind of situation that comes to mind).

Khaetra:
My neighbors.  Very long story short, he's an alcoholic who could never hold down a job and she works in a grocery store (neither have any kind of education).  He wrecked his car while drunk so he's on house arrest, she has to get rides to work because her car is broken and they don't have any savings.  The only saving grace is they don't have a mortgage but they have no health nor home insurance and they have legal and medical bills (he's had two minor strokes).  Neither of them are even 60 yet.

Chrissy:
I'll play:  a lady who's marriage had been tumultuous and, at times, abusive for 40 years (they married as teenagers).  She raised the kids/ran the house with no help from him while getting her first job AND multiple side-gigs, two degrees, and some tough certifications by the time she was 30.  The eldest was ~12 when she started making good money, but husband was a spender, so they saved NOTHING.  She wasn't too worried, though, because her father promised her a big inheritance (MILLIONS, he said).  But, not a penny if she left her husband.

Each and every one of the kids were high-performers.  They left for college, paying their own way.  She and her husband were in their 40s, making the best money of their lives.  She saved some and invested, but he developed some expensive tastes in liquor and cigars and a gambling habit.  The inheritance arrived in their very late 40s, but it was NOT millions.  By this point, the husband was accustomed to spending $5,000/mo just on the aforementioned recreation. 

She's still working today, and still married, 10 years later, a grandmother, almost 60, no retirement in sight.

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