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Old 12-10-2020, 06:14 PM   #61
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For me, winning the game means I achieved FI, actually RE, and then get to enjoy the fruits of my former LBYM lifestyle for at least 20 more years with reasonable health. Achieving FI, only to have a chronic health condition or accident happen, means your success was very shortlived.

I have a multi-millionaire friend who was living in the SF Bay Area, making tons of money in commercial real estate sales. He was all set to retire, and BAM! His car was broadsided, and he ended up with two steel rods in his lower back. He won the financial game, but that one accident reduced his later quality of life.
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Old 12-10-2020, 07:23 PM   #62
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I felt I had "won the game" of life back in 2000 when my daughter (only child) was born. Every minute since then has been awesome.
Financially, the win came earlier this year when I had the confidence to walk away from the office lifestyle at 59 1/2 knowing that we would be fine and our daughter would have a safety net for her life also.
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Old 12-10-2020, 07:31 PM   #63
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Must be Lake Woebegon
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Old 12-10-2020, 07:53 PM   #64
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I feel I won the game when I was born in the United States. No matter what somebody's situation or circumstances in this country, there are countless stories of success.



I feel I won the game when I arrived in this great country (legally, as a scholar) even only with less than 100 bucks in my pocket.
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Old 12-10-2020, 08:02 PM   #65
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At what point has one "WON THE GAME"? Interested in different perspectives, as there have been a few people who have posted that they 'won the game'. Everybody is different, but what is the minimum?


My minimum - everything paid for, retired, minimum 10k/month coming in off investments/pensions.
I’ve “won the game” when I pass without having run out of money.
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Old 12-10-2020, 08:50 PM   #66
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I first felt I was winning the financial game when my annual passive income exceeded what I saved with 3x summer jobs during my jr year in college. I w*rk my tush off to save $3500 that summer of 90, and when I saw my investments made more in interest in a year, I felt a great sense of accomplishment. I think this happened about 97.

big wins when I hit 20 years to vest in a pension at work in 2011. cracked the $1mn barrier in investments in 2014. by this time DW and I were lean FI.

won when we received enough passive income to live comfortably and RE in 2017.

I know nothing is ever permanent, so I am grateful and enjoying life today and looking forward to tomorrow.
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Old 12-10-2020, 10:14 PM   #67
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In comparison to many of our co-workers who have no plans/hope of retiring early, if we can get out the door before 65 years old, we are winning the game.

My own opinion on my situation, is to have my wife (also 55) retire in about 2 years, and me to retire at 62 when I can take SS early, with my pension as well, and we have enough to travel, and spoil the grandkids.
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Old 12-10-2020, 10:21 PM   #68
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Mega-corp offered a buyout 5 years ago and at that time I strongly considered taking it, but my end analysis was I wasn't ready, I hadn't "won the game" yet. At that time I had about $1M saved and qualified for $2K/month in pension. I was 56. I was sort of bummed because conventional wisdom was there would never be another package offer.

A year ago mega-corp announced a sale of the asset I worked at, and made another, quite a bit better package offer. The terms were I had to stay on an additional 10 months, which almost exactly coincided with my planned retirement date. I left with a package that put me comfortably well past my "won the game" finish line. I'm not superstitious, but I have a feeling someone is looking out for me, or at least they were with respect to my retirement planning.

One thing I experienced was the acceleration towards the "won the game" finish line over the last 5 years. The combination of kind markets, high end-of-career savings rates and the years of life being used up made the finish line rush forward and ultimately I blew past it.
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Old 12-11-2020, 04:22 AM   #69
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My most recent "winning of the game" would be this year, when I claimed SS at age 70.
Together with my pension/annuities, I seem to have enough income that I have an excess to invest every month.

Now a lot of this excess is because travel plans have been cancelled since March.

I retired in 2013, so for seven years, I did monthly withdrawals from investments in lieu of SS.
So I had very modest Sequence of Returns Risk.
But now I'm through with that, so I win...
Good deal!
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Old 12-11-2020, 04:38 AM   #70
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when I had enough stash so I could leave my "mind numbing" job at Megacorp last year at 64.
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Old 12-11-2020, 08:21 AM   #71
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when I had enough stash so I could leave my "mind numbing" job at Megacorp last year at 64.
Everyone has their breaking point. Sounds like your mental health was worth more than your j*b.
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Old 12-11-2020, 12:48 PM   #72
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The first time we 'won the game' was a few years ago when we had 30x our expenses saved (less pensions and SS) for retirement. At that point neither of us were eligible to retire with our full benefits. Maybe we actually won the first time when we decided to take jobs with pension benefits even when we started out earning much less than our peers.

The second time we realized life was going to be OK (can't say we won anything for this) is when DH finally was awarded his claim against the VA and was granted disability pay. He suffered for decades before getting that claim paid. The extra money will help us ensure we can give him the best care for the rest of his life medically and hire people to help us for home maintenance, lawn care, etc.

The third time we won the game was when DH finally told his supervisor that he will retire on January 31. Due to his health issues he never thought he would be able to complete his career and get full benefits.

The fourth time we will win the game is in May when I retire. We never expected to have this much 'winning' in our lives. We got married and immediately started saving but with DH sick we always were waiting for the day things may not work out. We kept working hard at our jobs despite the obstacles and there were many. We decided to balance saving vs spending money on travel while working and while healthy enough to do so. No regrets at all Somehow it all worked out or it will in May!
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Old 12-11-2020, 01:58 PM   #73
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$0 mortgage, $0 Debt (no car, credit card etc.), 1 Yr savings, $5K/mo off investments.
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Old 12-11-2020, 06:35 PM   #74
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I will win my race, when I have lived “extremely” large off my pension + SS + savings *and* I leave $1,000,000 to each of my 5 kids.

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Old 12-12-2020, 10:49 AM   #75
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When I hit FI in 2004 2 years before I retired at 48, when my passive income (stock dividends) exceeded my salary (adjusting for health insurance, 401k contributions, etc).
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Old 12-12-2020, 02:48 PM   #76
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Hmmm, well, if winning the game corresponds to FI, there have been little "wins" / goals met along the way.

FI (for me) means no debt, and (reliable) income to cover needs, and some wants.

What exactly constitutes "reliable" is the gray area . . .
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Old 12-12-2020, 04:28 PM   #77
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For me winning the game came in 2015 when evil megacorp decided to stop tormenting DH and let him go. I looked at the numbers and realized that we had 25 times expenses and we were okay. We're more than okay now.
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