Aha, the 'is it time to bail out & will I be OK' question!

From your brief review, it sounds as if the econ side is covered, in terms of your current needs and spending habits. And, you have another ~3yrs worth of income building/stashing, as I assume you are/will continue to work for another 3 yrs.

The part time idea from ~56 to ~62 is also good, though unless it is nailed down it may change or evolve, during the next few years.

The question of SS at 62ish vs 65, 66 or older, consumes Terabytes of storage on the net; fwiw, most of my Geezer buds all took it at 62, as none of us knows when we are checking out. The only ones that did not take SS at 62 were still employed, consulting, etc.

The health insurance issue is mainly a question of how well you are currently covered, and if any of your current plan would slide over, (other than COBRA), if you bailed at 56. I bailed at 53 in 2000, and we paid significant dough every year for BC/BS with a $5G major medical deductible. Didn't miss lunch because of the $6-$8Gs a year for our 'coverage', but it is a cost off the top or bottom. I hit Medicare last year, so our ins cost is down to $1300 a yr for me and $5Gs a yr for my CEO. But, health care costs are high, going higher by the day, and nearly unconscionable in this country, imo.

The med ins/cost/future cost is the only really vague part of your brief review...

I couldn't take another fookin day when I resigned; you may come to feel you want to work longer, a different gig, a less stressful gig, or that part time routine. My point is my CEO and I both had very good jobs, big dual income and saved like squirrels. But when we both walked early, the income stream came to a screeching halt after my resign contract was up. But, we were fed fookin up, with our careers...and 'part time' wasn't really a possibility for us.

13 yrs later, we are still fine/solid with a good sized portfolio, 2 houses, etc. But, it has taken careful planning, careful self directed investing, some luck and not getting sucked into boats, F Cars, et al.

The only surprises were 'adjustment', as in I used to be in charge of a $ Qtr Billion operation with a couple hundred people and suddenly I was 'in charge' of no one, esp the Boss of the house. And, there were some boring days along the way, even with lots of hobbies and activities...

Personally, I would do very little differently, and I am glad I have had these past 13 yrs as a RetiredBum. Hope to make another healthy 10, but as you know, none of us fookin know when our expiration date is up.

You have a good handle on your projections, but the med ins cost for the next few yrs , and then post job is a bit sketchy, (and maybe none of my biz), but Medicare is a long way off for you.

25 yr roof?! Now that is thinking optimistically!
My 50Cts...
Best Regards, mD

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Ol'UncleMotor
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The pt is rather easy for me, I have only worked about 9-10 months a year for the past ten, getting it down to 2-3 is just a matter of selecting the right jobs at the right time.

SS at 62 is so much lower than at 67 or 70 so I am not really counting on it... I'm thinking I will just spend from my savings at least until 67. Collecting SS starting at 70 would itself carry me so it is very tempted to wait till then. I am also thinking though that if the worst happened and I ended up living off the SS promised, I could also reverse mortgage the house to have a little extra. I'll have to look into whether or not I qualify.

This is the big unknown anyway you look at it. It can totally derail retirement if you get sick and must be feared (or at least worried about), but not really anything you can do about it.

I took 10 months off this year to see how the numbers would flow. I am happy to see that my numbers went forward - instead of in reverse. But this has been a great year for the stock market. But being cautious is why I plan to still work fulltime for the next three years.

I have plenty of personal (hopefully money making) projects on-line that should keep me from getting too bored, but to paraphrase you, "being free will be fooking worth it."

Thanks for your input.

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2006 X5 Sport 4.4i

Interesting blog thread....

Like many Baby Boomers, I vowed at a young age not to wait until retirement to have fun, do extensive traveling and enjoy life.
So many of us saw their parents slave away working hard and long hours at jobs, saying that they would have fun and travel once they retired. Then either while still working or very soon into their retirement they suffered a debilitating illness that prevented them from pursuing these goals, or worse yet, died at a relatively young age.
Both of my parents died at a young age, father at 59 and mother at 61.
That experience made me vow not to take my life for granted and to also plan for retirement at an age where I am still healthy.

As a 57 yr. old automobile enthusiast, my wife and I are now in our final planning stage for our eventual retirement. I would love to retire at age 60 and am working towards that goal. Depending on the value of our diversified financial portfolio once I reach that age will determine if I can afford to finally do something different. Now whether it is total retirement or working part time at some job that I find enjoyable, satisfying and stimulating, remains to be seen. I may do some volunteer work and possibly teach as well, in addition to our extensive travel plans.

Like some of the sentiments expressed by motordavid, I and many others in our mid-50's, share similar accelerating feelings about our respective workplace environment and circumstances, ranging from frustration, exhaustion, exasperation, boredom and anger. These feeling compete with our realization that most of us at our age have reached the peak of our respective career paths and recognize the reality of all the pros and cons associated with the position. While we may have experienced exciting, enjoyable and rewarding careers, both emotionally and financially, after 30+ years working, many of us are getting tired of it all and asking the important questions at this stage in life, such as:

1. Is this all there is for me?
2. Do I want to continue doing this?
3. If I want to do something different, do I have the courage to try it?
4. Do I want to or can I afford to forgo the security of a regular paycheck and employer-subsidized healthcare benefits?

For those of you who love your job(s) and look forward to getting out of bed and going to work.... you are very lucky and made the right choice for yourself.

For those of us who are in jobs, positions, professions where our overall satisfaction and enjoyment of our work may not be as strong, or at least not as strong as it once was, need to decide how much longer we will persevere before we really do need to make a change. Whether that change is making a lateral move to another company or firm or taking a different type of job or deciding to retire. I am a firm believer that if we are not satisfied with our current situation that it is up to us, ourselves to do something about it and not continue to bemoan the circumstances causing the angst or discomfort.

I also agree with the points made by Quicksilver and JCL on one's health and health care. One of the largest variables in retirement is your health and that of your partner. Whether you have and can afford to maintain adequate health care insurance before your reach the age where you are eligible for Medicare is a major concern and issue. Also, whether or not one has or can afford to get long-term health care insurance is also another important factor. It will be interesting to see how Obamacare ultimately affects costs and how it evolves and is modified to improve its deficiencies. I was originally supporting the universal health care approach and am philosophically opposed to our for-profit health care system, but do not expect that will change in my life time.

As far as motordavid's point on Social Security, my wife and I plan to hold off as long as we can before we tap into the Social Security system, I would guess that we will be 66+ when we finally do.

Also, my wife wants to continue working until her mid-70's (God bless her....!)
I support her wish to do so and look forward to being a house husband.
Finally, I look forward to spending more time pursuing my automotive passion, enjoying our M-B's and BMW's for all of my remaining years....

Finally, if you are really disappointed, disgusted, fearful and/or just fed up with the direction our country is going in, like TerminatorX5 stated, seriously consider leaving the US and relocate as an Expat to another country. There are tax consequences that would have to be thoroughly investigated to fully understand the applicable rules. Panama makes sense for the points he stated. I would also suggest considering Singapore for all of its benefits including the fact that English is the official language.

AVB-AMG

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My current & recent car history:
2020 BMW 440i xDrive Coupe (Wife's daily driver)
2016 BMW X5M (My daily driver)
2014 BMW M6 Coupe (gone)
2013 BWM 335i xDrive Coupe (gone)
2011 BMW 335xi turbo coupe (gone)
2007 Mercedes-Benz ML63 AMG (gone)
2007 BMW 335ci twin turbo coupe (gone)
2004 Mercedes-Benz E55 AMG (gone)
2004 BMW X5 4.4i (w/full Aero Kit - gone)
2001 BMW X5 4.4i (w/full Aero Kit - gone)
2000 Mercedes-Benz E430 Sport (gone)
1961 Mercedes-Benz 190SL (owned for 48 years)

buy property in Panama, transfer your monthly payouts there, get pensionado visa, import tax free household goods, car (tax free once every two years), buy into local medical coverage (excellent hospitals, on par, if not better than the US facillities, US trained docs), US currency (no exchange), most folks are fluent in english, major international port and air hub (under $300 round trip to US), super cheap living on the oceanside, rare hurricanes (they pass further up north), a lot of tax-free perks, the roads are built by US Corps of Engineers......
do not go to costa rica (too expensive), or nicaragua or belize (too poor, even though cost of living is low).
or, Philippines, as another alternative to panama...

I've thought many times about becoming an Ex-Pat... But for now I think I want to stay at home.

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2006 X5 Sport 4.4i

Divorce.

53 here. At a crossroads, thinking I will just retire now. Because I can, I guess.

To MD's excellent comments, I would just stress the health care cost. I agree that we can't do much about getting sick, apart from living healthy to improve the odds. But don't just plan for the best. I would hope for the best, and plan for the worst. Being sick, especially over an extended period, is very expensive.

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2007 X3 3.0si, 6 MT, Premium, White

Retired:
2008 535i, 6 MT, M Sport, Premium, Space Grey
2003 X5 3.0 Steptronic, Premium, Titanium Silver
2002 325xi 5 MT, Steel Grey
2004 Z4 3.0 Premium, Sport, SMG, Maldives Blue

I guess the only thing left to do is to go ahead and get the airplane built, and then drop out!

Good luck to us all as far as health goes.

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2006 X5 Sport 4.4i

At 72 years old completely. Life is based on health weather you live
in a mansion or in a trailer. Remember bad decisions regarding health or
your health care plan will affect everyone in your family. JCL is right.
Plan well and live healthy. The quality of your retirement depends on it.

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"What you hear in a great jazz band is the sound of democracy. “The jazz band works best when participation is shaped by intelligent communication.”
Harmony happens whenever different parts get to form a whole by means of congruity, concord, symetry, consistency, conformity, correspondence, agreement, accord, unity, consonance…….