When have I achieved the goal?

I've been grappling with the 'when is enough' question for some time now. I got a late start in the retirement savings game, then did poorly at it for about 10 years. Not much to brag about, actually. I got serious in 2007, just before the crash, so I have had 6 years to repair the damage of 12 years of relative neglect during my working life, and about 12 additional years of graduate and post-graduate education, when I didn't have much money to invest. I'm not complaining, mind you. Since age 37, I've been maximizing my pre-tax deferral for 16 years. The first 10, it amounted to little more than a savings account.

So here I am at 53 years of age, wondering how the horse-race to retirement is looking. I'm at the back of the pack, in the back-stretch. I either plan to switch into another gear, or accept a retirement that is more modest than what would have been possible, had I practiced what I now know from the first day I set a dollar aside for the future.

On the one hand, I can continue working as hard as my energy allows, keep socking away as much as the law and my budget allows,  and hope my health holds up. Or, I could plan an earlier exit, have more time to do other things of value  and accept that I won't have banked as much security by choosing to turn towards other interests. Now there's a dilemna. I can't get those years back, once I've spent them. Some years in the future will be bad years, from an investment standpoint. There'll certainly be some more hard times. Inflation will rear it's ugly head. Another world financial crisis will sweep across the landscape, on the heels of the last one. Just like hurricanes and flu epidemics, these financial ailments are part of the human condition.

What did my parents and grandparents experience with respect to their golden years? One grandfather died in his 40's, probably of a glioblastoma. A grandmother died in her 70's of diabetes. One grandfather had a very modest retirement as a widower, died at age 83 or so, demented. The last grandmother also had a modest retirement, died at age 87, perhaps, also demented.  They left behind a house, each couple, and a few thousand dollars.

My father worked like a slave, died at age 64, just prior to scheduled retirement. My mother is in the latter phase of a comfortable retirement, but much of it was spent looking after my disabled sister, who died when my mother was about 80. My mother ended up being worth about $2 million, between properties and my father's retirement savings. That's a big step up from the last generation.

At the rate I'm saving and investing, my wife and I may have more than that, but with inflation, we'll be in a similar position as my mother, perhaps. Comfortable, but not rich by any stretch of the imagination. My Mom's estate will split between 4 heirs, and that will add substantially to our wealth. My portion of that, which will accrue to me sometime in the next 15 years, will add perhaps 20% to our expendable resources.

Our estate will pass to a single heir. Depending on the stewardship of the estate, he could be wealthy in his later years, purely on passive income.  That's dirt poor to rich, in 4 generations. Not a bad story for an American family. I'll have to attend to the terms of this transfer of wealth, to assure that youth and indiscretion don't cause it to be squandered.

For my wife and I, we'd like to have the energy, the health and the money to do more in our retirement than sit around eating, reading and paying bills. That means using the time while our health persists to do things that others might not do. Perhaps it means starting earlier than some others, so the energy to do those things will be there.

This will take some life planning, as my son is 9 and he won't be independent for another 15 years.
If we were to wind up our current lives, leave our retirement funds in moderately managed portfolios, head off to the hinterlands to do God's work, we'd come home in 10 years to an income stream that would moderately support us into our later years, provided no global meltdown occurs. Were we to retire in a low cost country, we'd be very comfortable.

The biggest question is; why continue what we're doing? Why the big house and big mortgage? Why the 60+ hour work week, the stress, the wondering if I'll drop dead before salad time?
Well, I AM afraid of boredom. I am afraid of being confronted with the task of actually doing all those things I have thought I might do, were I not too busy. It's easier to dream about a bunch of them than to actually go out and try to accomplish them. There's alot of me that says: don't abandon my partners, to whom I am obligated and they to me. Probably bull@#$%, but still a powerful mantra in my subconscience.

I have a friend running for US senator. Now, that's definitely NOT an adventure I'd like to embark on. On the other hand, I'd like to do something that makes a big difference for someone who can't make it happen for themselves. I don't mean fixing people one at a time. I want to change life for the better for a lot of people. That would make me think all the effort was worthwhile.

I think I'll have to find an adventure that means I still work hard, at something I'm already capable of, in some place where the need is great and the hassle factor is low. That may mean medical missions, or some other non-profit endeavor. Right now, I have to put myself in a position where there aren't roadblocks, competing obligations. I have to get out from under those mortgages. I have to adequately replace myself so if I leave, my partners don't unduly suffer. I have to have a place to come back to now and again to recharge the battery, so to speak. Gotta figure all that out.
In fact, I think there's enough money in the bank. There are also too many bills.