Give Now or Give Later?

For me, it's 'Give later' for the most part. My mom's care right now is costing my dad $410 per day. My long term care "insurance" will likely be what is left of my portfolio.

For me personally, valuing the security of a robust safety net would take precedence. Neither answer is wrong. You don’t necessarily need exact numbers or a percent of your wealth, but can give a little more in Up years and less in Down years to the extent you feel comfortable.

Thanks for the shoutout @espamer. This is obviously such a tough question to answer. Not tough in the sense that you have already made an obligation to give and help others, but that you are trying to maximize the amount you give over your lifetime, while also ensuring you don't run out of money. That IS scary!

Chances are, if you do a series of monte carlo simulations, there's a small chance you end up with $0, but there is a very real chance you have 7 figures when you die. We just don't know what the market will return to you assuming you stay within a reasonable SWR. And also, we don't know how long you'll live! As such, it's pretty hard to optimize giving "it all away"

For me, there is no single plan of attack here. It's all about iteration. I'd say two things:

(1) I love that you are planning to give most of your wealth away upon your death. You can look at this bucket as an "Invest to Give" bucket a la Benjamin Franklin. Perhaps you are feeling a built guilty that you're hoarding money for yourself now, but if you can adopt the viewpoint that there could be better (or even just impactful) opportunities to give down the line and that you'd have more money to give because it's compounding, then it's a opportunistic way to look at it.

(2) Re-evaluate your current giving plan each and every year. Perhaps it's 10% this year, 11% the next, 12% the next -- see how your portfolio is doing. If the wealth pledge is scary, try starting with 0.1%, then 0.2%. (BTW is there a chance that your income pledge is comparable to a 1% wealth pledge already?)

I also like the idea of being very proactive and giving larger amounts when the markets are outperforming your 4% expectations (e.g. guardrails). This is a no brainer to me.

First off, this is great of you, and a great problem to have. What percent of your overall are you using for your own purposes? and what is your expected horizon? If say 3% for 30 years, you could easily continue to give another 3-7% of your investments (not just your income) and wind down over time / down years.

My main question, is there a specific charity or situation you want to help solve? If not, then I wouldn't just give away all now if not something you're passionate about. So figure that out first, maybe donate your time to a few organizations, attend fundraisers, hear some stories...

Once you have that you could easily take 25x your expenses (4% withdrawal conservatively) and give the rest away now to truly help. Or break this extra portion into chunks over the next 5-10 years.