I am approaching age 50 and become eligible to make “catch up contributions” into my 401k. But if it looks like I will have more than enough to fund my retirement needs, is it in my best interest to try to avoid the tax man or to accelerate my retirement date?

There is a magic formula.
Income in retirement = pension + Social Security + 4% of your portfolio.
When that is more than your income needs, you are all set to retire.

No need to overthink it.


FWIW, when we recognized that possible retirement was coming soon, we totally maxed out our 401K & IRA contributions. To the extent that our takehome pay took a nosedive for a year.
Well worth it.

I was able to snag the best way to retire. I smelled a layoff coming and told my boss that it it happened, I wanted to volunteer. So I retired with a handsome layoff bonus amounting to 1 year salary. AND could get the pre-65 post-retirement health insurance package.

We planned to file for SS at 62, because we know how to do math, and knew the bit about bird in hand. But we had a few years before 62. A payback period of 11 years is a bad deal. The utility of extra money is much more beneficial in the early years before your body starts to run down.

I initially delayed taking the company pension because, like SS, each month of delay bumps up the monthly benefit.
But then I ran the math, and saw how long it would take to breakeven with the small monthly increase vs. the ~$2500 foregone monthly. So I filed for that in a couple of months.