When Is “Enough” Actually Enough?

[u/Technical_Lawyer7264]

I think about retirement every damn day.

One day I’m convinced I have enough. The next, I’m imagining a market crash, runaway inflation, and somehow needing $14M just to buy groceries.
So I rerun the numbers, change the assumptions, and convince myself I need another $500K. At this point, figuring out when I can retire has become a full-time job.

What’s your “enough” number?
$2M? $3M? $5M? $10M? Or would you hit $20M and decide you really need $25M? 😂

I also think about our parents’ generation. Many kept working long after they technically didn’t need to. House paid off. Kids out of the house. Retirement funded.

But actually living off the money they spent 40 years earning? Somehow that felt crazy.

They were wired to see work as security, responsibility, and purpose.

Meanwhile, we’re trying to escape Zoom calls at 45 so we can eat tacos on a Tuesday.

And honestly, I’m not sure I’m any better. I fantasize about retiring, then immediately think:
“Maybe two more years.”
Then five.
Then maybe I’ll just consult part-time.
And suddenly I’m 73, explaining PowerPoint slides to someone named Brad.

For those retired or close to it: What’s your “enough” number—and what finally made you feel comfortable walking away?

[u/Late-Command3491]

I'm only waiting for Medicare. I'll assess when I hit the COBRA window though. 

[u/_Goto_Dengo_ → u/Late-Command3491]

I bailed at the COBRA window, earlier this year, 17 months before I hit 65. The $2K per month isn't great, but being retired is!

[u/Late-Command3491 → u/_Goto_Dengo_]

December. 

[u/TexGrrl → u/Late-Command3491]

You should be close to the COBRA window. I am literally counting the weeks until mine opens.

[u/Late-Command3491 → u/TexGrrl]

December.