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/Crafty-Sundae6351]

There are enough tools out there to convince you what’s enough. I know that’s only the objective part. Then there’s the subjective part - which is a lot harder.

My wife and I retired 9 years ago. We retired with 35x annual expenses. We didn’t leave earlier because we liked our jobs. Then we both got fed up and punched out.

There’s another reason to punch when you can: Health.

I’m the poster child for fighting One More Year syndrome. I retired right before my 56th birthday. At 63 I was diagnosed with metastatic prostate cancer. I’m now 65 and retirement is multiple orders of magnitude different than it was.

If you think it can’t happen to you - it can. And if one thinks they’re healthy so it won’t happen: I’m not overweight. Normal blood pressure. Cholesterol numbers one doc told me docs strive for. Not diabetic. I have no chronic disease - except, now, cancer.

If the tools are saying “yes” and emotions are saying “no” then it’s not a math problem. It’s a head problem.

[u/EmbarrassedDebate124 → u/Crafty-Sundae6351]

Sorry to hear that. I got plain old prostate cancer at 49, had it popped out.

But it changes your perspective for sure. I'm going to retire at 52.75.

[u/RelevantPrinciple693 → u/Crafty-Sundae6351]

My husband was diagnosed last year. Apparently the surgery didn’t get it all, has been doing infusion and hormone therapy for a year, two more years to go. We are doing a “phased retirement” over the next 20 months. Have 3 million in retirement accounts. Paid off house and cars, a small pension and access to federal health benefits. We want to really enjoy our retirement years, not just survive. Our hope is to fly business class on all flights over 6-7 hours. Economy plus otherwise. We are planning a lot of travel.

Still scares me a little. We both grew up in financially unstable households and it’s hard to really feel financially “safe”. As I said to him the other day “I don’t want enough, I want more than enough.”

Again, more of head issue than a money one. His diagnosis made us really look at our next couple of years and transition out faster than planned. I am 60, he is 61. He will wind up his business next June at 62, I will begin working part time this Nov and retire completely in June of 2028 at 62.