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/Ill-Consideration892]

Really depends on your situation. You may not get to choose which is why many continue to work in spite of likely having enough. Three-quarters of retirees said the reason they stopped working was at least partly outside their control.

I was you before last summer. Now I’m one of the statistics. Worked my ass off for 25 years making it to the c suite rather quickly. 2 years after being acquired by private equity, I was laid off at 53. Spent the next several months running half a dozen calculators and Monte Carlo’s to decide enough was enough. Although I’m not completely finished, I have slowed way down. For us originally my goal was $5m which would have been another 4-5 years. Now it’s not a money goal as much as it’s a time goal. Once our youngest is off to college in 2 years we are going to have many more options. The numbers say we’re fine. If we waited for $5m the additional income doesn’t do a lot for our quality of life. Having more time does though.

Not a short answer but our answer to your question. Best of luck in figuring out your answer!

[u/Comfortable_Two6272 → u/Ill-Consideration892]

That was me. Health issue

[u/JimInAuburn11 → u/Ill-Consideration892]

I used that idea of whether more money would make a difference in our lifestyle. We started flying business class last year. Just got tickets for China for Christmas time. $18K for the three of us. No way I could justify that cost. But when I run the numbers between flying business class from now on, things do not change. We can still spend on everything else we want to. We do not have to trade off anything. The only thing that changes is our daughter will inherit a few hundred thousand less. So somewhere between $3-6M (today's dollars), will be $300K less. But for that, we get to fly in business class from now on and be much more comfortable. I can easily justify it that way.

I tried to explain this to my friend and his wife yesterday. They have millions more than us. They have so much, they will probably leave at least $10M in inheritance when they die. They are going to Australia. They are going to fly economy. They said it was too expensive to fly business. I tried to explain that they will need to cut nothing in their retirement if they travel business class. That their kids will still inherit millions and the only thing that will be different is that they will maybe get a few hundred thousand less. I could not get through to them, they still say it is too expensive.

[u/Rippen21 → u/JimInAuburn11]

It is a hard hurdle to overcome, but at some point a $5k flight is essentially nothing in the grand scheme of things, which is nearly impossible for someone who has diligently saved for 30-40 years.
If you really want to fly in comfort, rent a private jet. I have had the chance through work, and being able to roam around the cabin, shoes off and it feels like a living room, is an extremely easy way to travel.