I don't think I will ever retire

This too for me. My husband and I are on the hook for our son’s private student loans. I’ve mentioned in many other posts that my son died after battling cancer. He was diagnosed 1 week after college graduation. We are co-signers and now have to pay up. We won’t be done paying for years.

I posted upthread that I like getting up and going somewhere every day, which is true but the financial boat we’re in is also a huge factor.

Certainly that describes my (and many other’s) 2020 and likely most of 2021.

I’m sorry to hear that.

We took out a life insurance policy on our daughter for that reason.

I retired 6 months ago at 61, and have generally enjoyed myself. There are challenges that need to be met, mainly how to fill the day and stay physically active.

I do have days when I do next to nothing, and I sometimes feel guilty about that, but less as each day goes by. The worst thing would be to just sit day after day.

Retired 18 months ago, and I can confirm this is the most wonderful part. I’m a “wanderer” and enjoy just meandering around places to see what’s there. Although I’d been considering it for a while, I decided on the spur of the moment to leave Tuesday morning – and drove away. Got back last night after a few hundred miles of exploring. Might go again next week, might not. I’ll know when I start packing my bag.

And this is the other wonderful part of retirement. My income is not related to my behavior. The checks come whether I’m sleeping in, or busy and productive, or camped by a shoreline with a fishing pole. It doesn’t matter where I am or what I’m doing, I get paid twice a month just like before.

To each their own, but I need “structure” about as much as I need a hole in the head. Living without it is like being a kid, but with a driver’s license and a credit card (H/T to @LSLGuy for this reference).

When I was 28 or so (a long time ago), I had a 3-4 month period the summer after graduating business school where I had already quit my old job and was waiting for my new job to start. It was fantastic. Sure, the first week I felt kind of weird going from a full-time job plus 2-3 business school classes at night to 100% free time. But I got used to it pretty quickly. It was nice having the free time without the stress of having worry about work or looking for a job.

I had a similar experience recently when I was laid off from my last company due to COVID-19. Obviously it was a bit different with the pandemic an having to look for a new job. But we had my wife’s income, plus I have money saved up and received about a half a year’s severance in cash and stock.

Point is, I have no trouble enjoying my free time. Plenty of shit I’d would rather do that have a bunch of conference calls or email douchebags about some business thing I don’t really care about.

My only concern with retirement is that, even though I’m healthy and in good shape, retirement tends to happen when you are “old”. Like, great that you have all this time to do stuff, but there’s a lot less stuff you can physically or mentally do.

Which is exactly why you need to do stuff right away after you retire, and not wait. Anything can happen. Driving around the country and staying in NY for a month was on my list, and I was glad we did it before Covid hit.
Retirement planning guides sometimes have you budget for the same amount of expense every year (after inflation) but in reality as you get older there is less to spend money on. My father spent almost nothing in his last years.

I would take it a step further and not wait to retire to “live your best life”. You don’t want to be one of these a-holes who works 100 hours a week only to get hit by a bus the day after he retires (what I like to call “retirony”).

Or at least a good life. (No best life even includes commuting.) When I was at Intel one manager was famous for missing the birth of one of his children because he had an important meeting. I doubt that kept him from getting axed when the time came.

I’m only 44, but I have friends who are appreciably older than I am. They are stark reminders of how I need to get things done and goals achieved now when I still have lots of energy and stamina, and not wait until I’m 64.

Eight and a half years ago, I got the chance to take early retirement from my senior management position
at age 55. I took it, we moved to a different town, and started an art gallery to show (and occasionally sell) my wife’s paintings and increasingly also my photographs. We only open when we feel like it. I think we found the right middle road between full-time work and ‘nothing left to do’.

I thought I was going to retire on February 1st. I haven’t done it yet. Purely financial concerns at this point. My girlfriend who is 11 years younger than me is going back to school to be a nurse and I am waiting to see what our new contract looks like. I may want to stay for a year if it’s a good bump in pay. It’s certainly not because of the work or worry that I will be bored. I’m 53 and life is too short to waste it working.

That sounds cool! Good luck to you.

I totally agree with this. My dad was an extreme workaholic and provided a great counterexample for me. I certainly worked hard and would work the occasional crazy long hours to meet a deadline. I also traveled the world and went to well over a thousand concerts. In 2019 I went to over 90 shows. I planned to break 150 in my first retirement year which is my retirony but times will change.