I am more and more getting irked by the "should not have worked so hard" crowd, or to be more precise, the ones that go "just quit and go backpacking". Great if you're young, wealthy and have a good social safety net (read: rich parents), not so much for the other 99% of the population.

I tried it once, going out of my comfort zone to do the backpacking thing, but it just wasn't for me. I'm not very social, have trouble entertaining myself, and end up spending a ton of money on food, drink and entertainment just to not be alone with my thoughts too much.

I agree. I did it towards the end of 2019 and completely torpedoed my life.

Because of COVID I didn't even get to do much actual hiking or backpacking as I planned; I went out to the west coast and everything shut down basically as soon as I got settled in.

Then I had a couple of deaths in the family due to COVID. The nest egg I had built up for the trip would have been really helpful, but I essentially wasted it to sit in an apartment. Now I'm searching for jobs nowhere close to where I was at because my industry took a massive hit.

Life's a dice roll. Hedge your bets.

I must respect your karma, but I'd wager you'd find something you're not expecting if you addressed the social anxiety, addiction, and chatty mind you allude to here (I understand you will probably object to these characterizations).

Some people take the state of their mind as a given and structure their life around that. Others learn that you can change your mind.

My experience is that the latter leads to profound riches. But then, I failed at the former.

That seems like valuable perspective. You are not one who likes to be alone with their thoughts too much. What's the version of quit and go backpacking for someone like you?

My brother did the same thing and like you did not enjoy it. He thought it was too boring without another person. I havnt dont it but I'm very comfortable with really limited social contact and live in my own thoughts. If I had two good knees I'd likely take some type of break to try it out.

Agreed. I've travelled a lot with my wife (We've been to 24 countries). I enjoy travelling with someone. A few times, I travelled alone... it's kind of boring alone. There are lots of people who say positive words about travelling alone like "empowering", "liberating"... but I didn't find that at all.

I'm equally as content during my travels if I'm alone or with another person but I do find that going with someone else tends to create stronger memories.

I went to Europe with my father and brother and remember those trips much more than ones I've taken on my own.

Quit and keep busy? i.e. quit and volunteer.

there are a lot of ways to "not work so hard" other than "just quit and go backpacking". I share your utter lack of interest in backpacking. to me, "not work so hard" means picking a good job, but not the most ambitious one possible. it means closing my IDE at 5:30 and finishing that last bug the next day. this leaves me with more time and energy to spend on non-work-related people and activities that I value.

and in a way, I suspect that backpackers and intense travelers have traded one form of "working too hard" for another. "making the most of your youth" is a FOMO perspective. I prefer to focus on appreciating what I already have.

The "I should not have worked as hard" deathbed quote has always bugged me. There are plenty of people who think they could have been more or done more. It's not a perfect example, but there are plenty of "Walter White"s who taught high-school science and think they were capable of so much more.

I find it is happening among some women I know who chose to stay at home and now, as the kids are getting older, are thinking about what they could have been. It's a harder choice than people realize.

I had a friend who said her tombstone would read "She had potential".

I feel like people often regret not taking the risk to go work (hard) on something they find meaningful.

Not sure if as many regret that they didn't put in the extra hours to get to the next level in a big corporation.

I think there are people who do regret not getting to the next big level. They thought they could have been a good (software) architect or director or principal, they thought they could have really made some lasting difference, but instead they were a cog their whole lives.

Success is important, feeling successful is important. It can be hard to be happy with "good enough".

Good reading on the topic of doing great work and fulfilling that potential you reference:

http://www.paulgraham.com/hamming.html

Just read it for the first time yesterday and plan on doing so many more times in the future.

"I should not have worked as hard" is an attempt to make people who work too much now to engage more at home. I honestly doubt this is a thing dying people say all that much. Frankly, if they valued their family, they would spend more time with them years before.

Arguably, being "authentic" in many ways covers this

I think it's more of a way to gain perspective on your life now. E.g., imagining what would be important on your deathbed is an exercise that can help you figure out what you think is important in life.

I have a lighter version of this: on your deathbed you'll regret the roads not taken.

If you spend your life as a family person, you might regret not making an impact on the community/the world. If you spend your life chasing impact, you might regret not enjoying family life. If you spend your life chasing money, you might regret either. Etc.

Either way, you'll regret something, so it's not a good source of insights for those who are still alive.