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It seems like you get a lot of your feeling of meaning and contentedness from social interaction. From what you’re saying about how travel, projects, etc don’t seem as fulfilling anymore, it really seems to me like you have some depressive tendencies.

I’m not a doctor, but just as a friend, I think you should really try to think of dealing with that existential sadness as a priority - not as an annoyance. Spending real time and energy towards improving your mental health could have real impact on every other aspect of your life.

2 books I recently read that point to social connection as essential to meaning and well-being are Lost Connections: Uncovering the Real Causes of Depression – and the Unexpected Solutions by Johann Hari, and Tribe: On Homecoming and Belonging by Sebastian Junger.

Do you have any recommendations for dealing with 'existential sadness', as you put it?

Seconded! This post sounds a lot like me a while ago, and depression was definitely a factor.

> found it mostly extremely lonely to travel alone. Got sick of seeing the same things (this place's contemporary art museum, that place's famous church). Of course I saw some amazing things but I now think I agree with some happiness researcher who claims travel is best in short < 1 week bursts every few months.

If you don't make accidental friends and events on your travels, they'll become a chore. Learned it the hard way. I travelled, was fun, then learned to avoid the accidents only for traveling to become lonely.

How it works?

- Try hostels (there are hostels where you can get your own room).

- Starbucks and approach anything (same gender, other gender, different gender, animal?)

- Go to random events

- Avoid online tools (like tinder and such). They are a waste of time. Most of the woman expect that you are there for a quickie and have their guards up. Most people turn their guards off when the interaction is "natural".

- Avoid approaching in touristy areas. They are usually for groups, couples, family, etc... leads nowhere.

edit: also don't decline to talk to people you are otherwise not interested in. Most of my interesting interactions started this way. Talk to this, invite me to party, go out together, find new friends, etc...

You won't remember the monuments but you'll remember discussions and human-based interactions.

I spent most of the last 5 years in Tokyo + traveling, mostly not working. Too bad we didn't run into each other. Happy to chat, have some suggestions. My email is in my profile.

Paul I think you've forgotten that you've removed your email from your profile. ;)

Pick up the guitar like I have been doing. I even wrote a quick article on how easy I’ve found it:

https://www.linkedin.com/pulse/learning-play-guitar-jay-paul...

Yup I picked up the bass guitar - incredible how quickly you can play most songs after half a dozen lessons and songsterr.com

>I agree with some happiness researcher who claims travel is best in short < 1 week bursts every few months.

Got a link to that?

I'm also interested in this because a lot of nomads (especially levelsio) think that staying somewhere for a few days/weeks isn't great and its better to stay somewhere for 6 months or so

Definitely weeks: days and then moving is tiring imho. And not productive. Months I find too long. Probably based on personal taste a lot as well.

And for nomads perhaps taxes; staying 6 months can be dangerous in some cases; even 60 days consecutive for some countries.

Dan Ariely's research for example shows that duration has little effect on our memory of an event. Check his TED talks.

Your post reminds me a lot of my own experience. I am quite socially anxious, which is a serious barrier to having 'enough' social interaction so as not to feel isolated. Meanwhile, I feel that my time is not spent doing something worthwhile, whatever that is. I am employed and in no position to take a longer break away from having to pay the bills, but if I won the lottery tomorrow I'm pretty sure I would struggle to find something to do that was meaningful. Anyway I hope that you find a way to feel a bit less shit.

Have you entertained the idea of settling down with a significant other? From what you shared, it seems like your problems stem from a lack of purpose outside of work and wealth building.

If you’re in one place for a year, try volunteering as an EMT. Gain some different skills, meet good people and get a different life experience.

Hey greggman, Drop me line if you want to commiserate!

I wonder if teaching would be appealing to you.

Are you married? Seems you have plenty of time.

I am glad at least someone is honest. So sick of hearing "This worked out so great" and then everyone shitting on the nay-sayers.