This could result in you being more than just psychologically uncomfortable. Tourists are, broadly speaking, expected to have hotel rooms booked; showing up at immigration without any advance plans is a good way to be denied entry to some countries. (Yes, even countries you don't need a visa to visit: Border officials can deny you entry on the basis of "this person's story doesn't add up".)
I'm about to embark on a 3 week trip through south east asia. Aside from my liveaboard where I'll be living on a boat and diving (which I have to book in advance), I haven't booked a single accommodation. It can be done; hostels all the way.
Though I expect some places outside Europe it might get a bit harder.
That sounds like a wonderful way to get kidnapped or murdered. Why do people recommend this? It seems only slightly less dangerous than going to the most dangerous neighborhood in the biggest city you can day-trip to, and start hurling slurs at passers-by.
The rest of your advice seems wonderful and I'd highly recommend it!
If you do this prepare for a raft of questions / meetings with you asking if you have a job interview or something today. Are you thinking about leaving? Are you sure you're happy here etc etc... :D
[0] https://www.youtube.com/watch?v=BEG-FXgAOGg
I believe most people are conformists and do not really care for those who stick out like a nail out the board; most will try to hammer it back in. If you're not a "culture fit", they might even let you go. Risky.
- Public speaking
- Taking on leadership roles
- Do things that are counter to your personality. Eg, if you're shy, force yourself to talk to strangers on the street
- Put yourself in situations where you will probably face rejection
- Do things that will make you stick out. Eg: showing up at work one day in a suit when everyone else is wearing t-shirts. Or vice-versa
- Take a flight to a random foreign country where you don't know the local language, and where most people don't know English. No hotel reservations in advance, no laptop, no smartphone, minimal budget. Figure out how to survive, have fun, and visit the city's major landmarks over the following 5 days. Bonus points if it's a developing country
Not that I'm particularly recommending all of the above. But they will certainly put you in an psychologically "uncomfortable" spot and help expand your comfort zone.