Group of skydivers social skydiving

How to Social Skydive in Japan

So you came to Japan ready to start a new life full of experiences and adventure.

At first, everything is cool, fresh and new. Novel. You’re excited about seeing all the places, and meeting all the people. You’re also excited about tackling this new beast of a language: Japanese.

But after that initial love affair with Japan, the novelty wears off. You start to get comfortable. You stay inside the house more. You’ve been working a lot. You’re tired. Visits to new cool Japanese restaurants become replaced with cheap and easy konbini bentos. Worse than comfortable, you start to stagnate as a human being.

Living in Japan comes with its unique set of challenges.

Those challenges include but are not limited to:

  • Risking embarrassment learning and using the language;
  • Breaking unfamiliar social norms;
  • Being judged as a clumsy, ignorant foreigner no matter how well you speak Japanese, and no matter how well you know the culture;
  • Not knowing how to make friends with Japanese people and expand your social circle in a culture where social groups are so tight-knit;
  • Not knowing how to graduate from just “teaching English to get that visa”, to doing the work you truly want to do;
  • And feeling isolated from society and getting bitter about life in Japan in general.

Not even saying these things are the objective reality of living in Japan. I’m just saying its easy to interpret many of the daily occurences as instances of these challenges happening. Basically, even if it’s all in your head, the struggle is real.

And these struggles mixed with the other normal stresses of life can start to weigh down on you, causing you to want to take it easy. It they can cause you to want to stay inside your comfort zone and NOT spend the effort it takes to build an amazing social circle of friends, and tackle your life aspirations.

“Nah man, It’s cool. I think I’ll stay home tonight and “relax”, rather than going out tonight and spending the effort to make new friends and find new opportunities.”

“I think I’ll take it easy tonight and study Japanese tomorrow. I mean, my Japanese is already OK I guess…”

“I really want to audition for that role in that new Japanese TV show, but I don’t know. My Japanese probably isn’t good enough. I’ll just skip the audition this time and try out next time.

Pack your parachutes, it’s time for Social Skydiving

Social skydiving is the art of challenging yourself by putting yourself in unique social situations that you may not have the chance to encounter on a day-to-day basis, in order to develop more confidence and consequently, improve your overall social life.

Just like feeling the fear of jumping out of a plane can be exciting, scary, and fun, so can placing yourself in novel social scenarios.

This can include talking to strangers in public areas, dancing in public, making absurd requests to strangers, or anything that puts social pressure on you such as singing Happy Birthday to yourself in a crowded restaurant (see video below!).

Social skydiving is also popularly known as rejection therapy and was made well-known by a badass dude called Jia Jiang in his 100 rejection therapy challenges.

I like to distinguish between “rejection therapy” and “social skydiving.” Whereas rejection therapy is for people who have social anxiety and want to use “therapy” to get to “normal”, social skydiving is to go above and beyond what is considered normal. On the level of application they are the same, but they have slightly different end goals.

You can read more into detail about what social skydiving in Japan is, and follow me on my social skydiving journey here.

To social skydive is to challenge yourself to an exciting adventure. Social Skydiving will change your life both in Japan, and anywhere you go.

Why is Japan a great place to social skydive?

Actually, any place is a great place to social skydive. However, there are a few great reasons I can think of for why I love social skydiving in Japan.

  • You can expand your social circle and meet cool new people and open yourself to new opportunities.

Sure, you can always make friends through social circles, your local bars, work connections, and etc.. But when you start challenging yourself with new, crazy social interactions you build more confidence. And that confidence will open up new doors of opportunity to meet people in ways that might surprise you.

Having those opportunities in a place where foreigners are often seen as being different can actually have a very cool effect! You might find yourself on TV, modeling for Abercrombie and Fitch, breakdancing and tricking with the best underground circles in Tokyo.

Who really knows! The possibilities are endless and depend upon who you are and what your interests are.

  • It gives you a fresh way of practicing Japanese.

One of the biggest problems that people have when learning Japanese is that they are to afraid to speak it (me included!). They are embarrassed about how they will be percieved by the Japanese people if they make mistakes.

I invite you to challenge that embarrassment by purposefully placing yourself in an absurd situation like asking the Japanese police to drive their car.

Not only does it help you overcome your fear of speaking Japanese but you are simultaneously practicing Japanese as well. This is exactly what Moses McCormick and Benny the Irish Polygot, two established polygots, talk about in this popular article.

  • It gives you insight into how the Japanese would react in a given situation.

One of the reasons you’re in Japan is to learn about the culture. Doing these wacky challenges in Japan has surprised me so much at the way the Japanese people will react. It’s unexpected, and its really a lot of fun.

It has taught me that my expectations of what will happen do not always match up with the reality of what will happen if I try.

The only thing I ask is that you always put the other person’s feelings first, and never do anything that would cause the other person shame and embarrassment.

Otherwise, please go out and embarrass yourself, as that’s a part of social skydiving. Place yourself in new social situations that may be intense or embarrassing, so that you overcome fear of that embarrassment and as a result live a more free, uninhibited social life!

How to start Social Skydiving today

Start small. Start with something you know you could do, but would make you feel a bit uncomfortable, and work from there. Remember that its impossible to do the impossible. I started by saying “hello ” to one hundred people on the street.

Make it too hard, and you won’t do it.

It’s like lifting weights. You don’t walk into a gym your first day never having worked out, and try to squat 500 lbs right?

Same with social skydiving. Just make it a bit outside your comfort zone.

Set a quota and stick to it. Give yourself a quota like “25 challenges” or “100 challenges.” You could even set a time frame like “30 challenges – one challenge per day for the next month.” I am personally committing to 25 challenges for my current project I’m documenting.

I also did a social skydiving challenge before, in which I first said “hello” to 100 strangers on the street. Then I did a second challenge in which I started conversations with 100 strangers.

At first I was very shy about all of this, but I started small and worked my way up.

No matter how hard it may seem in the beginning, I know you can do it too. No matter what level you are at in terms of social shyness/confidence, you always need to start with a challenge that is appropriate to you.

Document it! Please don’t skip this step because it’s super important to integrating your mental insights with the experience of doing the challenges.

You could write in a journal about it. You could blog about it. You could make videos and upload them to YouTube (heck, I do all three!). You must give yourself some opportunity to reflect on your experiences so that you can later go back and review the progression of your attitude and mindset.

This is not only super motivating, as you can literally see yourself growing into a stronger, more confident person but it also ensures that you learn all the lessons that social skydiving has to teach!

Find friends to social skydive with. This isn’t a requirement. But its amazing the difference you will feel in being motivated to do this if you have a buddy to share experiences with, and hold each other accountable.

When I did my first set of social skydiving challenges, I didn’t have anyone to share it with. I just did the challenges and wrote about them in my journal.

This time, I have friends who are also doing this to go out with and share my experiences with. We can also really push each other to expand our comfort zones – much more than if we were doing this alone.

Try to find someone interested to do this with you! I’m sure you will enjoy social skydiving much much more.

Go out, and sail the social skies!

That’s it for now. I hope you are as excited about going on this adventure as I am.

If you are interested in seeing me do and talk about my social skydiving in Japan project, give my YouTube a check.

For more written articles about social skydiving in Japan check out the official list of challenges in this article.

For articles about Japan life, learning Japanese, and living a fun and inspiring life in Japan, check out

For social skydiving in Japan updates and other Japan related fun, check out my Twitter:

If you enjoy the expression of lifestyle through photos, give my Instagram a look:

I really want to hear about your stories and experiences with Social Skydiving as well!

Author Bio
Tony Michael Head

Tony Michael Head

Tony is a 27-year-old fitness enthusiast who blasts his music at a questionably loud volume throughout the streets of Gunma, Japan. When he's not at the gym or conducting his wacky new "Social Skydiving" project, you'll find him in a park somewhere playing guitar, or working on his backflips.


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  • tonymichaelhead

    Thanks for the love, brother. I’m totally down for doing guest vlog/blogs if your up for it, so lets go SS and film!

  • Daniel Bamford

    This is so cool. Practical actionable inspirational… humble advice. Confidence and freedom from crippling social fear – such amazing things. Let’s go social skydiving, brother!