The World Is Broken And There Has Never Been a More Exciting Time to be Alive (in Japan)

Jay Winder
6 min readAug 24, 2016

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Everything around us was designed and built for a totally different world.

A world without instant access to the sum total of human knowledge through a tiny device in your pocket.

A world without software updates quietly installed to your devices, increasing security, fixing problems and instantly introducing new utility and features.

A world without tens of billions of increasingly interconnected people and devices.

The problem is that we’ve become blind to how broken things are. We’ve accepted them as part of our daily life. As only one tiny example, every time we need to update our address at the local government office, we dutifully sit and wait for hours, rather than ask the question “Wait, why can’t I do this on my phone?”

Silicon Valley veteran Paul Graham wrote an excellent essay on this called “Schlep Blindness”. (Also available in Japanese)

This whole situation is tremendously exciting for two reasons. It means there are millions of opportunities all around us, waiting for us to notice and fix them. Further, due to all the newly available software and technology, there has never been a better time to build a software company in the history of the world, and especially Japan.

Some people are pessimistic on Japan. They say that Japan is over. It was nice while it lasted, but Japan cannot compete in the global marketplace, and is unable to adapt to the new software driven market reality of 2016. They say there aren’t enough tech-savvy people to build or work in software companies, or that the tech-savvy people are wrapped up working on non-important projects in big companies.

Of course, I think this is total bullshit.

I’m very excited about Japan’s future. I’ve been lucky enough to build two companies in Japan, and I’ve seen firsthand the diligence, commitment and dedication of our team here.

I’ve seen the speed at which our team has adapted to new software and technologies.

It’s been exciting to see our customers start to realise the leverage and power they can get from great software, and it’s been enjoyable to see them lean in and start requesting features that can generate even more benefit for their business.

As an aside, Tim Romero of Disrupting Japan did an excellent podcast on this exact topic, called “Japan’s Coming Startup Boom”, which I highly recommend.

We’re also seeing an exciting shift in the marketplace. In a post-iPhone world, people realise the value of well-designed, beautiful software that is both highly functional and a joy to use.

Decision makers in companies are abandoning the idea of “No-one ever got fired for buying IBM”, and moving to the idea of

No-one ever got fired for selecting the right solution, regardless of vendor size.

The quality of the software and support are becoming the determining factors, as it should be.

Another misguided criticism of Japan is the availability of staff for smaller companies, or startups. This is also changing. Historically, many Japanese have aimed to join large companies, because it was perceived as the safe choice, socially and professionally.

These days, big companies are not as safe as they were. People are realising companies are not safe just because they’re ‘big’. Companies are safe if they’re competitive.

Japan is opening up to the idea that working in a startup is a viable career path. We’re seeing graduates choose to work at startups, not because they couldn’t get a job at a big company, but because they don’t want to work at a big company.

According to a 2016 survey, Japanese graduates seeking employment at a big company has dropped 7.8% since 2014. On the flip side, graduates who want to work at a startup has increased by 4.3%.

It’s still early days, but the trend is clear. Motivated and ambitious staff, regardless of age, want to work in a high-impact position doing something that matters right now. They don’t want to wait years.

Startups are uniquely able to offer this opportunity. They have no built in ideologies of what work women or younger staff or less experienced staff should or shouldn’t do — if someone is highly capable, they get responsibility and interesting work, regardless of gender, orientation, experience or nationality.

In any case, if you’re looking for a job or working at a company in Japan, the most important thing to realise is that you have options, and you can make your own choice.

Choosing what work you do is one of the areas in life where you can and must be selfish. You can’t do your best work when you’re unhappy, or reluctantly following what some else says you should do.

If you decide where to work based off advice from your university or even parents, you should know they have your best interests at heart. But it’s critically important to understand this advice was made for a non-2016 world.

There’s always the option of joining a startup company. If you pick the right one, it could be the most rewarding work experiences of your entire life.

If that sounds interesting, I’d recommend going to events and talking to people working in startup companies. Or even better, grab the CEO, and say “I’m interested in your company, could you give me more information about what you’re doing?”

Some people are perhaps thinking “I can’t just grab the CEO! They’re probably busy!” Nope. This is actually a great litmus test for company health. If the CEO is excited to talk to everyone about the company mission and if they’re trying to hire great people anywhere they find them, that’s a great sign.

In any case — follow your own path. Like Steve Jobs says,

Don’t be trapped by dogma — which is living with the results of other people’s thinking. Don’t let the noise of other’s opinions drown out your own inner voice. And most important, have the courage to follow your heart and intuition.

Best of luck.

(この記事の日本語版)

Thank you to Patrick McKenzie and Tim Romero for reviewing early versions of this post.

Naturally, we’re also hiring at MakeLeaps :) If you’re interested to join a team of Japanese and foreigners, tackling exciting real world problems for real people, I’d love to talk with you. We’re looking for interns and regular staff, English fluency and native/business levels of Japanese ability. If you’re not in Japan, we’re also open to remote workers.

Aside from that, I care a lot more about attitude (do you love helping people?) and ability to get stuff done, as opposed to qualifications, and even experience. If that sounds interesting, I’m interested to talk with you personally.

Please send me an email to jayw@makeleaps.com . Since half of our internal communication is in English, please email in English. Bonus: if you can send me a short 30–60 second introductory video of yourself, it’s very helpful.

Brief Introduction of Jay/MakeLeaps

Jay Winder is the CEO of MakeLeaps. MakeLeaps is the cloud business invoicing solution for Japan. MakeLeaps began in 2010, and is funded by Silicon Valley veterans such as Naval Ravikant (founder of AngelList), 500 Startups, and most recently Rakuten Ventures. Jay has been living in Japan since 2001, and running a company here since 2003.

Follow Jay on Twitter or Facebook.

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