Challenge Yourself in Your Late 30s, Not Your 20s

People in their 20s tell me, with the best of intentions, “This really is the decade for it, isn’t it!” So let me push back here too: “No, no, that’s not right.”

I’m not going to say something loose and half-asleep like “Challenges have nothing to do with age!” What I’ll say instead is: “If you’re going to challenge yourself, do it in your late 30s.”

Let me take a moment to examine what’s behind the common view that “if you’re going to challenge yourself, do it in your 20s.”

【Objection ①】 Your thinking is flexible, and you can take bold action unbound by conventional wisdom.

【Objection ②】 Even if you fail, you can still recover, over and over.

【Objection ③】 People in their 20s can pull three all-nighters in a row.

I imagine many readers thought “well, that’s true enough.” But notice something: there’s no actual logic for success in any of this.

Take startups, for example. I’ve never seen anyone found a company with the attitude of “I’ll get a good experience out of this.” Everyone falls in love with their own business model and founds their company imagining a big vision — great customer satisfaction, social significance, and trustworthy comrades all over the world. At that point, failure isn’t even a passing thought.

What should you do to succeed? What options should you take? Looking at it that way, I don’t believe the 20s are the optimal answer for most people.

When I was in the US, one thing I noticed happening very frequently around me was university professors starting companies. My mother, who used to work at a tax office, once told me, “Become a university professor.” In Japan, a university professor is generally seen as a stable profession with high status and high income. But the professors I got to know in the US had a different look in their eyes. Nearly all of them carried a sense of crisis and hunger similar to that of entrepreneurs, the kind of character best described as “intellectual hunters,” always on the lookout for an opportunity.

In fact, a distant, distant, distant relative of mine whom I met in Silicon Valley, Mr. M, was a professor at Carnegie Mellon Pittsburgh and also a serial entrepreneur who had founded three companies and successfully sold all three. Listening to him talk, it felt like the story of the eventual sale was already worked out from the moment he founded each company. He’d be researching some specific technology at the university, already know which companies wanted it, and once he founded the company he’d move straight into proof-of-concept or assembly work; once that succeeded, he’d sell the company. A very simple flow, and he ran it three times. He was, first and foremost, a researcher, so he had no intention of building a BtoC or BtoB business himself. He would elevate his research results to a level ready for social implementation, then sell that to the right platformer or research institute.

What a rational formula for success. It was eye-opening for me. But in America, this has been common sense for ages. Back to the topic of age: the aforementioned Mr. M is quite advanced in years. As for becoming a university professor, doing so in your late 30s would already be considered fairly early. And it’s not limited to university professors — what it takes is having already produced a certain level of results in a specific field, knowing the industry well enough to immediately spot potential buyers, and having the network and leadership to secure the right personnel the moment you start a company and move the process forward. Bring all these elements together, and you can stand on the same playing field.

Can you picture reaching that point in your 20s?

The world has a huge misconception. When companies like Facebook, Microsoft, Apple, and Google — founded by young people in their 20s, especially their early 20s — later become giant corporations, everyone gets intoxicated by that exciting story. But in reality, Netflix founder Reed Hastings was 36 when he founded the company, Oracle’s Larry Ellison was 33, Amazon’s Jeff Bezos was 30, Cisco’s Leonard Bosack was 32 — many of the companies at the top of the market cap rankings were founded by people in their 30s. For reference, Jack Dorsey was also 30 when Twitter was founded. Objectively, youth is not a particularly advantageous factor for success.

That said, there is an upside to founding a company young: you get to stay involved with that business for a long time. Larry Page, who founded Google, has already left the company — whether because he’d done everything he wanted to do or because his motivation burned out — but he’s still not even 50. He can still take on plenty of new things going forward. Incidentally, it’s well known that Eric Schmidt served as Google’s CEO in its early days. Eric was 46 at the time.

As shown through these examples, and from my own empirical experience, being especially young doesn’t seem to have much effect on making a challenge — especially founding a company — succeed. On the other hand, founding a company or launching a business is an extremely exhausting event. Most people, once they’ve done it, never want to do it again (Y Combinator founder Paul Graham is one example), and after pouring your whole self into something, whether it ends in success or failure, it wouldn’t be strange to feel dazed and empty for at least several months, or even years. Pouring in that much power and fighting through all sorts of difficulties comes more naturally when you still have some youth on your side. So, all things considered, I believe the best timing is somewhere around the late 30s.

I’ve always loved coming up with new products and business ideas, and I’ve kept my old memos, notebooks, and presentation materials. The other day, I happened to look back through them for the first time in a while. My ideas from when I was young are full of holes worth laughing at — fuzzy monetization here, a business matched to a market that was only briefly trendy there — but even so, each one had soul poured into it, and it made me think again, honestly, that there’s something good about that.

Originally published in Japanese at https://clazytech.com/2021/07/533/. Translated with LLM assistance and reviewed before publication.