Are there any 'winners' in the ice age generation? A story from a 40-something who has changed jobs six times

Hello, this is Ponzu.

'Winners of the ice age generation'.

I saw this phrase on social media the other day, and it made me stop scrolling.

Winners... who are they?

People who got into big companies? People with high salaries? People who didn't get laid off?

Honestly, none of those really resonated with me.

I myself am a high school graduate who has changed jobs six times, and I am currently working on AI promotion at a company listed on the Prime Market. From a general perspective, I might look like I'm on the 'successful side'.

But in my own view, I 'haven't achieved anything yet'.

Today, I'm going to write about my thoughts on what a 'winner' of the ice age generation even is.

The definition of 'ice age generation winner' has changed from the past to the present

When our generation was job hunting, the definition of a 'winner' was simple.

Get into a big company. Have a high salary. Get a promotion. It was an era where if you had these three things, people would say, 'He's a winner'.

But does that 'winning' from back then still hold up today?

For example, even if you got into a big company, early retirement offers are not uncommon now. Even if you have a high salary, mental health issues among managers are increasing year by year. I often hear stories about people who have been promoted but are the only ones working overtime while their subordinates leave on time.

In other words, the yardstick from back then is no longer usable.

The image of the 'hard-working, successful senior' I admired when I was in my 20s. They looked cool back then, but if you worked like that in this day and age, you'd probably run into compliance issues.

Did the times change, or did we change? Probably both.

What is 'winning' in an era where intense employees aren't valued?

In the past, 'working hard' was justice, no matter what.

Not minding working on holidays. Staying until the last train. Not leaving before your boss. At the first company I joined, that was the normal atmosphere.

But now, that 'hard work' can sometimes backfire.

Compliance, harassment, whistleblowing. Recently, the term 'right to disconnect' has also emerged. It is the right to refuse contact outside of business hours.

This is quietly important.

In short, companies are starting to say, 'You don't have to work that hard.' Even if you want to work hard, the environment is becoming one where you cannot.

Working furiously to produce results. The era where that was considered 'winning' might already be over.

So, what is 'winning' then?

I've been thinking about this for a long time, and I feel like I've finally started to see my own answer recently.

In today's world of diverse values, you have to decide for yourself who the 'winners' are.

There is one more thing that is decisively different from the past.

That is the 'diversification of values'.

In the past, everyone was looking in the same direction. Get into a good university, join a good company, buy a home, and work until retirement. If you were on this track, you were a 'winner'.

But now, there isn't just one track to begin with.

There are people who make 2 million yen a month as freelancers, and there are people who say 'this is enough' while valuing time with their family even on an annual income of 4 million yen. Some earn money through side jobs, while others build up internal company evaluations by focusing solely on their main job.

Which one is the correct answer, or which one is winning—others can no longer decide that for you.

If you open social media, posts like 'reached 1 million yen in monthly income' will appear. But you've never seen a colleague at your actual workplace say, 'I'm earning 1 million yen a month from a side job,' have you?

The true feelings of our generation that we really want to know are surprisingly hard to see.

That is precisely why you have to decide for yourself, 'This is winning,' instead of being swayed by other people's standards. That is what I think.

The conditions for 'winning' as I see them now, as a high school graduate who has changed jobs six times

So, what is 'winning' for me?

Speaking honestly, there are three things.

First, my main job. I am currently working on AI promotion at a Prime-listed company, and my immediate goal is to become a department manager. If the me from my 20s heard that someone who graduated from high school and changed jobs 6 times was aiming to be a department manager, I think he would laugh. But now, I truly believe it.

Next, my side job. My immediate goal is a monthly income of 300,000 yen. Centered on posting on note and X, I will use AI to turn my experience into content. It might not be a flashy number, but it is an amount that can make life for my family of four a little easier.

And then, family. This is the most important thing. With hybrid work, I work from home half the week and do the school runs for my children myself. On weekends, I prioritize my family above all else. This is the one thing I will not compromise on, no matter how busy I am.

A state where these three things are in balance. That is the condition for 'winning' for me.

Even with an annual income of 10 million yen, if I have zero time for my family, then for me, that is not 'winning'.

It is better to aim for a 'state where you can choose for yourself' than to be a 'winner'

Having written this far, I suddenly realized something.

The 'conditions for winning' that I am talking about are, in the end, just about 'being able to choose for yourself'.

• Commit to my main job this week

• Focus on my side job next week

• Prioritize my family on the weekend

A state where I can decide all of these judgments myself.

Instead of working overtime because someone told me to 'work more,' I can draw the line myself and say, 'That is enough for today.' As for my side job, instead of doing it secretly because I don't want my company to find out, I do it because I have decided for myself that it is necessary.

As I mentioned in an article I wrote previously about how to approach work, I believe that for people in their 40s, whether or not you can decide for yourself the 'direction in which you put in effort' is a big deal.

Simply put, I think that 'creating a state where you can choose for yourself' is far more important than 'becoming a winner'.

Winning and losing are about comparisons with others, right? But 'whether or not you can choose for yourself' is a matter that exists only within you.

The moment you stop comparing, you will probably feel more at ease. That was the case for me personally.

Main job is AI, and side job is AI. A side job is my 'own personal safety net'

What I am doing now to create a 'state where I can choose for myself.' That is using AI for both my main job and my side job.

In my main job, I work as an AI promotion manager, spreading the use of AI within the company. My role is to convey to the company, 'You can use it for work like this,' while using the three tools: ChatGPT, Gemini, and Claude.

For my side hustle, I run my posts on note and X with Kuro (Claude). I also build the structure of my articles by bouncing ideas off Kuro. I provide the raw material from my own experience, and Kuro shapes it into form.

Honestly, without AI, balancing my main job and my side hustle would have been impossible. With four children, it is physically impossible to do both while making family time my top priority.

However, the important thing here is the purpose of the side hustle.

For me, the side hustle is not:

• To quit my company

• To show off my achievements on social media

• To buy luxury cars or watches

It is my own personal safety net.

No matter what happens to the company, I have the ability to earn money on my own. Just having that sense of security allows me to approach my main job with more composure. It is paradoxical, but having a side hustle is exactly why I can focus on my main job.

The ice age generation is one that knows the fear of falling off the tracks once. That is precisely why I think we understand the value of a self-made safety net.

Summary of 'Winners of the Ice Age Generation'

What is a 'winner' of the ice age generation? The conclusion I have reached in my own way is this.

Winning or losing is not something decided by others. You decide for yourself, 'This is a win,' and then you go out and create that state. I think that is all there is to it.

The old yardsticks no longer apply. It is not an era of working like a maniac anymore. That is why I believe that creating a state where you can choose for yourself is what 'winning' means today.

I place AI at the foundation of that, both in my main job and my side hustle.

What is 'winning' to you? It might be worth taking a moment to think about the answer within yourself, rather than using someone else's criteria for success.

Well then, I will take my leave now.

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