Thinking about AI and Investing (11) – 5 Years Since Resuming Swing Trading. What Has Changed for Someone Who Couldn't Win?
It has been about five years since I resumed swing trading, before I knew it.
In the beginning, I couldn’t win at all; I would think I made a profit, only to lose it all in a big way. I repeated that cycle many times.
Even so, I kept at it without giving up, and as a result, I have finally started to win little by little recently.
So this time, I had Chappy (ChatGPT) read through my entire trading history from the past five years to objectively analyze my trading.
I feel like I have been improving little by little, but what do the actual numbers say?
First, here is my performance over the past five years.
I gave the trading history downloaded from the brokerage firm to Chappy and had it aggregate the data.
The results are as follows.
Yearly Realized Profit/Loss 2022: -203,466 yen 2023: -497,289 yen 2024: +247,351 yen 2025: +4,608 yen 2026: +726,148 yen Total: +277,352 yen
*2026 is as of October 26th. These are realized profit/loss figures before taxes, including spot transactions.
Man, looking at it again, 2023 was terrible (laughs).
A loss of about 500,000 yen.
Combined with 2022, I lost 700,000 yen.
I thought I was trading quite seriously back then, but looking at the numbers, it was completely hopeless.
It wasn’t until 2024 that I finally turned a profit.
2025 was basically break-even.
And this year, 2026, I have finally been able to generate a decent profit.
However, this year’s profit includes about 290,000 yen from the sale of a gold ETF I had been holding long-term.
Even excluding that, I am up about 430,000 yen.
Personally, I think I have finally started to grow little by little.
The most surprising thing was the change in win rate
Having Chappy analyze this for me this time, this was the most interesting part.
Annual win rate for margin trading.
Annual win rate: 2022 46.7%
2023 42.9%
2024 48.3%
2025 60.2%
2026 70.0%
In 2023, the win rate was only 43%.
That exceeded 60% in 2025, and this year it is 70%.
Of course, since split settlements are also counted as individual items, this is not the win rate of completely independent trades.
Even so, it is interesting that the numbers have changed this much.
I feel that as I look at charts and watch the order board every day, my intuition about whether something is likely to go up or down has become more accurate than before.
Of course, I don’t know how much I can trust that intuition.
However, as far as the 5-year figures show, it seems at least better than before.
The number of trades has also decreased significantly
Another interesting thing was the number of trades.
Annual trade record count: 2022 965 items
2023 738 items
2024 700 items
2025 322 items
2026 277 items
I used to trade like crazy back then.
And yet, I was losing.
I feel like I don’t force entries as much as I used to recently.
I feel like I used to take a position just in case there was even the slightest chance.
Now, when I’m not confident in my prediction, I’ve started to avoid entering unnecessarily more often.
Conversely, when I think something looks promising, I sometimes take a fairly substantial position.
Perhaps this is working in a positive direction.
However, I don’t know if I started winning because the number of trades decreased, or if the number of trades decreased because I started choosing winning situations.
I still don’t know that.
I was losing terribly with short selling
This is also something I found out through this analysis.
I had my margin trading data for the past 5 years separated into long positions and short positions.
Cumulative trading profit/loss: Margin long +367,417 yen, Short selling -637,786 yen
Since I often trade mainly with short selling recently, this was a bit surprising.
However, looking only at this year,
2026 profit/loss: Margin long +106,557 yen, Short selling +306,124 yen
Short selling is doing quite well this year.
In the past, there were often times when I would short sell thinking the price would go down, only to get squeezed, and the point where I cut my losses would be the peak.
That still happens now, though (laughs).
Even so, I feel like I’ve started to withdraw earlier when I sense that the market trend has changed.
At least for this year, short selling has become the core of my profits.
But, Chappy also pointed out my weaknesses
Looking at it this far, it seems like I am growing in a pretty good way.
However, there was also harsh criticism from Chappy.
“Your winning technique is improving, but there are still problems with how you lose.”
This is it.
In 2026 margin trading, I have made a profit of approximately 410,000 yen with a win rate of 70%.
However, in October, I suffered a loss of about 110,000 yen in a single day.
There were also several other days where I lost tens of thousands of yen.
In short, my old bad habit of
winning small and losing big,
has not yet been completely fixed.
I know it myself, but the more confident I am in my prediction, the larger I tend to make my position.
And it is precisely at those times that it moves significantly in the opposite direction.
According to Chappy, my profit factor for margin trading this year is 1.77.
It seems this means the total profit is 1.77 times the total loss.
The number itself doesn’t seem bad, but if I could reduce those big losses a little more, there is a possibility that I could leave profits more consistently.
Well, if I could do that, I wouldn’t be struggling.
What has changed in five years?
Thinking about it again, perhaps the biggest change is how I face the market.
In the past, I feel like I was obsessed with predicting whether it would go up or down and being right about it.
Now, I have come to think that being wrong in a prediction is inevitable.
No matter how much I think about it, I can’t know the future of stock prices.
More than that, I focus on how much I can grow my profits when my predictions are correct.
And how quickly I can withdraw when I feel the trend has changed.
Lately, I have been conscious of such things.
That said, I still get emotional sometimes.
Like trying to win back losses after a big defeat, or taking profits too early on a winning position.
Even after doing this for five years, it’s still quite difficult.
The final evaluation from Chappy is B+
This time, I also had Chappy give me a comprehensive evaluation as an investor.
The result is…
B+!
I’m subtly happy about that (lol).
To summarize the evaluation,
That’s how it felt.
Of course, since it’s an evaluation made arbitrarily by AI, it’s not an objective ranking or anything like that.
Still, it’s interesting to look back at my past trades with numbers.
Especially the fact that while my win rate used to be in the 40% range, it has risen to 70% this year.
I was genuinely happy about that.
In conclusion
It has been about 5 years since I restarted swing trading.
Honestly, there were many times along the way when I thought I wasn’t cut out for this.
Especially in 2023, I lost nearly 500,000 yen, after all.
Even so, I like watching the market itself, so I’ve kept at it one way or another.
And recently, I have finally started to be able to retain some profits little by little.
Of course, it might just be that my compatibility with the market happened to be good this year.
There is also a possibility that I could lose a large amount again next year.
Still, compared to myself five years ago, I think I have grown at least a little.
My goal going forward is not so much to increase my win rate further, but to reduce large losses.
And, if possible, I would like to become able to generate profits consistently every month.
Ultimately, it would be great if I could live off of investing alone, but that is still a story for the distant future.
For now, since I have gone to the trouble of continuing for five years, I think I will try a little harder.
It might be that it took me 5 years to finally reach the starting line (laughs)
Well then, until next time.