The difference is that if I apply for 10 jobs at once or put a bid in for 10 houses hoping one will succeed, I’ve lost nothing for trying 10 times.

If I gamble and try 10 times and win once - I have probably lost money.

Even if I interview 10 times and fail 9, I’ve learned something from each interview and I’ve gotten better. That’s also not true from rolling dice.

No it's not. Gambler's fallacy is "I just flipped tails so heads is more likely now". I read this article as "heads has a 50% chance of coming up so I'll get one eventually" (which is true - law of large numbers).

Indeed. "Just one more roll of the dice and I'll be ahead."

Worse, this guy isn't trying to get a job. He's just trying to get into grad school. Which is no longer a guarantee of a good career, but may be a guarantee of a big debt. Remember that "I did everything right" post on HN a few weeks ago? CS degree from a good school, but nobody wants junior CS people any more.

Is it ? In gambling your odds are fixed, but in real life, wouldn't you get better at solving problems with each iteration ?

When the outcome is positive, I see nothing wrong. Especially if you lose basically nothing in trying.