- Ask HN: What do you wish you had known before you turned 40? https://news.ycombinator.com/item?id=9092246
- Ask HN: What do you wish you had done/known in your 30s? https://news.ycombinator.com/item?id=30782994
- Ask HN: What's your best advice for someone turning 30 today? https://news.ycombinator.com/item?id=26068320
- Ask HN: How would you wish you had invested your money if you were 30 again? https://news.ycombinator.com/item?id=13179385
- Ask HN: What's Your Biggest Regret? https://news.ycombinator.com/item?id=33118584
[Shameless plug: I found all these on my llm-embedding based search engine I launched today: https://payperrun.com/%3E/search?displayParams={%22q%22:%22A...
It's much better than HN's default search: https://hn.algolia.com/?q=Ask+HN%3A+What+do+you+regret+doing... ]