What's the tougest challenge you gave yourself without knowing it was a challenge?

Like when I was in 1st grade and I was playing gen 1 and 2, i didnt know about the PC (or evolutions or anything) so my first 6 pokemon were my team. For like 10 playthroughs. If i wanted a late game pokemon, i would hold off on catching anything and just progress to the last gym with like a team of 3. In 1st grade.

But my biggest challenge was beating Pokemon Stadium 2 with just rental pokemon. I just assumed everyone was relying on rental pokemon. I didnt have the time or energy to do multiple playthroughs (for good movesets using tms) to transfer pokemon over from my red and silver versions. So i just toughed it out with the rental pokemon and basic items.

It didnt realize that like...no one did this. I thought everyone had beaten the game this way and I was just bad at pokemon for taking so long. Classmates beat the game in weeks. It took me like 4 months as a child.

But no. Rentals are usually trash (exception for little cup movesets) and winning the game with them was a huge handicap.