I obviously regret selling stuff but everything Iv done has led my collection to be where it is now. And I love it!
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Passing on a PSA 9 shadowless Chansey for $500 because I thought it was a weak 9. May have to settle for an 8.
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Oh man, Iāve literally only one regret in this hobby so far. This was before covid so prices hadnāt skyrocketed on them but I traded some ex PSA 9 slabs for some supposedly mint/nm e-readers. Guy had a good reputation in the community and I was still super green in the hobby. Ended up getting duped as the cards werenāt even close to nm, let alone mint. I probably lost several hundred dollars on that deal.
Honestly, it still eats away at me occasionally because in hindsight it was such a stupid deal. But Iām still okay that it happened since I only collect using disposable income and I learned a lot afterwards about dos and donts. Definitely have had cards I wished I bought but theyāre definitely not regrets. Iāve either just bought them for more or Iāll buy them later down the line. Canāt close every deal after all.
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Not being more engaged in this hobby and E4
Mistakes and failure is the greatest teacher of all
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Not buying the played af T Khan on Yahoo in September 2017 for ~$1,500.
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Not buying a Mario and Luigi Pikachu when it came out for $70 a pair.
Not buying a fan club eevee in its original mail for $450
Not having money on hand and missing out on all the deals Iāve seen get scooped up(my problem is that itās super hard for me to let go of cards and so my pokemon funding gets put at a standstill at times)
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I forget which Youtuber mentioned it, but there is a story about a financial advisor that has always stuck with me. The advisor had a client that would be unhappy regardless of which way their investments went. If the investments went down, theyād be upset for obvious reasons. But even when the investments went up, theyād be upset because they didnāt buy more.
Point being - or at least what I took away from it - that your attitude and outlook is independent from your external circumstances. You can choose to be someone who lives with regrets and is upset at what could have been, or you can choose to be grateful for what has come to pass.
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I regret buying a worthless extra copy of a trophy car
I regret buying my house when I should have spent it all on more Pokemon cards.
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I just remembered another regret when someone mentioned Mario and Luigi Pikas - not buying Charizard Poncho Pikas when they came out. And kept waiting and waiting to pick them up and now itās too late. So same thing as with the Shiny Ray. So I have 3 cards that I regret not getting. Thankfully at least I got Mario and Luigi boxes on release 
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As pretty much everyone, many āshouldaā, many good opportunities that I didnāt grasp, many cards that I wanted to own but I didnāt prioritize well, etcā¦
But in the end as was said, you always try to make the decisions to the best of your knowledge. And god I canāt count how many good decisions Iāve taken. Was it optimal? Sure no. Did I miss on some cards, did I not the signs of X item rising to the point where it would be unaffordable? Oh yes. Is it possible to always be right? No. I think the only way I could have real regrets is at the point where the answer to the question āDo I wish I never got involved with Pokemon card collectingā will be yes. And based on experiences, stories, people met alone, I can already tell it will never happen.
Itās good to learn from missed opportunities, and to know a lot you must learn a lot. And to learn a lot you must make āmistakesā a lot.
Remember the human brain is always biased towards the negative feelings (FOMO, remembering bad experiences over positive ones) just because thatās how we evolved, to avoid making mistakes again (that at one time could be endangering).
For every poor decision taken a lesson has been learnt, and down the line it resulted in a good decision being taken.
Keep positive!
A little over two years ago sealed base set boxes were in the high 2000usd to low 3000usd price range if I recall correctly. Some local dude had one for sale and we haggled the price back and forth over a couple days and we settled on the price of 1800 bucks. I had some money already but not the full amount, so I was going to have to take out a small personal loan, for like only around a 1000 bucks or something. I ended up dragging my feet on fully pulling the trigger and setting up a time to meet with the guy because I didnt want to go into debt. After a day or two of telling the guy I was working on getting the funds (which I really wasnt yet, I was being indecisive still) he ended up selling it. What really sucks is that I did end up deciding I was going to get the loan and I had already started the process at the bank. When I got up with the dude to let him know Iād have the funds that day is when he let me know he had already sold it. I really get bummed when that situation comes to mind. That was a steal of a price! I really blew it. I donāt know why I was so worried about a 1000 dollar debt. I think thatās my biggest regret so far. There is quite a few more though for sure.
Unless these wild prices go back down, without selling stuff I already own (which I dont want to do) Iāve likely missed my shot of owning a base set box. Hopefully one day Iāll get lucky and Iāll have the shot at buying one for that price again!
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I regret not telling my parents to buy and hold onto sealed first edition WOTC boxes because of how much theyād increase in price over the next 20 years. 4 year old me really should have been able to see that coming.
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Forgetting to move my childhood collection higher when my house was flooding. 
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I regret not maxing out credit cards and going to a loan shark to buy as many pokemon cards as possible.