It’s kind of relevant what the turn card is. Assuming its a total blank like 2h I think you probably need to fold, unless villain seems maniacal. If villain had raised CO or BUT calling down seems more reasonable.

At 21bb I might just check-shove this flop. When called you have >20% equity against everything other than sets, KK, A8 and T8, and you’ll fold out a lot of 2 over hands that have ~25% equity.

5 is an interesting card in that it allows villain to barrel some hands that picked up a flush draw, which may improve calling slightly. That being said, a card that strengthens your range significantly is a really bad one for villain to barrel (you have wayyyy more 5s in your range than villain), so I think folding is still the play here.  

I would be very interested to hear from more experienced players as these BB defend spots come up all the time, and you’re still relatively high up in your range with K8.

One tactic which I’ve been experimenting with is donking turn when middle or bottom card pairs. Doubtful it’s a good approach here because you’re risking a lot of your stack to turn a relatively good hand into a bluff, but something to consider for deeper stacked spots, especially if you have a hand that wants to semi-bluff.

I think my temptation to check-raise this flop is a remnant from when I first started playing, and indicative of a big leak in my short-stack play post-flop. Back in the ~2009 era I developed what may be a pretty odd strategy of trying to maximize fold equity when I had decent but vulnerable showdown value and roughly this stack size . It may have been good variance or just the different nature of play in that era, but it seemed quite effective. I think it got more folds than it would today because everybody was c-betting so frequently, but it also wouldn’t be uncommon (at least at micro/low stakes) to get called by a hand like 98s on this board and be in great shape. Kinda sad to think that my approach to spots like this still has at least one foot in 2009.

Another leak that spots like this highlight in my game is more mental game related. Not usually quite this deep, but especially around the 16-17bb mark I am probably too willing to gamble and tend to adopt a ‘double or bust’ mentality. My higher thinking tends to shut down when I flop equity, especially after defending the BB. Rather than applying my normal thinking about ranges and considering all my options, I’ve developed the bad habit of thinking “It can’t be that bad to get it in here,” which is obviously a pretty shameful approach to take as a professional MTT grinder.

A good reminder that there are many important areas of my game that still need a LOT of work. I was already extremely happy with my decision to finally join TPE, but getting called out by my favorite podcaster is an invaluable wake up call. Thank you good sir!