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That psychological barrier is the worst. As I said in my post the other day I remember tokens that I was waiting to hit $1 and I missed my chance by not selling when they were at $.95. Stupid looking back on it now...
I would say that 5% under the psychological barrier is a good trigger. Getting closer to the target and attempting 1% or 2% it increases the risk of not reaching it.
Yeah, I wish I knew that before. I had a nice token I bought at $.03, watched go up over $.90, but I was waiting for $1 and I missed out. I also forget with some tokens you can get out, then get back in lower in case it goes up again. That's a move I haven't mastered at all yet.