Starting to purchase expensive stamps without first acquiring the requisite knowledge to correctly gauge their condition and genuineness (or getting certs for the more expensive stamps).
Not following my own instincts when I was in my late teens and wanted to work in the hobby. I should never have listened to those who told me "you don't know enough". There were dealers at the time where I could have started out as a beginner and my desire to learn would have carried me through.
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