Speaking just for myself...
Both my arms are sleeved, the backs of both hands, my knuckles on both hands and I have a large tattoo of a skull and crossed spoons on my head and neck behind my right ear. Covering them would not only be inconvenient at this point, it'd look pretty darn weird.
I get all of my tattoos first and foremost, because I want them and I have no desire, under any circumstances to cover them. This isn't done to alienate anyone or to be in any ones face, so to speak. My tattoos are an expression of who I am. Just as my choices in clothing, hairstyle (shaved head), etc are expressions of those same things. They are my art collection. I feel more and more like "myself" with each new piece.
My personal definition of success doesn't include working in any industry or for any employer where these would be a problem. Some folks place their own personal comfort in their own skin above the amount of money they make, or level of societal success.
When I am older my skin will wrinkle and sag. I'll lose my hair (if I weren't shaving it), my teeth, my vision will worsen, my hearing too. It's inevitable. I can't and won't deny myself my self expression, my feeling of becoming more me based on what I will look like when I'm older. I simply don't care.
Being tattooed, for me at least, isn't just about aesthetics.
Maybe the person you saw is a professional tattoo artist or body piercer. Maybe they are a musician, artist, side show performer, fire dancer, or any one of a dozen other artistic professions in which being heavily tattooed might not only not be a detriment, but an advantage and an aid to their "success". Maybe they work in an industry where appearance is secondary to performance like construction, or (as is my case) the culinary arts. Hell, maybe they are independently wealthy and don;t need to worry about financial "success".
Words like "Freak" and "Success" are very, very subjective. Some folks think shaving off all your hair makes a person look like a "scary" or like a "freak"