You decisively missed the point. Yeah indeed for sure fear can be overcome by simply doing it successfully for the first time, but in order to actually be successful you need to prepare, always without exception. I'm sure you had prepared yourself for all of that, motorcycle classes before you got your bike, skydiving lessons before you were in the plane with a reputable pilot and instructor, leaving the Minecraft t-shirt in the wardrobe before offering a date. Good for you, but you didn't succeed just because you decided to. You did because you were prepared, and you were prepared because you were afraid from the beginning. If you followed the advice in the image to the letter, you'd have thrown yourself out of the plane afraid, but confident in your ability to figure out the parachute. Fear is necessary to hold us all back from recklessness.

I do think you're right. Some people certainly are too scared. The advice to simply do things regardless of being scared just isn't helpful or motivating to those people though. It's a real succinct-looking message, but it doesn't help them actually deal with the fear. Fear can be paralyzing and disabling when you least want it to be, just an evolutionary flaw. Overcoming it takes a lot of reasoning with that fight-or-flight part of the brain to flip that switch all the way towards fight. And I'm not talking "mad-scramble-thrash-and-flail-for-your-life" fight, I'm talking "kick-ass-take-names-and-make-a-name-for-myself" fight. Nobody that holds your attention does so with fear in their eyes. He or she does it with a plan behind them, and with knowledge and skills further back in their head. Success isn't just manifested and neither is confidence, both are borne from preparation.

Doing it scared is pretty crappy advice in most cases.

If you try to do a backflip scared, you will mentally sike yourself out, fault to commit, and land on your fucking head. Game over, all because in the moment you forgot how to make the rotation happen, or how to jump properly. You were thinking more about how afraid you are.

If you try to do a presentation scared, you'll have your audience thinking harder about the words you fumbled and stuttered than the ideas you're communicating. People don't really piss themselves, but you'll likely have sweat marks on your back and your pits, some dripping down your face, some shakiness that indicates low confidence and doesn't inspire confidence from others, et cetera.

If you're firing a gun scared, you may just drop it, or forget your trigger discipline. Accidentally turn it towards a friendly target while you're gushing to them about how much that recoil startled you, or just point it at your foot while you squint to see if your shot landed.

Driving on the highway for the first time? If you're scared, you might be looking at the mirrors more than the road, or the road more than the mirrors. You might drift from your lane or forget to maintain speed.

Asking out the chick you like? Newsflash bro, you might be afraid because you know you smell like shit, your teeth are unbrushed, or you're wearing a stupid "eat sleep game repeat" t-shirt, or just because you're simply batting out of your league, or you're shooting for someone with whom you have no rapport, no prior exchanges, haven't even traded introductions yet. Your brain will know if something's wrong and tell you accordingly.

Fear is an instinctual response to unknown prospects. Ignoring your fear is done by silencing the logical part of your brain, which yeah might let you do it, but also will allow you to do it incorrectly and distracted, so in certain instances powering through can just cause harm. Sometimes, doing it anyways is just what you need to do, but if it's something you only want to do then it might be better to step back and think about it before you're in action and on the spot. That's why I would revise this advice to "prepare, and do it ready."

Listen in on your brain if you're afraid. Brains should be rational by design, so there will always be a real reason it thinks it's not so good of an idea. Don't override it, pick it apart, and prepare yourself in advance to remove that confounding variable from the equation.