I can’t help with the understanding yourself, but I can give a natal interpretation a try.
You say, “Why can’t I make a basic decision without looking for clarification from people”, keep words to me “basic decision” (Mercury- and then the relationship between Sun and Moon). “clarification from people” (Descendant- and maybe Midheaven).
“I wish i was more assertive” (Mars or Midheaven, maybe)
Maybe on your own you can look at those places with introspection and then and the entire chart to understand what is going on with those placements then ask others. The descendant in Virgo can explain why you feel that others are needed to provide discrimination, common sense or your where your focus should be. But it seems by the wording of concern you somehow recognize it is better if that comes from yourself. Nothing wrong with hearing from others, but if your susceptible to it, too much of something shows lacking in the other. Right? Just something to think about.
Anyways,
Mercury is in Scorpio, a water sign and conjunct Pluto possibly contributing to the negative or jealous outlook. Moon, mercury, and Pluto in Scorpio and the 9th house, it makes sense that there is criticism. Since the 9th house is belief or philosophies. The conjunction can be seen as a hard aspect between those planets, especially the ones that are applying. Plus, you have Sun conjunct Saturn in Sagittarius! Saturn in mutable signs can make thinking more opinionated, negative, or worrying. This conjunct your Sun can cause a feeling of inadequacy and then in the 10th house which is your place in the world or “career”. I can see in the natal the measuring yourself up to some sort of personal ideal.
You have Mars in a harsh aspect to Saturn and Sun which can possibly show fear of self-assertion of course you have look at the whole chart, plus that square is sort of wide in my opinion. Your Mars is in the 1st house which has been said to be willing to approach a problem, but also in Pisces which can be unpredictable, moody, indifferent to pressure (especially conflicts or battles).
I’m assuming your Mars is quintile your Midheaven since its quintiles your Uranus which is conjunct your midheaven by about 3 degrees. There is can be a subtle dynamic at play there, then Mars is in the 1st house and the Scorpio planets. Which leads me to believe the intensity or urge seems to be there.
Midheaven is in Sagittarius conjunct Uranus. Jupiter is in Pisces in 1st house. Aquarius is in 12th house. Maybe you want to take a risk and be “different” or “original”, want to help a large number of people or have a feeling that your work helps a boarder good. But there is also a need for your place in the world to allow you to explore yourself and unknowingness, ignorance, or unconsciousness more. In hopes to achieve wisdom. Avoid putting yourself in places where people to take advantage of you, which requires thinking ahead, but not going through something with a negative mindset which can be blinding to this. A sense of selfless acknowledge by you or another is not equivalent to being helpful.
Maybe something in the arts that involve communication where you keep your individuality, somewhat show it, reaches a broad of people, but not out in the forefront. Maybe better in a team or group setting. The risky, but mysterious screenwriter, taboo exploring playwriter, eccentric songwriter, the direct, wild but honest radio host. North Node is in Aries it may bring clarity to be passionate, daring, fiery, and risk taking. This could work for the stuff I wrote in the paragraph above, but also your Pluto polarity point since 3rd house is communicative while Taurus is Venus ruled hence arts.
I can’t see the rest of your aspects to your Midheaven and frankly I’m too lazy to try and work them out on my own through the degrees.
That’s all I got, hope it wasn't unhelpful.
