More or less for the past ten years I have observed that there are probably only two main schools of thought on the matter of whether we should wait till we are ready to take a step or take a step and worry about the consequences later.
I spent a year at a ultra-othodox yeshiva for women (which in a way is an oxymoron in 
this case providing that we learned Gmara the way the men do in yeshivot), even though the majority of women that studied there, weren’t brought up religious and often weren’t even religious at the point of joinging the yeshiva. We were a group of women all over the spectrum of religiousness spreading from secular to ultra-orthodox, in the same space, at the same time, learning for 14 hours per day, 5 days a week and analysing every single bit of everything to the point of bleeding.
It was either a recipe for a disaster, or a recipe for a great success (I can’t possibly say “great success” without hearing Borat’s voice).
I chose that yeshiva, because I wanted to be challenged out of my box of practicality, being down-to-earth, being far more comfortable with things that can be measured, counted, invested and held. I do not find building castles in the sky exciting. I therefore made a deal with myself: I will see the world the way that it can be seen through a more spiritual approach while I get to learn some very tangible and challenging things like Gmara and Chumash. I am seeing another oxymoron here, but the one that works for me.
In a completely personal opinion, the general attitude to many things while being part of the program was that of preparation and waiting for things to happen. Not, under any circumstance, entering anything before we have worked on ourselves so we know that we can handle it. I thought that I would try, but I failed. It’s not my nature in any way to wait for anything to happen. Don’t get me wrong, things happen when they are meant to, but it doesn’t mean that I often wait for them. If something doesn’t go the way I hoped, I put it on hold and go set my eyes on another target. I am certain that I am not alone in my idiosyncracy.
“But, you’re not ready!” How would you know that? Even I don’t know that. My flatmate often says that people shouldn’t do things that they aren’t prepared to do. Like, you
shouldn’t enter a relationship, if you’re not a relationship person, or get a job which is being offered, if you don’t have all the necessary qualifications and experience… in other words, wait until you can before you do. I can understand this approach, but struggle to relate to it. Somehow, I always follow the policy of: if you see it to be beneficial, good for you and it feels right, do it before thinking if you actually can.
There is this moment of hesitation which fear uses to stop us from exploring what is outside of our comfort zones. Yet, nothing in this universe can grow by not outgrowing it’s previous size or capacity. Of course you cannot be a relationship person unless you are actually in a relationship and develop these traits. Similarly, you won’t have particular skills that are required in a particular job, if you don’t get them via work experience.
What I am trying to say, in a way of an early morning rambling, is that we can spend our entire lives waiting to be ready before taking the step to move forward, or we can just move forward and learn on the go. Life, comparatively to time, passes away very quickly and, just as time, is a friend to no-one. It doesn’t wait for us to feel ready. We are never ready, but as a very wise rabbi once told me:
“No-one sends birds to flying school so they will be ready to fly when they need to. No-one teaches them the routes on which they need to migrate annually. No-one sends cubs to a school to teach them how to be lions. No-one even sends children to a children school to teach them how to be children. But, somewhere during the course of our lives, doubt comes in, and we think that we have to learn everything in advance otherwise we will never be ready. Consequently we never take a step forward and we are always afraid of making a mistake. Just as the birds, the cubs and the children don’t need a school to teach them how to live, so don’t you. When the time comes, you take the step, even the smallest one, but without thinking how you will handle it later – and you will see how far you can fly”.
Nedida 