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I can totally relate! Sadly, I have no advice though.

I saw her climbing on a chair from the side the other day, and was SO EXCITED to see her do something 'different'.
But, she's so scared of everything else. Scared might not be the right word, but cautious, like you described, is perfect.
I can't even get her to step on a leaf on the ground. We had to walk through some loose dirt on the driveway at daycare and she looked petrified at the thought of having to step on it.

I don't really know what the future holds for her - is she going to be shy/introverted/cautious all the time?
I was (am!) extremely unathletic and should ask my mom to see if this is how I was as a child too - I don't want L to be as pathetic as I was

My LO is almost 3 and very, very cautious too (physically). She climbed 4 stairs by herself this past weekend…which is the most she’s ever done. We’ve never had to put up baby gates because she has NO interest in trying to walk up/down stairs by herself or get into places she shouldn’t go. Only within the past few months has she begun to climb up onto the sofa by herself, etc.

What I’ve done to try to encourage some risk-taking (if you can even call it that!) is to hold her hand, and then let go for just 1-2 steps/seconds, and then take her hand again – and then really talk excitedly about how great she did on her own, and ask her to high-five me for her “big girl moves”. Sometimes we'll call DH or a grandparent so she can tell them about whatever she did that was a "big girl move" - that seems to help too.

At school, I know she gets lots of encouragement from teachers and from her less-cautious friends to try things like the slide, which she now will do on her own, as long as it’s a very small sized slide. Peer pressure has definitely helped her some, so it might help your LO too!

I have an extremely cautious almost 2 year old, same issues. She won't walk on new surfaces, try new things, and she gets freaked out by a leaf on the ground, she's extremely introverted. I don't really have any solutions, but my current experiments with her is to make sure we're doing the same activities over and over again. We always go to the same playground, do the same classes at the same time, introduce one new thing at a time, etc. I have noticed that the more times we do something over and over again, the more willing she is to at least, like, put her feet on the floor. Oh, and the other thing that I am working on is making sure that I am okay with accommodating her having an introverted and cautious personality. My husband is very introverted and cautious, and his parents wanted him to be more outgoing, or thought it would be good to put him in highly social situations that just compounded his anxiety. So we have come up with some stuff already like small family birthday parties until she is old enough to decide what she wants, and then we will respect if she wants something small, that sort of thing. I also focus on the positive things about her being cautious and introverted, like that there's no chance she'll take a tumble down the stairs, and she's super easy to have in restaurants because she's so overwhelmed she sits in my lap quiet as can be!

@MrsF: in my experience, they are totally different children in school. Positive peer pressure at its finest! He eats well there and naps. She may surprise you.

@MrsF: we haven't. I don't think he is physically ready yet so I am not going to push it. He's going to be starting a toddler program right at age 2.5 for a few days a week and they help with sitting on the potty before each diaper change to transition to potty training. I'm crossing my fingers that will help. He just turned 2 last month and I am still helping with dressing and undressing, in and out of tub, in and out of car, and he's still in his crib with no signs of climbing out. I posted a thread the other day wondering when kids normally did all these things alone because I wasnt sure if I am babying him too much but there was a range of answers that made me feel like he was in an okay spot.

@yoursilverlining: I agree. In my circle of friends/family, the majority of kids weren't potty trained until around 3.5 or so.

My cautious LO is 25 months and just discovered climbing. It was very similar to the way she waited to take her first steps at 17 months and then practically ran the same day. She's very cautious and needs to know she can do something before she'll try.

She started climbing after we had a play date with a climber of the same age. She watched the girl over the course of an hour or two before she attempted to do what she was doing. I think the play date just came at the right time. It may have helped that the girls were being naughty (climbing over the back of the couch to land in the playpen). Her friend was getting a lot of attention from her mom by being scolded. I was sitting back hoping my LO would just attempt it.

Sounds like the childcare you have lined up will help.