"Everyone my age is further on"
One version of the dip gets a chapter of its own, because it doesn't need a housewarming to set it off. A birthday does it, or a form asking for your age. You're thirty-four, or forty-six, and you start doing sums. By now you should own somewhere. By now you should be senior, or settled, or have children, or know what you're doing. Everyone else your age seems to.
It's worth asking where the timetable came from, since nobody ever handed you one. My answer is an interpretation, but I think it holds. You pieced it together from announcements.
Think about what gets announced. People announce that they've arrived somewhere, with an engagement, a set of keys, a baby or a new job title. Nobody announces the waiting. You won't see a post saying "still renting, quite like it" or "third year of trying" or "same job, no news". So in any given month you hear from the few people in your circle who've just arrived somewhere. You hear nothing from the much larger number who haven't.
Run that for a few years and it feels like everyone. It's the effect from chapter 5 again, with a calendar attached. The people who come to mind are the ones who produced news, and you've taken the news for the norm. If you count the quiet ones, the picture changes. Of the people you were at school with, work out how many own a home, have a senior job and have a settled family. I'd be surprised if it's more than a handful, and I'd guess none of them got all three when the timetable says they should have.
The committee is at work here too. One friend bought at twenty-nine, another made partner at thirty-three, and a third had her children early. Your timetable takes the earliest date from each of them. No real person has kept to it, including the people it was assembled from.
You're also seeing arrivals without their terms. You see the keys. You don't see the size of the mortgage, who helped or what was given up for it. You hear about the promotion, and you don't hear about the three years of evenings that went into it. Whether you'd have wanted it on those terms is a separate question.
There's a fair objection, which is that some clocks are real. Fertility has a timetable. Pensions reward an early start. Some careers are hard to enter late. I agree, and those are good candidates for the kind of comparison you run, from chapter 2. If a real deadline may apply to you, get the facts from someone who knows, such as a GP, a pensions adviser or a person already in the field. You'll come away with an answer and some options, which the dip never gives you.
But the feeling of being behind hardly ever takes that form. "I should check my pension forecast" would be a useful thought. What the feeling tells you is that you're late for your whole life, as though there were one schedule and you'd missed it. There isn't one. There are many people arriving at different things in different orders, and some of them never arrive at some things and live well anyway.
So I'd make a small change in wording. When you catch "by now I should have", swap it for two plainer questions. Do I want that? If I do, what's the next step? Then "later than her" is only a fact about dates, and you can drop the word "behind", because nothing was ever scheduled.