Do you feel like you're fit?

Ha yes, as TavistockToad says it really is all relative. I consider myself quite fit compared to my co-workers and friends, but compared to people at my gym? Nowhere near.
What tells me that I am fit, personally? Being able to go further, longer, harder on both workouts and day-to-day tasks that I could have ever considered before. Everything is easier to do because my body is better equipped.

Actually I think it's the little things that make me realize how much fitter I am than I used to be, and indeed compared to the people around me. For example my daughter weighs 27kg and I can easily scoop her up in my arms and run a fair distance if the mood takes me - sure as hell my partner couldn't do that, or many other parents I am friends with. I can run up flights of stairs without getting winded. Physical jobs at home are much easier.

heck yes lol, I do 20000+ average steps a day, half of them are ran....I think that qualifies me as being fit and I feel fan-bloomin-tastic

(before my fitness journey began 3 yrs ago it bothered me to walk a couple of miles!)

The only thing I could think of to get an absolute (as opposed to relative to yourself or others) assessment was some kind of fitness test you could do. I did a web search and found a few, here is one example: sparkpeople.com/resource/fitness_articles.asp?id=1112.

For my own personal opinion, I've read a lot of your posts. I find it unlikely that someone that knows as much as you, is as passionate about it as you, and looks as fit as you do in your profile picture could be anything but fit. But that's just me :-)

What toad said, im pleased with where I am, but still working on it. Im a lot fitter, but i dont know where I want to set the bar. Is fitter than most people in your gym really fit? For weights then I know I have a whole series of cut and bulk in front of me to build myscle if thats the way i wnat to go.

My target has always been to get in the groups which are less at risk from medical complications.

Considering that 2 years ago I could not run 1/8 of a mile without thinking I was going to die, and now a 10+ mile run doesn't phase me at all, yes I would say I am fit, for me anyway. Definitely fitter than most of those that I work with and most of the other late 50's group that I know. I think icck hit it out of the park: "Being able to go further, longer, harder on both workouts and day-to-day tasks than I could have ever considered before. Everything is easier to do because my body is better equipped."

This is a great question and a great topic rabbit! Thanks for posting.
It's a hard question to answer because I don't think any of us truly see ourselves as others do.
If I compare my fitness now to where I started? Then yes... I am fit.
When I look in the mirror do I see a fit person? Mostly no... I mean, I see the good but I also see the flaws.
If I base my fitness on simple numbers then yeah, I am considered athlete level with all of my stats.
If I base my fitness on how I generally feel? Yes and no... I'm human, just like everyone else. As you mentioned I can do things physically I never imagined I could and I'm not afraid to try anything! But I still get tired, hungry, sore, cranky, etc. just like everyone else.
My workouts are highly intense and I burn well over 1500 a day in exercise alone (not about weight loss).
In my "fitness" mind, I am always in training in everything I do, always looking for the next challenge.
If I base my fitness level on what people tell me and/or how they percieve me? Well... I'd have to say yeah I'm fit.

So I guess my answer to the question is... I don't know LOL!

But I do know this: It will never be enough for me. In my mind there is no specific level of fitness high enough for me to stop.

I am happy, but will never be satisfied

I'd say there's not a standard definition of "fit." I'm sure there's some label somewhere if you can do X pushups, run X miles at X age... but I don't buy it. It's a very personal thing.

To some extent I think your trainer is right - what more can you do? What's your next level? My tae kwon do teacher is an amazing fighter - fast, strong, can jump way high - and he's an awful runner. So is he "fit?" Absolutely. Can the middle-age moms who run regularly and chat through his interval training classes run faster and farther? Absolutely.

In college, I used to swim laps. I've always been, always will be, a bad swimmer. Because I could swim during the day, I swam with a bunch of little old ladies some of whom could barely walk -- but they sure could swim circles around me.

I was diagnosed with rheumatoid arthritis at 21. So even for myself, there are days when my capability level is really different. I feel like I need to push as hard as I can - so the bar gets set really low some days and pretty high on other days. And that's OK.

So am I fit? Yes. I think we (Rabbit and I) are similar (48, mothers, etc.) I can do more pushups than I've ever been able to do. My clothes all fit better. I exercise regularly and at a challenging level (though sometimes I could use more challenge). I eat mostly healthy food in some balance - with a little junk thrown in for mental health.

As I think about aging, my balance is good. My core strength is good. My general strength is good. My cardio is so-so. My weight is good. My general habits (eating & exercise) are good. Can I be better? Of course. But for me, I guess this is my definition of fit.

If I compare myself to my immediate family and cousisn I am sure they cannot figure out how I have no medical issues like they do. Maybe because I have been exercising for years and years longer than some of them.