My teenage self would be shocked that I…
Quit smoking at 25
Cut my hair, and I now shave my head.
Actually worked in a factory.
Walked away from music for 5 years.
Found a way to make a great living playing bass guitar, and I get to travel lots because of it.
Met many of the artists from the records I used to listen to. And they know me.
I’m still alive and over 50.
Still be married to the same great girl I met when I was 18.
And that I’d miss my Dad so much after he passed away. It’s been 22 years and I still grieve.
My teenaged self would freak out that I’m not the editor-in-chief of Rolling Stone magazine, but instead a stay-at-home-mom of 3, with a Volvo station wagon parked in the driveway.
Wow, reading this has confirmed something I’ve thought for a long time: That I’m really just an extension of my 16-year-old self.
Because if you told that Detroit teenager that, at 28 years old, he’d be living in Washington DC, working as a journalist, engaged, and going to rock shows and music festivals regularly, he probably wouldn’t be surprised. Impressed? Yes. But not surprised.
Good question.
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That I’m not a comic book artist living off of twinkies and beer in NYC.
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That I have a ponytail down to my ass. (I was very well groomed back then, obsessively well groomed),
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Finally speaking with my father after 36 years and actually liking him.
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Being comfortable around women.
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Regretting not ever being married and having children.
I think sitting down with my seventeen year old self and explaining the choices I’ve made and why would be one of the hardest things I’ve ever done.
<poof> back to lurker town 
That I think my teenage self was by and large a little twat. That I got far away from Cowtown, Texas. That I actually like Republicans and think the CIA a useful organization.
And that I chase stupid teenagers off my lawn! (Well, living on the sixth floor of a condo building, I don’t actually HAVE a lawn, but I’d chase 'em off if I could!)
I never saw myself being married and divorced twice.
I never saw myself working in an office much less at the same job for over fifteen years.
I saw myself having kids but I never saw myself in the home stretch with a son almost twenty and daughter almost eighteen. It still amases me that I gave birth to both and by some grace of god I managed to raise them to adults.
I never saw myself living in the town I was born and raised in. I thought I would live somewhere else.
I never saw myself turning 40 but you can not stop time and I am faced with it this year.
My teenaged self would be horrified at how fat I am, and how conventional I look (I wasn’t a tearaway in highschool, but I thought that I’d get wilder once I left). She’d be pretty upset that uni wasn’t the natural fit she was hoping for, and that she wasn’t really going to grow out of depression.
On the plus side, I’m kinder than I was, better read than I was and I have a amazing group of friends, the likes of which I never thought I’d have.
Another thing is that I think my teenaged self would have been bowled over by how great adulthood is. Like quite a few other teenagers, he grew up thinking that his teenage years were going to be as good as it got. For my teenaged self, that was a pretty fucking depressing thought.
But man, I’m having more fun now than I’ve ever had. I don’t have to hang out with anyone I don’t want to, my work day isn’t much longer than my school day, and in spite of the fact that I have to deal with total wankers every once in a while, at least I’m getting paid a decent wage for doing it, and the wankers in the library aren’t anywhere near as bad as the wankers in high school. I mean, there’s just no comparison. And sooner or later, I’ll find another job, and I can always quit to go back to school to study something a lot more useful than the Etruscans, or whatever they tried to teach me in high school. I can’t quite remember.
What would have blown my teenaged mind (and what did blow my twenty-something mind) are all the choices I have. Starting with the army, I found myself with both free time and disposable income for the first time in my life. I could buy whatever I wanted to within reason, and suddenly I had a bunch of music and books. I could study history, or I could hang out with my girlfriend (Oh, that’s another thing: My teenaged self would have been amazed at my girlfriend. He’d had one or two girlfriends himself back in the day, but noone like her.) Much later, the girlfriend became my wife, and now we just . . . live. We decide what to do with our free time and what to spend our money on and what movies to see, and how to work out, and most of the time, it seems to us that getting older is like a $1.50 cover charge to the greatest club on earth. I’m sitting here typing this on a computer that I helped pick out, getting ready to go out for a little shopping, and then maybe we’ll hit the local Borders bookstore this afternoon and just chill for a couple of hours reading. Or maybe we’ll see a movie. Or stay at home and do nasty things on the couch that will guarantee that neither of us gets into heaven.
Right now, we like Boston, but we’re already starting to talk about moving out to the Pacific Northwest where the climate is milder and the job opportunities better. We choose where to live, how to live, and what to live it with. Choices. I actually had to figure out how to deal with all the choices, they were so overwhelming. It’s like my teenaged self escaped the Soviet Union and wound up in LA. Even good changes take a bit of getting used to. If I could go back, I wouldn’t even try to explain it to him. You have to experience it to understand.
Heh. Set the time time machine back to the late 1980’s and watch my college self’s head explode when she hears that-
I no longer smoke cigarettes, drink alcohol or take drugs.
I have a good man as a husband, and two beautiful children.
I show up for work on time and every day I am expected to, and “work 8 hours for 8 hours pay.”
I am not a successful actress, or even a struggling one (see my first item for how that went down the tubes…).
I have a nice house with a shrinking mortgage.
People not only trust me, but respect me and come to me for advice on a number of diverse topics.
I have taken out 4 of my seven ear piercings (but I did add a belly piercing, so she’ll at least now I’m not totally gone ).
I really am content to be a square instead of a player.
Ditto on that! I went to the most prestigious school I could get into and worked toward becoming an “academic,” because I assumed that that’s what smart, daring, strong women DO. And here I am, now, realizing that no, some of us become nurses! 
I think I’d also be surprised that I married so early (4 days after I turned 24) and that I want to have a baby as soon as I’m through with nursing school. I’ve realized that wanting to create and nurture my own family (which is currently just my husband and me, but it’s still a family I’ve created) is just as worthy a goal as wanting to have a good career, and while some people simply fall in to their goals, some of us look at our options and choose. I’m really looking forward to being a mother.
And, to round out the list, I think my teenage self would be totally un-shocked to find that I’ve spent my adult life in Chicago and New York City. I was never the type to hang out in a small town forever.
My teenage self would be shocked to discover that, at age 41 I:
• Still have most of my hair. I expected be almost completely bald by this time, like my dad was. Never mind that I attempted to pre-empt this by shaving my head for seven years. I let it grow back in last year and was surprised to discover that that little bald spot on the crown of my head hadn’t gotten much bigger.
• Have never been married, and have no kids.
• Voluntarily gave up driving for almost 15 years (okay, not entirely voluntarily; the first 90 days was a suspension for DUI - after that I chose to remain carless because I wasn’t ready to quit drinking, and when I finally did quit drinking I’d grown accustomed to walking and discovered better things to spend my money on than cars and gas).
• Would have ever gotten a DUI, because as a teenager I swore I’d never drink.
• Would be content with not having had sex in 12+ years (let’s hear it for 1995!)
• Would still be in the furshluginer restaurant business.
• Would love country music (I used to be a headbanger.)
Oooh, I forgot to add “Can actually speak French”. My high school French teacher was incompetent and after two years I had only a basic grasp of French. I can now discussed radio astronomy with my boss in French… 
Not only am I not an engineer or research physicist, I’m actually making a living through creative writing. I think my teen self would have turned suicidal at hearing that.
Moving to the opposite end of the world would have small potatoes in comparison.
That I would go to interview after interview, seemingly doing everything right & sending thank you notes afterwards, and still its always somebody else who gets the job.
That I put up with abuse, condescension and out-right lies from supervisors at a job that I hate without quitting, just because statistically its easier to get the job you want if you are already employed (even if you are under-employed).
I never would have believed that hard work and a good work ethic wouldn’t be sufficient in the workforce. Maybe I might have believed the ‘He’s over 40…f-him’ mentality though…
I was a poor marine biologist living in Southern California for a long time. My teenage self expected this and would have approved.
The part where I gave it up and went to med school would have flabbergasted him.
That I’m happy (overall) with my appearances.
The things I’ve done for love.
The things I’ve tolerated for love.
That I didn’t finish college.
That I’m not a pastor.
That I think gay rights are important and am now an atheist.
That I did an extended stint at blue collar work.
That I’d end up much more sympathetic to my gender than I thought. I was raised to think that the women had it figured out. Then I saw they didn’t. Then I saw neither did… then I saw we just talk right past each other WAY too often (and make it look harder than it is).
I honestly enjoy sports.
Women can enjoy sports (who knew?!? I sure didn’t!!)
That I’m pro-choice.
That one of my kids doesn’t do THAT well in school - despite the IQ to do so (argh!).
That I’d divorce at 32.
That I’d be marrying for a second time at 34.
(I was a protestant, snobbish, insecure one… can you tell?)
What wouldn’t surprise me…
I like my kids and having them around.
I use logic heavily for work.
My political interests.
All in all… I think what happened needed to happen. It’s been good for me - and to me.
After considering this question, I don’t think anything about my current day self would surprise my teenage self except for the physical changes of aging. In that category I would also have to include the realization that as you get older the passage of time seems to move faster and faster and that’s something that I could not have imagined as a teen.
Signing the front of the paychecks not the back.
One of the other posters reminded me: my teen self was homophobic and would never understand my attitudes today. I remember reading Plato in college and being appalled. Luckily, growing older can sometimes mean growing wiser too.
Another one is that I would probably not have believed it if someone were to have told me that I would spend most of my waking hours working on a computer. During my teenage years computers were something that only “computer people” had anything to do with. I was about 25 when I first started using a personal computer, an Amstrad, in 1989.