Is it worth it?

While I appreciate the clear-eyed and very reasonable questions being asked, I'll also point this out.
Not everybody is miserable. Not everybody is broke. Not everybody is stuck in a nowhere job. That doesn't mean it's all rainbows and unicorns, but it is possible to make a decent wage so long as you don't plan on living like Kimye.
But as you admitted, you come from upper middle class. Which is great. If that's the standard of loci that's your barometer, then yeah, you might wanna do something else with your life. And that's great.
At the same time, I kind of take issue with the idea that you'd have to slum it at some smaller paper to get started. Got in the biz nearly 20 years ago. Made 16k a year at small daily if never heard of until I saw the opening. Spent 2-plus years there and I consider the SE (who is still there) one of the greatest people alive. I worked my way up and now have a steady and pretty stable job in a metro. I'm not a millionaire but I make more now than I ever thought I would when I was 23.
Is the climate different now than it was them? Of course. I've seen good friends (who are far more talented than I) lose their jobs not because of performance but because of number crunching. That being said, it's not impossible to thrive. It is hard? Hell yeah. But it's not impossible. If it's in your blood (and only you can answer that) ten give it a shot. Sounds like even if it doesn't go your way then it's obvious you have the resources and the drive to find something else.
The best writer I've worked with actually replaced me (I picked him) in the bureau of a daily I worked at after I moved to the main office. He then replaced me in the main office when I took another job out of the area. He was fresh out of grad school and was brilliant. He waited five years, worked hard and wrote award-winning stuff. After a move to a bigger paper didn't happen, he bailed to do something else. He's happy he gave it a shot. And he hasn't looked back. He's happy now out of the business, married and has a life.
You're getting good feedback here overall. But there's a tenor of misery too. It's not alway miserable, but if you're a sadist, it helps.

 

The median salary for newspaper reporters is $35K. It is not decent. Let's be honest, here.

 

Dog8Cats had a good point about control that I definitely wanted to echo.

Chances are, a first job takes you far afield (unless you're really lucky). So most of your vacations will be spent returning to home or a college town. Big chunks of the year will be no-vacation zones. And you will be at the mercy of hiring folks for where you live at most stops. It could mean big moves to random reasons, but if you're chasing a better job, that's what it is. Unless you're at a really high level, you'd likely not be able to say you want to live in a specific place and make it work (easier in some other fields).

And early on, you're signing up for the lifestyle. It's not just the writing and covering of games (that's a pretty good part), it's those nights in the office when you're getting shelled on the phones, trying to throw pages together and then realizing someone forgot to hand type a page of faxed-in bowling scores. Then you probably sleep in and wonder where your day went. Unless you get an early job with minimal office work, that's also an element.

 

And my first SE (who is still at that paper) is maybe right around there after 25 years. Yet there are at least three alums (including me) who used it to get the experience they needed and have over on to eventually land "good" jobs (if there are such things). Though that SE told me recently his best guy now is leaving because he just graduated law school and doesn't want to be broke his entire life.
Point still stands. Not everyone is miserable. Not everyone is broke. Maybe this kid makes it. Maybe he doesn't. But in hopes of providing equal time, thought he'd like to hear that it is possible to do this and be somewhat OK with their life. Again, depends on if it's in your blood.
Am I scared the protective bubble I'm in will burst and it will all go away? Yep. Every single day. But is feel that way no matter where I was working, be it teaching, PR or whatever.

 

What percentage of people in journalism are:

1. Satisfied (at least somewhat) with their pay.
2. Not ridiculously overworked
3. Not legitimately worried about losing their job.

And for those who don't fall into any of those categories, how many are at the top of the profession? If you're at the top of the profession and working somewhere like SI, ESPN, USA Today, CBS Sports, they're probably not worried about job security the way a copy editor at the KC Star might be.

 

There was a writer I worked with early in my career who was at the same paper for 30+ years. He covered the top beat there, at a well-respected, but smaller college town paper. He was damn good and frequently broke news ahead of the bigger papers that covered the same beat.

When he retired, it was mentioned that he never made $40K in a year.

 

To be fair, those three questions could be asked of people in just about every field imaginable.

 

But every field imaginable has not seen its entire workforce cut by 33 to 40 percent in the last several years.

 

You know, there are options in journalism more varied than newspapers -- especially for college beat guys -- that haven't been discussed here much. Stuff like Rivals or Scout, pitching your services as an in-house contributor for an athletic department, initially working on spec for low wages at a Web site as a gateway to bigger things, but I think this part of your post almost gives you your answer.

If standard of living and providing like your dad did are two pillars of your adult ambition, there aren't a ton of journalism jobs that provide it.

 

The issue with the Rivals and Scout jobs are that some are great, but the majority of them are not and I know writers who have left decent gigs for those jobs and been let go within a year.

The people I know who are writing for a school or team's website seem to be incredibly happy with those jobs.

 

If I remember correctly, that was pretty much the absolute best possible time to get into the business. That was the peak right before the crash.

 

I can understand the "jumping ship" attitude for print media, but what about for digital media? Anyone here work for an online media platform (i.e. ESPN, CBS, SI, Yahoo, even Bleacher Report, etc.)?

If one were to land a job there, is the attitude still much of the same for those who've gotten in online?