Thoughts About Your Current Gig ...

This sounds like Dick/Don complaining about being fat.

Do you have to teach nights?

That's what I chose, as well - time, not money, though. As far as the job itself, it has its pluses and minuses. On the one hand, I miss working on big cases for big clients on big teams at my old Chicago gig. The matters were typically interesting and for either huge dollar amounts at stake, or pro bono matters that could be life-or-death. There was also a lot that was bad about it. I left for work at 6 a.m. and got home between 7 and 8. Some days - some weeks - I wouldn't have shit to do, because of the cyclical nature of things, and then, right when I'd be sitting down to watch the Bulls or Blackhawks game or the fucking Final Four on a Saturday night, buzz goes the cell phone. And the cases might have been big, but sometimes I'd be doing tedious work on them, like making a Power Point for some muckety muck partner. Also, you felt like you were constantly being judged - and you were, due to the up-or-out business model. I've been called a "failurist" on these boards for not making partner there, but the truth is, like 5 percent of people who start eventually make partner. It's a long road and you give up a lot, in both time and individuality. Pay's good, though, and you feel like you've made it. This is important: I left 100 percent on my own accord. I could have stayed at least 3 or 4 more years before being nudged out, and I'd have had no problem finding another high-paying job at a smaller but lucrative downtown firm.

My new job is in an office with 3 1/2 other lawyers. My boss is pretty domineering, which is understandable - it's his business. But he's a decent guy, and gives me a lot of freedom to write, for example, or go to court and argue, or plot strategy for some of our bigger cases. There's also a lot of keep-the-lights on bullshit that I have to do - harranguing deadbeats for pay for their fucking roofs, battling with little old ladies over late fees on their home loans. That kind of stuff. But I'm home a little after 6 and nobody bothers me at night or on the weekends. I coach Little League. I've seen the entire run of "Breaking Bad," and 1 1/2 seasons of "Stranger Things." But I can't say it's not weird sometimes to have a degree from the University of Chicago, five-plus years at a Top 15 national firm, and be working here.

If you asked me where I'm going to be in five years, assuming I'm still above ground, of course, I would have no clue. I can't figure out if I'm satisfied or not. As much as the media focus is on women "having it all," it's tough for men to have it all, too. And, generally, if women opt out of the rat race, people are sympathetic. Men have failed. And that's not me taking too much to heart what someone on the Internet says to intentionally trigger me - it's definitely part of the zeitgeist/in the air.

My biggest struggle - and this has been the case whether it was at my two newspapers gigs, or my big law firm job or, now, here, is that I feel that I'm really good at what I do, but nobody ever really has a way of knowing that, because I always for some reason end up buried on the bench behind other people, making them look good. Nobody who matters has ever known who the fuck I am.

When it comes down to it, I don't really like working for other people. But I suck at networking and I hate chatting up strangers, so I would have a difficult time with the client-building aspects of being an entrepreneur. Plus, we're not really in the risk-taking phase of our life. I'll talk to Mrs. Whitman at times about whatever it is I might find unsatisfying and her answer is typically some version of, "Well, yeah, most people hate their jobs. Get over it." It's a little rough, because she has a calling and I guess I don't.

Not a week goes by when I don't damn the six years I spent covering preps because I thought I was paying my dues.

Me, too, because that means I wouldn’t have been laid off.

When I lost my regular job a few years ago, without warning, I was pretty devastated. It was the career I loved, had always loved, and had had great success at. Yes, I miss the paycheck and, more importantly, the benefits, but mostly I miss interacting with many people every day.

I'm fortunate that I had also had a side gig for a number of years and it has kept me housed and fed, but I miss the daily interactions. Now, the most I really deal with people is to tell the server to take the steak back because it's undercooked (who am I kidding... I can't afford steak!).

My current gig is a Monday-Friday day job, where my work responsibilities stop the minute I leave the office every afternoon, and don't start again until I return.

I couldn't be happier and I really, really, really don't miss newspapers.

100 percent.

I got out of "the business" and into marketing about 6-7 years ago and have maintained steady employment and promotions ever since. While the paycheck and benefits are great, the non-work bonuses are the best part. I'm healthier. I have a better social life. I spend more time with my parents. I was able to meet an incredible woman who I am marrying in about 7 months (holy shit). I get to travel to places that don't even have high school football.

What I write about now is boring as hell, at least in comparison to covering sports. And there is always the usual crap that comes with working for any company. But my life is better by magnitudes.