Hi Main_Street - thanks for making us THINK about what we do. I've been doing radio since 1977. Here's my spin:
a) How do you know if you are "successful" in radio?
Success is relative. Like any other business. And it depends on what your measure of success is. Jocks who move from city to city their whole careers - shaking up thier family and lives - may be successful because they're earning good money (a liability these days). But I'd question the price of their "success". On the other hand, if you're pulling enough $$ to keep you comfortable in an inexpensive midwestern town, and you're happy, then you're successful too.
b) does anyone ever achieve success in radio and maintain healthy family relationships?
I'm still madly in love with the girl I met 20 years ago - we've been married for 11 years, and now have a baby girl. I used to work 15 hour days, and it was a strain on the relationship, but we always made time and got through it with no problem. One thing that's helped is NOT moving - I've always worked in CT or MA. Turned down many offers across the country, and have spent most of my career in Boston. We're living pretty large, so I guess I've achieved "success" and maintained a somewhat balanced, healthy life.
c) What's it like to work in a career where even your co-workers are your competition?
I've never seen it that way - my co-workers are friends and allies that can help open opportunities and get you gigs. Many are now lifelong friends. People I've worked with who are secretive and guarded tend to miss out on a lot of goodwill, as the radio community is a brotherhood. Just look at this message board! If you're good at what you do, have confidence in yourself, and a positive attitude - you'll have nothing to worry about from your co-workers.
But management is a different story. The recent layoffs from Clear Channel - sacking 20 year vets, then posting an opening for their job (WKSS) is a clear sign that the priority is cheap labor. The corporate mantra now is "work even harder, shut up about money, and maybe you won't get laid off." It's sad to see competent people who've worked hard for decades, possibly poured their heart and soul into a station, get shown the door simply because they earn more than management NOW wants to pay. That's your reward.
For that reason, I recommend NOT pursuing a career in radio until the industry stabilizes.