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Shivering -
As a journalist who has been on and off antidepressant medications for many years (and who has now accepted I'll be on them for the rest of my life), I can tell you two important things:
1. Your depression is probably affecting the way you perceive the questions you have to ask as part of your job (and the way you perceive others' perceptions of them). Treat the depression first. The real reason for this? If you switch careers now, you might choose the wrong one for your medicated/treated self, who will be different in terms of skin thickness, adaptability, and versatility.
2. I share your concern that people will be upset at your questions. Most people who feel this way are in one of two situations:
a. a public or official capacity, in which they signed up (or sought election or nomination or whatever), knowing they would answer to the public, or represent the public face of an institution. These people may not like the questions, but they were the ones who signed up to have to answer them. If they don't like the questions, either quit (great story then!) or don't do the deeds that result in the questions.
b. a private person whose life has somehow unexpectedly or unintentionally been thrust into the public spotlight (a current example would be the Kim family in California and Oregon). Asking these people questions is in some ways more difficult, but in other ways easier - you can empathize with them, and they want to talk, whether you believe that or not.
There is a very practical reason that newsroom jobs tend to all start as the obits clerk or obits writer - once you can ask someone you've never met about the life she shared with her husband of 55 years on the day he died, you can ask just about anyone just about anything. The real shocker, as any obit writer will tell you, is that people want to talk. We mourn as much spiritually and emotionally as intellectually and logically. What do people miss about their dead loved ones? Not just the unspoken love, or the hugs, or the smiles, but the wit, the insight, the pranks - the brains under the skin. We mourn verbally - we talk about our grief. And the newspaper is a way to bring the community into the grief.
I've written tons of obits, features on the prominent local man who died, etc., and the feedback has been invariably positive - even from the ones who hung up on me at first.
You may be a private person - I am very much so. So your discomfort may come in part from your expectation of how you would feel being asked these questions. But if you have had a family member or close friend die, think how you felt when friends of that person, folks you'd never met, reached out and asked how you were doing. It felt good, right? You didn't mind them asking, because they were gentle and supportive about it.
Just because you expect you would feel a certain way doesn't mean you're right about others - or even yourself.
So start every obit interview with, "I'm very sorry for your loss." Mean it - you do, after all (even if your sorrow is more that their loss means you have to make the call). Say, "I'm working on a story for the newspaper about your loved one, and I hope you can spare a couple of minutes at this difficult time to speak with me." Be genuine, be sorrowful and respectful. If the person on the other end of the phone breaks down, ask if there is someone else there who might be better to speak to.
On the other side of the spectrum, if it's a public official, remember that you and your readers employ the person, you (and your readers' tax dollars) bought their desk, their office phone, their filing cabinet, the paper in it (and the printer it was printed on, and the toner it was printed with). If they don't want you poking around, they shouldn't have agreed to do the job. They work for you, not the other way around. Be nice about it, but make sure they know that. Your boss doesn't hesitate to ask you hard questions - why should you hesitate for people who work for you?
And in all cases, remind them that you're just doing your job. You have to ask certain questions, and you're sure they understand.
Best of luck.
