This week I was struck by two very different tales about job-seekers.

One is Debra Dickerson, a writer who I respect and who I had the pleasure of having as a guest on News and Notes many times. Following a divorce, she has moved to Atlanta with her children and is broke: straight up, hardcore, broke. She is not hiding the fact and her writing is really wonderful, hard to read, and honest. From, “Brother, Can You Spare a Cone”:

I have the receipt from the returns in my hot little hands. My purchases total exactly $24.63. Tax included, thank you very much. Yet the clerk assures me that the card doesn’t contain enough money. How short am I? He can’t tell me. I should have told him I was using a store card. So the nightmare process of figuring out what to return begins. What good is bread without butter for the toast they consume by the loaf? Peanut butter or jelly? The claritin which allows me to breathe normally or…never mind.

It’s a recreation of that scene from Terms of Endearment when Debra Winger runs short at check-out, her kids are acting out and the cashier is New York City-rude. John Lithgow saves her but the kids and I are on our own.

Unemployment lines are shorter than the ones at Wal-Mart, with all it’s unmanned registers, and those snaked behind me are audibly angry at me and my unruly kids.

I want to cry. I want to give up. They kids won’t settle.

But I hold on. I hold on to moments of grace.

It is rare to see Americans write about struggles with money in this way, in part because of the way not having money is often framed as a moral sin. It is prosperity gospel turned inside out. If you are poor or broke, public policy and media debates often frame you as being deeply and inherently wrong in your behavior and perhaps in your being.

But in America today (as always) there are many people who are doing everything right… applying for jobs and working to save and still facing extreme hardship.

Then, there was a wonderful story by the New York Times’ Louis Uchitelle, who profiled a man who is floating, happily, on the bubble of his family’s money. Maybe a little too comfortably:

The daily routine seldom varied. Mr. Nicholson, 24, a graduate of Colgate University, winner of a dean’s award for academic excellence, spent his mornings searching corporate Web sites for suitable job openings. When he found one, he mailed off a résumé and cover letter — four or five a week, week after week.

Over the last five months, only one job materialized. After several interviews, the Hanover Insurance Group in nearby Worcester offered to hire him as an associate claims adjuster, at $40,000 a year. But even before the formal offer, Mr. Nicholson had decided not to take the job.

Rather than waste early years in dead-end work, he reasoned, he would hold out for a corporate position that would draw on his college training and put him, as he sees it, on the bottom rungs of a career ladder.

Future Darwin award winner? Maybe not, if his folks keep paying the bills.

I also think he does NOT represent his generation’s passion or common sense.

Like many people, I have had to make my own decisions in this economy. I chose to roll the dice and freelance while exploring new business opportunities. I have been lucky enough to find various ways to pay for what was essentially a year of learning to be an entrepreneur. In this past year I have done everything from earning money doing social media consulting for media companies and nonprofits; lecturing at universities on the future of journalism and the role of participatory culture and social media in journalism’s evolution; taking technology classes; moderating events of many shapes and sizes and constituents (including TedxOilSpill); and taking a LOT of meetings just to inform myself about the business environment and what role I might play in it. What I have not been doing a lot of is journalism. I found it was actually harder to support myself doing journalism than it was to admit that I could make more money in less time doing other things and to focus on raising the capital for my new project.

Our new media project is in process. I don’t want to jump the press release someone is probably generating but it will be in public radio and be very much multimedia, participatory, and social media-enabled.

The nonprofit which initiated the project is called Pop and Politics, the same name but not the same organization as the blog I started many years ago. This organization is focusing on covering a changing America, particularly issues of race, diversity, and community. Our content will reach people where they are, on multiple platforms, and we’ll encourage people to participate in how we select and report stories. We have raised money for the pilot phase; are working on the actual project; and are gearing up to raise more money. I have an amazing business partner; organizational partners in this work; advisors; and supporters. We are building the machine. (We will ask you for money, too, dear public media supporters! More information will be online soon about our project once the Top Seekret label comes off of the storage crates).

I look forward to being a working journalist again, but this decision to turn my full attention to business was deliberate. I realized after turning down a few jobs that I really wanted to create my own organization. Then I realized that doing that was going to take at least four times longer than I thought. I have no regrets and I’m really excited. But it is no joke! It takes focus (and savings!). For a time at least, I had to focus on the business side and not worry I was missing covering THE BIGGEST STORIES OF OUR LIFETIME like the oil spill. Okay, I did worry about that but I remained on-task.

It strikes me that we are in the middle of a huge landgrab in journalism, and who has the money to stick out the unpaid entrepreneur phase of both for and nonprofit company-building will have a huge influence in what journalism looks like, feels like, and how it serves us. I would like to see more support for non-traditional entrepreneurs in media, and not just for my own selfish reasons.

By the way, Debra Dickerson is both applying for jobs and looking for new ways to do her work. She is launching a drive to get her readers and fans (and new ones) to fund her next book. To wit:

I don’t know if you’ve noticed, but the internet has body-slammed traditional journalism and publishing into gibbering madness. No one knows anything about what’s going on, and in an atmosphere like this, my options are a) to continue writing for free (see: blogging/writing for websites none of which can pay a living wage), b) get a real job (believe me, I’ve tried), c) or hope that my DIY attempt to self-publish will succeed.

So, here’s my brilliant plan: raise $75,000 to support three or so months of reporting then six-nine months of writing, exploit a college kid as a part-time, minimum-wage research assistant (plus all the coffee he/she can drink), hire an editor to save me from myself before it’s too late and — TA DA — master the mysteries of self-publishing and the beast of technology.

You can read more about how she’s going about this and her hybrid free/paid distribution model in different media. I wish her good luck in all of it.