What are some of the obstacles to the job search? Speaking as someone who's been unemployed several times throughout my career, I feel I have some experiences to share.
One is that employers seem to hold it against you that you don't have a job. They've posted a vacancy, you're not attached to anyone else, but when you apply they want to know why you don't have a job and why you haven't had one. It's a value shift akin to dating relationships in junior high: you weren't attracted to X when they were single because they were single, but now that they're dating Y and unavailable, X is all you desire. That's how employers are, and they give this away when they ask whether you're still with a place and how much time you'll need to announce your departure. It's a very lazy, inexpensive form of headhunting, where you don't hire a headhunter but simply hope an employee will leave a place based on your charm alone.
Along with this: employers advertise only wanting to hire highly successful people who produce award-winning content. There are two responses to this. One is, "Well, duh." Of course you'll say you want to hire the best people, but the other response is that that kind of employee is not jobless and looking for a new office. They're in their old position, producing highly successful award-winning content. Why wouldn't they be?
And if such a person were let go through no fault of their own, the new employer (in the same breath as asking for them to fill a position) would immediately cast aspersions: "Well, sure you've been highly successful and have demonstrated to us you've produced award-winning content, but... why aren't you there anymore?"
Job searching is kind of like asking for help from someone with multiple personality disorder who is also a vessel for several possessing spirits. And these spirits don't agree with each other. It's like this:
Employer: Bananas for sale!
Applicant: I'd like some bananas.
Employer: Hold on. Why are you trying to buy bananas from us?
Applicant: Because I'm hungry, I have money and I love bananas. And you're selling bananas.
Employer: Can you demonstrate to us that you like bananas at all?
Applicant: Here are dozens of photos of me relishing bananas over the past 15 years. I'm a certified Banana Taster, and I have three references from banana moguls who swear I love bananas.
Employer: But if you love bananas so much, why aren't you eating one right now?
Applicant: Because my source of bananas ran out, and I saw you're selling bananas so I'd like to get right back into eating bananas.
Employer: Why aren't you already so stuffed on bananas you're sick of them by now?
Applicant: So you're selling bananas but won't sell them to anyone who wants to buy them, and you only want customers who are getting them from somewhere else and are sick of them?
Employer: Thanks so much for your time. We have a few more banana customers to evaluate and then we'll be in touch.
Another thing employers do in job postings is cite a specific, obscure program that few have ever heard of but which they insist is "industry standard." I don't blame them for looking for an employee who has skill in that program, but they're wrong on every other point. No, these goofily named programs (AccuTopix, ProAccuraForm, BizProAccuDesk, PerformoPro Plus, etc.) are not industry standard. Maybe that's what your buyer told you, way back when she was trying to convince you to shell out for a low-end platform that still met your requirements, but no. It's just a niche knock-off and you shouldn't alienate anyone for not having heard of NetDynamiCMSware Plus2.0. If you're looking for a smart, able employee, trust that they can learn this rinky-dink program that's no more difficult than memorizing the names and faces of their 30 new coworkers.
Lastly, there is a swelling, inflamed obstacle to finding work online. People like to say the best way to find work is through networking, but I feel this is only a response to circumvent this last obstacle. The problem is temp agencies. They call themselves "recruiters" or "talent placement" and they brainstorm for increasingly abstract and ridiculous appellations each year, but the truth is that they're an industry dedicated to creating an extra step between the employer and the employee, by which they siphon off extra money for the barest minimum of work. I know someone whose recruiter bills the client nearly as much as she herself is paid, and they self-righteously defend this rate, even though they refuse to advocate for her in regard to raises, promotions or workplace issues. The recruiter doesn't do any labor or production, only insists to the client they would like to be paid as much as the actual employee.
What does this mean to me? I'm looking for work in my area, somewhere I can bus to. I refuse to engage with rush-hour traffic anymore: it's damaging to my health and it deteriorates my environment, on top of being expensive and a waste of time. But when I find a reasonable job with requirements I meet and a nearby location, it inevitably turns out that it's only their recruiter's office that's in the downtown area. The worksite itself is closer to Nebraska or Canada, and they don't see anything unreasonable about a three-hour (one way) commute, while telecommuting is out of the question: who's going to sit in on their tedious pre-meeting meetings and listen to their meandering, circular thoughts for two hours if everyone's at home, working? How do we know they're not goofing off at home, instead of pretending to be busy in the office?