And therein lies the problem for some job seekers as they go about trying to define a new direction. It’s easier to be naysayer to a new aspiration than it is to nurture it to life.

The process of developing a Plan B is really one of internal and external conception: coming up with ideas for new paths in life; allowing yourself the space to, as one participant put it so rightly,  “daydream” about all the ways you could make money that you had never before dared envision; and then going out and testing the waters.

But we saw in the workshop that there are those who can’t get away from the notion of contraception: all the reasons why the workshop was wrongly named and all the reasons why you can’t do this job or that one. For example, one person briefly considered working at a museum given her love of the fine arts, but she was quickly reminded that there was fierce competition for those positions and they paid poorly. So much for that hot idea; it got a quick bath of cold water and sizzled on the workshop floor.

Developing a Plan B requires not only the courage to be unbound by the past or by negative thinking, but also a willingness to enthusiastically complete the workshop activities including (1) contacting old friends and colleagues to poll them on your strengths; (2) scoring potential Plan B “survival jobs” for your degree of acceptance in doing them; and (3) taking a long hard look at your interests/passions to see which ones you could profit from now.

Let’s face it: it ain’t easy coming up with new directions for your work life and there are lots of naysayers out there who are more than happy to squelch your idea before it gets off the ground. Parents who want you to fulfill their own dreams; colleagues stuck in a rut who don’t want to see someone else fly high — don’t forget what happened to Icarus; and fellow job seekers who can’t help but project their own natural and understandable frustrations upon you.

What’s a jobseeker to do? Simple. Choose your confidants carefully; let your daydreams rise up freely as cumulous clouds on a warm summer day, and curb your inclination to share too much too early. Wait until you have something of substance going before sharing it too widely.

We also took a few minutes to review some of the Plan B “survival job” choices that previous members had opted for and here are a few that proved particularly successful as transitional experiences for those who did them: Loews Paint Department salesperson; Whole Foods Cheese Department server/expert; Audi/Porsche salesman; Best Buy computer salesman; bakery owner; paralegal; mortgage broker; personal tutor to high school students; substitute teacher; acupuncturist; Boston tour guide; Williams Sonoma retail sales person and cooking demonstrator; wine salesperson and distributor; and housepainter.

As for the workshop facilitator, I learned my lesson: next time we do the Plan B Workshop, we’ll ban the Plan B contraceptives, but nourish the Plan B conceptions for those ready for finding new types of jobs.

For example, one of our members, Jacques, went into an interview prepared with a list of questions for the interviewer. The hiring manager ushered him into his office, sat back in his chair, looked him over, and abruptly asked, “Do you have any questions?”

Jacques whipped out his list of printed questions and away they went. His list contained a few favorites that he always asked, plus others tailored just for this interview and company. The interview was deemed a success.

As for the questions, you can ask open-ended questions or closed questions. Examples…

Closed question: What time am I expected to be at work?

Open-ended question: Can you tell me a little about what the workday is like here at Crab Apple, Inc.?

The former will give you a definite answer, but not much more. The latter gives the interviewer a chance to provide more information, and, hopefully, a way for you to build on their answer.

Key point: Your questions should not only be designed to elicit information, but also to generate an active conversation between all the people at the interview.

Just the other day, another member of our group, Dustin, went to a small company where the key players, who weren’t particularly schooled in interviewing, gathered for a four on one interview. After about 15 minutes of desultory conversation, they asked him whether he had any questions, whereupon he whipped out two pages of questions and away they went. (The party had begun!)

Here are some of the questions that members suggested along with the reasoning behind their usage:

Q. Why did you bring me in today?

Great way to find out what it is they liked about you and, even more vitally, what they are looking for in a candidate. Another way to elicit a similar response is:

Q. What was it about my resume that you liked?

This might be even better because it allows you both to talk about the resume, a third party to the conversation, as it were, rather than to force early judgments of your candidacy.

Q. In six months, how will you know if you’ve chosen the right person for the job?

This gets to the real reason they are hiring. Job descriptions are too often unfocused and without clearly stated priorities. A laundry list of what they’d like, but not of what they — and the hiring manager — really need. A variation of this query is:

Q. What metrics will be used to judge my performance?

This is a great question to pose to a manager whom you think is factually oriented, someone with the classic business mentality of: “If it is not measured, it’s not manageable; and if it’s not managed, then who cares?”

Here’s a question that may get to the core of the business problems of the hiring manager – something you’ll need to know to present your accomplishments in terms that will convince them that you are the right person for the job:

Q. What keeps you up at night?

Simple, straightforward and to the point. As long as the interviewer didn’t just read the John Cheever short story, The Swimmer, and is out trying to replicate the suburban hero who swims in neighbors’ pools at night!

Oh, and at any point that you’ve been asked and then answered a question, feel free to follow up with:

Q. “Did that answer your question?”

Not only does this make sure that you understand what they are looking for, but it also allows you to be brief and to drill down only if they invite you to.

For a good question on the culture of the company:

Q. How are decisions made in the company? Top down; bottom up? Are they made collaboratively or by fiat?

The answer to this question should be taken with a grain of salt, but as long as your b.s. meter is working, you should get some valuable intel.

Near the end of the interview:

Q. Is there anything that you see or sense that would prevent us from moving forward with the process?

Or something along these lines so you can elicit and then answer — on the spot — any objections the interviewer may have. Then…

Q. What are the next steps? What’s the timeframe here? When can I get back to you to find out how things are progressing?

And, finally, don’t forget to ask for the order!

Q. I’m really interested in this job; when can I start? !!!

Enough already for today! For a great book on questions, read 301 Best Questions to Ask on Your Interview, Second Edition, by John Kador.

No, this is the domain of the database, rule-based, computer-driven abstractionists. No dirt, no plants, no sunny days, no rainy days, no DNA, no bad moods, no vicissitudes… no fuss, no muss. Just clean, clear, rational office work for knowledge workers.

One of our members took the discussion to heart and got right to work polishing her LinkedIn profile. Eve had been working as an editor, proofreader and writer for a medical advertising agency downtown for seven years. It was time she did a LinkedIn Makeover!

Here’s what she did: under the Specialties she added:

Line editing, proofreading, AMA style expert, content management, process maven, style sheet creation.

She also changed her Summary slightly to read:

Versatile and adaptable communications professional well versed in both client- and agency-side operations in the medical device diagnostics, and specialty pharmaceutical industries. Sharp-eyed editor, proofreader, and content manager. Subject experience in biomaterials, cardiology, dermatology, nutrition, orthopedics, pediatrics, oncology, ophthalmology, and wound healing.

Note the number of specific industries she’s listed above; all the better to attract candidate-hungry HR recruiters

In Eve’s case, she just used her native intelligence to fine-tune her profile, but you can go about it in a more systematic way. (Keep in mind that when we refer to a keyword, it can be a single word or a string of two or more words; e.g. “content manager”.) Here are five steps to get you started:

1) Sit down and do some thinking. What words make sense for your career? Your background? Your career? And your future? Write them down on a list.

2) Pull out descriptions of jobs from your files that you were most interested in and/or applied for and/or held. Pull out the keywords and add them to your list.

3) Now, go to Google AdWords and enter one of the keywords that seems to be the most natural one for a search. (There’s that “natural” word again! How about we say your “best guess” for a search instead?)

4) Study your Google AdWord list. You’ll find a count of both “Global Monthly Searches” and “Local Monthly” searches. Add the ones that appear most often to your list, if they’re not there already. Keep an eye out for different spellings of keywords’ you may want to salt them in somewhere down in your profile. Now, do it again with other keywords.

5) Now look at other people on LinkedIn with the same general career track as your own. See if you can find more keywords in theirs, especially from people who might work or have worded at one of your target companies.

From all of these sources you’ll have plenty or words to choose from.

Now put them in a food processor, add about two tbsp of extra virgin olive oil and blend at high speed for about 15 seconds. You should now have a list of keywords to add to your LinkedIn profile!!!

You can add the keywords in a list to your specialties section, but you also will want to be sure that they appear, or at least the key keywords appear, in your summary statement and in the detailed portion of your profile.

As for Eve, her polishing of her LinkedIn Profile didn’t take long to generate results. Literally, within two days she got an email from one of the top agencies in the city! They were looking for a freelance editor/ proofreader for a very busy account. The HR manager said that Eve popped right up on her LinkedIn search “because her key words were great!” She’s now got a job that fits her — and her LinkedIn profile — to a T.

Now see if the same magic that happened to Eve doesn’t happen to you soon, too!

His mantra of “Don’t settle”, for instance, was particular nettlesome to some as they are beset by bills and family obligations — and frankly, it’s not fair to ask them not to settle if it means jeopardizing the health and futures of their family members. Others, however, have followed their hearts and intuition, as he urged, and despite protracted periods of unemployment appear to have reaped (or about to reap) the rewards of holding out.

One aspect of Jobs’s speech that doesn’t get quite as much attention is how he talks about death. He did have pancreatic cancer. Imagine sitting at your college graduation listening to this slightly hoary, if iconic, guy talking about death. Graduation is about stepping into life… isn’t it?

He said then, “Remembering that you are going to die is the best way I know to avoid the trap of thinking you have something to lose. You are already naked. There is no reason not to follow your heart.”

Many people don’t realize that Jobs is/was a long-time Buddhist. His statements on death and your life’s work may have surprised if not darkly challenged many in the audience both at Stanford and on Monday. Yet it’s perfectly consistent with Buddhist philosophy. After all, the Buddha was supposed to have said that “death is the greatest teacher”. And, in fact, meditating on one’s death is a fairly common Bhuddist practice. So it’s only fitting that Jobs should have said and meant it too, so deeply so, that, “…Death is very likely the single best invention of Life. It is Life’s change agent.” Just as Steve Jobs was an incredible change agent.

Now it is up to us to be challenged by his death to “ follow our hearts” and find the work that is right for us: maybe not right now, maybe not at your next job, but ultimately, to do what you must do.

If you see a job listing that interests you, you should immediately start tracking that company. It’s a little like the college interview process: you must show your interest in the company/college by following them/visiting the college to be taken seriously as a candidate. You should have some recommendations — how many is a matter of opinion. Just be sure to avoid reciprocal ones as it looks a little fishy.

LinkedIn is far more robust than just a list of connections though. There are groups to join where, by the by, juicy job leads may be posted. Don’t have a good target list yet? There’s a functionality to search for particular kinds of companies in your area. Use it. And, also, let everyone know you’re in the game by updating your profile with changes and/or news bits on a regular basis.

Finally, what to do about targeting your profile to a particular job opportunity? Good luck on that one. There’s no practical or easy way to do it. Like many aspects of the job search process, you can’t control everything. If you think there is no such thing as luck or chance or fate or kismet or “God’s plan” or whatever you want to call it, just ask Red Sox management this morning about that!