For job search, you need to be optimist — and cynic

Amy Lindgren owns Prototype Career Service, a career consulting firm in St. Paul, Minn. She can be reached at or at 626 Armstrong Ave., St. Paul, MN 55102.

Halloween is just around the corner. Do you know what you’re going to dress up as? If you’re hunting for a job, one obvious answer is to go as a job seeker. But wait! That doesn’t make sense: Employers don’t hire job seekers, they hire people to do jobs.

Anyway, how would a job seeker dress up — as a giant resume?

As I’ve been thinking about our national costume holiday and wondering what I should don for handing out candy at the door, I’ve been reminded of the frequent conversations I have with job seekers about wardrobe choices.

When it comes to interview preparation, it’s pretty easy to give general advice — comb your hair, shine your shoes, etc. But providing wardrobe advice appropriate for the actual company that’s doing the interviews? It’s another thing entirely to imagine the right outfit for a specific but unknown workplace.

I take the “dress-for-success” theory seriously, but it’s hard to maximize the concept when so many workplaces stretch casual Friday over the entire week. These relaxed standards are mostly good for employees, but all kinds of trouble for the interview candidate.

So I default to the standards. Wear what you’d wear on the job, but one step better. Look the part, but as if it were a really special day at work. Women, tone down your look just a bit (limited makeup and jewelry); men, spark it up a bit (add a tie pin or wear a colored shirt). Dress in layers, so you can remove the jacket for your outfit if you’ve inadvertently overdressed.

Dress choices aside, there’s another kind of “costuming” that comes to mind when I consider job search. This is a metaphorical dress code that involves hats, derived from the common metaphor of wearing more than one “hat” to indicate having more than one role.

In this case, I’m not talking about the multiple hats a job seeker wears in terms of tasks. We all know that on any given day, a person in job search will be a researcher, a sales representative, a telemarketer and a subject matter expert while conducting his or her job search.

The hats I’m referring to are more about attitude than tasks. I’ve got two in mind that I’ll sometimes ask a job seeker to imagine wearing: an optimist’s hat and a cynic’s hat. Since we’re talking metaphors here, we don’t need the actual hats for the exercise.

The more important point is to have the metaphorical hats ready to pop on at any moment. And to sometimes wear both simultaneously. The optimist hat is my go-to accessory for most aspects of the search. If someone says, “You should call Harry — I think he’s planning to add staff,” I want my job seeker to think, “That could be me!” and not, “I bet he’s already got somebody in mind.”

Basically, I’m trying to rewire the job seeker’s thinking so the default message is positive rather than negative. This comes from my observation that, in the absence of actual information, people in job search tend to imagine the worst.

But not everything in job search is rosy, even for the natural optimist. Donning the cynic’s hat when reviewing job postings will remind you that many posted jobs have already been filled and that some jobs list more criteria than the work requires. With both hats firmly in place, you can do some research before applying, or limit the time you’ll spend on the application.

The cynic’s hat is also quite handy when you receive an offer and the interviewer tells you, “This is the top of our range.” That doesn’t mean they’ve topped out their budget — just the range that they set before the process started. So, while the optimist assumes the offer is the highest possible, the cynic knows there’s almost always more money available, but only if one asks for it.

As you can imagine, the job seeker who wears both hats at once makes a terrific negotiator. Cheerful cynicism is a hard combination to beat when it comes to making a deal. The best part? You don’t have to worry about how the hats look. You’re the only person who will know you’ve got them on.