The Job Hunt: Why Is It So Damn Difficult To Get Hired?

We often share our ideas about how to motivate Millennials in their careers, but there’s more to the story we need to talk about: how to get the job in the first place. The modern job hunt is nothing short of nightmarish for hunters and we can’t imagine the process is easy (or affordable) for recruiters either.

The path to employment has been elongated and complicated since the inception of recruitment platforms like LinkedIn, Indeed and Glassdoor and since Millennials made it a habit to jump from job to job.

The Job Hunt is such a thick topic that we will zero in on only one layer in this story: the layer where a potential employer pits you against other candidates with multiple interviews, assignments, letters of recommendation and a battle for who will take less salary — over the course of six months and then STILL doesn’t hire you.

A top PR woman in Toronto wrote me an email one day, whilst I was employed elsewhere. Her note said to me, “will you please come aboard?”. This was our second time pursuing a professional relationship together and I was open to a conversation, so I went in for an initial meeting. Then she asked me in for a second meeting with two other people, and then I was sent home with an assignment: to design a comprehensive digital strategy for her business.

After that? A test to gauge my savvy with social media metrics and, based on how the questions were being asked, I could tell she wouldn’t know why my answers were correct. After that, a request for a letter of recommendation (I forwarded her a glowing one from my former Director) and after that, a request for a phone call with another former employer. I decided pulled out of the race with a reconciliation. If PR lady didn’t yet feel confident in me, she would never have confidence in me and I suggested she go with somebody else.

A recent Dear Prudence column by Slate shares this modern story about The Job Hunt:

Dear Prudence,
I graduated college two years ago and spent a year looking for a job in my field. I went to more than 30 interviews, got lots of positive feedback and follow-up interviews, but never a job offer. I’ve done networking events, signed up for mentors, been to job fairs, asked for advice, gone to career councillors, tried staffing agencies and found nothing. I truly am open to critique and tough love if it means I could find my way to success. I’m not even being picky at this point. I’m willing to take anything that requires a college degree and pays a living wage with a chance to move up. The problem is I’ve been working the same reception job full time since graduation and I’m really starting to resent everyone here. I took a year off from trying to find other jobs, and now I’m ready to get back to it. How do I keep my positive face on at work? Job searching stresses me out. I’m unfulfilled, unstimulated, and very unhappy.

—Staying Positive

The job hunt can be so incredibly demoralizing. It can make you feel small, insignificant and invisible — especially when you’re creative and thoughtful cover letter receives no response at all.


The Job Hunt is a broken system that needs a full re-write to fuel the Millennial job hunt. Employers need new tools for uncovering exactly what skills they need to fulfill a job. LinkedIn needs to improve their user experience to streamline the job hunt by facilitating more productive conversation and less hash-tagging. Organizations need to empower human resources to value IQ and EQ in their recruitment process, and young professionals need to learn how to put a positive spin on a tough experience.

Job search fatigue is typically a mixture of physical and emotional exhaustion. When we become fatigued, our body and our mind are communicating with us. Our work is then to pay attention to where the fatigue derives from. Are you losing steam because you aren’t really that excited about the jobs you’re applying to? Are you physically tired because you have to search for a job after a day in the office? Are you discouraged because you haven’t heard back on your applications? Only once you’ve isolated the cause can you start to think about strategies to help you push forward.

Josh Durand

Perhaps the best advice we’ve heard about a demoralizing job search to take time off. Career and life coach Kristina Leonardi has helped hundreds of people over the last eight years improve their job performance. She suggests booking time off from your job search to become significantly more focused on what you want.

Depending on your circumstances, take time off to do a major reboot on your search. Instead of thinking about how to get your next job, ask yourself why you want it in the first place. Yes, we all need a paycheck, but what is your deeper motivation? What do you do love about the work that you do or desire? Why are you interested in a particular company or role? The more specific and clear you can be about who you are, what you have to offer, and what you want to experience, the more focused and excited you will be about potential opportunities.

Kristina Leonardi

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