Stuck in a Prolonged Job Search? Here’s 8 Things You Might Be Doing Wrong

A woman with long hair looking upset while looking at her laptop screen.

“I have never faced a job market like this.”

I hear a version of this statement multiple times a week from those in the job market. They are confused, stressed, and on the brink of throwing in the towel.

Often, they need help figuring out what to do.

So, if you are feeling lost in your job search and need to know what you should be doing differently, I have some suggestions for common scenarios I am hearing about.

It is essential not to be like the proverbial ostrich, put your head in the sand, and think the issue will disappear. It may, but it could be years. I do not know anyone that has that long to wait!

Instead, consider what you can do to change the trajectory of your job search.

Taking 6+ Months to Find a Job

For some of you, this job search feels like you are running a marathon. In the past, you may have gotten your jobs in weeks or, at most, a few months. Now, it is 6+ months, and you don’t know what is happening. Are you unemployable? Are there no jobs (though you are applying to many)? Is it the bots?

Is your goal(s) clear?

I emphasize career clarity for a reason. Having a clear goal provides a roadmap for your job search, relieving the stress of uncertainty. Many of you may not have thought through what roles are the right next step for you and what value you bring to the role. Not just your experience but the knowledge and skills you possess. Can you speak to accomplishments you have had in your work, education, or volunteer work that would resonate with employers? It would help if you did this at the beginning of your job search. Then, you can make a plan to address how to find these roles and how to communicate what you offer in your resume, LinkedIn, and interviews.

Those with a prolonged job search often haven’t done this work upfront. If that is you, now is the time to do this. Start by conducting a self-assessment to understand your strengths, values, skills, and interests. What do you offer that is unique or of value? Who needs this in the marketplace now? Start by strategizing how to attract interest from those who need what you offer.

Develop a structured job search plan.

Many people searching for jobs need to take the time to organize their job searches. They are often haphazard, with some weeks very focused on activities and others with minimal effort. This approach can leave you feeling overwhelmed, discouraged, and missing opportunities.

Even if you are a free-wheeling type of person, some organization is needed to keep you on track. First, make sure you are tracking your job search activities. You can use a simple spreadsheet or job search tracking tools like Teal (https://www.tealhq.com/tools/job-tracker), JobScan (https://www.jobscan.co/job-tracker), or project management software like Trello (https://trello.com/) or Notion (https://www.notion.so/). That way, you can better assess what is getting you traction, AND you have a repository of all your job search information to access easily.

Next, come up with a plan for your weekly activities. Concentrating on what you need to accomplish rather than the hours you want to work is better. Also, while applying to jobs online may feel like you are accomplishing something; remember the 80/20 rule. 80% of your results will come from 20% of your effort. So, where are you seeing the most results? Lean into those activities. This will help you feel more in control.

Network actively with people outside your immediate network.

You knew I was going to mention networking. Why? Because so many of you are not doing it or only doing it haphazardly. I know, this may be your least favorite part of a job search, but I am telling you if you have been looking for over six months, you need to lean into this because what you have been doing isn’t working.

Now, I hear many of you say I tried it, but my network was of no help. So, let me get you to rethink your approach. Think about moderately weak ties to network with. Who are these people? They can be former classmates or alumni, co-workers from previous jobs that you did not interact with much, members of professional organizations you know only casually, or even distant relatives (that cousin you see at Thanksgiving dinner). This group runs in different circles than you, so they have different networks and information that they can pass on to you.

Tailor resumes and cover letters for each job application.

This can seem burdensome, but if you know which roles you are targeting and have written a resume focusing on your value for these roles, this should not take too long. Maybe you switch a bullet point or two and add keywords from the job description, but it should not be a full rewrite of your resume.

If you are using a jack-of-all-trades resume to apply to multiple types of roles, then yes, editing that document will take time.

While this may not be that much fun, think of it like book editing. The writer submits their manuscript to the publisher, but a good editor goes through it and makes changes to tell a better story—one that you, as the reader, will enjoy better. The same idea applies to tailoring your documents when you apply for a job.

Appealing to everyone means you appeal to no one.

I get it. Especially if you are unemployed, you look at your bank account and think, "Okay, I'm desperate now. I will take anything." Then you abandon your strategy and start trying to appeal to everyone and anything.

Here is the problem: You are now confusing recruiters. They do not get a coherent story when reading your information (because you have changed your resume to include every possible skill and experience you have had). They get a hodgepodge of information. They find it confusing, and when recruiters are confused, their immediate reaction is to move on to the next.

So, please do not do this. It rarely works. Instead, if you need to get a temp job or take on side work to pay the bills, do this. There is no shame in working a non-career-related job to pay your rent. But if you get an offer for a non-career-related full-time job and you have to take it, then have a plan for continuing your job search. Do not become complacent. If you want to thrive in your career, taking a detour is fine, but please do not make that detour permanent.

Consider upskilling or reskilling through courses or certifications.

Are you looking at job descriptions and seeing requirements that you do not have? Maybe it's a specific technology or digital skill? Perhaps you could use a brush-up on some business management skills, like project management or business analysis. If you have been out of work for 6+ months, this may be a good time to develop new skills or enhance the ones you have. A recent certification proving competency in an in-demand area could differentiate you from your competition.

Practice and prepare for interviews to increase confidence.

Focus on your interviewing skills if you are getting interviews but cannot seal the deal. Many job seekers have blind spots about how well they perform in interviews. A fun conversation does not mean the interview went well. Your interviewer may have been engaging and the conversation interesting, but it doesn’t mean you convinced the interviewer that you were best qualified for the role. 

If you have been out of work for many months, evaluating how well you are doing in your interviews will be worthwhile. Since employers rarely give feedback, you may need to reach out to a trusted friend or colleague who will provide you with honest feedback, or career coaches like me can assess your interview performance. 

Even if you are new to your job search, getting help with your interviewing skills can have a huge ROI. Connecting the dots of your story to that employer is a strategic skill that many job seekers struggle with. A coach can help you with that strategy.

Consider side projects or freelancing to build a stronger portfolio.

You may need to do this for additional money, but you may also want to consider it if you get feedback that you do not have “experience” in a specific area. Depending on your work, this could be easier or harder to do, but something to explore. For example, if you are a bit light in project management experience, could you lead a project for a local charity or community organization? Or, to showcase your problem-solving or critical thinking skills, put together a case study on an issue relevant to your profession or industry.

While this may not be as good as work experience, you can tick off the box that you have something similar.

Conclusion

There are very few things worse than a prolonged period of unemployment. It saps your confidence and puts you in a state of constant stress. You start thinking that there is something wrong with you.

I am here to tell you that nothing is wrong with you. Sometimes, your situation is due to a strategy that is not working, and sometimes, it is bad timing for your job search.

Don’t give up! If your strategy and activities are not working, analyze each one separately. Are you following best practices? Is there something else I should be doing?

In my experience, these issues lead to prolonged job searches. Address those that apply, and you should start seeing better results.

Shelley Piedmont is a Career Coach who focuses on understanding your unique skills, interests, and aspirations and provides personalized coaching to guide you toward roles where you can truly thrive. Whether you are stuck as to what your next career move should be or need help with resumes, LinkedIn profiles, or interview preparation, Shelley is here to help you. Please set up an exploratory call to find out how she can help you reach your career goals.