How to Find a Job in 2020: The Ultimate Guide from Career Contessa

Is it time to find a new job? As the year draws to an end, many women naturally take stock of their lives. What works? What doesn’t? Are your relationships healthy? Is your apartment in dire need of a deep clean? As your romance with the summer months draws to a chilly end, you might find yourself re-evaluating relationships, living situations, your lifestyle and, of course, your job. If you find yourself happy with all of the above, that’s incredible. If you find yourself less than satisfied with your employment situation, it might be time to start looking for a new job. And because every job search situation is different, we tackled a few different job search options. Whether you are looking for a job in your field, in a new industry, or across the country—we’ve got you covered in this guide.


Long gone are the days when you might take red ink to the Classifieds section of the newspaper. Instead, the first place a modern jobseeker looks is on the internet.

Job searching on the internet is both easy and difficult. On the bright side, you can apply to a slew of jobs with a few clicks. But applying exclusively online can lead the modern jobseeker into an abyss. And because many job boards send your resume straight into an Applicant Tracking System (ATS), you might be left wondering if an actual hiring manager will ever even see your resume.

The Hack: Speak Like the ATS

The trick to beating the ATS lies in the job description itself. When applying for a specific job, refer to the job description. For example, if the requirements mention fluency in Adobe CS, make sure your resume (and your cover letter) mention that you are, indeed, fluent in Adobe CS.

Scan any job description for the “keywords” associated with the job at hand. Tailor your application to highlight these skills in order to send the ATS wild for you! Your application is sure to be shared with the hiring manager if you’ve used the proper keywords in your application materials.



Studies have shown that 70-85 percent of jobs are filled through some means of networking. Hiring is an expensive (and time-consuming) process for any company. Finding a qualified applicant who is already connected to a current employee will generally to translate to an attractive hire option.

This is also where the internet becomes a bit of a drawback—if an applicant is attempting to conduct a low-visibility job search, activating her entire social network is going be tough.

The Hack: Utilize Your Connections

Every social platform has some variation of private messaging. Go ahead and slide into the DMs of your friends who work at your dream company or your former roommate who knows someone (who knows someone else.)

The job search is a pain universally recognized. Everybody has had to depart their comfort zone in order to ask for small favors in their own job search. So even if your connection is a small one, use it. Find a social network (or email if you have access) in which your contact is most active, and don’t be afraid to reach out.


When composing these messages, be specific, be personal, and be gracious. If you do score a connection (or even if you don’t) always make sure to follow up with a word of thanks. If this kind of cold contacting freaks you out (don’t worry, you have nothing to lose), download our networking templates, where we’ve done most of the writing for you. You’ve got this.



Is it time to sprout wings and leave your hometown? Do you live in a fast-paced city where rent is growing too unaffordable (aren’t we all?) to survive? Whatever the reason, it might be time to find a job in a new city. Job searching in a new city provides its own set of challenges. Most companies will communicate whether they are open to a relocation hire within the application. However, sometimes landing the job is still…complicated.

The Hack: Be Honest About Relocation

I struggled with what tip to share in this section. The really hacky tip I avoided sharing (even though I am going to do it now) is listing a different address on your resume. There are circumstances in which I think this tip works. If this address belongs to your sister, with whom you could stay semi-long-term, then use the address. If the address is an abandoned field (or entirely made up) do not use it.

The truth is that a local address might get you in the door in a new city. However, you want to be forthright in the application and interview process. If a potential employer finds out you don’t live in the area that sets off all kinds of dishonesty bells and whistles.

This is seemingly obvious advice, but here it is anyway: be honest in your application process.

If you can stay at your sister’s local apartment, be upfront about it. Tell your potential employer that the address listed is a viable long-term option, but that you are serious about permanent relocation upon employment.



Finding a job in a new field is a daunting (but exciting!) process. As a person who has switched career paths in the past, I am here to tell you that it is a real possibility.

What I’m not here to tell you is that it can happen in a day. It’s not likely that you can transition from social media specialist to a board-certified dermatologist this week, but you can make moves to get that train started. If you’re motivated enough to seek them out, resources exist to learn the fundamentals of some of the most well-paid jobs hiring today.

The Hack: Freelance at Your Dream Position

Not everyone is in the position to take a substantial pay cut to essentially re-enter the workforce as an entry-level employee. However, with the gig economy growing at lightning speed, you can wet your feet with freelance work in your desired field.

If you are a 9-to-5 accountant who dreams of being a graphic artist, it’s a very possible transition. The growing gig economy means that freelance projects are constantly being offered at sites like Upwork and Fiverr. Once you clock out of your accounting job, pick up a freelance job or two. You can use smaller jobs like these to build your portfolio. Once you’ve built a body of work, you might find yourself in the position to begin applying to jobs in your new field.

The Other Hack: Tell a Story in Your Cover Letter

Be very upfront in your interview process within a new industry. Any smart employer will recognize that passion and determination can outweigh even the most refined skill sets.

When applying to jobs in a new industry, I’d recommend outlining your new journey in your cover letter. Use this time and space to illustrate why your experience looks… different than the other applicants. It’s rare that an employer gets to read an interesting story in a cover letter.

It is never too late to switch it up. The modern employee is going to work approximately 5 decades before retiring. Make sure those years are as happy and fulfilling as possible.


By Jeanette Hickl
Jeanette Hickl Jeanette Hickl