9 Remote Work Job Hunting Challenges and How to Overcome Them

In today’s world, remote work has become increasingly popular for a good reason.  With the right remote job you can work from anywhere in the world.  You can choose to work from a tropical beach bungalow or the comforts of your own home.  Your stressful daily commute is eliminated and you can enjoy the benefits of a much better work-life balance.  

But even with the rise in remote work options since the pandemic, finding the right remote job can be challenging.  Too often remote jobs will come with stipulations.  For example, companies may insist you live within a certain radius of the office or attend periodic meetings in person.  Or companies may request that workers only live in certain states.  Companies may even reduce salary offers based on where candidates choose to live.  

I recently decided to change jobs and encountered a number of challenges in my remote work job hunt.  While I am not a recruiter or employment expert, these are my real life experiences that may be helpful for others to hear. 

In this article I’ll be discussing some of the challenges I encountered so you know what to expect as you embark on your own remote job search.  I’ll share ways I learned to overcome these challenges that could help you find and land your ideal remote position.

Challenge #1:  Finding legitimate remote jobs

One of the biggest challenges in finding a remote job is the difficulty of finding legitimate remote jobs.  

There is an abundance of scams and illegitimate postings online.  They may be trying to get your personal data to sell. Or they may try to do things like try to coerce you into sending them money for equipment you’ll need for the job.  

Even on reputable sites like LinkedIn, you still need to read the job postings with some skepticism.

Solutions to finding legitimate remote jobs:  

  • Use legitimate job boards and then cross-check the job listings.  
  • After you find a job listing on a popular job board go look for the company on LinkedIn.  See if the specific job listing is also posted on LinkedIn.  Look through the people listed as part of the company on LinkedIn and read their job titles.  I’ve seen some companies where almost everyone has another company listed as their primary employer.  Stay skeptical!    
  • Visit the company’s website to make sure it looks like a reputable business.  A company that offers remote jobs but doesn’t have a professional website should prompt you to proceed with caution.  
  • Look up the company on Crunchbase to verify other company details like the number of employees, revenue, etc.    

Challenge #2: Finding remote jobs that are truly remote

Many jobs are listed as “remote” but are actually hybrid or require weekly or monthly meetings on-site.  If you want to be a digital nomad and travel while you work remotely, these arrangements may not be ideal.  It’s one thing if the company is willing to pay for your travel to fly back for meetings.  But if you have to fund your own trips to the office, you might think twice.  

If you plan to live locally but the thought of getting stuck in rush hour traffic even once weekly is too much to swallow, then a hybrid job may be less attractive.

You also have to consider if you are ok with travel as part of your job.  Sometimes companies use the term “remote” to mean a job where you work from a home office but then have to travel to various project sites.  Most job listings in this situation will list a percentage of the time they expect you to travel.

Solutions to finding remote jobs that are truly remote:  

  • Look for “remote first” or “all-remote” companies.  You can start with a google search using these terms and your field to get an idea of what is out there.
  • Thoroughly read the job descriptions.  Do a google search for the job title and company.  Check the same job description on multiple sites to verify if the position is truly remote. Review the company’s website career and company culture pages for more information.
  • Check out job boards that exclusively or primarily list remote jobs.

Challenge #3: The intense competition for remote jobs

As remote work has become increasingly popular, more and more people are competing for the same remote jobs.  This makes it difficult to stand out from other candidates and secure a remote job.  I’ve seen remote jobs on LinkedIn with 600+ applicants.  The odds of landing popular remote jobs are worse than getting into Harvard or Stanford!

Solutions to the intense competition for remote jobs:  

  • Optimize your LinkedIn profile. Use keywords related to your job and list your most in-demand skills.  Grow your social network on LinkedIn to increase your chances of having mutual contacts with hiring managers or executives.
  • Highlight your remote work experience and applicable skills in your resume and cover letter.  Employers know that remote work requires a certain level of discipline and self-motivation. You’ll want to showcase your prior success in this area.  Even if you haven’t worked remotely before, highlight any experience you have had with self-management and working independently.
  • Consider taking a remote work skills course. This will give you an edge and boost your resume, especially if you have no previous remote work experience.  Utah State University offers a low-cost Remote Work Certificate.  You can become a certified remote work professional or a certified remote work leader. Coursera also offers courses on managing remote teams (GitLab).  After completing these courses you can display your digital certificates on LinkedIn.
  • Consider asking your current boss to go remote before you leave your current non-remote job in search of a remote one.  You might be able to tailor your current job to achieve your desired work-life balance.

Challenge #4: Hiring Managers are using artificial intelligence tools to screen and eliminate you before a human ever gets to see your resume

To streamline and improve the recruitment process, hiring managers are using AI tools to screen and eliminate candidates.  AI tools allow hiring managers to be more efficient and review a larger pool of candidates in a shorter time.  This saves companies time and resources to screen and shortlist candidates.  But it also means you may need to apply to dozens of jobs before a human ever sets eyes on your resume.  

Solutions to the hiring managers’ use of AI tools:

  • Use AI tools to master your remote job search. Increase your odds of getting the job by learning how recruiters are using these tools to scan your resume, manage the hiring process, and evaluate you as a candidate.  Equip yourself with equal power by using AI tools to super-charge your resume, interview skills, and perceived employability.
  • Be patient and consistent.  Don’t take it personally when you get an automated rejection email.  Reassess your tactics. Review your resume for ways to better highlight your skills and accomplishments. Keep applying. Don’t lose hope!

Challenge #5: Employers want candidates who have the essential remote work skills of communication and collaboration

Communication and collaboration are essential for successful teams but they can be even more challenging when working with a remote team.  Companies may even list “high emotional intelligence (EI or EQ) as a job requirement.

Solutions to employers wanting the remote work skills of communication and collaboration:  

  • Highlight your communication and collaboration skills in your resume, LinkedIn profile, and during your interview.
  • Provide examples of times when you worked with a remote team.  Be ready to describe a situation where you were able to use your communication skills to resolve or diffuse a group conflict.
  • Use communication keywords or buzzwords in your LinkedIn profile and resume like emotional intelligence, conflict management, teamwork, and feedback loops. 
  • Take a course in teamwork skills or emotional intelligence from Coursera, Udemy, EdX, or a similar platform. Display the certificates you earned on your LinkedIn profile.

Challenge #6: Employers want candidates who have experience with various software tools and apps for remote work

Employers will want to know that you have experience and proficiency with the various software tools and apps they use to work effectively.  These may include project management tools like Trello, team collaboration tools like Asana, communication and collaboration tools like Microsoft Teams or Slack, etc.

Solutions to employers wanting candidates with experience in remote work tools:

  • Highlight your experiences with remote work tools in your resume and LinkedIn profile.
  • If you are unfamiliar with certain tools common in your industry then start educating yourself. Take an online course. Watch youtube tutorials. Consider getting certification through the software companies themselves.

Challenge #7:  Time zone differences between you and your team or employer

Working remotely often means working with team members who are in different time zones.  Your coworkers may even be spread out across the world with little to no overlap during typical work hours.  This can make scheduling meetings and collaborating on projects more challenging.

Solution to time zone differences between you and your team: 

  • Communicate your flexibility with your schedule to potential employers. Mention your flexibility with your schedule in your cover letter and during your interview.  Employers will appreciate candidates who are willing to work outside of traditional business hours to accommodate team members in different time zones.   

Challenge #8:  Geographic restraints of certain remote jobs

Unfortunately, tax laws haven’t caught up with the reality of remote work. Tax rules are different for workers in every city and state in the US.  It can be complicated and costly for companies to make sure they are following local tax laws for every place their employees live.  

When a company issues you a paycheck, they are required to withhold federal, state, and local taxes for the location in which you are physically present while doing your job.  This means that many companies will insist that you live where they are already registered with the local tax agencies.   

When companies put restraints on where employees can live it also reduces your chances of taking advantage of places in the US that are paying remote workers to move.

Solutions to geographic constraints of remote jobs:

  • If you really want a job but don’t want to live in the required geographic area, ask about working as a contract employee.  Contract employees handle all their own tax work.  The company will still need a complete a 1099 tax form for each contractor but the rest of the tax burden will be up to you.  This puts a lot more tax responsibility on your own shoulders to make quarterly tax payments so you don’t end up needing to pay penalties.  You’ll also have to pay self-employment taxes to the IRS. This can cut into your paycheck so you’ll want to be prepared to negotiate a salary to compensate.

Challenge #9: Home office and internet requirements

Employers will want to be sure you can complete the demands of your remote job from home.  They may provide a home office stipend but it is unlikely to cover everything you will need to work comfortably and productively.  

Solutions to home office and internet requirements:

  • Anticipate what you will need for your remote work (home office) toolkit. A quiet space without distractions. A desk with plenty of work space (or a standing desk).  A comfortable chair. Fast internet connection.  A coffee machine or tea kettle. Good lighting for your zoom meetings. A computer with adequate processing capabilities depending on your job type. An ergonomic keyboard. A printer. Other basic desk stuff like a stapler, staple remover, pens, and file cabinet.
  • Consider subscribing for access to a local coworking space where you can enjoy comfortable desks and chairs, high-speed internet, coffee, and snacks.  Coworking spaces can have inspiring creative energy, help to prevent the loneliness that can be inherent in remote work, and provide opportunities to network.
  • If you plan to travel internationally while working remotely, consider staying at coliving spaces. Many coliving spaces provide coworking spaces with high-speed internet.

In conclusion, finding a remote job can be a challenging process, but with the right mindset and approach, you can overcome these challenges!  Equip yourself with the right tools and solutions from the beginning to make the process easier and increase your chances of finding your ideal remote job.  

Remote work has the amazing benefits of flexibility, autonomy, a better work-life balance, and the ability to become a digital nomad.  Don’t give up the dream! Be proactive, patient, and persistent in your search and you will eventually find success.  

Jamie Dubois

I am a freelance writer, wanderer, kayaker, rock climber, and adventurer.

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