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About Your Remote Work Coach

After a decade of working remotely with SaaS and Fortune 500 companies, Darren Cronian now teaches others how to land remote jobs they actually want — through honest advice, coaching, and simple tools that work. Read more >
Last Updated: 16 September 2025

I know how exhausting the remote job search can feel. You’re scrolling through listings and sending out applications that seem to get lost deep in the internet. It’s easy to think you’re not talented enough or that the competition is impossible to beat.

In most cases, the problem isn’t you; it’s that you’re making a few common mistakes that quietly kill your chances before a hiring manager ever sees your potential.

I’ve worked remotely for more than a decade and coached people through the same struggles you’re facing right now. I see the same five mistakes pop up again and again, and they’re almost always the reason why talented people get ghosted or continuously receive rejections.

In this guide, I’ll walk you through each mistake, explain why it’s holding you back, and share fixes you can start using right away. By the end, you’ll have a clear picture of what’s going wrong and how to fix it.

Common Remote Job Mistakes and How to Avoid Them
Mistake 1: Using the Same Resume for Every Application

One of the biggest traps remote job seekers fall into is sending out the same resume to dozens of applications because it feels productive. You’re applying to more jobs, so your odds must be better, right? Unfortunately, it doesn’t work like that.

Remote companies often receive hundreds of applications for a single role. If your resume looks generic, it gets skimmed and passed over by application tracking systems, so a human never even reads it.

Here’s how to fix this: treat each application as unique.

Read the job description carefully and highlight the specific skills and experiences the company is asking for. Then adjust your resume to focus on those.

If a company is looking for someone experienced in project management tools, don’t just list “project management”; instead, share your experience with specific tools like Asana, Trello, or Notion. It takes a little extra time, but it shows the hiring manager that you actually paid attention to their role.

Mistake 2: Not Showing You Can Work Remotely

Being good at your job is one thing. Being good at your job while working from a kitchen table, juggling time zones, and staying productive without a manager looking over your shoulder is something else.

Remote companies know this, and they’re looking for signs that you’ll thrive while working from your home. If your resume and cover letter don’t mention remote working skills, you’re missing an opportunity to stand out. Reflect on instances when you’ve worked independently, managed online communication, or achieved results without constant supervision.

Did you lead a project with teammates spread across countries? Have you managed deadlines while working alone? Mention that. Hiring managers want evidence that you’re not just capable, you’re ready.

Mistake 3: Applying Blindly Without Research

It’s tempting to click “apply” on every job that looks decent, but this usually backfires. Remote companies can tell when you haven’t done your homework. Your cover letter ends up vague. Even worse, sometimes the role isn’t even what you think it is. Many so-called remote jobs are actually hybrid, and some listings are flat-out scams.

Spending ten minutes on research changes everything. Look at the company’s website, read about their team, and check if they really operate remotely. Mention something specific you found, maybe a project they’ve worked on, a value they highlight, or a tool they use.

This small step shows that you’re genuinely interested in their company and not just chasing any job with “remote” in the title. It’s the difference between looking desperate and looking prepared.

Mistake 4: Ignoring the Job Description Keywords

Here’s the hard truth: many remote companies use applicant tracking systems to filter resumes before a human sees them. If your resume doesn’t contain the right keywords from the job description, it may not make it through that first set of checks.

This isn’t about gaming the system; it’s about speaking the same language as the company.

Go back through the job posting and note the exact words they use. Suppose the role description says “customer success” instead of “customer support”; mirror that language in your resume. If they list “HubSpot” as a required tool and you’ve used it, don’t just say “CRM experience”, say “HubSpot.”

These small changes make a big difference because they align your application with what the hiring team is already looking for.

Mistake 5: Giving Up Too Early

This last one is more about mindset. Remote roles are in high demand, which means even strong candidates face rejection or silence. The biggest mistake I see is people applying to a handful of jobs, getting discouraged, and walking away. I understand why it happens; it feels personal when you’re ignored, but giving up guarantees you’ll stay stuck.

The people I’ve seen land great remote jobs are the ones who keep going. They learn from each rejection, adjust their approach, and keep sending thoughtful applications. Sometimes it takes dozens of tries. Sometimes it takes months, but persistence pays off. Every “no” is one step closer to a “yes,” and every application teaches you something about how to do it better next time.

Action Points to Take Away
  • Pick one job description right now and tailor your resume to it.
  • Add at least two examples that show your ability to work remotely.
  • Research the next company you apply to and include something personal in your cover letter.
  • Review the job description and incorporate its key terms into your resume, focusing on skills, experience, and relevant personality traits.
  • Set a weekly application target without burning out.

Before you send out your next application, take a step back and ask yourself: Am I falling into any of these traps? Fixing even one of these mistakes could help land you a remote job interview.

Remote job searching isn’t about being perfect; it’s about being willing to adapt, and that’s something you can start doing today.

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