What I Learned After Failing To Land A Remote Job

I must be a gluten for punishment. Or perhaps I am just overly optimistic. Maybe both. Whatever the reason though, over the past year, I have applied to nearly 100 remote jobs and only one has been a successful opportunity. This was pretty frustrating since, up until this point, I had landed every job I have ever interviewed for. While I don’t have a magical answer on how to land one of the golden remote and/or part time jobs out there, I definitely have learned a few things along the way.

(PS it looks like no one has a magical answer on how to specifically get a remote job. Seriously, try googling it.)

I love to teach. I found my dream job in Columbus, Ohio, where I was a supervisor at a private educational company. However, a month after my first daughter was born, my husband decided to make a career change. This led to us moving away from the flexible dream job I had there.

As a fairly new mother, trying to teach full time at a public school was a frustrating experience. Not only was I barely making money after paying for $800 a month for daycare (the cheapest one I could find), I was always the first to drop off my daughter and one of the last ones to pick her up. I couldn’t believe how many hours I had to give to public school. Wasn’t teaching supposed to be a family friendly career? Eventually I decided to leave.

After teaching in public, carter, and private school settings, 2 years of specific Applied Behavioral Analysis, several years of work with families and adults recovering from addictions, experience training and supervising educators, and some experience with social media management, website management, and administrative work, I thought surely there would be a remote or part time job out there for someone with my skill set.

Well… apparently not. Or at least, I did not play the game correctly. I did have several job offers that ended up not being good options for me. Eventually, what really worked was starting up my own private violin lesson business. Thanks to TakeLessons.Com, some students are even online.

So for now, I’ll take what I can get. However, here’s what the hours of applying and researching have availed me:

1. Companies use software that scan your resume before humans look at it.

I didn’t know this until about 20 applications in, but most companies use software that scan your resume for “key words” before any humans lay their eyes on it. That means, if your resume does not have the same wording as the descriptions in the job posting, your resume may be tossed out without a chance.

To combat this, I highly recommend narrowing down your job choices. Then read the descriptions and requirements closely. Rework your resume so that your related experiences and skills use the same descriptive wording as the job requirements. This method actually ended up working for me at Western Governors University. Reworking my resume allowed me past the software screener. Although, even with three recommendations, several LinkedIn relationships, personal emails with the direct supervisors, I still did not get an interview there… I have no idea what they would looking for. Anyways, to my next point.

2. Remote jobs in any field, especially in education, are competitive.

Why do you want to work remotely? Believe it or not, hundreds of other people want it for the exact same reasons. I was astounded to learn that Western Governors University (a 100% online university) had several hundred applications for most of their job postings. Coupled with the fact that many educational jobs often are appropriate for those with degrees and experiences outside the educational field (i.e. humanities, social work, etc.), an entry level job can suddenly become very competitive.

So how do you stand out? My approach was to make as many connections as possible. I reached out the the recruiting department, the supervisors, and had friends in the company write me recommendations. I actually was never asked to interview.

I still believe that making connections is a great tactic, but I have also read that you may need to think of ways to show you are more valuable than the rest of the applicants. That may mean learning about the job, then giving possible suggestions on how you could make the company better.

3. Branching out into a different field may seem easy, but it takes a lot of hard work.

I this idea that because I had some basic coding skills, WordPress management experience, and social media management skills, that I could get a remote job doing something like that. This was my most unsuccessful attempt.

I realize now that I was not selling myself as creative enough or skilled enough. Companies want to see proof of your accomplishments and skills, not just read about them. How can you prove it? Well, I sucked at that. But I know some people do it by sending in portfolios, links to websites they are currently managing, or emailing actual startup companies about how you can improve their company.

Additionally, different career fields are looking for different types of resumes. Do your homework. What do employers want from a ____(insert your career field here)___ candidate? Make your cover letter appealing to read, but also tailored to the specific job.

4. If it seems too good to be true, it probably is not true.

At one point during this job chasing adventure, I had the opportunity to pay for a social media marketing training class. The idea was to take the class and then get set up with a job. The class actually was insightful, but the company never placed me with the part-time and remote job that was promised. As soon as I finished, another class was required to be hired.

Another company promised money for taking surveys, and even another for doing random odd screening jobs on the internet. Neither of these ended up paying much, and the second one kicked me off due to a glitch in their system.

5. Know what jobs would actually be a good fit for you.

Early in this process I looked at VIPkids. People have had a lot success teaching for online english tutoring services. I got the job and started the training process and realized this was just not for me. First off, the hours were very early in the morning, and second, it required a level of energy that I could not even produce with a sugary, caffeinated beverage. I ended up loosing a lot a time messing around with that job.

Once, I was a final candidate for a social media job. On the last interview I was asked to prepare for some very business related questions that I had no clue how to answer. If I was desperate I would have studied the crap out of those questions and then tried to pull it off. But I decided that if I had to work that hard to do everything the job required of me, I was probably going to hate it.

What I would recommend is the research the company and the job’s duties thoroughly before applying. If you can talk someone who is or has worked there, that’s a bonus. If your skill set matches the task, go for it, and let your skills shine.

6. Many private contracting positions require you to do the leg work get customers.

Many companies have had this brilliant idea to start educational companies, that require the individuals to go seek customers. Well why didn’t I think of that? “Hire” teachers and then say, go find some kids to teach. Sounds a lot like MaryKay for teachers.

Anyways, there are plenty of these companies out there. They range from small micro schools, to “stay at home” preschools, to writing summer bootcamps. These companies are NOT all created equal. This is just a warning to make sure you’re aware of what you are signing up for. If you are ready to own your own little business go for it. You will just need to be ready to put in the work they require.

TakeLessons.com was a great fit for me because they do all the advertising for you. They do take a percentage of your pay, but they do not require me to go pay for advertising or track down students.


There are definitely remote jobs to be had out there, so I hope that this article helped problem solve for you, rather than discourage you. Eventually I looked closely at my skill set, and decided to figure out what was the MOST marketable. It ended up being my SPED degree and my 24 years of experience playing the violin. Privately and through TakeLessons.com, I have been able to put together a little part-time business. It is possible to find a job that can work around parenting, but it may take a little creativity.

If you are looking for a side job, considering reading my other post about flexible side jobs for teachers.

This article from The Remote Nomad, is the best information I have found to become prepared for remote applications.

Good luck in the job search! Comment below if you’ve had any other remote job successes, or maybe even more entertaining, comment your own remote job failures!

2 thoughts on “What I Learned After Failing To Land A Remote Job

Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.