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I Train Remote Workers, Here Are The 5 Biggest Mistakes That I See

This article was written in collaboration with Remote Work expert, Camille Attell.

In 2016 I walked away from my 20+ year career as a corporate trainer to work remotely. I worked over twelve different remote jobs and even started a remote business from my RV. I made a lot of mistakes along the way. 

By learning the good, the bad, and the ugly, I eventually started Remote Work School where I train and coach aspiring remote workers, and I help them find remote work either working for someone else or themself. In this article, I will share the five biggest mistakes that I see.

Before you move on, let’s make sure that this article is worth your time to read. If you can relate to any of these scenarios, then keep reading:

  • You are putting off looking for remote work because you don’t feel “ready”
  • Staying at a job you don’t want
  • Applying to remote jobs but only hearing back from crickets
  • Waiting to start the remote business you’ve been noodling on
  • Undercharging for the services you provide
  • Not negotiating your pay
  • Thinking you aren’t qualified to do what you really want
  • Spending time thinking about possibilities but not making progress

If you read that list and thought “ouch that’s me,” don’t feel bad. You’re not alone, and nine of ten people relate to at least one or more of these. I know this because I have worked with over 700 people over the last five years and these are really common barriers for most people.

So let’s dive into these top five mistakes and help you avoid them so that you can get real traction on your remote work journey. If you want to get more resources to help guide you in your remote work journey, click here to get my free remote work series.

Mistake #1 Undervaluing Your Skills and Strengths

Most people who want to work with me, make mistake #1 more than any other mistake, and that is undervaluing their skills and strengths. What this means is thinking that what you have to offer “isn’t enough” or that you are “not qualified” or thinking that because you are new, you should charge less or not negotiate your pay.

This happens because a lot of job descriptions are written for the perfect candidate. I used to work in human resources and write job descriptions. I can assure you that we never found actual humans who fit the job descriptions we wrote. They rarely had all of the qualifications, and often it was the candidates who showed initiative more than anything, who were selected for jobs and special projects.

Here’s the fix: the way to avoid undervaluing your skills is to focus first on your transferable skills, and then how you can transfer those skills into different job types, industries, or niches. For example, a woman I worked with named Christine, quit her job in 2019 thinking she’d get a new job right away. Little did she know she’d be competing with millions of people who had lost their job in 2020. She panicked at first, but then did a skills inventory and looked at expanding her options. I’m happy to say that today she works 100% remotely as a virtual assistant.

If you want to learn more about how to do a simple skills inventory, click here. Insert aff link

Mistake #2 Waiting to be ready

My husband has a funny saying when we are getting ready to go out. He says “I’m getting ready, to get ready.” I hear this as “We’re going to be late.” 

I bring up this funny example because it’s not so funny when it involves getting remote income. You see, many people wait for the “right time” or tell me that they will be ready in six months from now, but need to “get ready” first. When I ask what they’ll be doing to get ready, they shrug and give me a blank stare.

This concerns me because we are living in unprecedented times when there have never been more remote job and business opportunities than now. Not only that, working remotely is no longer optional. You literally need to know how to do it. If 2020 didn’t make that obvious I don’t know what will. 

Here’s the fix: get ready now by picking one of these options. 

  • Option #1 Have a remote work resume. This includes a professional summary and remote keywords.
  • Option #2 Update your Linkedin profile. This includes a quality photo, professional identity and remote keywords.
  • Option #3 Teach yourself a few of the key remote work tools. These could be Google Workspace, Dropbox, Trello, Slack, Canva…just to offer a few. If you have no idea what these are then you definitely should start now with signing up for a free Google account and at least learning more about file sharing. Luckily you can find free training on Google and YouTube for just about anything.

If you want to learn more about remote work resumes click here.

Mistake #3 Getting too attached to a specific job title or type

Here’s a sentence you should never say “I have only ever done X so why would anyone hire me for Y?” For example, “I have only ever been a truck driver, so why would anyone hire me as a project manager?”

When you use words like “only, just, or never” you are communicating that you undervalue your skills and are not a great person to hire. When you undervalue yourself, it might mean you take less pay, too. 

In addition, it means you’re really attached to your job identity, and that attachment can prevent you from seeing how you are more qualified than you think, or how you can transition into new opportunities because you may be thinking that if you were always a truck driver, teacher, administrative assistant, etc. that’s the only job you can ever do.

Here’s the fix: you should consider that you could do different job types, in a different industry or something else entirely. You should also be open to new work types, like freelancing. Often I see people who come from traditional jobs and think that working for someone else is the only option. 

If you are semi-retired or working in retirement, freelancing or creating a service-based business is a really good option to consider.

Take for example my client, Kathi. She worked for an airline and in 2020 was “encouraged to retire”. We all know that’s code for getting aged-out of the workforce. Kathi had no idea what else she could do. By doing a skills inventory, looking at other possibilities, and understanding her income needs, she was able to become a financial coach working with clients—something she never considered before!

So, don’t get so attached to anything that it blocks you from seeing other options. 

Mistake #4 Looking at online job platforms first, to find remote work

It seems logical that if you want to work remotely you look on platforms like Indeed or Flexjobs. Or if you want to freelance you might look on Upwork. 

Don’t get me wrong, online job platforms can be great! The problem is when you start with online job platforms and skip over the other steps. For example, if you haven’t done a skills inventory, or you don’t understand your strengths, or you don’t know what to charge, then online job platforms are more overwhelming than they are helpful. 

Not only that, there are more than 100 online job platforms! If you don’t know what jobs you qualify for and you undervalue your skills and strengths, how do you know which platforms are the right ones for you?

Here’s the fix: what you should do instead is tap into your immediate network. This could include your friends and family or past co-workers. I’m not saying that you should shout from the hilltops that you’re looking for a job. What I am saying is that you should start early and let people know that you are going to make a transition. Let them know what you do, who you help, and if they can they put you in touch with the right people. 

I just helped a friend of mine with his job transition. He worked at one company for over 25 years and at 55-years old his prospects weren’t looking great. By sending simple and fun emails to his network of friends and family he landed a great consulting job!

Make sure you have a remote work resume that you can send them, too.

You should also create a profile on LinkedIn as that is the top job platform in today’s market for both jobs and clients. You should also work to improve your LinkedIn profile, so that hiring managers, recruiters, and clients can find you in searches.

Mistake #5 Thinking too big and making things complicated (and overwhelming yourself)

I’m going to be candid and tell you that I used to be the queen of complexity. I’m a big picture thinker and I have a thousand ideas everyday. The issue isn’t being an ideas person, the issue is when I try to implement all thousand ideas at the same time.

If you’re an ideas person, too, or like to research, or understand everything before you start something, then you are likely to get bogged down in a mess of your own making.

For example, maybe you want to start a remote business. And you start googling businesses that seem like the one you want to start. You see a beautiful website that is exactly like your business idea, then you find another one, and so on. Before you even have a chance to write down your business ideas on a piece of paper, you give up because “everyone else is already doing it.”

This is an example of thinking too far in the future and falling into the trap of comparing yourself to other people. Plus, you might think you could never build a website that is as pretty.

Listen, pretty websites are great but that isn’t a business. There are far easier things you can do now without a website, or social media, or all the things you think you need.

Here’s the fix: the best thing you can do is start small. Think about your top 3-5 skills, which ones you like, and then how you can create a service from that.

There’s a man I work with who became an RV maintenance technician. He thought it would be a great business idea to build a course teaching people how they could do their own RV inspection. It’s not a bad idea except that he didn’t know how to actually sell the course. 

So we started working together and came up with easier steps he could take to make money now while working on the course for the long term. Simple things like getting on calls with clients to help them do a self-inspection. Perhaps using something like Facetime so he could see the issue. Then maybe gathering small groups of people online so he could leverage his time. Then later build a course that he could then learn how to sell.

Sometimes we are so lured by the promise of passive income and fancy business ideas that we overlook the obvious income generating ideas that are right in front of us.

Go step by step and build up to more complex ideas, if you even need to. I have a friend who decided to offer copywriting services. She had no formal education and in her first year made over six-figures… just by telling people she was a copywriter on facebook.

Focus on the simple things.


I hope you found some ideas, inspiration, and helpful tips in this post. The good news is that right now is the best time to get into remote work—whether you want to work for yourself or someone else. Avoid the mistakes in this article and get yourself out there now so you can benefit from the opportunities that are waiting for you.

For additional information click here to get my free Remote Work Roundup and learn about the different remote work options.

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