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I Worked a 9-to-5 For A Month And This Is What I Learned

6 min readAug 5, 2025
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The easiest way to say this is: it sucked. But in this article, I’ll go through WHY it sucked, what I learned about the hiring process for companies and individuals, what companies expect from their remote workers, and more reasoning why leaving 9-to-5 work and becoming a freelancer is the best way forward. So, let’s take a look at this failed foray into the world of regular work.

Landing a Remote Job

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As most of you know, I’m a freelance writer. I’ve done freelance writing work for many companies over the years, ranging from blockchain/crypto companies to Software-as-a-Service (SaaS) and Artificial Intelligence. At the end of July, I lost a significant client and had a bit of time on my hands to fill. Since my earnings from Medium can’t even buy me a pack of bubblegum at current market rates, I decided to look for a remote job. How hard could it be, I wondered to myself.

I set a solid routine to apply to 10 remote work jobs a day. So, at ten positions a day, until I landed this job in the dying embers of August, I had applied to 250 remote jobs. Out of the 250 jobs I had applied for, less than 10% even bothered to email me promptly. Out of the remaining 90%, 5% even emailed me at all. And yes, I did check my spam folder. So, out of 250 jobs, 25 of them bothered to tell me anything. I’m starting to see why people say there’s no work to be had in the regular workforce.

Of the 25 that replied to me, 10 rejected me outright (which is fine; that’s their prerogative). Two asked me to do a free trial article for them, which I declined because if a company is not paying for my time, I am not working with them. Of the remainder, I did a paid article for some of them, and they didn’t like my style, which is also entirely satisfactory. My writing isn’t everyone’s cup of tea. The one that eventually hired me, though (not going to mention names, of course), made me feel like it might have been a good fit.

That was until the project creep came in, and the compensation remained at the initial (non-negotiable) mark.

People Want You To Work But Don’t Want to Pay You What You’re Worth

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Now, this is crucial, especially for the writers out there. Many people will treat you like your job is now easy, and they could just hire an AI to do it. Sure, they can, but they’ll probably get far less than they paid for. Many of these people who are hiring you don’t even know what they want, so they think AI can both give them a direction AND the work they need to be done.

Even worse, a company that throws out a call for writers like this probably isn’t looking for the top of the stack. They’re not looking for someone who can solve their problems, identify their client pain points, and help them sell their product. They don’t want a language whiz who can take complex ideas and break them down into simpler ones. All of these are things I do as a writer. And I would be glad to do it for any company that needs that done, regardless of the industry. Just so long as they pay me.

I live in a third-world country. It’s not something I say because I want to “throw shade” on my island; it’s the truth. We’re a “Developing Economy,” according to the World Bank. Our minimum wage recently breached $US2.57. However, as a writer, I work at international rates. Even if I decide to work for a local client, I work at the rate that is paid to a freelance writer internationally. It really sucks when a company wants to hire from the third world but wants to pay you a third-world rate, especially if they’re a first-world company.

The Clock Watching Never Ends

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One of the things I forgot about since I was in control of my own schedule for so long was that if you’re working for a company, you’re required to be “on the clock” for that company for a certain stipulated amount of hours. That holds true as a remote worker as well. Now, I have nothing against being on the clock. When I work for myself, I’m on the clock for myself as well. I dedicate time to completing work and finishing it in the time I set for it. But it’s a different thing when the clock belongs to someone else.

When you sign up to work for another company, you no longer have control of your time. Now, please don’t get it mixed up; you may also have some difficult clients as a freelancer. Some clients want things done as soon as possible. However, the difference is that you can tell that client, “No, this is my time that I have set aside for myself,” and they are likely to respect you for it (or find someone they can abuse easier than you). You can’t tell that to an employer that you signed up to work a certain amount of hours for.

What I Learned Working a Remote Job

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I guess it takes going back to basics to learn about yourself. But I learned a lot. I learned corporate culture doesn’t care about its workers. I learned they’re willing to kiss ass to get you on board, then abuse you with work without proper compensation. I learned that this is something many companies do because they don’t care about quality work; only someone they can get to do something for them for as little as possible. And I learned that I’m not cut out for regular employment.

Probably one of the most important lessons I learned from this was the reasons I left regular employment in the first place. I left because I wanted control of my own time. I left because I wanted to be able to do the things I wanted to do without someone looking over my shoulder or telling me I owed them my time. I wanted to earn independently and be responsible for my work habits. Adapting to this isn’t easy, but the freedom is worth it. As it stands, I’ve “fired” that job and have time once again to look for real freelance clients. And I think it’s one of the best decisions I’ve made in my life as a freelancer.

Are you interested in learning more about this or the stuff I run into as a writer? I love doing little slices of the things I enjoy as a writer. You’ll find many more of these sorts of articles or my forays into game development, personal finance, and emerging technology on my Medium page. Feel free to subscribe via email so you don’t miss any of my updates. Also, if you’re a company looking for an actual freelance writer, I have some capacity; how about you hit me up?

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Jason Dookeran
Jason Dookeran

Written by Jason Dookeran

Freelance author, ghostwriter, and crypto/blockchain enthusiast. I write about personal finance, emerging technology and freelancing