My biggest online writing mistake

And how you can avoid it now

James Presbitero Jr.
Upside Down
3 min readOct 16, 2023

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Photo by Richard Jaimes on Unsplash

Right out of college, I started writing online.

I was “discovered” by another freelancer, who kind of took me in as an assistant. She loved me, loved my attitude, and blessed me with steady, reliable tasks.

We entered into a “partnership”. She would look for clients, while I would help in research and writing the copy. We provided great outputs.

For a recent college graduate, it was a very well-paying job. Not to mention, the pandemic hit soon after, and everything was on lockdown for years. I was very lucky to have a great job, so I hung on to it and really learned how to work.

That was my mistake.

Yes, I became complacent. I had a great job, but I was merely a component in someone else’s system. Building something, becoming a stand-alone content/copywriter, learning to get clients — it never crossed my mind to learn all these things.

It was a great job, but it was fragile. So when uncertainty buffeted our niche, I shattered.

Clients started taking off with unpaid invoices. Our trusted niches suddenly went dry. Worse, my business partner was suddenly neck-deep in personal and family troubles that left her unable to focus on our business.

For a college graduate in a third-world country, not having a steady income is a terrible feeling. It’s so easy to lose confidence.

Fortunately though, if I can be proud of something, it would be my stubbornness (or mental fortitude, if you prefer a prettier term).

After stewing over my anxieties, I decided to learn this whole writing thing for real. My plan now is not just to be someone’s assistant. I want to learn. I want to build a community.

And I want to be one of the best dang writers on this side of the globe.

It sure is difficult, though. There’s so much I have to learn now, and the future is still uncertain. Maybe that’s why only a fraction of the population starts to create content. I’m learning the craft, to be one of those.

But if you want to avoid my mistake, then you should be doing this (and what I should’ve done from the very beginning).

  • Become antifragile. Never be complacent, always upskill, and diversify your source of income. Don’t put all your eggs in one basket like I did!
  • Build digital assets. Start writing, posting videos, making podcasts, etc. It’s never been easier, and it will make you stand out if you do it right.
  • Learn to pitch. Approaching clients is another skill entirely. Even if you have a day job right now, learning how to make money on your own is a core skill that will save you if the worst happens. Don’t be like me!

Since you’re already here on Medium though, chances are you already have a plan. If so, good for you!

Please share your story, if you like. I’m interested to learn your online writing journey in the comments.

Any advice would also be appreciated.

Hey! This is in response to Jordan W.’s interest to read my online writing story in the comment section of another article. Thanks Jordan.

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