Why The Overnight Blog Success Stories And ‘$1000 My First Month Freelancing’ Posts Aren’t Totally Honest

It can’t all be smooth sailing and calm waters. Where are the folks that washed up on the rocks?

Colby J Smith
6 min readDec 10, 2020
Photo by JESHOOTS.COM on Unsplash

Now, I don’t like to be cynical (that’s a total lie, I’m British, moaning is in our blood) but there’s something that doesn’t quite sit right with me about all these success stories that I see posted on Medium and just about everywhere else online.

You know the ones I mean. “How I quit my job overnight through my blog about goldfish bowl maintenance ” and “How I turned over $1k in my first month on Upwork.”

No doubt there are success stories out there, and I’m not trying to tear anyone down or rain on any parades, but I feel that poetic license is being overused in some of these cases.

When I joined Medium (a colossal ten days ago at the time of writing this), before I’d given the algorithm a chance to learn my preference or followed any writers or publications, the first stories that appeared in my feed are these exact kind of stories, designed to gas you up, to give you that buzz of excitement, telling you that blogging can be more than a bedroom past time or side hustle to add to your 9–5, or whatever it is you do to make ends meet.

And I understand that there are people out there, lots of them in fact, that are making a killing from this profession. But I get the sense that these posts don’t tell the full story.

When truth meets reality

I’ve clicked a lot of articles that have had the phrase ‘overnight success’ or something to that effect in the headline, and a lot of what I’m reading is about people who have been on the grind for months and years, and woken up one morning to realise their income is enough for them to quit their main job or stop worrying if the bills are going to be paid at the end of the month.

These are great stories, and I commend these writers and hustlers for sticking at in when times got tough. You are the true heroes of this art form, carving out an existence in the big bad world of online moneymaking.

But grinding for 48 months and finally making a decent income isn’t an overnight success. That’s like waking up on New Years Day and proclaiming that the world has made one complete rotation around the sun overnight.

You’re completely discounting the other 364 days. You’re completely discounting the hustle, the learning, the mistakes, the failures, and the hard times.

And similar to how the earth needs to pass through Autumn, Winter and Spring to reach the glory days of Summer, I think these times of hustle, learning, mistakes, failures and hard times are essential in any line of work to develop your skills.

You don’t get the gains without the sweat, body aches, meal prep, and pushing through when every part of you is telling you it would be so much more simple to just give in.

I want to hear the stories of how you wrote what you thought was going to be your magnum opus, only to see it get a tiny handful of engagements and rejected by every publisher under the sun. I want to hear about you eating twenty-cent noodles for weeks on end when money was short. I want to hear about your friends and family begging you to go back to your office/prison desk job.

I want to hear all of this, then I want to hear that you smashed all the doubters to smithereens. You made the impossible trench run and against all odds, you fired the torpedo right down the middle of the exhaust port.

And I think that most budding content creators on the internet want to hear this too, because the majority of them haven’t reached the end of their story. Nobody who is at the top of the mountain wants tips on the assent. It’s those who are still climbing that need a leg up and a healthy dose of motivation.

The happy endings, the high-fives, and the milk and honey are so much sweeter when we’ve seen the protagonist being dragged through the mud for the whole film. But you know this, you’re writers.

Bogged down on Upwork

Now onto the magicians who are going from zero to hero on any one of the freelancing platforms that are out there.

I’ve read plenty of these stories as well and I’ll bet you have too. They will tell you how it’s possible, with no experience on these sites, to get your proposals accepted, demand higher wages from your clients, and fill up your profile with five-star reviews from trendy startups and silicone valley giants.

Again, no doubt it’s possible for a few of us to get this kind of running start, but there’s definitely something here they’re not telling us.

Maybe its the degree in sales or marketing or journalism they’re displaying on their profile. Maybe it’s the CV with years of experience working for various copy-writing firms. Maybe it's the extensive list of network connections on LinkedIn they’re leverage to gain traction.

I don’t know. But as someone who has none of these to kick start my freelancing career, let me tell you it’s a shark tank out there. I barely finished high school, let alone university. My background is working on construction sites and in kitchens, and my only real online writing experience is trying to condense political arguments into 140 characters.

When you’ve got none of these shiny medals and zero experience on your Upwork or Fivver profile, these platforms essentially become a contest of who can undercut their competitors the hardest. You’ll accept peanuts for a job that’s going to bore you to death, just for the opportunity to get a bit of positive feedback and to build your portfolio.

This isn’t a sob story.

I knew it was going to be like this, and I know it's going to continue to be like this until I can put the fancy logo of some reputable company that has hired me at the top of my profile page.

This is what I signed up for.

Am I sure that I’ll make it out of this rut someday? Yes. Do I understand that it’s going to take a whole lot of determination and persistence? Yes. Is reading the success story of the one-out-of -a-hundred people who managed to turn these platforms into a full-time, rent-paying gig within the first few weeks going to help me? LARGE NOPE.

Maybe these posts can inspire you for a week, or even a month, but if you fully buy into these stories and it doesn’t work out for you in the time frame you have given yourself, the effect on your motivation is going to be a lot worse than if you had sat yourself down and been realistic about it from the start.

It’s called the grind for a reason. Unless you’ve got access to some real-life loot crates, you can’t level up from newbie to veteran at the click of a finger. Yes, you might get a double XP bonus every now and again with a viral blog post or really lucrative gig, but don't count on these.

Maybe you’ll see a ‘how to make it as a writer' post from me one day. Don’t expect it any time soon, unless you want tips like, 'take any and every job that comes your way regardless of the pay' or 'wallow in self doubt 24/7’.

One day you’ll see it, and I’ll be sure to include the times where I was sitting in a flat I can’t afford to furnish and relying on my super supportive girlfriend to pay the rent. But I’m not there yet.

So come on Medium. I want to hear the real rags to riches stories. I want to hear how low you got before you turned things around. I want to hear about the websites that fell completely flat on their faces and the twenty-hour projects that you got paid $10 for.

Because that is the point in the story arc that this particular protagonist has found himself at, and I bet you there’s a whole load more of us scrabbling our way up the summit, than there are those at the top, admiring the view.

(this isn’t coming across as a rant is it? don’t they demonetise rants?)

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Colby J Smith

In November 2019 I took a one-way flight out of the UK to find a new life out in the world. Little did I know a global pandemic was around the corner.