‘Hustling And Milestones’

Adesua Ayomaria
6 min readJun 30, 2024


Photo by Good Faces on Unsplash

Pardon the title of this one; the last milestone of work given to me on Upwork has just been approved, so in the spirit of the money coming and the many things that I have planned in my head to use it for, I might be a little over the moon here.

‘Every hustler has a payday’. In this sense, the best news for a freelancer on Upwork is to get that mail notification: ‘Your last milestone has just been approved…’ With this message, you heave a sigh of relief and thank your stars that everything is aligning, at least now, and there is a little purpose in life after all.

I got this notification, and for nothing, or probably because I am currently giddy, I opened my medium tab. This is me typing, at this point, just penning down whatever comes to mind. Now that I am thinking about it, I should take some time to talk about my struggles as a freelance writer.

As they say, after all, to a writer, especially one like me, everything is content. So stay with me as I milk this in a way. Hustling on Upwork is never a predictable game. It is solely about consistency, hard work and a little luck. I like to add this last part because we cannot relegate luck.

It is as subtle as anything, and although some might argue that luck is just years of preparation that happens to stumble upon opportunity. For luck to work, you must at least have substance. Upwork throws up a fair challenge to its freelancers, and the scales sometimes need to be balanced.

You must be able to stay up at least, submit proposal after proposal, update your profile, find a way to say the right words and pray that something clicks for you to be the one chosen amongst the hundreds, possibly thousands, jostling for the same job. Talk about luck again.

At this point, my mention of luck starts to sound boring or feel escapist, so I would stop mentioning it. But if you are familiar with Upwork, then you catch my drift here. You must stay at it, pulling all the plugs and praying to whatever you believe in to give you that edge. Some people found a winning formula and stuck to it, while others had to ‘grapple for something in the dark’ to at least have a chance.

Isn’t that life? Anyway, I am on ‘Cloud Nine’ today and I Have just little time to discuss many of my freelance struggles. Again, if you are thinking about talent, I know that I am a good writer, and when I talk about any topic, best believe that I will know something or, better still, someone who knows something about it, I just know how to pull the best plugs.

Anyway, as I have said, I am on cloud nine, and I want to do my best to celebrate Tobias, who decided to take a chance on me and has consistently sent me gigs upon gigs, writings upon writings, as we work together to build his YouTube channel. We had a brief video chat, and it just felt right. I knew I wanted to help him in any way possible to build that channel.

I have done something like this before, I can pull this off. Do you know who I am? Ayomaria I remember how I once wrote a whole ass company whitepaper in the night, armed with a bottle of ‘Fearless’ and although my head was spinning by the morning, I got that shit done.

Or was it how one of my gees once dared me to complete a niggling 1000-word document on a bet, and I finished it in record time. I always find the right words, or a mix of the right ones, to give you what you want or what would make you stay. Just the way you are scrolling on this screen and reading the scribblings of a dramatic ‘Extrointrovert’ if there was a word like that.

Anyway, I am lucky that this Night, Tobias sent me a new milestone,and we both might be up to something here. After so difficult a time, I can at least smile at myself that all hope is not lost on my writing career. In one corner of my head, somewhere amidst the many struggles of everyday life, all hope is not lost.

Well, for everything, one still has to be grateful. Upwork provided me with succor when all seemed hopeless. The app helped me stay afloat during many tough times, and I can look at myself and be thankful for the many insights and how it has helped my growth and that of thousands of others. It is one solid platform that is here to stay.

However, as the ‘Chief Complainer and Solutions Provider’ that I am, I would suggest that maybe it’s time for the platform’s administrators to focus on freelancers. We already bid for jobs, buy ‘connects’, and purchase badges, all with hard-earned cash, so we contribute in no small way to the freelance ecosystem.

Photo by Windows on Unsplash

It is a relationship. Upwork provides us with individuals and platforms in need of services, and we, in turn, as freelancers, provide those services.

It may be time for Upwork to vet its clients to sanitize the system better and correctly.

A friend lost over $800 after completing his side of the bargain because the client found a loophole through which contracts can be cancelled and escrow money safely disputed and returned.

She did just that, and Upwork returned the money to her. Talk about nights of writing, research, and brainstorming before we arrive at that point. It all went to waste, and when we went on a media search and proceeded to pull media threads from the little information we could get from this patient, we found out she did not exist.

The company she was ‘Impersonating’ at that point does exist, but the CEO politely clarified to us that the same job we were contracted for had, in fact, been done about three years ago. We found evidence of this claim on all the company’s social media pages. So basically, we were ‘Phoo-Phooed,’ and nothing was done about it at the time of this writing.

Upwork could take the time to consider freelancers' yearnings effectively, leading to a better work environment and platform. While I continue searching for the writing job that I must be a part of, you could also reach out to me and let’s work together because I am tired of walking the streets of Lagos; something has to give yunno.

I might not have hit all the points directly and solidly, but if you are a freelancer on Upwork, then you understand what I am all about. Or better still, maybe there are some significant hacks to the platform or the system as a whole that I have yet to get, so I would be happy if someone could be kind enough to show me.

Photo by Daniel Thomas on Unsplash

But for now, I am on cloud nine, and I love my life. I hope Upwork fixes up in no time. Before I end this, I think there should be a slogan for writers. I will have something before I come back, but until then, stay winning my people.