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Upwork is Scary but I got Pickle Patches Now


exasperated holden stephan roy

This job searching is overwhelming. At first there was this hubris that my CV was good enough. The universe has since made it abundantly clear to me that something must change. Over the last 4 and a half months there has been this gradual shift from not trying hard to taking it all more seriously.


Little by little I took on different projects and started new things, but everything has felt (but is not) aimless. Sometimes this blog will be crazy adventures but today it’s honest, open insecurity.


For all my skills analyzing others and figuring out stuff for them, when it comes to me, I’m a hot mess. This month of May is going to be a rebranding process to understand how I fit into the world of income.


As I started to edit this someone messaged me down to buy 2 hoodies, so there are silver linings.


12 years is a long time


The last time I was unemployed was the autumn of 2009. That summer was one of the darkest phases of my life. Due to poor life choices, I did not hold down any kind of job.


I remember having this gig at Canadian Tire, where had I just shown up on time, I would have had a permanent role. Instead, I goofed around and was let go. Stoney S. Babe and I were colleagues for that little stint.


Somewhere around the end of the year I started working at the Dunkin Donuts on Grand and Sherbrooke. It was an overnight shift and again, I did not take it very seriously. I worked just enough to not get fired.


Hating the overnight life, I ended up finding my way into a call center position. Back then Craigslist was a viable way to find a job and that is the last time I job hunted for real. Using Craigslist.


I went from lowly call center agent to managing my own team holding down my own projects. Along the way my music/content journey started and up until December of 2022 I had the safety of a comfortable income.


I was “no kids” aiight. I could maintain a pretty fun lifestyle and invest in my life while wasting money. Had I had kids, there is a 0% chance I could live the way I was/am. But then it ended one day.


Timestamped reality


Now I’m in this limbo. Thankfully I’m living off the choices of a younger me, but that is timestamped. Before letting myself hit the point of sadness, I will need to find a job.


This break from the normal has been an interesting experience. It’s the first phase of my adult life where I had both purpose and the time to pursue things. Unfortunately, it also came with a couple of months of sheer demoralized lack of focus.


Now I find myself in this perpetual state of self-imposed catchup. Certain things like recording music never seem to become a priority. I’ve spent a lot of time feeling stuff.


The end of last year was a strange time. I couldn’t answer simple questions like what made me happy. It sounds dumb but I’ve been going through a process of trying to understand what I enjoy in life again.


I’ve started to focus on what I want out of life again, apparently being a writer is a priority. I’ve always enjoyed writing I just never wrote for myself like this before. I worry that I may talk too much on my anxiety, but people also told me I’m trash at letting them in.


This blog is what I really feel about things, through a lens I’m comfortable sharing. Because I am not comfortable sharing how I feel with my friends, family or hell even Bonnie. I am still learning a lot about opening up when it matters. People care.


The freelance adventure begins


I have dabbled in freelance work across my life, but the opportunities fell into my lap. As you can tell by my current level of success, reaching out and grabbing life by the horns is not my strength.


Most of my wins come from linking up with someone bolder who breaks the ice for me. I know I need to be more assertive and create my own moves. I am slowly learning how to do that.


In some cases, it’s easy, I know how to throw an event now. Once they are profitable, it becomes throw enough events and that’s a chunk right there. I can write, so find enough people who need me to write for them and we Gucci.


I’m a project manager, I can do voice work, and there is all this other stuff I can do. My life has had me learn skills on the fly and just do things as needed. Now I need to learn how to package myself into something marketable.


People have seen a complete revamp in my style/fashion sense. This was an effort to understand how to dress better. I am now learning how to do the same thing for my corporate/hustler identity.


I’ve procrastinated a lot over the last few months. Little things set me off and the next thing I know an entire hour has disappeared. But that can’t become the normal so today I opened an Upwork account.


My first experience was tech issues


I had tried to sit down a month ago and create the Upwork account. I ran into a strange bug creating my account and gave up. Moved on to some other thing, probably writing a blog.


This has become the new “productive” time waster I have to procrastinate on more important tasks. However, I also need a portfolio, so here we are in the Catch 22 of time management.


Still, I couldn’t create an account with my main email. I could bore you with the steps, I know how to write bugs in a way a developer can replicate. But suffice it to say I had to use a backup email to move forward.


Then I got into the site and filled out my basic information and went through a relatively simple sign-up flow. You import your CV information, where because my highest degree is a DEC, I have no valid degree.


Then you do the part where you introduce yourself, caption, description and add some keywords for the bots. This part was overwhelming and made me realize that there was a lot more to learn. The logistics of using the website are easy enough, knowing what to say and how to brand myself is daunting.


The basics of an Upwork


I chose to start with the version where I look for gigs. There are apparently also “projects” which is a whole other side of Upwork.


You create your account and choose your skills. You add relevant portfolio experience if you have some, I don’t yet. I came to realize all my bootleg freelance work was not formal and thus I need to figure out this portfolio thing.


Sure, I have a blog, but that is proof I can write, not proof I can deliver on projects as requested. It asks for a video introduction I have yet to do, because again how does one create this? Oh no, today is not a solutions day, I feel bleh and needed to vent.


You need to set a rate. How much do I bloody charge on a website where I know nothing? I set a number I am comfortable starting with. I don’t have any credibility in this world, so I need to at least clock a few clients.


It’s asking me for certifications and other experiences. I definitely want certifications now. I suppose this blog and my content hustles count as “other experiences”.


Basically, it’s a dating profile for your work life. I know the tone I wrote this in, and I am going to go watch videos on how to make my stuff tighter. Once I have some success, I’ll share what I learn with you.


Looking for gigs on Upwork made me feel small


Full disclosure, I spent a small amount of time doing this so far. Account creation is probably going to take a good 30 minutes to an hour. You really want to think about what you put down.


Then you get brought to a feed, like on Indeed, with available jobs. Now comes this part where you read the job, see if you think you can do it and make what they call a proposal.


This makes sense, you basically put your rate (or the company has a set rate) and then you write a cover letter to express why you are dope. Then you need to use a currency known as connections to bid on the job.


You can apply, with 2 connections, but you see right away people are using 14 and go oh, I should probably bid more if I realy want this job.


Upwork’s knowledge base article on this was like, you’d spend money on dinner, buy the damned currency. You start off with 50 and then can earn 10 a month for free. Or you can join their premium program to get more a month. Or you can buy them outright.


If you want to apply to jobs on Upwork, it is literally pay to play. I’m not saying it shouldn’t be like this, Upwork provides us with a tool to connect with jobs, once the connection is made that’s future money in my pocket.


The other side of Upwork is creating projects


This is presenting yourself as a consultant. You get to charge for Zoom call. You create a series of requirements that a potential client will fill out, like their business information and goals.


Then you meet with them on Zoom and go over their project. You can flex your expertise and offer insight. I’m sure there’s more to it than that but I wanted to get a basic understanding of how I could make money on Upwork.


You can think of the gig side as you are a worker, and people need your skills to accomplish their goals. You can think of a project as you are a manager and people need your skills to think on their behalf.


This is cool as I have wanted to move into this kind of work for awhile. I’ve already had a few one-off clients where I’ve been able to provide help starting their projects. A lot of the time people suffer from the same thing I’m suffering from, they need someone to tell them what to do.


The reality is this is going to take a lot more time than the couple of hours I looked at stuff today. But this is a start towards the future where I can feel more confident in the direction I’m going. The process of tightening my Upwork (and soon Fiverr) profile is basically the same as tightening my CV.


Oh yeah, I joined a board of directors


I nearly forgot I had a meeting at 4:00 PM today. This was to go over a project to restart the newsletter for Notre-Dames-Des-Art. Turns out we are to be what is called a working board.


There are two kinds of board of directors (that I know of). The ones that advise and the ones that must do things because there is no staff. Board members are voluntary positions for the most part where you offer your expertise to guide the ship.


Turns out I joined the board during a transitionary period. The staff that was there before is there no longer. This means if we want the organization to thrive, we must take on some work to get things moving. Then, when the ball is rolling, daddy government can hopefully give us operational funding.


Either way, this is a great experience to learn things and get some hands-on experience with tools I’ve never used before. I partly fear the idea of taking on more work without pay, but to get pay I need more relevant skills it seems.


Or at least some kind of results I can boast over.


New merch more work


I had to go meet 7:Thirty from Regulators in Lasalle after I had that meeting. I ordered some patches in the brand-new pickle design. Patches are cool because they can be sold individually while also being something that can be added to other merch items.


They came out great to be honest but like everything else, there’s the impending, “Now what?”.


I still have these new hoodies and tank tops. Thankfully the Made in Montreal man hooked me up with some mock-ups. After this blog is done, I need to edit videos, then go work on my store to make sure all these items I have for sale are listed.


The process of sitting there and working on this site doesn’t excite me. However, ignoring the things that don’t excite me is going to leave me in a position where I am fucked. So, it’s time to focus on getting things done.


I know there are greener pastures in my future. Even amid my “hard phase” this is pretty privileged, and I know it. I count and appreciate my blessings and the people who love me.


I just need to learn to be more honest with where I’m at and find my drive to get the boring done again.


Live Long and Prosper Everyone

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