Lessons in Navigating My First Couple Months of Freelancing

I’ll be honest, I’m still not 100 percent clear on what I’m doing. When I started my first side hustle with freelance writing, I was certain it was going to be a lot easier.

I first thought my profile on Upwork and my first couple of gigs on Fiverr were “complete” after a couple of weeks of YouTube tutorials and reading tips and tricks articles. I thought my first stories for Medium were bulletproof. I thought I had done my research and I had an idea about what I’m doing. The truth is, I don’t. Not 100 percent anyway. I tried freelancing about six years ago and I had no clue what I was doing then. Right now, I have some ideas, but it is not a crystal clear picture for me.

In my research, I decided platforms like Fiverr and Upwork would be good starting places, especially when I wasn’t completely sure of myself or where to begin with it. I’ve grown frustrated that with a little over a couple of months, I still have yet to land an elusive client on either Upwork or Fiverr. But during this time, I have learned a few things about myself and this trade.

There’s a lot of work and steps to freelancing

I think this is the biggest issue I’ve had to tackle with beginning this freelancing journey. It takes time and persistence. You can’t respect instant success.

When I first attempted a freelancing journey six years ago, I thought my name, my education, and the fact I had taken writing classes were good enough. It wasn’t and it lead me to abandon it within a couple of months out of frustration.

At the start of 2021, feeling a combination of pressure to bring in extra income and start branching out from my main job, I looked back to freelancing. New Year’s Eve, with my choice of libation in hand, I promised myself I am going to making writing a profitable thing. I was going to be a freelance writer. I started a WordPress blog again and let it, along with my ambitions, languish until about July when I came back to it with fresh eyes. It was then I realized that I really had no clue where to begin.

Discovering a niche

This is still an area under construction. I thought freelance writing could be the simplest thing as I’ll just write blogs or I’ll just write content! It is a big, vast world with people writing about everything and anything. Competition can be fierce.

Medium was a platform I first tested the waters by writing about some of the things I learned working from home after over a year into the pandemic. It didn’t perform that well. I started my WordPress blog back up, writing about writing and mixing in a couple of updates. I thought that was it. I was writing and could call myself a freelance writer, but that wasn’t the case.

I actively started researching platforms like Fiverr and Upwork, gaining the courage to join. I posted my first gigs on Fiverr focusing on content writing, resume writing, and beta reading. On Upwork, I found it much more daunting because I had to apply to jobs with proposals rather than post something and let people come to me.

At this point, I thought I had it figured out. I was wrong again.

A stand out profile and repolishing skills

I thought after a month of applying to jobs and having gigs up something would materialize. But I still had nothing to show for it. So back to YouTube and reading various articles about freelancing. One key takeaway: first impressions were everything. My focus turned to my profile and I started to make it stand out more, or at least, as comfortable as I was with doing so.

I highlight my education. I tried to find the same profile pic that I used with LinkedIn. I rethought my focus on writing services and skills, expanding to include things editing and hot keywords like SEO optimization. I went back to relearn and expand my knowledge of skillsets I thought I had mastered like copywriting.

Even as I retool and tweaked my profiles, I began to also polish and refine my gigs and proposals. I repriced my gigs on Fiverr and reconsidered my hourly rate on Upwork or what I should bid on projects.

It’s still not perfect, but it’s getting there.

Trial and error, flexibility, and persistence

Probably the biggest lesson I’ve learned with navigating freelancing is persistence, flexibility, and never giving up on it. I’m constantly retooling my gigs and my proposals. Even the way I write a story for Medium, I am experimenting with each new story to see what works and what doesn’t. This month, with Medium, I’ve actually seen my first earnings. Granted is cents compared to the dollars one might expect, but it is something. It is something tangible to show for my efforts. And it is also validation for continuing on this path and navigating this hustle to figure out the best results.

I recently redid my WordPress blog into a portfolio and blog using everything I have learned over the past couple of months. I’m proud of that effort. It may not be the success I thought I would have before beginning this journey, but I am happy with it thus far. That alone is enough motivation to continue to pursue freelance writing and see the possible rewards.

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