How I Made My First $1,000 Online in 3 Months

Blake Reitnauer
The Digital Dollar
Published in
3 min readJan 23, 2024
Photo by Alexander Mils on Unsplash

Like anything, it takes time to get started. The fight from $0 to $1 is the hardest step to gain initial velocity.

The most common reason people fail at virtually anything is that they quit right before the effort they are putting in gets them their first results

For you, I know that will not be the case too…

To cut to the chase, I made my first $1,000 online freelancing on Upwork.

Here are the steps I took to make it happen in 3 months…

Identifying My Skillset

First, I started with what value I had that people were looking for. At the time I was doing a great deal of work in the Market Research and Competitive Intelligence space for a degree, so I ran with that.

When identifying your own unique skillset think about the line of work you are in, or even what classes you are taking for school. This can be virtually anything you have expertise on.

Searching for Contracts

With that I started researching open contracts in the Market Research niche looking for opportunities that I had the relative experience to take on.

Take a minute to read the contract description and make sure what it is asking fits your core competencies. Your job success score will matter for reputation on Upwork and that is determined by the person who hires you.

Start pitching the contracts that fit your skills and continue to look for more opportunities. Keep in mind that the people posting these jobs are often wanting someone to start immediately, so even if you are not the most qualified person pitching the contract it always pays to be the first one.

Without any portfolio or past Upwork history it is hard to find that first contract, I needed someone to take a chance on me.

Pro Tip: A well written proposal goes a long way too, here is a great resource if you are looking to nail your Upwork proposals from the start.

Closing MyFirst Contract

The way I closed my first contract was easy, after the prospect responded to my proposal I scheduled time to do discovery on their project and let them know I understood their problem. Then I could pitch my execution plan and timeline for the project, if that was accepted I was able to finalize the project compensation and get started.

After two months of persistence, I finally closed two back to back contracts that led to over $1,000 by the end of the month.

The hardest part was in fact getting started, and being persistent until I got my first shot to build my portfolio.

Once you have some previous work behind you and get better at pitching your skills, the contracts that follow become much easier to land. Plus you are able to charge more for your services as you progress.

Thats it, just monetizing skills you already have.

Let me know below if you have tried out freelancing and if you had a similar story to mine. I’d love to hear your experience as well!

Photo by krakenimages on Unsplash

Thank you for reading!

BR

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Blake Reitnauer
The Digital Dollar

Startup professional sharing ideas on sales development. RevShare newsletter ↘️ https://revshare.beehiiv.com/subscribe