Month 1- Freelance Report

(Last Updated On: March 22, 2016)

freelance report month one


I’ve been out of the freelancing game for a few years while working for just one company. This was not a very strategic move, but that’s okay.

In my first month back at freelancing, here’s what happened:


Four years ago, I started out freelancing on elance, which is now Upwork, so I returned here to look for work. I know how to use the platform and returning to it felt like a homecoming, which made me more confident. This month I created my profile on Upwork and bid on 4 jobs. When I was working on my profile, I discovered Freelance to Win and signed up for the free, five day “Upwork Hacks” course. This course has helped me tweak my profile and feel more confident about holding firm on my rates.

Out of the 4 jobs I bid on, I was offered one. I actually turned down this job, which is a topic I’ll write about in a future post.

Cold Pitching

On Gina Horkey’s blog, she wrote about how she cold pitches clients. Cold pitching means that she sends an email to a person or company who has not actively advertised work. Gina’s post, along with this follow-up post about one of her students who cold pitches his work over the telephone motivated me to try it.

I sent out cold pitches to three major education publishing companies. I heard back from one of the companies within the first week!  They hired me to join their pool of freelance assessment item writers (Yep, I write standardized test questions. It’s a dirty job, but somebody’s got to it.)  I don’t have any work yet, but they will contact me when a job comes up.

Warm Pitching

Getting hired by this company boosted my confidence. It also made me think that my pitch email was probably pretty strong.  I found four more education companies that said they were always looking for new freelancers to join their team. So, I sent pitch emails to all of them.

Hurray, another company hired me as a sub-contractor! Again, there was no immediate work, but when a project comes in, they will get in touch with me.

A third company asked to see work samples, which are currently under review. Keep your fingers crossed for me.

Former Clients

The final place I looked for work was with two of my former clients. During my two years away from freelancing, both of these clients had emailed me to see if I was available. I wasn’t then, but I am now! I emailed both clients this month to describe what I had been doing for the past two years, ask about their current projects, and tell them I was available to help. They both replied almost immediately, and I’m emailing and Skyping with them both to figure out what work I can do to help their businesses.


Writing great pitches takes a lot of time.

I found two strategies to help me speed up the process:

  • Save every pitch to use as a template for future pitches.

I customize my pitches for each prospect, but saving all my pitches made this easier because I could cut and paste parts of different pitches together.

  • Find a niche.

My niche is writing assessment items for K-12 education companies. Finding a niche allows me to re-use many parts of my core pitching template. For example, all assessment companies want to know if I have teaching experience and have written assessment items before. It’s easy to re-use the bullets that describe my experience in those areas for every pitch. It’s okay if you don’t have a niche yet. Just know that once you find a niche, pitching will be a lot quicker.

Finding work is a slow process.

It’s been a month, and while I have plenty of promising leads, I don’t have any actual work. I’m okay with that because I’ve done this before. I know that some of these leads will turn into paying work. If you’re new to freelancing, stay patient and keep pitching. Eventually you will find work.

Be open to new opportunities.

I spoke with one of my old clients, and when he told me the rate his company has been paying teachers to produce curriculum, I balked. I asked him a few questions about the quality and type of work he’s been receiving, and he immediately asked if I might be willing to consult.

This was a huge revelation for me. I’ve reached a point in my career where I know more about my niche than some of my clients. I can and should be advising them, and not just producing content for them. In the next few months, I would like to delve deeper into the world of consulting and learn more about how consultants get started, how they find work, and how they market themselves.

Freelancers need to network.

I’ve always hated networking. I wanted to live in a perfect world where my skills get me a job, and it doesn’t matter who I know. Well, I am changing my tune. Getting in touch and lining up work with my old clients has been much easier and less stressful than cold pitching or applying to work on Upwork. It’s time to put on my big girl panties and network. I don’t have a strategy for this yet, so if you have any tips, please share. I’ll start researching and trying some things in the coming months.

Your Take-Aways

Here are some lessons you can take away from my first month:

  • Even though I took a two year hiatus from freelancing, I am not a beginner. If you are, it’s okay to have different goals and different results.
  • Relationships are key. You should plan to use your network and grow your network if you want to grow your freelance or consulting business.
  • My proposals and pitches get rejected all the time. Yours will too. It’s normal, and it’s not a reflection on you or your work. If you need a little more of a boost about handling rejection, check out last week’s post.
  • It’s all about the long game. I’ve always been in a big rush when it comes to my career. Now that I’ve gotten older and wiser, I’m able to slow down and see the bigger picture. If you are just starting out with freelancing, know that you are not going to see immediate results. Keep putting in the work, and eventually things will come together.


If you are new to freelancing, what questions do you have for me? If you are more experienced, what is your best advice for new freelancers?

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