Recently, I have had the opportunity to explore freelancing as a new gig. I’ve been playing in the marketing and sales space for quite some time and wanted to dust off some of those skills that I was only tapping into occasionally. While I’ve had the benefit of leading some amazing marketers and developing relationships with some key CMOs, CIOs, CEOs, and other leaders during my time in the sales and customer success space, I found that I didn’t have the time to tap into one of my true passions: writing and learning.

Since I’ve also had quite a bit of experience in hiring freelancers in the past to support many of my marketing efforts, I had a bit of a leg up over brand-new freelancers who weren’t sure where to get started. In my case, I explored freelance platforms such as Upwork,, and Fiverr, to determine the platform that would provide me the flexibility I needed, and the opportunity to take on a lot of diverse writing projects.

New Freelancer? Know that Freelancing is About Selling

Let’s be clear. I had to really WORK to get started, and I had to MARKET my abilities quite broadly. I practically jumped out of my seat when I got my first writing job. And now it seems that the freelance writing jobs keep coming. So, I figured that I must have done something right. As such, I determined that I wanted to take some time to provide new freelancers with some tips on getting started in the world of freelancing.

1. Freelancing is a sales role

I alluded to this previously, and I’m not kidding. You must sell yourself if you want to get gigs and eventually turn your side hustle into full-time employment. You’ll be writing proposals and literally selling yourself. Whether it be in writing or via a follow-up phone call that some clients require, you need to be ready to demonstrate your value proposition.

You need to be prepared to speak on behalf of yourself. And this is where the marketing comes in, too. You need to create some assets that speak to your abilities… assets that you can use as a sales tool as you try to land jobs. In my case, I have a document that I maintain that looks a lot like my cover letter, and I have categorized the type of writing I have done, and when I find a piece published, I add the hyperlink).

2. Prepare yourself for rejection

And I mean a lot of rejection. Getting clients to want to work with you takes some time, especially if you don’t have a portfolio. It is highly likely that you’ll start by working at far lower rates than you ever imagined, and this is normal. And it is a gift. When a client is willing to hire you with no perceived experience, they are taking a chance on you. Seize that opportunity, and write like it is nobody’s business.

Then, once you have knocked the socks off your client, you will realize that you now have a portfolio… a portfolio of one, but a portfolio nonetheless. And part of the rejection process is the “never hear boo” part of the process, which means that many times, you may submit a bid or a proposal for a job but never hear back anything. In many cases, from what I have been able to tell, not only do I not hear back, but it appears that the client didn’t hire anyone or move forward with the project at all. This is a frustrating experience, especially when you have taken time and care to present a proposal that you feel is lucrative and appeals to their needs. Prepare for this. It’s part of the process.

3. Prepare to shift your working hours

While this might not be the case for all freelancers, I have found that many jobs seem to come my way in the late afternoon or evening. I suspect this is the case because marketers and those needing freelancers are so busy during the day that they simply don’t have time to post available projects until the end of the workday. If you are freelancing part-time and have a day job during the day, then this will work well for you.

But, if you really want the gigs, try to check the freelancing job boards in the late afternoon so you can jump on the projects that interest you.

4. Be responsive and offer reasonable turnaround times

While clients are definitely looking for high quality (this is a priority), they also appreciate a high degree of responsiveness for proposed edits, questions or clarifications, etc. And if you can turn your project around fast, even better. When I started, I could turn around a blog in one day or less, sometimes even the same day. If it was a topic I was passionate about or little research was needed, I could whip out articles and would often exceed expectations.

Most clients don’t expect same-day turn times. That said, occasionally, you will find clients looking for just that. If you can deliver and they like your work, you can assume more work will come to you from that client in the future. For example, just this past weekend, I had a client reach out to see if I had time to write two quick web pages, both on a topic I had quite a bit of experience with.

As each piece was only 500 words, I had both delivered in under 90 minutes. He was thrilled! And he shot me a note later in the afternoon to see if I could take on two more, and I did. I was able to deliver four high-quality pieces for him in one afternoon and still had time to enjoy the holiday weekend.

Stay Focused – Success Can Come

If you commit to the freelancing experience and have the drive and talent to be successful, you will be. Take the time to explore your skills and be open to feedback (both positive and constructive). If you do, you will find that freelancing can be incredibly lucrative and rewarding. And businesses need freelancers for far more than just writing assignments. While that tends to be my sweet spot, there is always work for other skills. You’ll see freelance roles open for Excel and PowerPoint wizards, graphic designers, resume and cover letter assistance (I dabble a bit in this, too), and a plethora of other needs. The work is there, and it is always coming in.

Leave a comment