How to Book Your First $500 in Freelance Work this Month

cold-1284030_1920-1Ever wonder how other freelancers got their start and somehow command thousands of dollars every month, and even replace their full-time income? 

When I first started freelancing, I earned $400 a day as an assistant video editor on commercials and worked my way up to $600 a day (plus overtime). The work was long and hard, but landing work was not. I was living in New York and post-production houses were plentiful. It was rare I was out of work for more than two weeks at a time. My average booking was for two week assignments (one lasted over a year) and netted $4,500 minimum.

But when I became a freelance writer, I felt like I was reinventing the wheel. How did I start? How did I book more than a few random $100 jobs here and there? How did I scale?

It turns out, the methods I used weren’t all that different than landing video editing work on commercials. I just had to know where to look and how to find the right clients. The trick is getting started.

Anyone with ability can start freelancing. Your ability might be:

  • Writing
  • Project Management
  • Social Media
  • Accounting
  • Errand Running
  • Tutoring
  • Graphic Design
  • Transcribing

In the case of errand running, you don’t need to be  an expert at anything. What you need is time, the ability to get the job done, and personable customer service skills. You can do this.

Start by identifying one or two freelance jobs you can tackle, and break down your hourly rate. Now think about your goal. I like to start with $500. It makes an impact in your day-to-day life, allows for more fun, can pay down bills and is ambitious. You need a goal that’s exciting and worthwhile enough to pursue. But $500 isn’t unrealistic either.

So take a hard look at your estimated hourly rate. If it’s $10 an hour to transcribe some audio, then you have 50 hours of work ahead of you, and need to find enough clients to sustain it.

You can still do the transcribing, but think about what else you may need to do to supplement your freelance goal income for month.

Choose a High-End Specialty

You may only be able to charge in the neighborhood of $20 an hour for math tutoring to a middle school kid in your neighborhood. But what about test prep? Now you’re looking at $50 to $100 an hour to help kids master the SATs, possibly get a scholarship, and help their parents save on college. That’s valuable. And now you only have 5 to 10 hours of freelance work to hit your $500 goal.

That’s why I made so freaking much as a video editor in New York. Sure, I was in the right location, but I also had the right specialty. Advertising pays way, way more than an independent film or TV show. My friends at MTV made less than me, and we were essentially doing the same work.

So what’s your high-end specialty if you’re doing something like errand running? It could be picking-up furniture at IKEA in your van and saving people the $99 on up fee to deliver locally. Maybe you pick-up several orders at the same time, twice a day. If you’re charging $60 per order, then you could be looking at $500 or more in a single day. And if you’re good with your hands and have a toolbox, you can offer to put it together for $100 a pop. That could put you in the $1k category for a single day of freelance work.

Don’t discount those “low-paying” freelance fields. It just takes the right positioning.

Set Your Rates

Your hard work deserves payment to match. So get it out of your head that you need to write $10 articles to earn your way up to $500. There’s much easier, more rewarding, and more lucrative ways to do it.

Start by spying on your competition to see what they’re charging, and split the difference. For example, if you want to work on designing a landing page or flyers for a local business, see what other people are charging for this. Now let’s say you see rates ranging from $200 to $500. Set your rate at $350.

You want it to be somewhere in the middle. Rock bottom prices signal rock bottom talent. People won’t take you seriously, and you’ll be a magnet for clients who want everything for nothing and low-ball your already low offer. People smell desperation from miles away and will try to cheat you out of what you’re worth.

But if you set your price too high, people may balk, or expect you to be head over heels amazing. That’s a lot of pressure for a new freelancer.

Find clients

I’m not going to lie. It can be really frustrating finding clients right out of the gate. And even seasoned freelancers get frustrated and find themselves in a slump. But you can usually bust out of that pretty quickly one of two ways:

  1. Reach out to your social media networks
  2. Cold email people like crazy

The first is going to be easier, but isn’t always the preferred. Maybe your day job is a battlefield and you don’t want anyone to catch wind of the fact you have a side hustle going. Or maybe you’re trying to do something your best friend failed at, and it’s just awkward.

Your other option is cold emailing people. Most people are intimidated by cold emailing people, but I absolutely love it. Just like sending query letters to publishers and editors, cold emailing is reaching out to people who may be interested in your service. If you do it right, it’s highly effective and doesn’t have to be gross or salesy.


As a seasoned freelancer, I frequently book work with just a handful of cold emails, but it can take awhile if I’m working on a new initiative. For example, I recently started approaching businesses with a content marketing strategy service, and while I got a lot of interest pretty quickly, it’s taken time to actually nail down and book the work.

Start by sending out 25 cold emails or tap your network. See what happens. If nothing happens, there’s either something wrong with your offering or the market you picked. Can your market pay? Or are you tying to hit up small travel blogs with a website redesign for $500? They’re not going to pay you for that, sorry.

Send an Agreement

Once you land work, send over a basic agreement created in a Word document outlining:

  • What you’re offering
  • When you’re delivering it
  • How much the client agreed to pay
  • When they’re going to pay you
  • How they’re going to pay you (preferably cash or PayPal)

Once you’re done, save the file as a PDF and ask them to sign it. I make it super easy for my clients and suggest they use DocuSign. It’s easy, free, and just takes a minute to set-up.

Do Exceptional Work

Look. Doing a half-assed job isn’t going to do you any favors. Competing as a new freelancer sometimes comes down to how much the person likes you. Are you reliable? Do they love you? Do you make everything super easy?

It can be hard to execute on things as a new freelancer, especially if you’re in a field like writing. But you can make it work. Hire a proofreader or editor from UpWork (freelancers hiring freelancers!) or send to your BFF to get the job done well.


It’s way easier to re-book an existing or former client than a brand new one. I use to have a big problem following-up because I was afraid of rejection. I wasn’t as afraid of it when first snagging that new freelance work. But once I completed it and turned it in, I was afraid they didn’t like it and would recoil if I asked for more work.

Once I started asking, I got booked again and again. People want things to be easy. They’re not looking for Pulitzer Prize winning lawn care service. They want to work with the guy or gal who shows up on time, does the job well, makes it all easy and maybe goes above and beyond and pulls the weeds too.

What do you think? Ready to dive in? Still a little uncertain on how to put all the pieces together? Leave a comment below and let me know what you’re’ struggling with.