A Path to Freelance Success – Part 1

My freelance career has been remarkably successful. I’ve worked with an amazing array of individuals and companies from around the world. I’ve gone places I never thought I would. I authored a book when I was 24, something I wanted to do sometime in my life but didn’t think would come until much later.

The money hasn’t been bad, either.

I had no idea what I was doing when I started freelancing. I figured I’d just wing it and hopefully things would work out in the end. I certainly didn’t jump in blindly – I did my research – but I never codified my plans in any way.

Discovering the Path

A couple of years ago, I was on a business retreat with some awesome associates of mine. Each person on the trip was invited to present to the group on a topic they considered interesting. I sat down in the weeks leading up to the event and thought about what I could talk about that would be applicable to a group of freelancers from disparate backgrounds and a variety of disciplines. I wanted to present on something that they would be able to apply to their professional lives.

That’s when I came up with the process that I credit with my success as a freelancer. I believe anyone with a marketable skill can follow the steps I’ll outline and be successful.

I’m not saying this is the path you MUST FOLLOW to have success as a freelancer. I don’t deal in absolutes like that. It has worked for me and I hope it will work for those of you who are interested in freelancing and aren’t sure how to get started.

In this post, I’m going to go through the first three steps of the path. Tomorrow, I’ll reveal the other steps. I look forward to hearing what you think!

Figure Out What You Like Doing

If you want to build a business as a freelancer, you need to choose the services you offer wisely. You’re going to be doing something every single day in order to pay the bills, so you better make sure you like doing it. Otherwise, you might as well go work as a nameless and faceless drone in some thankless corporate job.

I love developing software because it gives me a chance to craft unique solutions for a myriad of different problems. I get to think things through logically and architect artful solutions. I learn something new every day and I get a deep sense of personal satisfaction from knowing people use the things I build.

Figure Out if There is Money in What You Like Doing

To freelance professionally, you need to be marketing a service that people are willing to pay (and hopefully willing to pay well) for. No matter how much you like doing something, you’re not going to make it as a freelancer if the service you offer has no market.

Here’s how I found out that people were willing to pay for software development in general and WordPress plugin development in particular.

  • I found job boards centered on the service I was providing (like WordPress Jobs and the FreelanceSwitch Job Board)
  • I looked on Craigslist and saw there were job postings for freelance software developers
  • I found people already doing what I wanted to do

No matter what service you want to offer, you should be able to do the same.

Write a Plan

Once you determine that you can make money performing a service you can provide, you have to dig deeper and do some planning.


The first thing I did was figure out how much I needed to make per month to live the life that I wanted for my wife and I. After that, I worked backwards to determine a plan to start making that much money. In my first few months freelancing, I gradually built my business up and hit my “need this much money to live” goal.

The most important thing about financial planning for a freelancer is to be realistic. You can almost certainly make the money you need to get by if you plan appropriately, but you can’t expect to go from nothing to full income in a few days unless you already have a captive audience, prospective clients who will pay for your services without further convincing, and the ability to provide those services in a business context.


The most important question you should ask yourself is “How am I going to get the word out about my services and the fact that I’m now offering them?”

If nobody knows you’re in business, you won’t be able to make any money. You need to find clients or have them come to you and request your services.

There are a variety of ways to do this, the simplest being word of mouth. Tell all of your friends and family members that you’re freelancing and let them know what you do and how people can get in touch with you.

As a follow up, you should register a domain name and put up a business website. Make sure it has a clear call to action that prompts people to contact you and that it clearly demonstrates your ability.

How do you demonstrate it? If you’re a developer, have code samples or links to your GitHub profile. If you’re a designer, portfolio pieces and a link to your Dribbble account might be in order. Writers should have writing samples in a variety of formats. Bottom line, demonstrate you’re good at what you you want people to pay you to do.

Part 2

Tomorrow, I’ll go through the final steps of the freelance path I discovered and flesh out a bit of the endgame. Getting started is tough enough, so if you have any questions or comments about the steps outlined so far, please let me know in the comments!

Update: You can read part two now!

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