For some, becoming a freelancer is something that suddenly happens, either out of necessity or spontaneity. But that wasn’t the case for me — I wanted to be a freelancer for nearly three years. I wasn’t ready when I first began thinking about it. I wasn’t ready after a year. Or two. I wasn’t ready a month — or even weeks — before I made the final decision. The thought of quitting my day job to be independent seemed insane. Today I want to share how I finally mustered up the courage to do it.

As of this writing, I am in the midst of my first week on the job. My goal is to be transparent in my experience so that others may learn from it. I’m not saying that this is the only way to do it, but it’s the way I did it. 

Constant learning

I took inventory of what was holding me back and worked to address those issues.

For example, editing DNS settings freaked me out. I didn’t know my mx from my a record. The thought of launching a website on my own scared me shitless. So, I listened to the server admins and asked them a lot of questions when we launched websites at the web agency I worked at. Over time, I became more comfortable with DNS settings. I may not be an expert now but I know enough to at least ask the right questions when I get stuck.

But it’s about more than just learning DNS settings. I observed other freelancers by hanging out in online forums that freelancers frequented and learned from their mistakes and successes. I participated in account management and project management where I worked and I was able to refine my communication and organizational skills. I read Mike Monteiro’s Design is a Job (you should too)

Let’s get comfortable talking about money. — Mike Monteiro


I wrote a blog post about Google Analytics that earns around 700 visitors a week. It comes up second to Google’s own documentation in search results for many keywords. I put a note at the end of the post that said I was available for consulting on the topic. Soon after I received emails from people asking for help. I did some consulting on evenings and weekends. Some of the people that I helped turned into good connections and some even sent me more work.

By the time I became a freelancer I had already made a decent amount of profit on my own. This was a tremendous boost to my confidence.

Personal marketing

I set up a blog years ago and even though I didn’t post on it with any kind of regularity, I posted enough to gain some attention. I earned some links and hundreds of social shares. Not only was this satisfying but it also expanded my network and positioned my site higher in search engines.

If you’re considering going freelance someday, I recommend starting a blog now. Scratch that — start a blog now even if you’re not considering a career as a freelancer.

Also, read Austin Kleon’s book about personal marketing called Show Your Work! Here’s the gist: share your experience, expand your network, profit.

“Imagine if your next boss didn’t have to read your resume because he already reads your blog.” — Austin Kleon

Leveraging my network (the final piece of the puzzle)

When I got serious about the prospect of becoming a freelancer I sent out feelers to people in my network.

Many people that I talked to were positive about the idea and assured me that we could work together if I made the jump. Some were even so sure that they offered to put me on a project immediately. This taught me that it doesn’t hurt to just ask.

By the time I had some potential projects lined up I felt that I was so prepared that the decision was easy after that.

So that’s it

It turns out that I was training to be a freelancer for years. This post makes it seem like this was deliberate but the truth is that it’s only when I look back on it now that I realize that I have been preparing for this for quite some time.

Interested in staying up to date with me on my journey as a freelancer? Follow me on Twitter to keep in touch!