Looking back at my freelancing history it’s easy to see things that I should have done differently.

It’s not regret. It’s knowing more now and having a better understanding of how business and freelancing works. My hope is to give some advice to help new freelancers who are starting now.

The biggest thing I’d change would have been to establish myself as an authority earlier on. You might know me as the freelancer who did Redmine work but it took almost two years before I specialized in that.

Those first two years were rough. Some months were great. Plenty of clients. Plenty of work. Income growing.

Other months were horrible. Projects ending with nothing to start. Spending time marketing with no results. Classic feast and famine cycles.

At the time I was studying marketing. Not because I enjoyed it, but because I had to find a way to fix my business. (It wasn’t until a few years later that I started to enjoy marketing)

When you need to find a client now in order to pay your bills, you get really motivated.

The problem I had was that my services were still generic and unfocused. I wrote software using Ruby on Rails. Like thousands of other people.

Much of the marketing advice I got suggested narrowing down my services, target clients, and honing in on a niche.

Things that wouldn’t work for a generic service like “Rails development”.

Around the two year mark I was working with one long-term client who switched to Redmine for their project management. I’ve been using Redmine for awhile by then and had built up a bit of knowledge about its internals.

This client had some friction with the system, so we started a small project to remove that friction and make Redmine flow better for them.

This small project was successful and led to another. And another. And another.

It didn’t take long for me to notice that the knowledge for each project was building on top of the last. Basically I was getting better at working in Redmine. Not Rails stuff, but Redmine architecture and how its systems were interwoven.

Around that time I started very casually mentioning that I was available for Redmine development. This attracted another client. And then another. And then a contract was renewed.

Eventually over the next few months I specialized and focused only on Redmine development. Instead of working on anything Rails related, I was only taking Redmine projects.

Each time I finished a project, not only did my knowledge increase but my portfolio of successful projects increased. Each project had components that would be open sourced as a plugin. These plugins fueled my marketing and status even more.

Around 2012 this specialization hit its max. I was busy developing for Redmine full-time, was referring other Redmine projects away, and had enough of a marketing system to hire another developer.

(I decided against hiring and have now shut down my Redmine services. That’s a story for another time)

What can a new freelancer learn from this?

Specializing takes time, energy, and a leap of faith to do. But it can be a significant boost to your business. For four years Redmine and related development was my full-time career. Every month was an improvement over the last month in some way or another.