13 Strategies for Becoming a Successful Freelancer: Strategy Thirteen and Conclusion

This blog post is the last in a series of eight adapted from a talk given at TOS-Con 2021. Learn more about TOS-Con here.

Break Rules Constantly (but Thoughtfully)

Statistically, you’ve almost certainly applied for a job and gotten no response whatsoever. Many people have experienced this aggravating situation hundreds or even thousands of times.

This happens because you’re playing by someone else’s rules—and in many cases, those rules are dumb, arbitrary, or both. To be clear, I’m not saying you should ignore every client’s policies and just approach them however you want. That’s a recipe for disaster. Still, many clients are using rules or systems that are not effective at getting them the results they want—but they don’t know that, or maybe they know but don’t have the power to change it.

Crash.co advocates breaking rules in order to get clients or hiring managers to notice you, usually by sidestepping the established hiring process entirely and instead sending a value-packed pitch directly to the decision makers you want to impress. Even better, you can proactively identify a problem that the company is having and solve it for free—before they even know who you are. This can be a great way to distinguish yourself from hundreds of other applicants.

You can strategically break rules once you’ve already got clients, too. Your ultimate objective as a freelancer is to make your clients happy, because that’s what enables them to make you happy by paying you and, hopefully, by referring other clients to you. You make clients happy by solving their problems, so if the best way to solve a problem is by tactfully sidestepping an obstacle, then do that. Once in a while, a client will chide you for doing this, but most will greatly appreciate your willingness to take action and get things done.

I have a client who once needed a lot of graphic design to go with an article that I was writing for them. They needed to make a spreadsheet with a few hundred rows of data that they could then use to make infographics, but they didn’t have anyone in-house to collate all the data. All of the senior people were too overloaded with their own tasks to do it themselves, and they couldn’t pay me to do it because I have a flat-rate agreement with them and they couldn’t pay me more for extra work outside my normal scope.

This problem brought the article to a halt for a few days, at which point I decided to take action. I paid my assistant to collate the needed data and sent it over to the client. I didn’t ask them for permission, I just did it, and I didn’t charge them for it. It cost me $90 to pay my assistant to do it, so yes, I “lost” $90 on that particular assignment—but it got the project moving again and scored me major points with the client. Essentially, the $90 was an investment in my relationship with that client, who is now even more likely to give me additional work and to refer me to their colleagues.

You’re Ready to Get Started!

There’s so much more to say about how to launch your freelancing career, but these thirteen strategies should be enough to get you moving in the right direction. If you’re interested in coaching (either writing coaching or general freelance coaching), feel free to email me or visit my website.

Finally, I highly recommend the following five books. You should be able to read all of them in about twenty hours. Each one is densely packed with powerful tips and strategies, and if you put them to work in your freelancing career, you’ll be off to a great start.