Freelancing rules I've changed my mind about

It's been four years since I started working for myself and my thinking's shifted

Illustration: Léo Hamelin

On a Friday afternoon four years ago, roughly about this time, my freelancing journey began. In one 72-hour period, I lost my job and I made the decision to start working for myself as a solo writer.

The four years since have been a wild ride. In so many ways, I feel like I’ve finally hit my career stride. But I’ve also changed my mind about some of the “rules” of freelancing I thought I had to follow. 

I haven’t written a list in a while, so here’s a rundown of some of the key ways my thinking towards self-employment has shifted over the years. 

Simultaneous pitching

I used to think sending out a pitch to multiple editors at the same time was a big no-no. I reasoned that I myself used to be an editor and I would’ve been furious if I greenlit an idea only to then find that the freelancer had shopped it around it. I don’t think that anymore. 

For starters, when I was an editor I’d never been full-time freelance; I look back now and cringe at how that lack of understanding influenced how I worked with freelance writers for the worse. More than that, though, I’ve come to realise that while you should always be respectful to your clients, you need to put your own business interests first. Taken purely as a strategy, waiting to hear back about a pitch until you send it out again is not very effective. This is business, after all. 

It isn’t always good to meet

On aggregate, the majority of meetings and calls I’ve taken over the last four years have been a waste of my time. My default has been to think, “This might be a great opportunity!” or “It would be good to meet this person.” Indeed, it might be a great opportunity or good person to meet, but the problem is my parameters were always too vague and subjective. A good opportunity to do what exactly and, more importantly, for whom? I still haven’t got this licked yet, but recently I’ve been trying to formulate some kind of framework (a decision tree of sorts) to help me more accurately assess whether something actually is worth my time. 

Work wives aren’t just for complaining to 

Ok, this point isn’t something I’ve technically changed my mind about but rather whether my thinking has evolved. I’ve written before about work wives and how important they are for freelancers, but lately, I’ve taken some of those relationships to the next level. I’ve been working on creating a way to combine the best bits of working in a team with the independence of freelancing. The goal is to create a team infrastructure that benefits each person’s individual business. If that might sound a bit abstract, that’s because the project is still in its infancy but I’m convinced this is the future of my freelance business so watch this space.  

Runway over retainers

I used to think retainers were the holy grail of the freelance business model. Now don’t get me wrong, I definitely wouldn’t turn my nose up at an opportunity to write a regular column, but it’s no longer an active goal of mine. While they might guarantee work without having to cold pitch, retainers don’t necessarily guarantee income. The few times I’ve landed a retainer, it’s been on a rolling basis and when I lost them (which inevitably happened eventually), it was with no notice. Now I’m focusing on building a long runway*, a startup term for the amount of time a business has until it runs out of cash. It’s a different way of thinking about building wealth as a business and should also inform what kinds of projects I have taken on and when. 

*In my book, I call runway my “benefits package”; savings I use to cover a lack of income. This is different to my emergency fund, which covers unexpected bills; benefits package/runway gives you income when you don’t have it and an emergency fund covers unexpected costs.  

There are no rules 

I love order, plans and processes but I don’t really like rules. So why I thought I should follow them when it came to my freelancing is beyond me. Perhaps the biggest thing I’ve changed my mind about over these last four years is thinking that one day I would just “get really good at freelancing” and that would be it. Turns out, there is no freelance nirvana. It’s a journey seemingly with no known destination. That’s as frustrating as it is rewarding and to get there, rules will get broken.