I got my first job out of school back in 1998. I was responsible for building and maintaining a website for a Hamilton-based magazine publisher. Less than three months into it, the publisher fired me: we appeared to have fundamental differences of opinion on what my job actually was. I thought it was a technical and editorial position, while he thought I should be selling ads and building business partnerships.

A year later, I was hired by a securities firm in Toronto as part of a team building a new intranet (remember those?). I had just gotten engaged with the amazing Erin Thomas, and we had rented an apartment together in town, in advance of our wedding in September 2000.

Three weeks before our wedding, my entire team was laid off in an internal management war that my side apparently lost.

Months later, I had a new job, with Compaq Canada. I was a content producer for compaq.ca. There were good years there. And then HP and Compaq merged (or something). I managed to survive the initial layoffs, but then three or four rounds later, in 2006, they got me.

I was sensing a pattern here. When you get hired by a company, you are building a relationship with the employer that’s founded on loyalty. That’s the theory, anyway. In practice, at best you’re a cost centre that needs to be justified. At worst, you’re a pawn in a game you have no control over.

The part of the story I’ve left out in each vignette above is the after effect. Losing your job is fucking hard. As an employee, living paycheque to paycheque, having that flow cut off is like having your world torn away. Each of those periods were devastating pain points in my life.

My solution was to incorporate my own business. After all, I can’t fire myself.

My business is contracting: from then on, I was selling my services to companies. They can fire me, not renew my contract, go out of business, or just fall off the face of the earth, and it’s not a disaster; it’s just a part of my business’ life cycle.

Contracting is not for everyone. Sometimes it’s not even for me. There are definitely pros and cons. Let’s look at The Ugly first:


  • You should incorporate your business. It’s a great idea for protecting yourself from liability, and taking advantage of the special privileges that corporations enjoy with your local tax agencies. But it’s annoying and expensive.
  • You need to supply your own benefits to replace those an employer might provide. I went through my local Chamber of Commerce.
  • You need to hire an accountant at the very least, and perhaps a lawyer too (I’ve avoided the latter thus far). Make sure you hire a good one, though. I had a bad one, and I got fucked so hard that my grandchildren are going to feel it. That’s another story.
  • You can never rest. If you’re currently employed in a contract, things might be going great, but that other shoe is going to drop at any moment. Diversify your income as much as possible in order to survive that shoe.

It’s not all bad news, though.


  • Freedom. Oh by the Beard of Zeus I love the freedom. A job is a commitment to work when and where the boss tells you to work. A contractor can work from anywhere and anytime she likes. Its the work product that matters, not the time spent in a chair.
  • Income. Whenever I test the J-O-B job market, I find the salaries disappointing compared to the revenues I pull in my average year. To be sure, an employer is also providing benefits with that salary. And I have to pay myself out of that revenue, along with benefits and payroll taxes. But I have more levers to pull to control what I make, than I would as an employee.
  • Diversity of work. It’s pretty hard to get bored with your work when you contribute to multiple jobs a year. 2014 was crazy: I did work on things as diverse as a hockey app, a trade show app using iBeacons, an internal business tool with some significant PDF involvement, and a few more. You learn a lot of different skills; the number of clubs in your bag multiply faster when you contract.

I hear there are regular jobs that have some of the pros I list here: they accept remote workers, pay them well, and give them varying responsibilities. But they’re pretty darn rare, and I’ll never believe they won’t unload me at some point of their own choosing.

As I write this, I’m just coming off a contract that ended with the suddenness of a balloon popping (the curious can always keep track of my current state through my Now Page.). I’ve fielded contacts with opportunities that include those looking to hire full-time employees, and those looking for freelancers. It seems, as usual, that the former are more plentiful.

And while some of these full-time jobs look really interesting, I have to take a deep breath and remember why I’m here.