Billing and Procrastination


I am so bad at actually tracking my time for billing purposes. Seriously – I’m currently living off of my Visa, for the sole reason that I haven’t billed my current contract since… DECEMBER. This is lame. Anyone can see the direct relationship between billing and getting paid, but for some reason I just want to spend my time ACTUALLY WORKING instead of playing ‘accounts receivable’.

I need to get better at this, pronto. Even writing this blog entry is just more procrastination. I think I’m much happier with a project manager, in a salaried position, where I know what I’m supposed to be working on every day. I miss knowing what my coworkers are doing, especially when that means that we don’t inadvertently duplicate each others’ work. But most of all, I miss not having to try to remember what I did last week, or the week before, or the month before that. Once again I’ve worked myself into a hole. *sigh*.


It doesn’t have to be big to start, it just has to be a start.

I met with my accountant yesterday, and he gave me some valuable insight into the financial aspects of my quest to remove myself from the office.

Another week is ending, and I still don’t have a signed contract with my new Evil Masters. I’m cautiously optimistic, but I’m sure glad I stuck to my guns and didn’t serve my two weeks’ a month ago like I wanted to. I made that mistake once before…

When I lived in Calgary, Alberta, I was working my dream job for a few months – I had been drafted from the customer service center of a large ISP straight into the R&D department! This was unbelievable luck, and I was on cloud nine, but unfortunately it was not meant to be – the manager of the department was notorious for challenging the status quo. This was actually a really good character trait for an R&D department, but it drove the CEO and the General Manager of the company batshit crazy, and eventually something snapped. Disciplinary action was taken; my manager was made the manager of customer service for two weeks, and the four R&D guys were scattered to the wind to work in other departments for those two weeks.

My new department was connection support – you know, the guys that answer the phone and talk you through your problems getting onto the internet. The guys that know long modem initialization strings by heart, and all the different versions of Winsock. The guys that work four days on, four days off, in twelve-hour chunks, clinging to their humanity.

As an additional kick in the teeth, the best four of the eight-man tech support team had recently quit, citing poor working conditions and pay, and had taken jobs at the other ISP in town for better hours and pay. There was a standing offer at this other ISP of a job for any of us, should we choose to jump ship, but I wanted to get back into R&D more than anything, so I stuck it out. Four techs became six, with myself and another of the R&D guys joining the team.

It wasn’t actually that bad – though the insidious part of the four-days-on, four-days-off working schedule is that sometimes your weekend is Monday through Thursday. There’s not much to do on a Monday night in Calgary, so you end up drinking in seedy bars with people of questionable reputation, and eventually that takes a toll. Soon the schedule included work nights, and my exemplary punctuality began to suffer – I overslept on several occasions, and started to become surly with customers.

Any tech insider will tell you that the average lifespan of a technical support phone worker is eighteen months – after this period, it’s likely that someone will get an earful when they call in with a simple problem, not realizing that they’re the forty-fifth person that day with the same stupid goddamned one-click solution, you moronic sonofabitch idiot luser motherfREAD THE GODDAMNED MANUAL @#RT(GEW!@#@$! AAAAAAAAAAGH!!! .

One day I came in late, and was met with a bad scene – apparently out of four techs scheduled “on” that day, only one had shown up on time, and the General Manager was pissed. She and I got in a little argument over it, with the culmination being her yelling back “You can’t even handle a simple tech support job, you’re never going back to R&D!”. That was enough for me, and I handed her my resignation letter thirty minutes later.

A friend of mine was working in the Network Operations Center over at the other ISP, and thought my resigning was great. He said, quote, “DUDE! Awesome! Send me your resume right away. You’ll be in tier one tech for a day, tier two for a day, tier three for… about a week, tier for for a week or two, and then we’ll promote you right into the NOC with me, it’ll be rad!”. That sounded pretty good to me. I sent over the resume.

I got called in for the interview immediately, and went the next day. They made me do an interview quiz, with a lot of winking and nudging, and said to expect interview number two in a few days. Lo and behold, interview two, three days later. Interview two was very similar, with a lot of “sorry to have to do this, we all know you’re hired, it’s just red tape…” apologies and smiles. After interview two, they said to expect interview three in a few days, with that interview being the meeting of the team and the serving of the official job offer.

Well, I waited.

…and waited.

After a week and a half, I pinged my friend, who said “Dude, I have no idea what’s going on, you’ve been greenlighted and they should be making an offer!”. So I waited.

After two and a half weeks, I started getting nervous – I didn’t have any money left (who has savings at age twenty-three?) and rent was coming up. Still no word.

Finally, at almost a month, word came down – the ISP had had a hiring freeze issued by their head office, and they were not to hire any new people for at least three months! This was a serious problem – we were already a collective of five people living in a two-bedroom apartment, just trying to make ends meet. It got pretty bad there for a while – to the point that to this day I make regular donations to the Food Bank. Eventually I found a new job, and took it at pay that was faaaaar below market rate, just happy to have a paycheque again.

I don’t regret any of that time – I made a few friends that I’ve held on to for the decade since, and learned a lot of tough lessons. The biggest one, however, was NEVER quit your job until you have the next one lined up and the papers signed!


I had a meeting with my accountant. We spoke at length about the move from being a regular salaried employee to being a contractor working from “home”. He told me that to be able to write off a home office, it would have to be a portion of my house used exclusively for working, and specifically for meeting clients. We’ll see, I think I can handle that.

The biggest take-away I got from the meeting, however, was that as a contractor I should have any funds from the new Evil Masters deposited into a separate chequeing account, and then pay myself (and any work-related expenses) out of that account. That way should the government choose to audit my income, they can pull the account transactions and will have a clear record of all income, where it came from and where it went. It would not be anywhere near as easy if the paycheques went into my regular chequeing account…

Revenue Canada: “So, uh, where’d this $100 come from?”

Me: “My Mom. Birthday cheque.”

RC: “You’re a contractor, this is your work bank account, we want to see the receipts for that…”

The accountant also said that it’d be important to get the bank to send over physical copies of all cheques written or deposited into the account. This will make it much easier come tax time.

Another thing that he said that I thought was interesting:

“Every time you start thinking about hours and billing and materials and such, forget about computers completely and pretend you’re a plumber. Everything you bring to the table is worth money on that invoice.”

Nice. Keeping that one.

I was really hoping for some outside-the-box magic bullets regarding taxation, but I wasn’t able to come up with any. He did make it clearer to me that I’m not so much starting a new job, but rather I’m starting to work for myself – and that helped me to make a big mental jump. If I’m working for myself, contracting to the new Evil Masters, I can also gather other contracts, both short and longer term, and begin to build up my own business as opposed to working to build someone else’s empire.

It doesn’t have to be big to start, it just has to be a start.

Anyhow, the new Evil Masters are still in negotiations with their client, from whom the money to pay for my services will flow. Apparently this client is a real ball-buster when it comes to service agreements, so they have to be verycareful with the wording of the contracts… and each change has a two-day turnaround with the lawyers. I haven’t given on them yet, and I haven’t served my notice – though I’m still watching Craigslist for other opportunities.