Moving is a stressful. If there's one thing that Joanne & Co. taught me it's that nesting is important, and even more so when you're an adult and you're moving your entire life around (as opposed to your sleeping bag for a month).
Things I did to make it less stressful:
Used Augusta Movers. They weren't the cheapest of the companies I surveyed, but the owner was super-responsive, it was very easy to set up, the team was punctual and hard-working, and they did a great job packing things up. They also stressed in every email that you have to pay HST even if you're paying cash, which I appreciate. At no point in the process were there any surprises, which is about the highest compliment you can pay to movers.
Ordered Frogboxes plastic boxes, as opposed to buying or scavenging cardboard ones. You're an adult now; you can do better going to the LCBO every day and getting Alberta Premium boxes. These things are clean, strong, convenient, water-repellent, and easy to move. You can put fragile things in them and not worry they'll be crushed, you can half-fill them and they'll still stack, and they make loading and unloading a breeze - they stack perfectly and uniformly. They'll end up costing a little more than cardboard boxes (~10% in my case), but not having to deal with the mess and cleanup of all that cardboard made it worth it in a second.