How much money do you need in order to live comfortably in Toronto?
URBAN PLANNER: A couple can be comfortable making $100,000.
LAWYER: That sounds low to me. I’d say $250,000.
URBAN PLANNER: That’s crazy. If you look at the stats on income, that’s actually in the top four or five per cent of how much people make here. That’s not anywhere near the middle.
HEADHUNTER: I was going to say $130,000 for combined, with comfortable meaning you can go out on the weekend for drinks, you can go out for dinner once a week, and the rest of the time you’re packing your lunch and not going overboard.
LAWYER: The reason I say $250,000 is that the real estate market is over the top, so if you want to buy a house and do a renovation, you’ve got to have resources. Every once in a while, I like picking up at a moment’s notice and taking a trip to New York or wherever, and not having to worry. That’s comfort to me.
DEVELOPER: I’d say $190,000. I like to go out for dinner—I don’t think I’ve been to a supermarket in five years—and I like to go to plays. I go out every night. But people can live comfortably on a combined salary of $80,000, depending on how they spend it.
SURGEON: The definition of middle class has changed significantly in the past 30 years. Even if you’re not making money—some of my friends are musicians and professional kayakers—you’re still expected to own toys that reflect money. Everyone’s got a laptop, everybody’s got an iPod, everyone I know travels. I mean, I’ve been to 70 countries. If you’re going to be a part of a certain level of society now, that’s what you have to do.

So how do people who don’t earn much pull that off?
SURGEON: Credit. To define yourself as middle class is a big abyss of grey. When I started as a surgical resident, I was making $40,000, but I had a $200,000 credit line. I live like I have a bigger salary since I know in a few months I’m going to be making $400,000.

Are you earning as much as you expected to make at this point in your life?
DEVELOPER: I fully expected to make my first million by 25. And at 25, I was still doing my master’s, so I amended that to 30, and now I’m 29 and realize it’s probably not going to happen. And I don’t know what to do. I’m kind of in this weird phase: how can I quickly make this million and meet my goal, because I can’t let myself fail twice in a row.
ENGINEER: Well, headhunters call me all the time, offering me more and more money, but for me it’s about quality of life, so I’d rather have my five weeks’ vacation than make oodles of money.
URBAN PLANNER: Absolutely.
CONSULTANT: You’re such a Gen Yer.
HEADHUNTER: Yeah, the Y generation rebels against companies because they saw their parents getting screwed by being so loyal, working so hard. So they don’t give a crap. If they want to work till five every day, that’s what they’re going to do. And they don’t care if they don’t get a promotion right away.
ENGINEER: A lot of my friends who chose the academic route, getting one degree after another, are in their mid-30s and just starting their careers. They’ve lost 15 years of earning power. But lately, with a lot of boomers retiring, I’ve been noticing a huge demographic shift. If you have the right credentials and happen to be in the right place, you can move up the ladder quickly. This is particularly true in government, where my friends who were pretty much poor in their 20s and 30s are now in senior management.
URBAN PLANNER: Something like 40 per cent of public sector workers are going to be eligible for retirement within the next five years, so there’s going to be a big exodus in government and a lot of opportunities. We’re already seeing the beginning of it.

What do you give to charity?
LAWYER: I try to give 10 per cent every year.
URBAN PLANNER: Hmm. It’s hard, don’t you find?
HEADHUNTER: I went to Africa last summer for two months to work, and I spent a lot of money to do that, buying school supplies and building a roof on a school. But really, let’s be honest, I got just as much out of it as the kids got. I give to charities in ways that either let me travel or do something I feel good about.

Have you ever made a purchase you regret?
DEVELOPER: I just bought a Jeep. It was $32,000 and kind of an impulse buy. I didn’t really research the car. I had actually ordered another car, a Toyota FJ Cruiser, and as I was doing the final test drive around the block just before making the pur­chase, I passed by a Jeep dealership and saw the Wrangler and realized the Cruiser had some considerable drawbacks: it took only premium gas, it was too big to fit in an underground garage. I said, “I don’t want this car anymore,” returned it, and went over and bought the Jeep.
HEADHUNTER: I go on binges—I won’t go into any stores for a month, then I’ll go crazy for a month. I buy things because it makes me feel good. I’ll say to myself: This looks great. I’ll love it when I lose weight and can fit into it. I find things in my closet with tags still on them after a year of having bought them. I got a pair of heels at Holt’s once, but I can’t wear them. They hurt my feet after just five minutes. They cost $220.
ENGINEER: I’ve been buying art and then realizing afterward I don’t like it. It’s an expensive habit, which is kind of dangerous. But I’ve learned to re-gift.
SURGEON: I travel so much now, and every time I have the itch to be in nature, it’s $500, $600 to get out of town for the weekend. I travel at the drop of a hat. If I have a bad day, I just literally go on Expedia. Or I’ll be invited to a party in San Francisco and think, What am I saving my money for anyway? We’re all going to die from global warming. And I just book it.
DEVELOPER: When I was in Palm Beach the other week, I bought a really ridiculous pair of shoes for $500. They’re slippers by Stubbs & Wooton that you can wear with jeans or even a tuxedo, but they look like slippers. Pope John Paul II had a pair! They’re the coolest. Mine have a big skull and crossbones on the front of them. You can only wear them in the summertime, so they’re sitting in my closet waiting, and I’ll probably never wear them.