Anytime I talk about our family (and my past), I’m inevitably sized up financially by whoever I’m talking to. Nobody will come out and ask directly, mind you. They cleverly say things like, “Wow, that must get expensive,” or “Good thing your wife’s going to be a lawyer.”

Six kids. One mom in school. Two exes that receive support. “You must make a ton of money,” someone said to me when I was doing a photography gig in Toronto a few weeks back.

Finally. Somebody, somewhere had the guts to come right out and ask it. So here’s the truth – and it’s something anyone can benefit from, whether you’re blending a big family or growing a modest one.

It’s not how much you make. It’s how smart you spend.

First thing’s first, I make the sort of living that any professional with a two-decade-old practice makes. I work for myself as a copywriter, photographer and speaker. I’m constantly behind on my cashflow, but I’ve gotten good at shuffling this here and that there. It’s a good life and I work hard.

That said, there are still a lot of mouths to feed and backpacks to buy. So I’m smart about it. Here’s how…

I plan.

I spend a day a month asking the question – how much money will I need in six months. This question can be asked because I run a business. This way I can forecast how hard I’ll be working over the next few months to find new business.

Planning not only allows me to anticipate most expenses, it also means I can get the biggest discounts on things. Paying for summer camps months in advance nets me 10 per cent off with one group and 15 per cent off with another.

One more thing. Planning reduces ad hoc spending, which can get anyone into trouble. I go to the grocery store with a grocery list and I stick to that list. We throw out less food than any family I know. We also have a pretty manageable food budget.

I weigh time versus cost.

When I lived in a big city, I didn’t own a car. On days when I had to go somewhere, I’d ask the question, “What do I have more of, time or money?” That allowed me to know if I should grab the subway or jump into a cab. I use that same thinking today when it comes to whatever I buy. I could work another two hours today if I got us pizza for dinner. If I get all the kids $300 iPads, I won’t have to buy $1,200 computers later – and I’ve got a handy tutor (at less than the cost of a handy tutor). Big question, big savings.

I’ve come to love Value Village…

I have three girls and VV is fantastic for nearly, new clothes for all of them. The same goes for toys and books. In fact, we look forward to big sales like the library book sale, the sale rack at the grocery store and a whole lot more. I may not be dressing in the finest designer stuff, but I’ve created a good look for myself, in part, because I wait for 40 per cent off at the Gap and places just like that.

…and Kijiji.

At the same time, I’m a photographer and gadget blogger. This stuff can add up quick – unless you sell it at the right time. I upgrade constantly, but it doesn’t cost me $800 every time there’s a new iThing. I sell my old one and pay the difference. Because I don’t spend a lot on things like trips or a big car, I’m able to make this work with our lifestyle. It also helps that this attracts high technology clients! 

I keep trying to get better.

The idea of smart fiscal management wasn’t something that parents taught kids when I was a kid. I’m not great at it, but I continue to get better.

Here’s the important part, I’m starting to figure out how to impart this to my team. I’m encouraging the older ones to start small businesses in their teens. I talk about saving up for what you want with the younger ones. I create incentives for them and talk about savings. And I know that over time, I’ll get even better at all of this too.