In the Four Hour Workweek, Tim Ferris talks about his simple, yet unconventional strategies for winning the Chinese National Kickboxing championship with relatively little kickboxing experience. How knowing the finer points of the rules and focusing on their weaknesses led him to win first prize in the tournament, simultaneously pissing off the whole of China. My mom was doing this Four Hour Workweek stuff — using existing rules and structures to her advantage, outsourcing her workload — before Tim Ferris joined his Highschool wrestling team. Back when he was still wearing tighty whities and Spiderman pajamas.

When my little sister and I were in grade school, my mom had an unusual hobby. She had a regular job, 9 to 5, like other working moms. But after the dinner plates were cleared, she would set out  her envelopes and folders on the dining room table, filled to the brim with UPCs and entry forms, and she would sit down to “do her contests”.

Mom had refined it into quite a system. On the weekend, the four of us (dad, mom, sister and I) would pile into the old minivan and go the grocery store. Back in the early 90s, if you looked, you could find dozens of contests in just one trip to the supermarket. Mom would stop at every little cardboard display, pull off one of the ballot forms, and stand there for a few minutes reading and scrutinizing the rules on the back. If the rules said one entry per person, she would take 4: one for each family member. If it said one entry per person, per day, she would take half the ballot stack. If the rules didn’t say anything about entry limits, she would rip ten ballots off the top, leave those on the counter for other people, and then take the whole rest of the stack. I remember she had this giant, black purse that she would stuff everything into.

Then we get to the outsourcing bit. Tim Ferris had India. My mom had my sister and I. To save her work and time, my mom would have us help fill out the contest entry forms. “Contest Time!” she would yell, smiling. It was fun for us, because it meant that soon more random prizes would be coming in the mail. Then the next week at the supermarket,  she would drop off the entry forms we had all filled out (the ones that didn’t need to be mailed) into the boxes, all the while scouting for new contests.

In her contest heyday, my Mom won over $30,000 dollars worth of goods. Every other week we would get a phone call or a letter in the mail saying someone in our family had won something. My eight year old sister won a set of winter tires for the car. I won a new barbecue. My dad won $500 worth of camping equipment and a 21 foot canoe. A few months later my mom won yet another canoe – a beautiful 19 foot Labat blue canoe — in a draw at the liquor store.  We literally had to reorganize storage spaces in our house to make room for the prizes. There was always a package for us at the post office: Walkmans, Rollerblades, cameras, giant stuffed animals… and my favorite at the time, a Sega Genesis and Sega CD gaming system (that’s right, Sega’s unsuccessful precursor to the Sega Saturn – that’s probably why they were giving them away…). Then there were the gift certificate prizes: $400 worth of CDs, a $1000 travel certificate from CAA, $1200 worth of groceries, mall gift cards, movie passes and concert tickets. She once won a computer backup device and traded it to a friend for 400 shares in his startup company and a few years later sold the shares for $2000.

Then there were the travel prizes. When I was 14, Mom won a week-long trip for two to New York and a stay at the famed (and absurdly expensive) Waldorf Astoria hotel. Mom and Dad planned to go alone but my sister complained so much that they ended up buying us plane tickets and taking us with them. My mom would always make the joke that we were like the Clampetts from the Beverly Hillbillies, heading to the big city. I don’t think it was too far off. We had to buy new clothes just to walk around in the hotel. In New York, we did all the typical touristy stuff: we toured around central park on a horse and buggy (I remember my little sister yelling “that man is peeing! Right on the street, he’s peeing!”); Dad and I went in a stretch limosine to a New York Rangers hockey game to see Marc Messier play; and Mom and my sister bought tickets to see Cats on Broadway – but my sister threw up in the cab ride there so they went back to the hotel.

Then when I was 16, Mom struck big again and won an all inclusive 10-day trip for four to Ireland. The prize included a vehicle rental (the appropriately named Ford Picnic: probably because it you could drive it through a park without tearing up a single blade of grass or waking up any old people) and prearranged stays for us at B&Bs all around Ireland. We had a great time — although I’m sure my parents were about to kill my sister and I by the end of it, with all of our bickering in the back seat. I remember coming back to Canada and excitedly taking my four rolls of film in to be developed, only to realize I had taken a hundred pictures consisting entirely of green rolling hills, farmers fields, winding roads and sheep.

It’s funny how when you’re a kid, you think that everything that happens to you is so normal and happens to everyone. I realize now how cool my mom’s hobby was and how it instilled in me a sense of adventure and appreciation for seeing the world. Nowadays, Mom doesn’t enter as many contests. She still wins an Ipod here, a digital camera there. With the Internet making contests easier to automate (“bot” computer programs, etc) it’s gotten a lot tougher to win, and my mom has other cool hobbies to keep her busy (like her book club). In fact, as I was just “fact-checking” (reminiscing) this post with her on the phone, she told me she just won a $100 West Jet gift certificate this week. (And in case she reads this) I’m still waiting for the day that she calls me saying she’s won me a 2008 BMW GS… Although I guess I’d settle for a Harley.