From Entrepreneurial Disasters to Grocery Store Glory
Welcome to another episode where we prove that terrible teenage jobs actually shape you into a functioning adult. This week: Jacqueline's running disaster, Ryan's travel chaos, and a comprehensive ranking of every Ajax teenager's employment nightmare from 1998-2002.
00:00 - 03:30: Fake Smile Science & Our Ideal Audience
Ryan discovers that fake smiling doesn't work when you check yourself in the mirror - turns out his "biggest smile ever" looks like a straight line across his face. Meanwhile, they establish that their ideal podcast audience is literally just themselves sitting in a conference room listening to themselves.
Key Quote: "What if all 12 of those people are you and you're the only person listening to your podcast?"
03:30 - 09:00: The "How Hard Could It Be?" Brain Disease
Jacqueline reveals her latest victim status: trail running. Despite never running in her entire life, she went from zero to five-mile runs at nine-minute pace in one month because "how hard could it be?"
The Damage Report:- Tore a tendon in her ankle- Made it worse by "stretching" it with a tennis ball daily- Now trapped in a walking boot in 100-degree weather- Surrounded by hundreds of dollars of unused running gear
The Gear Confession: When Ryan correctly predicts she bought all the equipment first (Hoka shoes, running pack, outfits, the works), her response: "I am furious that you know me that well."
09:00 - 16:30: Ryan's Travel Disaster Continues
Classic Porter family vacation chaos: flights canceled, hotels lost, arriving at 2 AM missing the entire point of the trip (a fireworks festival). The highlight: Ryan's family group text game called "Guess What Flight We're On" featuring a departures board where every flight is on time except one that says "CANCELED."
Travel Philosophy Update: When Ryan was single, canceled flights meant impromptu adventures. Now with kids, it's just expensive chaos and missed ice cream for breakfast.
16:30 - 25:00: Childhood Chores & Jonathan's Birthday Party Fact-Check
Worst Chore: Dog dirt pickup (Ryan and Dan's exclusive domain while Jacqueline got feminist exemption) Best Chore: Ryan loved cleaning the garage to read 1970s trucking magazines; Jacqueline organized cassette tapes (even though none matched their cases)
Jonathan's Birthday Party UPDATE: After fact-checking with Jonathan himself:
It was his 12th birthday (not 6 or 7)
Taylor the boxer-rottweiler ate cake/pizza and vomited during the party
Dad built a "shrine" over the vomit with a dustpan and pizza box
The movie was Alfred Hitchcock's The Birds (black and white)
Kids ended up lifting weights in the basement
One kid declared it "the worst birthday party ever"
25:00 - 31:15: Technology Generation Gap
Jacqueline's quest to buy her daughter a camcorder leads to a Target employee who genuinely doesn't know what a camcorder is. After taking over the employee's phone and finding the product herself, Jacqueline jokes: "I work at Target now. If anybody has questions about camcorders in 2025, send them my way."
The Irony: Their kids want cassette players and camcorders while having phones that do everything better.
31:15 - 48:15: THE TEEN JOB TIER LIST
C-TIER: Entrepreneurial Disasters & Babysitting Nightmares
Ryan's "Dependable Neighborhood Kid" Empire:
Complete business plan with mom at kitchen table
Two paying customers: Auntie Gale ($25) and parents (negotiated down to $10)
Cost Auntie Gale ~$100 per lawn cut when you factor in snacks and hospitality
The Failed Fish Stand: Ryan and Dan's brilliant plan to compete with Food City by selling live fish from Crothers Creek. Caught fish all day, put them in a kiddie pool overnight, woke up to find them all dead, then dumped the corpses back in the creek.
Babysitting Horror Stories:
Jacqueline's career ended when a family "forgot" to mention they all had lice
Ryan's refusal to wipe an 8-year-old's butt while the kid maintained downward dog position for 15 minutes
The great baby escape incident where Ryan fell asleep and a toddler walked across the street
48:15 - 1:09:10: B-TIER: Grocery Store Legends
The Porter siblings dominated Ajax grocery stores, working at competing chains and literally getting into fist fights over which store had better prices.
Jacqueline's Loblaws Deli Disasters (3 years):
Lost fingertips in meat packages while slicing deli meat
Got demoted to scaling fish (badly)
Eventually told customers the deli was closed early so she could eat leftover chicken wings
Worked for "the scariest woman I've ever met" named Gina
Ryan's No Frills Empire (6 years, age 15-21):
The Hidden Camera War: Original owner installed illegal surveillance disguised as motion detectors. Ryan retaliated by going through his desk and finding video cassettes labeled with employees' break times.
The "Feasts": Every department contributed stolen food to massive break room meals.
Pat the "Doctor of Philosophy": Coworker who declared himself a doctor of philosophy, then immediately sliced his hand open with a box cutter trying to cut chicken. Got 22 stitches.
Janice's Birthday Cake Tragedy: Pat ate an elderly coworker's 80th birthday cake, then filled the container with Coke. They watched Janice cry as other employees tried to console her with a replacement cake from the bakery.
The Frozen Salmon Prank: Put a whole salmon above ceiling tiles in the women's changing room, forgot about it for a month until it decomposed and made the entire second floor uninhabitable.
The $2,000 Traveler's Check Adventure: On Ryan's last day, he borrowed $2,000 from the store safe to show Japanese immigration he had travel funds, got stranded downtown when the family van died, and barely made it back before they thought he'd stolen the money.
1:09:10 - 1:16:10: A-TIER: The Good Stuff
Mall retail (with employee discounts)
Video stores
Pet stores (Ryan's friend got to hang out with iguanas and birds)
Electronics stores with tax-off discounts at Best Buy/Future Shop
The Bank Marriage Proposal Incident: Ryan's dad randomly walked into a bank where Ryan's old friend worked (she was engaged) and told her he and mom "would be more than happy to welcome her into the family if they got married." Dad waited in line with actual customers just to deliver this message.
1:16:10 - 1:21:20: S-TIER: The Holy Grail
Movie theater employee (Jacqueline still wants this job)
Amusement park lifeguard (Canada's Wonderland, Wild Water Kingdom)
Jacqueline's Office Job Glory: Worked 4-8 PM answering phones at a renovation company, spent entire time on instant messenger. The twist: her music was accidentally the hold music for clients. Keith Has Teeth (her nickname system for identical twin bosses) eventually told her to stop playing inappropriate music for customers on hold.
Ryan's Welding Reality Check: Thought he was destined to be a welder after one good bead, until Superman (the dad from his babysitting disaster) showed him his completely shredded hand and said "If I don't need a Band-Aid, you don't."
1:21:20 - 1:30:00: Why These Jobs Actually Mattered
The Real Lessons: These weren't just jobs - they were world-expanding experiences. Working with people from different backgrounds, ages, and life situations instantly broadened their perspective beyond small-town Ajax.
Jacqueline's Take: The adults she worked with became trusted advisors during teenage years - people who could give advice without parental baggage.
Ryan's Philosophy: "You meet that one person who has a completely different life than you... those things help shape you as a teenager trying to wade your way into life."
The Independence Factor: These were their first truly independent experiences where parents couldn't intervene once they walked through those doors.
1:30:00 - End: Unhinged Text of the Week
From their sibling group chat about Ryan's permanent residence application. After requesting everyone's addresses, Jacqueline immediately responded, but Ryan then specifically asked for Jonathan and Dallin's addresses "for sure," leading to hurt feelings about her "inferior American address."
The Reality: Ryan actually knew Jacqueline's address but had no idea where Jonathan (recently moved) and Dallin (Vancouver apartment hopper) currently lived.
International Chaos: They all live in different countries with different address formats, making Christmas cards "the worst."
Episode Takeaway: Every teenager needs at least one terrible customer-facing job. Not for character building, but for world expanding. Plus you'll have stories for life about decomposing salmon and awkward parental marriage proposals.
