So I''m writing this guest entry to solicit some of your best..and when you were growing up. A guy I went to university with was so broke he participated in those pharmaceuitcal testing weekends. He was paid handsomely, but sprouted a tail about 2 years later. Good for balance, bad for meeting girls.

Here are some of my early gigs with some positives and negatives.

+ Free hot dog and coke at 9th hole
- Lining up along a wall at 6am to get selected by old white a slave auction

+ Little kid allowed to swing axe at stuff - what's not to like?
- The pay was an ice cream cone

Newspaper delivery boy
+ Independence
- 5am wake up to start prepping papers / collecting - some pricks would dodge paying by saying they didn't receive their paper

McDonald's - Quarter Pounder grill
+ Made my own (free) big macs with 4 or 5 patties and a hundred pickles on it
- You are coated by grease and smell like meat... all the time.
Bonus fact! I once had to dress up as The Professor character and along with others like Grimace and Mayor McCheese, I was sent outside to greet kids, none of whom had ever heard of The Professor character

Coat check at Royal York Hotel
+ Easiest fucking money ever
- 8am Saturday morning shifts after Friday night fraternity parties
Bonus fact! One older guy who worked there wanted to watch me have sex with his wife

Security Guard
+ Look tough in uniform
- Was told once to go look for a crazy hobo who was somewhere on the 10th floor of a darkened office building...who was armed with an 8 inch screwdriver

Private Investigator
+Lived at a hotel in Ottawa for a summer, fantastic dough, killed many
- If people knew who I really was, could have been many

Retail sampler
+Met lots of chicks
- Standing all the time, pretending to give a shit about the product

Pizza delivery
+Free pies
-Giant risk of being shanked delivering to rathole apartment buildings

+Working outside in the summer
- Hard bloody the summer

Hobo Gauntlet Radio Episode 6 is now online for streaming or download. These 1 hour shows include a bit of commentary, but I mainly spin some of my favourite alternative tunes that span the decades. Episode 6 features Tones on Tail, Lemon Jelly, The Pogues, James, The Propellerheads and more. Get the link at my blog at or directly at

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Al The Royal Pain

Packing Celery In The Holland Marsh - 2 summers
+ The life lessons learned as a 9 year-old working with Jamaican immigrant workers (who were only making $1.50/hour more than me) (they had lot's of kids from lots of different girlfriends/wives)
- Celery's a thing

Delivering The Toronto Star - 1 summer
+ nothing
- Same as @Ryan G.

Delivering The Sears Catalogue - Once
+ nothing
- Getting $0.09 per catalogue delivered and my mom spending way more than that on gas driving me around to deliver them because they were too bulky and heavy to deliver on my own

Grocery Bag/Stock boy - 4 years
+ flirting with the checkout girls
- Working for a crazy (possibly made) Italian owner

Pizza Delivery - 7 years off and on
+ Driving everywhere (I was 16)
- It took me at least 20 years to enjoy pizza again
Bonus - Losing all my tip money playing poker at 3am with the owner and other drivers after a shift.

Clerk at a Beckers - 2 Days
+ I got addicted to scratch and win tickets
- I didn't last long at this job (due to the above)

Direct Energy Sales Guy - 2 weeks
+ This is when I learned that I was not cut out for sales
- I was the annoying person who tried to get you to commit to a contract on your heating bill

Assistant Manager Little Caesar's - 4 years
+ I was 18 when they offered to give me my own store to manage...I looked at my manager who and flashed forward to what my life would be like in 20 years...then promptly said no.
- It took me at least 20 years to enjoy pizza again

February 19, 2015 @ 3:05 PM

Toronto Mike Verified as the defacto Toronto Mike

Game booth manager at the CNE
+ being around the Ex for 20 days in the summer
- it was seasonal

+ hmmmm... that's a tough one
- low paying, short shitty shifts

Grocery Clerk
+ having fun with the other grocery guys, nice long shifts, decent money
- working the overnight audits

February 19, 2015 @ 3:14 PM


Worked as a Drug Store clerk while in high school, lotsa fun selling condoms to all the young beauties coming in. Interesting time.

Worked at a charcoal factory up north one summer. Tough job, but great fun and a load of beer.
Taught me all about hard labour.

February 19, 2015 @ 4:02 PM


McDonalds Kitchen
+ learned a lot about how a well structured environment can make a difference
- the smell of Big Mac sauce used to get ingrained in my hands and I never eat one again because of that

Golf Course maintenance
+ free golf
+ spending my days on a mower
- the smell of rotting onions from the Holland Marsh
- almost got electrocuted while digging up a sand trap

I had a temp job that basically involved unboxing and throwing out old merchandise that was returned from stores to a company's warehouse.
+ they paid me
- so boring
- cheesy canned music being played in warehouse
- since it was a temp job, they fired everyone when they didn't think people were doing a good enough job, then they hired me back two days later. That was awkward.

Server - East Side Marios
+ fun people to work with, good social life
+ decent discount on food
- unlimited salad and bread (people don't really think about the extra effort that means for a server
- I was working in a small town and you literally knew the day that people got their unemployment cheques.

February 19, 2015 @ 4:02 PM


Waiter/bartender (late teens, early 20s)
+amazing pay for that age
+beautiful people everywhere
+cheap quality food
=server life is totally fucking different from normal life. Not necessarily better or worse.
-exposed to horrible horrible people/"guests" we have to share society with
-hours didn't match my friends' schedules
-ridiculously late hours
-potential for terrible shifts
-not something I wanted to make a career out of

I really loved it overall, but didn't want to make a career out of it.

February 19, 2015 @ 6:11 PM


Wonderland......very social even I picked up what a blast

Waiter.....too true about very nasty people but also fantastic fun at times. I miss Christmas tips., underpaid ,difficult, best, job I ever had. Hanging with the crew ,trying to sleep with waitresses. Drinking until daybreak and working the brunch...stealing steak for dinner

What I do now..... Caretaker...great benefits govt job blah toilets sweeping floors so effing boring

February 19, 2015 @ 6:17 PM


Stock Broker

- made some tailor rich
- loved the stock market
- hated the work environment (old boys club)
- Met a bike courier at Sneaky Dee's? and decided I'd..become..a.

Bike Courier

- allowed to have my hair in dreads
- fairly decent money at the time
- "cool factor"
- learned to master the art of riding a bike
- always get a good nights sleep or the day is long.
- it hurts to get hit.


- can speak fluent "CB Radio"
- long hours but great freedom
- how to get fat in 90 days.

- 3rd party contractor
- I was not permitted to discuss anything I saw to anyone
- I was not permitted to list that I was "employed".
- Some things cannot be unseen.

Paper Delivery Guy

- 2006ish. Became self employed & needed the cash flow
- Delivered newspapers in the "hood" of downtown Kitchener
- Returned to my car around 4 AM to find a topless street prostitute sitting in the front seat "hiding" from some thugs.
- Met a single mom with 2 kids (in the car) who delivered papers to "buy diapers"
- Met an entire Indian family that delivered newspapers (their kids included) to "pay the bills".
- Above to examples made me realize my life was pretty good.

Self Employment:

- good times, bad times you know I've had my share.
- keep at least 40K in cash at all times
- unable to define "vacation". ever
- worked on average 357 days a year, taking only stats off
- final four months, averaged 300 hours billing each month.
- the CRA, ah the CRA (I was incorporated)
- Get a GOOD accountant.
- Don't buy a BMW
- Learn to say NO.
- It's not a job. It's a lifestyle and you live it.

February 19, 2015 @ 7:01 PM


babysitter for semi-well known politician at the time
+ super nice people
+ always left me $ to do stuff with their one beloved kid
- just wanted to hang with my friends all summer

carpet cleaning sales over the phone from a guys basement
- guy was whacking off and watching dr who while I sat in the same room
- told my mom - that was my last day (maybe two weeks into the job)

office cleaner
- office dwellers are pigs

factory worker making travelling toothbrushes
+ loved this job on the night shift
+ my poor mom brought my lunch every night at 2:30 and I sat in the car with her and ate
+ loved the money at the time (summer job) I think it was $4.50/hour
- my boss was called hammer head herb and he was about 100 years old. fixed everything with a hammer. told us to put our hands into areas marked "do not put your hands past this mark"

current job - office dweller
+ great pay
- mostly terrible people
- mind numbing boringness

February 19, 2015 @ 7:21 PM

Al The Royal Pain

This thread is some enjoyable reading!

February 19, 2015 @ 8:10 PM

this guest

'selling condoms to the young beauties'
love it
that sounds like a song Speysidephil.

took a job in a bakery once
early 20s
started at 4 AM - had to get up at 2:00
nobody would speak English
Even when giving me directions on what to do.
a 3 day career then I packed it in.

February 19, 2015 @ 11:49 PM


Highschool Caretaker
+ Great people to work with
- This was a summer job so discovered treasures some students left in their lockers (old lunches, dirty gym clothes, garbage... all of which sat for a couple of weeks in a hot unair-conditioned building)

Worked Reception (small town police department)
+ Hilarious calls from lonely seniors (a lady trapped a neighbour's hamster under a laundry basket in her driveway and wanted police to deal with it)
- Very few phone calls overall

+ Meeting a wide variety of people
+ Making people of all ages happy
- Pay was unpredictable (could play for an afternoon and make anywhere from $5 to $30 an hour)

February 20, 2015 @ 9:07 AM


Woolworth's lunch counter - I lasted 3 days. Got tired of the dirty old men and the blisters on my feet.

The Bay - selling teen fashions - I was so useless as a salesperson they put me in the change room handing out the numbers. Then they got wind of the fact that I was giving my honest opinion when the customers asked how they looked. Mysteriously, my hours were cut to zero ;-)

February 20, 2015 @ 10:50 AM


All my jobs while still going to school.

First job- delivering newspapers by boat and mini bike around Lower Buckhorn Lake from my parents cottage. Lots of fun, but had a few wipeouts on the bike and remember one time my buddy in front of boat and he was holding a stack of papers and I turned to sharp and he went flying out of boat into the water.
Delivering Swiss Chalet Chicken from Bloor and Prince Edward Outlet.
Huge delivery area from this store. Went from 401 in the north to Dufferin in the east to Lake in south and 427 in west. Meet some interesting dudes who were fellow drivers . A lot of guys who were doing two or three jobs . Had some weird deliveries to people like the lady above a store on Roncesvalles who I walked up stairs to her apartment and she answered the door totally nude and she was so stoned she started to put her hands into pockets that weren't there , looking for money. When I got back down to street she was half hanging out window yelling at me. Also delivering to West lodge Ontario housing apartments at midnight got a little intimidating. Thought I was going to get rolled on more than one occasion. Weird how the people who could least afford to tip you gave you the biggest tips. Another guy I delivered to had a walk down apartment and it was totally dark with not a single light on. Well the guy had some terrible deformity on his face and he was also blind , so no need for any lights. He was a nice person who was just dealt a crappy hand in life. Going there the first time was kind of spooky. Some of the other people I delivered to were Gordon Sinclair- Sam Shopiwitz- Ronnie Hawkins- Borje Salming- Leon McQuay.

Working the B.P. gas station and car wash at South Kingsway and Queensway was a bit of an eye opener. Saw some crazy accidents with people driving right through the car wash and crashing into the washing equipment or flying through till they hit the big dryer at the end and cracking their windshields. The way that the company controlled the money coming into the car wash was to use a wand that swung over when a car would be taken through the car wash on the moving rollers.Then the car counter was supposed to match what you had in cash or tickets. Well some of the employee's would just tape the wand back on a busy winter day and pocketed some major cabbage. I could never figure out how they never got caught.

February 21, 2015 @ 7:17 AM


This is great...

Delivered Brampton Guardian
+ Earned spending money for Grade 8 trip to Ottawa
- very cold in winter
- collecting money from people who never had it and always wanted you to come back later

Opening summer Sunshine Beach (now Wild Water Kingdom)
+ awesome tan
+ worked with friends and met some great new ones
- not so bad bus ride or long bike ride
- rain days mean no-pay-days (lots of rain in July 1986)

+ great store discount
+ learned a lot about good customer service
+ my direct manager was John Eaton
+ good and consistent hours even through university years
- I actually can't think of anything that was a negative to this job..

Customer Service Drug Distribution Centre (3 summers)
+ 9-5 summer hours to be able to have half decent social life
+ good discount
- the summer when smoking was still allowed at the desk I inhaled at least a pack a day
- known as the Master Stapler. I went through 36,000 staples in first summer.

Promotional Products Company
+ two of my best friends today are from that job
+ consider the owners to be my other parents
+ learned a lot about trials and tribulations of running all aspects of a small business
- small company didn't make quite as much money as other friends I had who got into bigger companies

Commodity Trading
+ it's what's given me a pretty good life today
+ not having a plan B makes things scary and exhilarating
- very hard on a marriage

February 21, 2015 @ 11:34 AM


I used to work for the Pop Shoppe and carry cases of pop to customers trunks, and wrangle the carts all for the kingly sum of $10.00 a day!

....also used to go door to door in a hospital and deliver newspapers to all of the sick part of that job was the Candy Stripers...worst part was delivery to the infection disease units :(


February 21, 2015 @ 1:05 PM

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