Tell us about your best/worst job

I had such a good time last year with our Labor Day radio show on the best/worst job you ever had…

… that I think we should do it again.

  1. Listen Labor Day 2016: Your best/worst jobs

    September 5, 2016

So on Monday at 11 a.m., I’ll fill in for Tom Weber, open the phone lines, and explore the deep recesses of your limbic system to talk about your labors and what it taught you, if anything.

Like the “pickle guy” we had last year, who worked at a now-closed pickle plant in northern Minnesota, every job teaches us something, even if we only learn we don’t want that job. But some teach us about life. What job comes to mind for you?

It’s a Friday on a holiday weekend, so we might as well start the conversation now in the comments section below.

Meryl Cooper, for example, a PR type, writes that she learned good real-life lessons from really bad first jobs. She surveyed some acquaintances and found they did too.

Branding communications professional Jill Hamilton-Brice remembers back to her time as a nursing home aide—and specifically the lesson she learned on her worst possible day there. On Christmas Day, she spilled every last piece of pie. Horrified at what she’d done, she confessed her major screw-up to her boss. The two of them jumped into the car and drove all over town to buy up every last pie they could find in the few local corner stores that were actually open—all so that the residents could have a special meal instead of canned pudding.

She was so impressed that her boss cared so deeply to get this fixed, despite the fact that the residents, who suffered from dementia, would likely have not have noticed the difference between that pudding and pie. It underscored the importance of stepping up, acknowledging mistakes, and doing the right thing even when no one is looking.

I wish I could say some of that was my experience too. But it wasn’t. One of my first jobs was in a Dairy Queen franchise. I was “the boy” who worked in the back, slicing onions for the onion rings, making cole slaw, and sometimes whipped cream.

I didn’t do any cooking unless someone ordered spaghetti, in which case I’d pull spaghetti, cooked earlier, out of gallon jar, put it in a strainer, hold it under hot water, and then send it out front.

What did it teach me? Not to eat at the Dairy Queen in my hometown, which has now been demolished.

Let us commiserate and educate together below. And then give me a call on Monday and let’s talk.


  • Dave

    My first job was at a local resort up north. I would rake the beach of seaweed and dead fish, clean the fish-cleaning shack, collect the garbage (a lot of NASTY diapers) and haul it all in an old pickup to the local township dump in the woods………BEST JOB cuz I got to drive that pickup as my first vehicle……3 on the tree, starting on a upward slope, no hand-brake….and I was starting out in 3rd instead of 1st gear…..really taught me to dance my feet and be gentle with the clutch 🙂

  • jon

    Tech support for the fast food industry.

    I got to remotely connect and troubleshoot the POS systems (point of sales, but the acronym you were thinking of fits to.) Let me see first hand how the fast food industry worked… without having to go into them all that often.

    My boss there smelled of stale cigarettes to the point where you could smell when he entered the building (super gross, pretty sure he was going through a carton every couple of days, the storm drain in the parking lot clogged with his cigarette butts on more than one occasion)

    I got written up at that job once for when a general manager called in to report that one of his stores was having an issue, and asked us to call them fix it, and then call him back to let him know when it was done… I made the mistake of asking for his phone number, he insisted he gave it to the last person he talked to about this issue, I said the last person didn’t put it in the ticket, so if he could give it to me now I’d be able to call him once I did all the stuff the last person didn’t do (like contact the store and fix the problem). He reported me to the CEO of the company for it…

    Other fun things I learned from that job:
    Your credit card information isn’t protected at all once it goes into a computer (it’s supposed to be and there is a threat of massive fines for not protecting it, but that didn’t seem to matter at the time).
    Some fast food restaurants will make your burgers differently if you go through the drive thru, giving you 2 pickles instead of 3 with the understanding that people in the drive thru really don’t have time to stop and complain unless something is really screwed up.
    It’s not as important to actually be accomplishing something as it is to look like you are busy.
    When the CEO turns the heat off at night when he leaves the building, while there are still people working in that building for another 9-10 hours, is an OSHA violation (also those locking plastic covers for the thermostat are pretty easy to bypass with a bent paper clip).
    Never store a computer that has lived for years in a KFC in a confined space (like the trunk of your car) the smell of stale chicken grease takes months to go away, even after emptying an entire can of febreeze in there…

    But that set me up for every job I’ve had since… And taught me that labor laws aren’t without teeth when enough of your co-workers also report the violations…

    • Sam M

      Interesting perspective. Perspective and reality can sometimes be a little different.

    • >>Some fast food restaurants will make your burgers differently if you go through the drive thru, giving you 2 pickles instead of 3 with the understanding that people in the drive thru really don’t have time to stop and complain unless something is really screwed up.<>It’s not as important to actually be accomplishing something as it is to look like you are busy<<

      Truer words have never been spoken. Just carry a clipboard / folder / laptop and look like you are going somewhere and most won't even look at you twice…

      • jon

        Carry a clipboard, wear a lab coat, mutter to yourself and walk quickly…
        You quickly look to important, busy, and/or crazy to bother…


  • Annie Possis

    When I was in high school in the late ’70s, I had a job with a food broker, going to Minneapolis grocery stores dressed in a giant Mr. Peanut costume and handing out peanut samples to shoppers. Inevitably I’d talk to some little kid who would wail, “Mom! Mr. Peanut’s a girl!” My parents made me quit after three weeks because ‘it wasn’t dignified’…though I wouldn’t say I’ve ever actually BEEN that dignified. 🙂

  • Rob

    My first summer job was at a tree nursery. It was great to be outdoors every day, riding the water tank tractor around to water the trees, enjoying the scenery and the wildlife at the same time. Thanks to the workout of planting and digging up trees and bushes, pruning trees and cutting out snag with a chainsaw, I was in pretty good shape. Plus, I got to operate the tree spade, a piece of equipment used to dig up and transport larger trees to customer sites; totally cool. And to feel like I played a small part in helping to keep the planet green was mighty satisfying.

  • John

    Hmm. . . I’ve had some pretty good jobs, and some not that great jobs, but nothing at the end of the spectrum in either direction.

    As I cruise the internet, I see a fair number of “articles” (read clickbait) that promise stories of the worst jobs ever. Sometimes I click, and they sound awful.

    I wonder how common truly awful job experiences are, or if, like so many things, they’re the ones we hear about, because they’re interesting to us.

    I’ve learned about some unusual jobs over the years. Did you know “cricket farmer” is a real job? How about “pontoonist?” I haven’t done the former, but I worked at a summer camp one year during college. The camp was located on two islands, and my primary job (in addition to maintenance assistance and a few other things) was to haul supplies and kids’ luggage to/from the islands on my trusty pontoon boat. Probably only a couple hundred yards, but still tough in the dark on a northern MN lake. It was fun, physical, outdoor work – one where my introverted self (less so now than then) could be working with people all day, but still slip away to a quiet corner of the island in the evening to recharge.

    I hope I remember to listen in on Monday. This sounds like a fun conversation to be a fly on the wall for.

  • Gary F

    Tire warehouse worker. Unloaded semi-trucks full of car tires. As they rolled out of the truck I had to stack them in the proper stacks then put them away. Semi-truck tires were stacked ten high. You could only ask for help on numbers 8,9,10. Number seven sucked. Even though you wore gloves and long pants the black rubber wouldn’t wash out of your skin so your inside middle digits of your hands and thighs were black all summer.

    A good summer job for a 19 year old kid to learn that I need to make living with my mind and not my back.

  • First job: Bag boy for a local grocery store.

    Worst job (by far): Paper delivery as an adult. It. Just. Sucked.

    As an aside, I’ve never really had a truly horrific job (save for that paper delivery job). Most places have office politics and the odd irritation…

    • John

      I think paper delivery as a kid was my favorite job during that era of my life. (1-2 hours starting at or before 5AM, alone, freezing cold or nice out or raining or something in between for a 2-3 mile walk).

      I had two different routes when I was a kid. I never kept either for more than a year though. In small town MN, newspaper delivery was a 364 day a year job (I think there was no Christmas paper), and there were no substitutes – you had to find your own. So, I quit..

      It’s too bad, really. I don’t mind getting up early, and I enjoyed the work. (it paid more per hour than anything else I was doing at the time too – bonus). It just wasn’t possible for me to be on every day while managing school and my other 1-2 jobs. (newspaper paid well, but was only 1-2 hours a day, so I needed something more to put gas in my car).

      • I can see where a small route as a kid wouldn’t be so bad. As an adult with a larger route, it was just awful…

        • John

          It was good (though didn’t feel small – especially on Sunday when I had to go do 3-4 bundle drops before I would go out on foot with two bags slung across my back), unless it was -40 or there had been more than a foot of snow the night before. Those days I could live without.

          (long underwear, sweatpants, sweatshirt, snowmobile suit, hat, goggles and double mittens – I looked like Ralphy from “A Christmas Story.”)

  • lindblomeagles

    I’ve had several jobs and none of them were remotely what I wanted to do, which has taught me now in midlife to chase your dreams. Money is important, but, if you’re doing something you’re not thrilled about just to pay bills AND you’re not making a lot of money doing it, life gets pretty depressing quickly. My best experience at a job, college, spring, 1990. Both supervisors were absent due to a stomach virus, leaving me and two coworkers responsible for cleaning and stocking campus dishes after dinner, which just happened to be spare ribs and baked potato — two items you can’t toss into the sink’s disposal unit. My coworkers were worried. Real worried! We were supposed to be done by 7:00 p.m., and they had their studies to get too. I assumed lead, as a sophomore, over two seniors, directing one to stock and the other to get behind me as the dishes rolled in. From there I worked as fast and as hard as I could, clearing all those bones and potato skins so that my sidekick could get the dishes prepared for the washing machine. Not once, did I allow that conveyor belt to stop, and my sidekick picked up her intensity and followed suit. Just 3 people plowing away at incoming dishes without a word spoken. When we turned the machine off, it was 7:00. All the dishes were clean and stocked. It was a big moment for me. My first REAL command, Sadly, I decided to switch campus jobs the following year, and ironically, that dishwashing job was the last time I was in command of a workforce in my career.

  • dschille

    My first job ever. It was the only place I knew that would hire a 14 year old. I worked at Evergreen Industries in Inver Grove Heights. My entire job was to tie pine cones on the wreaths that Cub Scouts sell during the winter. Mind numbingly boring and I could never tie those cones on fast enough for “management”

    To this day the smell of pine is not pleasant

  • BReynolds33

    Worst job: I was hired to do hot tar roofing. My job was to haul 5 gallon buckets of tar, one in each hand, up an extension ladder, drop them off, walk to the other ladder, climb down, and grab two more buckets. Lather, rinse repeat for 8 hours.

    Required work attire: long sleeve, heavy cotton shirt (read: flannel) to protect my arms in case the tar splashed onto me. Jeans. Work boots. Hard hat. Gloves. In August.

    Why we couldn’t just pump the tar up, I never found out. I made it two and a half days, and left at lunch on the third day.

    Best job: It may sound cheesy, but it was working with my dad, painting houses. When we worked in new construction, I remember feeling like I was finally part of the club. The carpenters, the flooring guys, sheet rockers, electricians, the foul language, dirty jokes. As a teenager, it was like I had cracked the code, and had been accepted into the club of men.

    On older houses, repainting the outside, the memories are different. Sitting on the tailgate, eating a hot sandwich that was never meant to be hot, drinking a cold soda.

    Somewhere along the line, I learned how to work, too. And hard. But it was never about the work.

    • >>Worst job: I was hired to do hot tar roofing.<<

      THAT sounded awful…


  • Jon E.

    My worst job was working at the Mall of America at a store that has now closed. The people I worked with were awful. They had figured out a way to steal money on credit card receipts so that people were charged for what they bought, it showed up on their cards, but it never logged in the POS system. It would just look like lost inventory. Hundreds of dollars a day went missing.

    The first time I worked a closing shift, the guy I was closing with counted the register and handed me 100 dollars (a lot of money when I was 18) and I was so appalled, I gave it back.

    They also smoked in the back room (strictly forbidden) and there was even one time I walked into the back to get help-because I was on the floor by myself and swamped-and they were snorting coke off the desk.

    My best job was working opening shifts in grocery at a co-op. I worked 5:00AM-1:00PM and it was extremely hard work. Hauling 40 lb. boxes of produce for 8 hours a day and working in coolers is not for everyone but it gave me time to do all the things that I love in the afternoons. I loved being able to cook and ride my bike every day after work. It also taught me that a bike commute at 4:15 AM on the trails of Minneapolis is magical and I recommend it to everyone at least once. I left that job because it just didn’t pay enough to support me. If it had paid a living wage I think I’d still be there.

    • MarkUp

      //If it had paid a living wage I think I’d still be there.

      I know the feeling. I wonder how many people share that sentiment, and what the nature of the work was.

      • And then there are those who work JUST for the medical insurance benefits.


  • BJ

    I’ve had a lot of ‘jobs’ if you count babysitting and newspaper delivery.
    1. Sold Greeting Cards (the old back of comic ‘win a prize’, if they didn’t have a prize you got a buck per item sold) – 4th and 5th grade, banked some great money.
    2. Newspaper delivery, about 2 miles from home – had to bike it or took to long to get there, winter was hard biking on snow and ice (pre mountain bike days, narrow tire 10 speed).
    3. Babysitting
    4. Trophy Maker
    5. Burger King – cook/cashier
    6. Perkins Dishwasher
    7. Umpire (baseball park and rec leagues)
    8. Cart pusher at Grocery store (pre those electric pushing things – PS 100 carts gives you a heck of a leg workout)

    After High School
    9. Sold Vacuums door to door
    10. Radio Shack – Sales and then Manager
    11. Carlson Companies -Marketing support
    12. Video Store Manager
    13. Go Kart Track and Arcade Manager
    14. Support Scheduler
    15. Software Support Rep (Automotive recycling Inventory systems)
    16. Software Sales Rep (Same thing as above)
    17. Convenience Store Manger
    18. Auto body shop – Administrator
    19. US Census Bureau – census taker
    20. Software Developer (Political Campaign)
    21. Software Developer (Identity and Badge Creation)
    22. Software Developer (Accounting)
    23. Software Developer (Survey and Medical)

    I’m missing a few Dairy Queen shoot that was between 9-10.

    • BJ

      Learned a lot at every job.

      How to be a leader.

      How to make things look better than they are (it doesn’t have to be perfect, it just has to look that way).

      Most important one: You can, and should be able to be, replaced by someone else. Any business that a person can’t be replaced is a business that is doomed to fail.

    • BJ

      Best Jobs:

      Software Developer (Political Campaign) – Working with about 400 campaigns was pretty cool. I knew a lot of elected officials, people who are in the news. They called me for advise on getting elected and raising money. I was good at it.

      Cart pusher at Grocery store – Physical work, with lots of down time, could read a whole book during the shift and still get praised for good work. Legs never in better shape.

      Worst Jobs:
      Vacuum sales was straight commission, that wasn’t bad, but the gimmick was free carpet shampoo – my feet where wet all the time….

      Auto body shop – Administrator – Owner was a nut case and his daughter was the ‘boss’ except she was idiot, so my job was to keep Mr crazy from finding out about the idiot stuff his daughter did, plus doing what she was supposed to do. Very high stress, got yelled at all the time, Mr Crazy actually made me cry.

    • >>19. US Census Bureau – census taker<<

      Ha! I was a Crew Leader for the 1990 Census (Northern Hennepin County). That was actually pretty fun.

      • BJ

        I loved it as well, 2000 census. That job, being PTA president, and being Foreman on a jury shaped a lot of my polical views.

  • KTN

    Living in Crested Butte Colorado in the early 90’s working in the ski industry, I worked construction in the summer. One project was raising a house, built by, as the owner said, “hippies tripping on acid and drinking wine”, so there was some issues with the place. I was tasked with crawling under the house to dig with a hand shovel new footings. Not horrible, but kind of tight quarters – and then there was the hantavirus scare at the time. Hantavirus is transmitted by mice, and what’s under a house with no foundation – mice. Didn’t contract Hantavirus, but it did give me pause every time I crawled under the place.
    Best job – coaching ski racing in Crested Butte.

  • MarkUp

    Worst Job: I worked for a book distributor; they would order books in bulk for libraries and my job was to pull books from the bulk order shelves for individual orders. It was 8 hours of dead silence, listen to your headphones, and stick to the monotonous work. It was a test of mental fortitude every day. I was fired for talking too much (ask anyone who knows me; I’m one of the quietest people you’ll ever meet). An older family friend told me that was the best reason to get fired he had ever heard.

    Best Job: Working in a scene shop at college. Hands on work building sets, hanging lights, painting, making props, working with a team. So much of my college degree focused on abstract ideas that tangible work was a rewarding change of pace. I earned minimum wage, but took a lot of pride in what we produced. As college wore on, I would find any reason I could to spend more time in the shop.

    Today I work with a software development company and I volunteer at community theaters. I never figured out how to make a living off theater work, but if I could I’d change careers in a heartbeat.

  • David

    Almost Every single “family owned business” I’ve ever work at, and there has been a lot, has been absolutely horrible. There is nothing worse than being taken advantage of while your boss pretends to be your buddy. You learn fast what the meaning of the word nepotism is, and that you are better off looking for a different job then thinking you actually have a future with the company.

  • Greg Nixon

    Best job: Easy choice. Dairy Queen in high school. My friends all worked there. It was more like getting paid to goof off appropriately with mostly free ice cream thrown in. What a blast!

    Worst job: Another easy choice. Banking. I don’t even want to try to explain it.

  • boB from WA

    Second worst job: working as temp I was assigned to inventory car parts in an old warehouse. It was dusty, hot work and somewhat mindless counting parts over and over.

    One of my best jobs was being a model for the local community college art dept. I was paid $4/hr ($1.75 over the min at the time) to pose for 3 hours.