Crappy Jobs on My Path to FIRE

[Hey guys! Please welcome 5 AM Joel back to the site today as he starts transitioning into his new role here while I go the opposite way at the end of the month… Really really enjoyed this post of his, and hoping you do too! See ya back on Monday!]


Check out that old name tag up above…

Yep, I used to work at McDonald’s. Started back in 1999 when I was 14 years old and worked there for almost 5 years while attending high school!

I remember …

  • They made me work the weekend graveyard shift, 11 p.m. to 6 a.m.
  • I was labelled a “pretty boy,” working the front counter with the girls instead of flipping burgers with the boys out back.
  • People made fun of my uniform and my ears stuck out of my visor like an alien. 
  • My pay was only $5.25 an hour (and my parents made me give away 10% of it to charity).
  • I swept, mopped, scrubbed toilets, picked up trash in the parking lot, cleaned fry vats, etc.
  • I missed many parties and hangouts with my friends and schoolmates.

But here’s what I gained …

  • By the time I finished high school, I’d saved enough money to buy my first investment property with my parents. Thank you, McDonald’s!
  • I have an amazing work ethic that makes me stand out. Thank you, McDonald’s!
  • Name-calling doesn’t affect me whatsoever (well, tbh it hurts my feelings a little, but I’m way tougher than I used to be!). Thank you, McDonald’s!
  • My ego is small; no job is too crappy, smelly, or beneath me. I’ll shovel elephant poop if it stands between me and success. Thank you, McDonald’s!
  • I appreciate every single free second I have in life. Thank you, McDonald’s!

I keep all my old name tags and badges as reminders of times that helped build who I am today. Here’s another crappy job I had …

Australia Post!: Working harder, not smarter

Joel's old work badge for the AU Post

When I was 20, I decided that working full-time wasn’t good enough. I wanted more money! So, I picked up an after-hours job sorting mail at the Australia Post factory downtown. I worked 9-5 at my regular day job, then 7-midnight at the post office. 13-hour days, 5 days a week.

I remember …

  • I rode my motorbike across town, in the rain many days, freezing cold and shaking by the time I arrived. My hands were so frozen sometimes I’d have trouble holding and sorting the letters.
  • My co-workers teased me because I was the only one who didn’t do drugs. Some of them were ex-felons, and I went to work sometimes scared that I would get beat up because I didn’t fit in.
  • The management was quite horrible. One boss in particular had it in for me, and publicly berated me regularly.

But here’s what I gained …

  • In the 6 months I worked there, I banked a cool $10k, after tax. This money eventually funded my move to the USA. Thank you, AUS Post!
  • Trading my time for money, I realized, ultimately wasn’t worth it. I never worked night shifts again and learned the difference between working smarter vs harder. Thank you, AUS Post!
  • I learned how to navigate and survive under bad management. It’s all about taking the high road. Thank you, AUS Post!
  • I developed my strengths in remembering numbers, sequences, and attention to detail. Thank you, AUS Post!

More crappy jobs, and more awesome life lessons learned …

One summer I worked as a server at Outback Steakhouse. I was fresh off the boat from Australia, with a thick Aussie accent. I learned I could make more money telling jokes and spending quality time with one table than I could scattering my time across multiple tables. I’m better with quality work vs. quantity work.

At Abercrombie & Fitch, my job was just to stand around and smile at tourists. (I was the only model hired for my accent, not my looks!) As fun as that sounds, it was the most boring job I’ve ever had, and I only lasted 3-4 shifts there. I learned that my brain has a “use it or lose it” clause. Another good life lesson I learned: You become the people you hang around. Watch out!

Most of my career has been in sales roles: phone sales, field sales, customer service, and consulting. I’ve been hung up on, yelled at, laughed at, rejected, and failed at more sales presentations than I can remember. But all of these hard times are matched equally with times I received praise, solved client problems, saved people money and time, and added value to lives. My biggest takeaway from sales is: The more value you provide others, the more you will get paid in life.

More to come in the future!

As much as I’d like to think all my hard work in life is done, I’m still learning. Every day, no matter what I’m doing, a challenge pops up out of nowhere. Sometimes they are fun to solve and other times they absolutely suck.

But on the other side of crappy jobs and tasks is invaluable lessons.

Do you agree?  What crappy jobs did you have in high school? (Or do you have a crappy job now!?) What did you learn?

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  1. Backpack Finance May 15, 2020 at 5:50 AM

    I worked my fair share of crappy jobs. I actually did make quite a lot of money through them but I blew it all on a 6 month trip to South East Asia. I wish I would have been smarter with my money back then and bought a property like you. But hey, no regrets in life!

    My best crappy job was lifeguard in a pool. Can’t even begin to describe the horrors during summer time.

    Cheers and good luck on your new journey here!

    1. Joel O'Leary May 15, 2020 at 11:26 AM

      Traveling while your young is important and I’m sure you learned a ton. No regrets on experiences like that!
      Wow – I never pictured a lifeguard to be a crappy job. It always looks so cool in the movies but I’m sure real life is different.

      1. J. Money May 15, 2020 at 11:41 AM

        Haha same! Especially for getting dates, no? :)

  2. Lisa O May 15, 2020 at 10:39 AM

    I have liked all my jobs even the fast food one at The Red Barn! I will say some days are better than others but that is just Life!

    Best of Luck here on the site. Looking forward to getting to know you.

    1. Joel O'Leary May 15, 2020 at 11:52 AM

      Great attitude Lisa. That’s life!

  3. Mister DS May 15, 2020 at 12:05 PM

    I also did some time at McD’s! I remember I stayed long enough to get my first $0.10 raise, but then minimum wage went up $0.25, so I was back to making minimum like the new guys!

    I got really good at mopping floors, cleaning toilets, and holding my tongue while taking verbal abuse from rude customers.

    I also remember using my employee discount to hook my high school buddies up with 20 piece boxes of McNuggets!

    I remember the manager was always worried about getting in trouble if the average hello to goodbye time through the drive-thru exceeded 2 minutes, which it always did. At the end of the night he would take the metal trash compactor stick and waive it over the magnet outside the drive-thru window to log a whole bunch of 0-second times and bring his average down. :-)

    1. J. Money May 15, 2020 at 1:09 PM

      Stop! Haha…

    2. Joel May 15, 2020 at 7:11 PM

      haha dude that’s hilarious! I remember people messing with the KPI’s too. One guy in the kitchen would eat old food ingredients to make sure his wasted food tally was lower at the end of his shift.
      Love the McNuggets discount – I gave away a lot of food to friends and family. One of best the perks!

  4. Amy May 15, 2020 at 12:06 PM

    I too worked at McDonald’s as my first job at 15. Looking back I wish my parents had taught me money management and that I had started saving right away. Unfortunately I spent all my money on clothes, movies, food, car insurance, and the other things teenagers ‘need’, haha.

    My worst job would be when I picked up a second job picking flowers for a massive wholesale nursery. I spent 3 weeks picking tulips by hand and was asked to leave (nicely fired?) because I didn’t pick the stem low enough to the ground so they were too short. To this day I don’t think that was true, but I didn’t fit in with the others doing the work (older women, different culture, language barrier) and think they wanted me to leave so one of their friends could be hired on. No hard feelings though, it gave me an understanding of manual labour (bending over all day was horrible even at 17) and I will never complain about paying $4 for a bunch of 5 tulips again!

    1. Joel O'Leary May 15, 2020 at 12:28 PM

      Go McDonald’s! Yeah I’m lucky my parents taught me to save. Their rule was 10% charity, 45% save and 45% spending. Even with that I had enough money to buy all of my teenage “needs”. I still blew a lot of money on crap that I wish I saved.

      Sounds like you learned a lot from the nursery gig. You’ve just changed the way I look at flowers forever!

  5. freddy smidlap May 15, 2020 at 12:25 PM

    hell, i worked 2-4 years at mcdonald’s too. it was great. the girls who worked there weren’t so ghetto in the 80’s so that was a bonus.

    i used to be a french quarter bartender in new orleans during a mini retirement. my roommate was an overnight bartender 1am to 7am in a popular bourbon st. spot and we had a great time. then he noticed his coworkers dying pretty young and decided that life wasn’t a long term solution for him. it really is about the company you keep. he quit that gig and became a lawyer.

    1. Joel May 15, 2020 at 12:48 PM

      Wow – what a turnaround for your friend. He could have been dead by now if he stayed in that line of work.? That’s a scary thought.

      Yes McD’s has become ghetto in a lot of areas. But some in cities around the world it’s still a decent place to work. Most of Australia is still stuck in the 80’s, so maybe not that bad still down there! haha.

  6. Dave @ Accidental FIRE May 15, 2020 at 1:46 PM

    My brother worked at McDonald’s for almost 10 years, the acne that he got from the grease in the air was horrendous. It did teach him how to work hard though.

    1. J. Money May 15, 2020 at 3:57 PM

      From the air and not over eating it??

      Wow… would have never guessed that!

    2. Joel May 15, 2020 at 7:14 PM

      Ah, yep I remember being a filthy greaseball every time I finished a shift. My clothes and hair would stink like fry oil. Even now when I walk into a McDonald’s (a rare occurrence) the smell hits me and takes me back.
      Cheers, Dave! Have a good weekend buddy!

  7. Helen Wall May 15, 2020 at 7:15 PM

    My first job at 14 was helping with the charge accounts and billing at a drugstore owned by friends of the family. I would make a copy of each statement, one at a time by dipping it into some chemical solution (this was 1965) and I licked the stamps for the envelopes….for 75 cents an hour! I thought I was rich. Worked for them about 5 years after moving into a clerk spot. Learned punctuality and people skills. So glad stamps no longer require licking.

    1. Joel May 15, 2020 at 8:51 PM

      Haha my mind immediately went to that Seinfeld episode where George’s fiance (Susan) dies from licking all those toxic envelopes! Glad you weren’t hurt!
      Punctuality is such a great lesson to learn early – good one!
      Have a great weekend,

  8. J.R. May 16, 2020 at 10:02 AM

    I guess time dulls some of the memories. But thinking back on it, my first job did a fair amount of good. I worked at The Taco Bell (for some reason we referred to it as “the” Taco Bell). It was a summer job for me in high school and college. The job itself taught you to show up and clock-in on-time. But also there were a lot of friendships in that crew. There were a lot of us in roughly the same age range and we were always hanging out. Nothing to do on Friday night? Head to the Taco Bell and see who’s there. Almost always you’d find some of the crew hanging out even when not scheduled to work. No cell phones or emails then (early 1990’s) so it was harder to stay connected. We’d often help close the store at 2am even though we weren’t working so that we could all hang out. Then go to breakfast at 3 or 4 in the morning.

    I got my best friend a job there. He got promoted to management. He used the money to fund his college and eventually got a masters degree. He met his wife working there. They’ve been married over 20 years now with two kids.

    Good memories. A lot of good can come out of our crappy jobs.

    1. J. Money May 18, 2020 at 9:31 AM

      So cool!!! Love that y’all hung out there even when you weren’t working, haha… I suppose many of us did that back in the day since it really was where all our friends were :) Funny you called it “THE” Taco bell too. I don’t know why but that reminds me of how much my wife makes fun of me for saying “David Grohl” all the time instead of just “Dave” :) Our brains can be weird!

  9. sfmitch May 16, 2020 at 12:16 PM

    I’d prefer to say low paying rather than crappy because I enjoyed almost all the jobs I’ve had.

    I got my first job at 14 working at a Stewart’s Root Beer stand (hamburgers & hot dogs). $3.35/hour. Takes a long time for that to add up! It was family owned and operated and I worked there for years. Great people. Worked the fryers, griddle, expediting, couterman, carhop (took orders and delivered food to people eating in the their cars (no roller skates)), etc.

    Baked bagels.


    Bank Teller.

    I think those were all my jobs before going to college.

    Then I delivered pizzas.

    Worked at an auto parts store. Helping customers, dealing with inventory, etc.

    Service writer at an auto repair garage.

    1. Joel May 17, 2020 at 10:32 AM

      You’re so right! I never really thought of my work as ‘crappy’ because I always appreciated the opportunity to work. As much as I might complain, I secretly enjoy struggling times. :)
      You’ve got an awesome list there! Fun stories I’m sure from those places :)

    2. J. Money May 18, 2020 at 9:32 AM

      Ahh!!!! Did you come across a ton of old coins or currency at the bank?? One of my dream jobs to do later in retirement!! Haha…

  10. Christine May 18, 2020 at 10:52 AM

    My first and worst job was as a banquet waitress for a country club. I think I made something like $4.25/hr. Which was minimum wage at the time and we couldn’t get tips. They treated us like complete crap. I remember they made us carry around these ridiculously heavy platters in baskets with apps. Your arms would fatigue and get numb. Once, for a wedding, I was at that point when people were clambering for the last kebab and as I turned, I stepped on one of the ridiculously long ribbons they attached for decoration, and the kebab the guy was grabbing somersaulted onto the back of the mother of the bride. It didn’t go well! And of course, serving at events where kids from our high school trotted around like princes was great fun too. I ended up quitting during their biggest event, a golf tournament, after the management refused to prevent us from being sexually harassed by the golfers. I guess it was my first #metoo experience. And the manager was surprised and disgusted that I would be so bold. I learned that an organization and team is only as good as it treats its employees, and management by being a blowhard or terror is no management at all. This was further confirmed by my first job after college where my supervisor ruled over her employees like a tyrant. I also learned that you gotta know when to fold em. Some situations are just not worth it.

    1. Joel May 18, 2020 at 1:11 PM

      Wow – I’m so sorry you had to go through that! Glad you stuck up for yourself – and I hope your story helps others do the same… Because harassment is NEVER worth it.
      Thanks for sharing, and I’m glad you’re stronger because of stuff like that!

      Flip side… I used to work at a banquet hall too, catering for weddings. My experience was different, because they paid me well and I’m a hopeless romantic that loves weddings! Or maybe I just watched the Wedding Singer movie too many times and wanted to be like Robbie. ;)

  11. Michael @ Financially Alert May 19, 2020 at 3:48 AM

    Oh man, I love that ID card, Joel! I think a lot of us did our time in food services.

    My first job ever was working at the Hollywood Bowl in L.A. The only problem was I lived an hour away. I literally worked there for one concert and made a little over 20 bucks at $4.25/hr for 5 hours.

    I wised up a little in college and got paid $5.25 working in the dining hall. And I always gave generous portions of mashed potatoes! ;)

    1. Joel May 19, 2020 at 9:53 AM

      A 1 hour commute isn’t that bad in LA, right? :) haha just kidding, no wonder you only lasted 1 shift there! I hope it was a good concert!?

  12. Ben May 20, 2020 at 4:56 PM

    As soon as I got my driver’s license at 16, my parents put me on the job hunt for gas and fun money, so up through college graduation:

    From 16-18, worked part time at Lowes’ Foods; at the time I hated it because all I wanted to do was hang with my girlfriend, but in retrospect it wasn’t that bad, and definitely gave me an appreciation for grocery store workers/

    Once I started college I mostly just worked over the summer, with a couple exceptions:

    Summer between Freshman and Sophomore year: I first got a job at Champs’ sports working in the back stocking shelves, which wasn’t too bad, got paid $7/hour when minimum wage was $5.75, so *shrugs*…then, I got an offer from my dad’s old boss (he works in IT), asking if I wanted to consult for 5-6 weeks on a bank merger job (essentially what we did was load software onto computer towers for 2-3 weeks, then take them out to all of the branches, 20-30 in total, and set them up making sure they could perform all the necessary banking functions)..this was my favorite job to date, and I got paid $10/hr, plus mileage, so I was making bank (for a 19 yo anyway). Then after that was finished I went back to champs for a couple weeks (although they screwed up my time sheet, so I got paid like $11 for like $100 worth of work, lol).

    Summer between Sophomore and Junior year: This was an interesting one – got a job at Aeropostale making $6.25 (minimum was still $6.25), worked there for 2 weeks, then quit to take a dishwashing job at an upscale restaurant for $8.00….this job was awful and I was fired after 3-4 weeks for not being fast enough; my least favorite job ever…I still had half the summer left, so I made $50/week helping to mow my church’s graveyard, and helped a friend with a blueberry farm pick blueberries for $7 per probably a half gallon jug :).

    Summer between Junior and Senior Year: Worked as a temporary bank teller for $10/hr….narrowly beat out the consulting job for favorite, I loved it.

    During Senior Year: I refereed Intramural soccer and football..the rate was by game refed, and I don’t quite remember what that was, but I made about $900 in a semester before quitting to finish up my studies strong.

    This was also in addition to the income I made online gaming that I mentioned in the side hustle post, to the tune of probably $4000 or so over my four year tenure.


    1. J. Money May 21, 2020 at 8:34 AM

      Man that was fun to read, haha…

      I also was a dishwasher for a while but I actually loved it!! You got to be messy and blare music in the back and got paid more than a lot of people there! At least base pay… No one unfortunately tipped you ;)

      I think I’d enjoy that cemetery gig too. I already hang there for free so to be paid for it would be a bonus, lol…

  13. Max @ Max Out of Pocket May 24, 2020 at 8:40 AM

    I had a similar progression, Boston Market in high school to DHL courier delivery packages all over Michigan! My wife was actually born in Australia (Wollongong).

    Take Care,


    1. 5am Joel May 27, 2020 at 5:36 PM

      Awesome Max! Must have visited some cool places for DHL.
      Has your wife still got the Aussie accent? Or did she move a long time ago?