A list of the most random jobs I’ve had – how about you?


A friend just tagged me in a tweet on the different jobs we’ve had, and thought it would be fun to play along here too to get to know each other more :)

We’ve all done some interesting things to help pay the bills at some point, right?!

Here was the message I was tagged in:

random jobs tweet

Went back to see what others in the chain had done, and it was pretty amazing the variety of skills in our community! Everything from police officers to paper boys, models, log peelers, rock pickers (?), sign makers, seamstresses, prayer ministers and even puzzle store owners, haha… None of which I’d personally be good at, except for maybe the rock picking ;)

Here were the 5 gigs I ended up sharing:

  1. Bowling Alley Attendant (“Cosmic Bowling” even – remember that??)
  2. Timeshare Rep (*ick*)
  3. Stamp Factory Worker
  4. Photo Editor
  5. Airline agent (<— the best!! You practically see the world FOR FREE!!)

My friend Hélène joked that we’d break Twitter if we listed ALL our random jobs from over the years (she was the puzzle store owner – hah!), but it reminded me that I *did* once post them all up here for all to see which makes playing games like this a lot easier :)

Wanna reminder of this FULL list of jobs over my illustrious 39-year career?? It got pretty random there for the first 30-something positions! Haha…

Here they are, along with my best recollection of pay:

  1. Babysitter ($5/hour)
  2. Lawn Cutter ($5-$20/lawn)
  3. Pet Watcher/Walker ($10/day)
  4. Camp Counselor ($4.75/hour)
  5. Commissary Vendor Stocker ($800/mo)
  6. Day Care Associate ($6/hour)
  7. Bagel Maker ($6.25/hour)
  8. Bowling Alley Attendant ($7/hour)
  9. Prep Cook ($7/hour)
  10. Book Store associate ($7-$8/hour)
  11. Gadzooks worker ($6.75/hour)
  12. 7-Eleven sandwich maker ($8/hour)
  13. Construction Site Trash Hauler ($8-12/hour)
  14. Timeshare Sales Rep ($400-$800 a sale)
  15. Stamp Factory Drone ($10/hour)
  16. Photographer ($0 – $10/shot)
  17. Kid Shelter Volunteer ($0)
  18. Assistant Photo Editor ($50/issue)
  19. Photo Editor ($100/issue)
  20. Assistant Photo Editor Intern ($10/hour)
  21. Boat Rental Worker ($10/hour)
  22. Totaled Car Washer ($5/car)
  23. Dish Washer ($11/hour)
  24. Old Navy Associate ($9/hour)
  25. TV Show PA (Production Assistant) ($0 // apprentice)
  26. Travel Agent ($10/hour)
  27. Airline Ticket Agent ($9/hour)
  28. Customer Service Rep ($28,000/year)
  29. Customer Service Assistant Manager ($32,000/year)
  30. Realtor ($3,000+++++/transaction)
  31. Customer Service Rep at a Startup ($35,000/year)
  32. Customer Service Manager ($45,000/year)
  33. Product Manager ($48,000/year)
  34. Customer Service Director ($55,000->$78,000/year)
  35. Project Manager ($78,000)
  36. Graphic Designer ($78,000)
  37. Blogger/Entrepreneur ($100,000+/year)
  38. Blog Coach ($50-$100/hr)
  39. Money Coach ($50-$100/hr)
  40. Fintech Advisor ($100-$200+/hr and/or stock)

40 different jobs in almost 40 years on this Earth! Not too shabby!

Funny how some of the least glamorous ones ended up being some of my favorites too…Like the dish washing and lawn cutter gigs. Something so soothing about working with your hands though while contemplating life and listening to music! And that dishwasher one paid more than almost all other positions at that restaurant too!

Here’s the list in more detail if any of them particularly looked interesting to you: My Entire Work History

As fun as it was changing things up every now and then though, I’ll admit it’s nice to finally have a more solid career to build upon over the years and grow… I’ve had the same gig now for just over a decade, and no way I would have guessed it would have been around blogging! Haha… I swear my parents still think it’s mad I don’t use my college degree! ;)

But hey – that’s why you try out a bunch of different stuff, right? Never know what’ll eventually stick and change your life/career/finances… Gotta keep going until you find your right path!

Now that you know my complete life story, though, it’s time to hear more about yours :)

What are some of YOUR most random jobs you’ve tried over the years? Have you finally found the one you’re passionate about, or are you still on the hunt?!

Totally recommend listing them all out one day if you’re especially feeling bored or introspective… It’s a trip going down memory lane like that, and who knows when it might come in handy!

PS: For a list of jobs I *haven’t* tried yet but are equally as interesting, check out our side hustle series that now features over 70 ways to make money on the side! –> Side Hustle Series

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  1. Kate April 30, 2019 at 5:50 AM

    1. Cabaret dancer in Japan
    2. Hospital bed maker in my own country
    3. Beer “promoter” at festivals in Argentina
    4. A temp receptionist job in a part of the country where I literally couldn’t understand one word of the local accent in England
    5. English teacher in Korea

    Bonus round: Favourite “your fired” moment was getting sacked from McDonalds as a 15 year old for eating a chicken nugget!

    1. Kate April 30, 2019 at 5:52 AM

      One more! Drawing the crosses on the hot cross buns in a bakery. Probably my happiest job ever!

      1. J. Money April 30, 2019 at 7:39 AM

        HAH!!! You live an adventurous life over there!!

        My mother was actually an English teacher while we were stationed over in Korea too…

        What year were you there? We could have crossed paths! ;)

  2. Max Out of Pocket April 30, 2019 at 7:01 AM

    I also have very fond memories of some of my less glamorous jobs. Dish washing and delivering packages as a courier were my favorite! Sometimes it is better to just be part of the process (dish washer) vs. managing the process (i.e. restaurant manager). That way, the job is usually done when you leave work for the day and the stress doesn’t follow you home!

    Did you work for the actual airline at the airport? Discounted flights by chance? Cheers!

    Max OOP

    1. J. Money April 30, 2019 at 7:41 AM

      Exactly!! There’s some beauty (and freedom!) not thinking about work 24/7 – even though it’s such a sought after thing it feels like in our world…

      And yup – I worked for Continental Airlines back in the day and could fly anywhere in the U.S. for like $30 round trip, or anywhere in the world for around $50 or $100 I believe…

      Was bonkers… some days I’d fly out to another state just for the day, or head out to London just for the weekend :) Unfortunately you didn’t get paid much so I couldn’t do much while there – haha – but it sure was exhilarating!

      1. Max Out Of Pocket April 30, 2019 at 2:39 PM

        Wow! Could be a good gig for post FI life!

  3. SL April 30, 2019 at 8:23 AM

    My more obscure jobs:
    1) Waste disposal manual labor (I literally shoveled waste)
    2) Dietary assistant with elderly care
    3) Package courier
    4) Assembly line packer (for OEM Corvette parts whee)
    5) 3rd shift Waffle House wait staff (I LOVED the Friday 3rd shift! ALL the stories there)

    1. J. Money April 30, 2019 at 2:03 PM

      I would imagine!!!

      Waffle house was always a fun last stop before calling it a night ;)

  4. Aaron April 30, 2019 at 8:35 AM

    This is always a fun exercise – sometimes you forgot all the life experiences. You were paid well as a designer! (many of mine revolve around golf)

    1. Softball scorekeeper
    2. Golf range picker
    3. Golf course maintenance worker
    4. Golf pro
    5. Designer

    1. J. Money April 30, 2019 at 2:07 PM

      Well I snuck in as a customer service guy, eventually working my way up to manager and then product manager, and then over to graphic design when they found out I had a degree in it, haha… And all the while just kept me at the same salary which was nice :)

  5. Adam April 30, 2019 at 8:39 AM

    Some of my favorite jobs were along the same lines — slinging donuts and coffee to regulars every morning at 6am the summer after high school, or hanging out in the back of a bicycle shop building bikes and playing guess-that-conductor-and-orchestra with the other mechanic with the classical pieces that would come on the radio.

    I was thinking about that today, given all the responsibilities and troublesome moving parts in my current job (production support manager, sort of). It sure would be lovely to go back to making half to a third of what I do now and enjoying my work that much more. Maybe in the last few years before FIRE, when the investments are earning more than I’m socking away, I’ll skip out on this pressure and try to get a soft landing at the local coffee roastery…

    1. J. Money May 1, 2019 at 7:46 AM

      That would be the life!!! There is definitely something to be said about it!!

  6. Chris April 30, 2019 at 8:40 AM

    Church musician

    Picker and sorter at a cherry orchard
    Farmer’s market
    Another farmer’s market
    Another farmer’s market
    Another farmer’s market (all for two different companies)
    Medical transcriptionist

    Medical transcriptionist
    Piano teacher
    Temp agency – clerical hospital work
    Local telemarketer
    medical secretary

    OTHER – homeschool teacher to my child

    1. Chris April 30, 2019 at 8:41 AM

      Oops – I just listed all jobs I could think of, not just random. lol

      1. J. Money May 1, 2019 at 7:47 AM

        Super fun to read though!!!

        Almost thought you said candy STRIPPER there too for a hot sec, haha…

        1. Chris May 3, 2019 at 7:40 AM

          Nope. You have at least one old-fashioned Christian lady who read your blog and enjoys it. :)

          1. J. Money May 3, 2019 at 7:50 AM

            Haha… And we love you for it :)

  7. Colleen April 30, 2019 at 8:57 AM

    1. Ice cream server (ugh….the smell!!!)
    2. McDonald’s (one of my favorite jobs – I think everyone should work fast food)
    3. Pizza Delivery
    4. HR Assistant
    5. Recruiter

    My Husband’s:
    1. Camp Instructor
    2. Swing Dance Instructor
    3. Starbucks Barista (oh the perks!)
    4. Zoo Worker (handling snakes, alligators, big cats, etc)
    5. Graphic Designer (freelance and for churches)

    1. J. Money May 1, 2019 at 7:48 AM

      That zoo one sounds fun!!!

  8. Josh April 30, 2019 at 9:07 AM

    This will be fun for me ’cause mine will be pretty rare.

    Jobs since graduating college (actually I tutored math in my last year of college):

    -Information guide to visitors & tourists by day, then stargazing program coordinator by night.
    -Telescope operator at professional astronomical observatory (small radio array)
    -Telescope operator at professional astronomical observatory (very large optical telescope)
    -Telescope operator at professional astronomical observatory (one of the largest optical telescopes in the world).

    1. Minimal Millionaire Mom April 30, 2019 at 10:33 AM

      Was it at Yerkes?

      1. Josh May 1, 2019 at 7:24 PM

        Not at Yerkes, but I’d rather not give it away. ;-)

    2. J. Money May 1, 2019 at 5:38 PM

      Haha… Okay, you win!

  9. Brian April 30, 2019 at 9:31 AM

    Saw the “5 Jobs” blow up on twitter recently. It was fun to read the replies. Here’s mine.

    1. Paper-boy (do they still exist?)
    2. Deli clerk
    3. Gas Sation attended
    4. Deposition videographer ( I met Axle Rose doing this)
    5. HS Teaching assistant

    1. J. Money May 1, 2019 at 5:41 PM

      I hope they still exist – print is awesome!! And I’m always seeing them in front of peoples’ doors, so unless Amazon’s unleashed all the robots…?

  10. Minimal Millionaire Mom April 30, 2019 at 10:40 AM

    How fun!

    1) Swim instructor (while in high school)
    2) Taco Bell (had job for 4 hrs, had to clean refried bean pans and clean men’s bathroom, returned uniform in drive thru…I’ve got Adam Corolla beat)
    3) Health insurance claims examiner (while in college)
    4) Homeschool teacher
    5) Walk Chair/conference organizer for charity

    Nothing to do with what I went to college for and future career.

    1. J. Money May 1, 2019 at 5:42 PM

      4 hours!! I once dated a girl for about that much time too, haha…

      Do you do charity stuff still or no? I’ll have to tap you whenever I finally get my Big Idea :)

  11. Natalie P April 30, 2019 at 11:25 AM

    First ever paid job: Kohls Point of Sale during Christmas (never again!)
    Favorite part-time job: Newborn Baby Photographer
    Favorite college job: Arts and Culture Intern (paid $17.50/hr, got my own office, not bad for a broke student)
    Most useful job: Call-Center/Box Office for a nationally recognized theater
    Current job: Box Office/Admin/Development Associate for a non-profit

    Volunteer work:
    Most meaningful: DAT at the Red Cross
    Most fun: Bartender at a beer crawl
    Most oddball: a tie between German Shepherd Photographer for a rescue and fetal demise photographer for a hospital

    1. J. Money May 1, 2019 at 5:44 PM

      Wow those are random and equally fascinating, haha…

      I could look at babies all day long – that’s such a good one!

  12. Angela April 30, 2019 at 12:54 PM

    Fun! Can’t help but participate with my crazy jobs:

    1. Lifeguard/Swim Instructor (Not really crazy, but the most fun summer of my life! I’m sure turning 21 that summer didn’t have anything to do with it . . . )
    2. Diaper tester – technically, I was a chemist, but my company made the superabsorbent polymer in diapers and I tested the diapers it was in
    3. Cruise Ship Director – yes, just like Julie on The Love Boat – so much fun and I saw so much of the world!
    4. Church musician
    5. Now I work in the nonprofit world as a fundraiser and have worked for a variety of orgs, such as higher ed, a homeless shelter, a youth development and sustainable farming org, and currently an org that places service animals.

  13. Brian April 30, 2019 at 2:07 PM

    I delivered Ice for a couple summers. It was commission based, but averaged out between18-30/hr depending on the day. While it stunk to work 4th of July, I made BANK that day. I think the most I made in one day was around $1000. A local factory losts its AC and had to keep their products cool, so I spend all day dropping pallets of Ice off. It was super easy and great.

    1. J. Money May 1, 2019 at 5:46 PM


      But where the heck were you delivering all these ice creams to?! In bulk to stores or single cones to all the neighborhood kids?! :)

      1. Brian May 2, 2019 at 10:28 AM

        Not Ice Cream. Just plain old Ice…. Frozen water.

        I forgot that we also made a killing delivering to the football stadium here and to the race track and drag strip out here. So.. much.. ice

        1. J. Money May 2, 2019 at 1:34 PM

          OH, duh haha… much more sense now! :)

  14. Donna Freedman April 30, 2019 at 3:04 PM

    When I was 9 or 10, my friend and I would pick strawberries from a farm and daffodils from an abandoned field and sell them in front of her house.

    At 11 I was considered old enough to babysit (!) and made 75 cents an hour. By the time I hit 13 or so it went up to $1 an hour.

    At age 13, I picked tomatoes in a greenhouse. Good Lord it was hot and humid in there!

    At age 14 I traded week-on, week-off duty with my sister at the home of the local GP. We were on call for child care 24/7, i.e., responsible for them every second even when their parents were home. We also did housework. All for the staggering sum of…$25 a week.

    At age 16 my parents separated and I became the housekeeper for my father and brother. This was old-school stuff: clean every day (seriously, how dirty could the place have gotten in the previous 24 hours?!?), wash towels after one use, hang all laundry outdoors, iron all shirts and slacks, cook all meals and desserts from scratch, can and freeze garden produce. The pay was…zero dollars. It was expected of me because I was the female in the house. (And yep, I *still* get angry when I think about the fact that my dad and brother never lifted a finger.)

    Couldn’t get a job-job in my area until I was 17 because there was no public transit. At 17 I got my driver’s license and scored a weekend gig at a bakery; either my dad would drop me off at 11 p.m. and pick me up at 7 a.m. or he’d borrow a friend’s truck and let me take his VW bug. I can’t remember what I earned but minimum wage was $2.10 so it was probably that or only a little bit higher.

    Still babysat, and occasionally worked on a chicken farm owned by a friend’s family. I also did a trade with that family: Every week or two I’d bring over some freshly baked cake, pie or cookies and they’d give me two dozen eggs in return.

    After graduating from high school I took a summer job at the glass factory. And good Lord was it hot in there, too….! Worked shifts, earning $4.08, $4.18 and $4.34 per hour. (Funny how I still remember that.) A lot of double shifts and I never did get used to the sleeping pattern.

    During my one year of college I cleaned houses, babysat and did work-study in the college’s public relations office. I don’t remember what the work-study pay was, but it helped get me through.

    Dropped out because I’d had a nervous breakdown and didn’t know what I was doing. Cleaned more houses, babysat some more and finally got a job typesetting and proofreading for a small printing/publishing firm. Can’t remember what I earned but I bet it was close to minimum wage.

    Then I got pregnant, had the baby and did secretarial work, typesetting and proofreading again, and ultimately got a job as newsroom clerk at The Philadelphia Inquirer. The pay was pretty good (thanks, Newspaper Guild!) but it was tough to make a living because child care cost a whopping $35 a week. (Those were the days.)

    That job was life-changing, though: I began freelancing for the features section, and met and married the guy who would be the reason I moved to Alaska (where I used the freelance clips to get a job as a full-time reporter). Alaska and the features section turned out to be great backgrounding for 23 years later, when MSN Money asked me to start the Smart Spending blog. Apparently features writers are bloggers in training.

    Weirdest one-time job I ever had, though: Getting paid $35 to watch a porn film made by women as part of a university study. Most people pay *to* watch porn; I got paid *for* watching it.

    1. J. Money May 1, 2019 at 5:55 PM

      HEYO!!! haha…

      And I hope you turn all this into a blog post now for YOUR blog – that was equally as interesting as it was long!! When you participate you really participate! Haha…

      Thanks for taking the time – I feel like I know all your work secrets now :)

  15. FullTimeFinance April 30, 2019 at 5:24 PM

    Camp counselor
    Swim instructor
    Computer repair man

    Cutting it here as the rest are corporate and these are more interesting honestly as they have no tie to what I do today.

    1. J. Money May 1, 2019 at 5:56 PM

      I always thought life guarding was a sweet gig… Did you enjoy it as much as it looks?

  16. Carolyn May 1, 2019 at 2:13 PM

    1. Paper girl – I inherited the route from my brother who inherited it from another brother.

    2. Dunkin Donuts/Burger King/A&W – I only lasted about a month at each job; hated working in fast food but usually needed cash for something.

    3. K-mart cashier – One time I had to push around the blue light for the blue light special, which has scarred me for life (traumatizing for a teenager who was praying nobody she knew saw her). And I had to wear an ugly aqua smock.

    4. Retail salesperson – I worked in the dress department of a high-end department store in Chestnut Hill, MA. I didn’t last long at that job because a majority of the people who shopped there treated salespeople horribly.

    5. Library employee – I worked in the basement of the college library, where they stored the cards for the books that were checked out. We made sure the cards were organized correctly. Also, if somebody couldn’t find a book on the shelves, they could send the call number to us in a pneumatic tube, to verify whether or not the book was checked out. Soooo boring.

    1. J. Money May 1, 2019 at 6:14 PM

      I’d like trying out that librarian one!! Love being surrounded by books and they never talk back to you!! :)

  17. KellyJean May 3, 2019 at 9:35 AM

    1) Babysitter – (pre- 15) $20
    2) Govt worker – (15 years old) – summer work – take home pay $500 per month
    3) Retail – (pre- college) – $21K annually
    4) Administrative Assistant – (Some college) – $19K to 26K annually
    5) Software Engineer (still some college) – $31K to 56K
    7) IT Consultant (grad degree) – $75 – $112K
    8) Business Owner/Manager – (self-employed) – $83K
    a. Airbnb – current company http://gladco.co
    b. fashion/life/financial blogger – (working on it as it is one of my future goals)
    c. Software Application Re-packager using Wise – IT Instructor (dissolved first company)
    Volunteer work:
    1) candy striper (past)
    2) homeless shelter (past)
    3) ESOL helper to church (past)
    4) Financial Fragility Support Group – Co-host – future

    1. J. Money May 3, 2019 at 9:53 AM

      Cool! I love that you went from the higher paid consultancy work to running you own business now :) Which I’m sure will only surpass that $$$ the further as you go! What’s the blog url so we can all check out?

  18. Stone C. July 25, 2019 at 2:57 PM

    In chronological order:

    1) Sonar Technician on a Submarine
    2) Team lead in a grocery store (talk about a downgrade =^P .)
    3) Fabricator in a Machine shop.
    4) General Labor in Solar energy field construction
    5) Electrical Procurement Specialist in solar energy field construction (never be afraid to pursue a promotion!)

    1. J. Money July 25, 2019 at 3:10 PM

      fascinating!! I’d love to learn more about solar stuff and especially incorporating into homes… we get so much sunlight at our new place that I need to see if it would make sense to set up :) funny that you went from soNar to soLar!

      1. Stone C. July 26, 2019 at 5:47 AM

        The price of panels has come down a lot over the past couple years, especially with so many solar farms now being built in the U.S. (My company alone is going to build 16 this year!) So they are cheaper than ever. And hey, aren’t you supposed to be on sabbatical right now? hahaha.=^]

        1. J. Money July 26, 2019 at 7:35 AM

          learning never takes a break! ;)

          thanks for the insight!