Save. Spend. Splurge.

Businesses and Jobs I have had since the age of 7

I’ve held a number of odd jobs over my lifetime so I thought it would be fun to list them out.

I will tell you that even though I haven’t really worked like a donkey in the past 5 years (I’ve been taking a semi-retirement of sorts, working one year, taking one year off and alternating), I used to be a really hard worker when I was younger.

I’ve just gotten lazier (in a way) as I’ve gotten older and less money-grubbing, which is both good and bad depending on how you look at it.


I was recruited into the paper route world by my older brother who tricked me at the start by making me fold all the fliers and do all the work for 25% of the pay.

He basically used me as a mini-slave, but after a few months I cottoned on to his sneaky ways and took over the business completely while he went off to work stacking shelves at a local grocery store.

By the time I was 10, I had done something similar and employed other children in my neighbourhood to deliver to certain sections of my route, and gave them a small cut of my route money and the promise of free ice cream treats to do it.

Basically I turned myself into a manager!


I did this only for a year less (my memory is a bit hazy.)

Anyway, what I did was go into thrift stores, scour the racks for things that looked nice (I looked at the label first, then the condition, then assessed whether it was nice or not), and re-sold it on eBay with a nice, comprehensive listing of what it was, the sizing and so on.

I didn’t make a ton of money off this mostly because it was a lot of time and effort to scour thrift stores to find things to re-sell, then having to package and ship it, not to mention having to spend time creating listings for each item (and measuring everything!!), but I at least turned a profit.

The good thing about all of this at the end was I learned how to sell online to faceless masses.

I understood how to list a product, give it a nice spin (I tried to make my listings funny), and how to manage business with having to deal with things like finding the cheapest way to package and ship an item.

Ultimately it was too much work for me for the amount I was getting paid, so I stopped doing it.


This is the rite of passage job for every teen I think!

I found a job making burgers and flipping fries, and worked part-time all the way until college.

I took every night shift (5 p.m. – 9 p.m.) I could find, all the weekend shifts they could offer me (11 a.m. – 8 p.m. for instance), any canceled shift, as well as all the overtime working during busy holiday hours.

I can’t really remember how much I made, but minimum wage was around $7.25 at the time I think. I also got really sick of fast food from having to sell it all day.

I kept doing this all the way until college because I moved away from my home town and had to quit my job.


After my little stint on eBay I started looking at other ways to make money with less work, and it seemed like going online was the best.

I stumbled across this “business” purely by accident because I was obsessed with gaming online, and ended up realizing that other people would pay REAL MONEY on eBay to get a cheater’s head start in a game that took me about a year to master and build up from scratch.

I made some serious cash off it (serious for a 16-19 year old anyway), and had fun doing it.

I also learned a lot about customer service because I was interacting with “live” customers from the shop I was running online, and listened to what they requested for and wanted. I became extremely efficient and organized at managing my online inventory and overhead.

You can read all about how it happened here: Turning virtual millions into thousands

I only quit doing this because it really wasn’t enough money even though it was a fun hobby, and because I needed really good grades to get into college, so I stopped a year before my applications started.


Another business I started offhand from another hobby/interest of mine just because I thought coding websites was a lot of fun and interesting.

I have since let my skills go to ground (I’m totally rusty and useless at doing anything very technical for the web now) but I used to be pretty good.

I was targeting small and medium-sized businesses in town to help them set up websites on this newfangled “World Wide Web”, as well as just having an online presence even if it was just a placeholder to tell people where they were located and what their store hours were.

I basically told them how to display their business online in the best light (based on what I thought was required).

Even today, when I go to business websites and I see that they don’t list their hours, a map or BASIC information, I do a *facepalm* because I really want to offer my services.

Sometimes when I am browsing Etsy, I just KNOW I could triple the business volume of some of the businesses on there if they would make a few key but important changes to their online shop…

(See? Being a bit of a shopaholic really does pay off!!!!)

Anyway, I did this all the way through college because I could work in between classes (sometimes DURING class), as well as at night or on weekends in between my other full-time job of being an assistant superintendent of a building.

(Yes this was all while going to business school, which is why my grades in college weren’t stellar like the other kids in my class.)

It was so flexible hours, I made my own schedule, and the money wasn’t bad for the time I spent.


By luck I found this job that let me live relatively rent-free if I would just help out around the building. I wasn’t the one working full-time during the day, I was the person on-call for the nights and weekends.

Worked out well because I still had to go to class (yes.. annoying business school classes).

I just had to clean a lot, deal with whiny, entitled residents (some were students too!), and manage office affairs to help keep things going while the main superintendent took a break for the night, weekend or went on vacation.

BLOGGING (AGE 22 – ???)

This has been my worst paying job since I was 7!

Haha I kid. Kind of.

I started blogging way back when I was in $60,000 of student loan debt, and chronicled how I got out of it in 18 months. Then I stopped, giving it all up, swearing to never do it again (it was a lot of internal pressure to perform), then started again with this blog.

Anyway, my blogging “income” has been on average $0.25/hour in 2012 considering the hours I’ve worked on the blog (a hobby) and what I get out of it.

Good thing it isn’t my bread and butter or I’d be FREAKING out!

Still, I’m rather competitive with myself, so it stands to reason that I’ve been channeling a lot of free time and energy into doing this schtick, which is the reason why I regularly schedule 2 years in advance because I’m afraid I will get swamped and not have time to blog.


Which brings me to present-day Me.

I have now found the perfect marriage of what kind of work I like to do, as in having a more flexible working schedule, and using my brain instead of my brawn (hah! BRAWN!) to make money.

Having a business that deals with a product like selling clothes is not easy, and is a lot harder than if you just sell your brain, but getting to the point where someone wants to pay for your brain (your expertise, as it were), is just as difficult in the beginning but it gets easier as time passes.

Looking back, I can kind of see in my history how I developed my rather independent, don’t-wanna-work-for-anyone-but-myself streak.

I’m lazy and that helps with my creativity in finding jobs or professions that embrace my laziness.

Looking back, I can’t believe I did all of that. It feels like another person entirely!!



  • Karen

    I hate to say it but I barely worked when I was younger. I was only allowed to work during the summers and breaks in high school. My parents wanted me to focus more on education so I could get into a good university and get a so-called good job. I wish I had fought back more on that and worked part-time in high school. It would have been nice to earn my own money and probably learn better time management.

    I worked as a camp counsellor (never again) and worked in office retail.

  • Tara Faircloth

    Love your blog! I am a fellow freelancer, and have had whirlwind job history as well. My main work is directing operas, which involves A LOT of travel, and I also own a duplex and airbnb my half of it when I am away.

    I’m sorry if I missed this elsewhere, but I am curious what is the nature of your consulting work now?

    Thanks for your time!

  • Derek @ MoneyAhoy

    Wow, you are quite the entrepreneur! That’s an interesting job history – I can definitely see how those all led up to freelance consulting.

    Most of my jobs were technical related which involves me sitting at a desk 8 hours a day. I am only just in the past couple of years starting to brand out onto my own with various side hustles.

    Good luck with the freelance gig!

  • SP

    I did work a lot, but it was less interesting standard stuff: grocery store cashier, retail, waitressing, lab/school related jobs.

  • Ramona

    Wonderful list of businesses. We do meet on 2 of them 🙂

    Age 15 – I’m poor, but have good grades. So I teach younger students (10-14 year old) English. I’m Romanian, for those who don’t know this detail, so knowing English well was a huge advantage,

    I didn’t make millions, but I could buy a new pair of jeans or pay for a very very expensive TOEFL book I just had to have. Yes, I was a geek and wanted a huge English book 😀

    Then I started working as a radio DJ at a local station.

    For 10 years.

    During my radio stardom, I also got interested in web design, so I started getting clients in 2004 (2 years after I started being interested in this).

    I also started a blog in 2007 (Romanian), which brought me many clients and some money as well.

    Now I also work as a freelance coach, while still doing web design work.

    My radio life abruptly ended in 2009, when the station closed down.

  • SarahN

    I’ve done so many jobs, and for much of my time at university, I had 4 -5 simultaneous jobs as none had the hours to completely cover me every week. Plus I liked to save money, to pay both fees, but also to travel. SO I did babysitting whilst in high school, which included a school based program to escort younger boarding house students to medical appointments, and their parents were charged $10 – so sometimes you ‘won’ and sometimes you ‘lost’ depending on where you were taking them to. Sometimes local, often times, in the city. In any case, getting out of the dorms was a bonus!! I also worked in school holidays for a florist. I did two weeks unpaid and then my mother suggested I ask if I could work paid, now I’d learnt how to be a ‘junior’ and the boss said yes. I worked in that florist for fits and spurts for many many years, including the occasional Sunday to help her (it wasn’t in the same city as my university, but I could day trip).

    At university, I did: sports coaching (water polo, netball and softball the last of which I knew nothing about!!), note taking for special needs students (paid for by the university, thanks to socialised education $23 per hour), scribe for special needs students in exams (never the same subjects I notetook), admin relief for lunch (taking student calls at university) which also meant I helped stuff envelopes, man events, whatever they needed that I could help with (cheap manpower, but great contacts for me!), Kmart cashier (always the 10am open on Sunday’s as I wasn’t a party animal and would always be there), left that to work in a homewares store, but they didn’t treat me well and I found a better job – boarding house supervisor where I spent the weekend supervising girls (the weekday live in person got a break that way). After a few terms of that I ‘upgraded’ to a full time role doing this at another school, which gave me week nights and some weekends and fitted my penultimate semester’s schedule. That was about $45k per annum, so it was an awesome upgrade to finish my studies with (and the ultimate semester, I had resigned, moved to my parents and smashed out the last of exams). I also was a ‘resident advisor’ for two of those years, which got me a reduction on my rent in student accom (winning), but I had to stop that when I spent too much time at the BFs, and then moved to France. IN France, I was an au pair in the second semester (live in with one family, hated it, quit and live out for a fantastic family I still talk to 10 years later!), I ‘wrote’ English talks from a CD (HARD and a ‘per track rate!’). After returning from France, I subscribed to SO many panels for surveys and mystery shopping, so earned a lot of incremental money with doing those too.

    I learnt a lot with all the piecemeal jobs – just the other day, I used mail merge skills from my admin days! Sports coaching helped so much in management of staff (who’d have thought!), as does babysitting and au-pairing. I’m also a weapon at saving money – when balancing 5 jobs and 5 pay cycles (weekly, fort nightly, monthly or ‘whenever’), so I always had buffer money, and always paid rent in semester chunks to take some stress away and get 1 week ‘free’. I’m also a demon at time management. And these were the days before smart phones – so it was all manual diary and scheduling! And I did (relatively) well in my studies for the most part. Even I’m a little (humbly) proud looking back!

  • Taous

    I worked as an usher as a major theater from age 16-19. . I got to meet a lot of people and most importantly see a lot of musicals, opera and concerts. I also got to enter for work throu the stage door which was thrilling for as aspiring actress.

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