How I’ve Made All My Money - Elizabeth Stapleton
Elizabeth Stapleton
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How I’ve Made All My Money

First things first, this is not a post about starting a business and growing it into amazing income, and it’s definitely not a get rich quick story. In this post, I’m going to share with you all the ways I’ve made money. Every single job and gig, going back to when I was a kid.

Sure some people get wealthy from one job or by inventing something or starting a wildly successful business. But most of us, work a job and side hustle to get ahead. While I still have tons of debt, I’ve managed to build up a decent amount of savings, over $30k in retirement savings, and have never paid a bill late.

I’ve made money over 30 different ways. Pictures are included, though they peter out as the jobs list goes, on, my mom wasn’t always there to force me to take a picture. In no particular but somewhat chronological order, here is how I’ve made all my money including the pay rate for each job:

1. Babysitting

I think I started babysitting when I was around 12 years old. I even got certified, yup the local community college had a class about babysitting that included CPR training. Though, I only remember ever babysitting for two different families. Frankly, babysitting was never really my jam. Just a way to earn a little extra money for stuff I wanted. I was really good at saving for things I wanted (I saved and bought myself a TV when I was 10).

Pay Rate: Not sure, whatever babysitters made in the late 90’s.

2. Cleaning Out Files

When I was 15, I got a job at my Mom’s office, clearing out old files. They could only get rid of files that were at least seven years old. So I took my boombox and hung out in a storage unit, going through all the files. I earned enough to buy my letterman’s jacket ($200), I still have it, picture included below.

Pay Rate: Pretty sure it was minimum wage.

It still fits! Yeah, it really does just say field. I threw shot put & discus so put field instead of the flying shoes, because running around in circles is for suckers, throwing metal objects is where it’s at.

3. Boomers! Team Member

If you’ve never heard of Boomers! it’s a family fun park. It includes an arcade, mini-golf, go-carts, bumper boats, etc. This was my first real job when I was 16. I’m still convinced it’s the reason why I don’t like children. As a team member, I floated around to working in different areas. I worked at Boomers for over a year until I went away to college.

Pay Rate: Again fairly certain it was minimum wage which was around $6.75 an hour.

First day at Boomers! Thanks mom for making me take a picture so I could have it for this blog post 14 years later.

4. Artist

I’ve mentioned on here before that I dabble in painting. I did it much more regularly when I was younger. A family friend or two even paid me to paint stuff for them. Below is a picture of me painting a piece on the wall of a client’s bathroom.

Pay Rate: $40 – $200

This was over a tub, and I was standing on the edges of the tub to paint. I remember being super proud (still am) of how the stone archway turned out.

5. File Clerk

In addition to working at Boomers! I worked at my Mom’s office (a different one than before) pulling and putting away files, sending out mail, etc. in the mornings. I didn’t have a morning class because it was reserved for the class I was taking at the community college which was actually at night. So I would go to work, then school, then sports, then work. Honestly, I have no idea how I did it back then, especially since I didn’t drink coffee.

Pay Rate: Minimum wage I thin

6. Party Hostess

After working at Boomers! for a while, I got promoted to Party Hostess. This meant serving food and cake. Helping to hand out presents and keep track of who gave what as well as distribute wristbands for the kids to go play after the party.

Fun fact, serving ice cream cake is a bitch. Also if you are going to have a party for 3-year-olds with a total of 40 people in attendance AND have an ice cream cake, you should definitely tip. I did not receive a tip. Did I mention I don’t really like kids?

Pay Rate: Slightly above minimum wage, I think I got a $0.25 per hour raise.

7. Security Desk Attendant

When I went off to college, it meant moving across the country and of course finding a job. I got one in my dorm as a security desk attendant. I would scan everyone’s IDs when they came in and sign in guests. The desk had to be manned 24/7 so as the newbie I was the last to pick my hours.

I’ll never forget that first semester I had a 2:00 a.m. – 5:00 a.m. Saturday night shift. I also had a few other late night shifts that caused me to oversleep once or twice and miss class. It was a really good job overall; I pretty much got paid to do my homework and watch movies on my laptop.

Pay Rate: $7-$8 an hour, somewhere in there.

8. Soccer Referee

I grew up playing soccer in the local rec league. When I was 16/17, I started to referee as well. I’ll be honest I was a terrible referee, and 9/10 the parents had every right to yell at me. But every once in a while I did make a good call. Since I was a terrible ref, I only did this for one season.

Pay Rate: $20 per game (not a bad way to spend a Saturday)

Me being a mostly terrible referee, if I was ever your referee, I am sorry.

9. Cashier

I spent my first summer in college back home, I had an internship and ended up getting a job as a cashier at Big 5 Sporting Goods. It was great for putting my math major skills to good use. I was responsible for putting away merchandise, helping customers find what they needed and then processing their purchases.

On occasion, I would also prevent theft, when people would try to sneak things into the stuff they were purchasing (always check the inside of shoes).

Pay Rate: pretty sure it was minimum wage so between $7-$8

10. Peer Tutor

My second year of college, was when I was taking the highest level math class for my major. The students of that class were asked if they would be interested in tutoring. Always looking for a good hustle, I said yes, I was always in the Math Lounge (yes, there was a math lounge, and it was awesome!) anyway, may as well get paid.

I think in the two years of having that job, I tutored approximately 5 people. So it was another job where I got paid to do my homework and hang out with my math major friends.

Pay Rate: $11 per hour

11. Sales Associate at Victoria’s Secret

My second summer in college I stayed in Massachusetts and got a job at the mall working as a sales associate at Victoria’s Secret. I mostly worked in the fitting rooms, measuring for bra sizes and helping figure out what bra would work best.

BTW if you are ever shopping at Victoria’s Secret, go straight to the fitting room. They will measure you, and they have bra boxes, which have the top 6-8 bras in every size. So you can try them on and then go on the sales floor and pick the bra and color etc. and you aren’t going back and forth.

To this day friends and family ask me to help them measure to see what size bra they should be wearing. Guys that summer always thought it was cool/sexy that I worked there until I explained that I got flashed by 70-year-old women on a daily basis. Guys stopped being dumb about it after I explained that.

Pay Rate: Minimum wage, except Sundays because in Massachusetts you got paid time and a half.

12. Resident Assistant

After working for ResLife as a security desk attendant for two years, my senior year I also worked as a Resident Assistant. It definitely had its ups and downs, and I was glad when I graduated. Probably one of the biggest pains was that my school was a dry campus completely. This meant no drinking, even if you were 21.

Note to all college students, so long as you aren’t being unsafe, obvious, or throwing it in the RA’s face, the RA will likely let it slide. I cannot tell you how many times I would have preferred to be taking a nap rather than filling out paperwork from a resident being dumb.

Besides busting residents when necessary, I also got to be a human smoke detector one time and break the rules by exploring the underground tunnels with a fellow RA. The song below came out when I was an RA, and it was hilarious, still is.

Pay Rate: Not nearly enough, somewhere between $100-$200 per week I think and free parking

13. Painter

Different from Artist above. The summer after I graduated college, I worked on my college campus as part of a paint crew. We would touch up dorms, classrooms, and offices. However, we were very efficient and usually ran out of work. So then we were instructed to stay out of sight and just continue to look busy. I got paid to do my summer reading before law school started.

Pay Rate: $8 an hour?

14. Law Clerk

My second year of law school I got a job at a business immigration and civil litigation law firm. Being a law clerk means you do all the grunt work. It’s great practice for being a lawyer. You draft briefs, memos, do research, and then the lawyer looks it all over and signs their name.

While it was a great learning experience, I didn’t have any interest in that area of law, but the job market was tough. I sometimes wonder if I’d gotten to work in an area I cared about, if I would have enjoyed being a lawyer a bit more.

Pay Rate: $10 per hour and then a raise to $12 per hour (BTW clients were charged $80 per hour for my work)

15. Merchandiser at Macy’s

Not sure if that title is a real word, but it meant that I got up really early to be at work around 5 a.m. to put new merchandise out on the floor and set up new displays. While it was really early, it meant that I didn’t have to interact with customers.

During Black Friday it meant keeping the floor stocked and cleaning up after the mayhem. I kid you not; I went in around 2:00 a.m. on Black Friday (store had opened on Thanksgiving) and there was a mannequin that had been taken apart, we later found the dress it had been wearing. Someone had violated a mannequin and then didn’t bother to buy the dress. People be crazy.

Pay Rate: Minimum wage

16. Foto Finish Race Worker

This was a gig I found on Craigslist when I was visiting my family in Virginia Beach. All I had to do was at the end of the race (it was the Rock N’ Roll Half Marathon) was direct runners to where they could have their picture taken. My voice was hoarse by the end of the day, but it was really fun gig overall.

Pay Rate: $75

17. Pet/House Sitting

Growing up and as an adult, I have looked after people’s pets, usually dogs. It meant going over to their houses bringing in their mail, watering plants, and taking care of the animals. I love when I get these kind of gigs, because it’s super easy.

Pay Rate: $10 – $30 per day

18. Website Testing/Review

I have and occasionally still do complete website reviews for User Testing. You just have to sign up, and then they will notify you when there is a test available. Then you log on and usually answer a question or two to see if you are a qualified candidate for the test. Then you take the test and get paid.

Pay Rate: Varies, but usually $10 per test.

19. Sold/Flipped Books

I first started selling books I had no intention of rereading a few years ago, then I kicked things into high gear when I was getting ready to move from Massachusetts to North Carolina. Recently I flipped some books that I got at the thrift store.

Thrift stores are great places to buy books to flip because they usually cost $0.50 – $1 each and can be sold for a few dollars. I wrote more about selling books in my Easy Things to Sell to Make Extra Money post.

Pay Rate: Varies, I use BookScouter to find the best rate.

20. Sold DVDs

Again I started doing this a while ago, it sort of coincided with my implementing a more minimalist lifestyle. It really got kicked up a notch when I was getting ready to move. I still sell some of my DVDs from time to time just to clear some clutter.

Pay Rate: Varies, I usually got the best rates from FYE

21. Document Review

During a merger or lawsuit there is usually a ton of paperwork that needs to be reviewed, either for discovery or to ensure proper notification to all parties. Often extra attorneys and/or paralegals (some states only allow lawyers to do doc review) will be brought on to review the documents. It’s boring and tedious, but the pay in much better than minimum wage. After taking the bar, I got a document review job, reviewing documents to help finalize a big merger.

Pay Rate: $25 per hour

22. Stadium Security

I worked on a “roam team” during NFL games. Our job was to walk (occasionally run) a specific section of the stadium. We’d respond to fights, assist police in keeping patrons from walking into a situation, kick out the drunks, and check the area including restrooms before and after games to make sure everyone’s cleared. If we were bored, we’d go yell at smokers because there is no smoking in the stadium.

It was our job to make sure the rules of the stadium were being followed. Overall it was a pretty fun job. Unfortunately, I ended up with some knee injuries (not from work) that make continuing the work really difficult. If you want to know more about working at a stadium, you can read my guest post about it over on Budgets Are Sexy.

Pay Rate: A little under $100 per game + meal + parking

23. Contract Attorney

As you may know, I picked up some work drafting briefs on the side to pay off my credit card debt. A friend’s firm was overwhelmed with work and paid me to review documents and draft briefs. Each brief took 5-8 hours; it was similar to the work I did as a law clerk. I would review the documents, draft the brief and then send it back to the firm for one of their attorneys to review and sign.

Pay Rate: $300 per brief

24. Solutions Consultant

Until very recently I worked as a Solutions Consultant for a legal research and litigation solutions company. While I did a lot of different things, a lot of it boiled down to teaching how to best conduct legal research on our company’s platform and conducting sales demonstrations. It utilized my legal knowledge and gave me tons of experience presenting to audiences of all sizes (there is nothing like presenting to a room full of judges to hone your public speaking skills).

When I initially started, I had a salary and the opportunity to earn some commission when I discovered upsell opportunities that closed. Though they changed the pay structure about half-way through my time there to just have a salary, though every company utilizing solutions consultants is different.

This job also required travel and the amount of travel I did, kept increasing as time went on. When I started I covered three small states; I eventually moved to a new location covering three larger states. By the end, I was covering the majority of 5 large states. I was never home and had no life. I’m really grateful for everything I learned in this role but was also very glad to move on when I got laid off.

Pay Rate: varies by location and company $55k – $76k per year

25. Affiliate Marketing

Affiliate marketing is basically providing refer-a-friend links on a website or social media. The company you referred your friend to says thanks with a small amount of money. It is one strategy I use to help keep this site going. Though I never share links to anything I haven’t’ personally used and loved.

Right now I don’t make tons of money through affiliate marketing (some bloggers make upwards of $50k a month from affiliate marketing), but it helps with the costs of running the site. I’m working to increase my affiliate income by implementing strategies I learned from the Making Sense of Affiliate Marketing course.

Pay Rate: varies by company $0.20 – $100 per referral

26. Driving for Lyft

I started driving for Lyft in August 2016. When I started it was just to check it out for a potential blog post; I ended up really enjoying it, though. Admittedly I don’t drive for Lyft nearly as often anymore; I almost always drive when they are offering guaranteed rates. They do this on nights that are likely to be extra busy. Basically, they guarantee you’ll earn a certain amount per hour even if you don’t end up with too many rides. On Halloween they offered $40 per hour, I ended up driving for two hours, I only had 3-4 rides but still made close to $100.

Get started driving for Lyft today.

Pay Rate: Varies $15-$45 per hour

27. Sold Stuff on Craigslist/Facebook Yard Sale Groups

This is something I did a lot when I first started implementing a minimalist lifestyle, back then, I had a lot of stuff to get rid of, nowadays not so much. Though before donating something I always try to see if I can sell it on Craigslist or Facebook.

Pay Rate: Depends on what you are selling, the most expensive sale I ever had was when I sold a kiln for $1000+

28. Freelance Writing

I had dabbled in freelance writing for a while when I decided to get serious in April/May 2016 and took 30 Days or Less to Freelance Writing Success. I started to really focus on finding freelance jobs in July and as a side hustle earned $3k on the side in 6 months. This was all while traveling almost every week. It is now my full-time job. In January I made over $2k, check out my latest income report to learn more.

Related: Side Hustle Series: Get Started Freelance Writing

Pay Rate: varies by client, typically $0.10 – $0.40 per word

29. Selling Stuff on Etsy

I started an Etsy store in early 2014, after getting a sewing machine for Christmas the year before, I started making bags and loved it. Ultimately I had no clue what I was doing selling on Etsy and didn’t do a good job of promoting my store.

While I did have some sales (including one to Paris), I decided to shut down the store in early 2016 because I was no longer bothering to keep the store up to date. Having the Etsy store even motivated me to sell at a craft fair that was unsuccessful.

Pay Rate: In total, I probably made a few hundred dollars.

30. Selling Courses

Back when this site was Friday Night Shenanigans, I sold a few different courses using Teachable and did make a little bit of money. However, since going through a rebranding, I’ve taken down the courses to rethink them and what I want to offer in the future.

Currently, the only course I have available is an email course, Money 101 is FREE and is designed to help you get a handle on basic personal finance concepts.

Pay Rate: $10 – $97 per course sale

31. Proofreading/Editing

Having freelanced as a writer for a while and running this site, I’ve branched out into offering proofreading and editing services. I’ve only had a few clients so far, but I find I really enjoy the work. It’s nice to do something other than writing sometimes.

Pay Rate: $2-$4 per page

What about you?

Those are all the jobs I can remember doing; it’s possible there is a gig out there I’ve forgotten about but, 31 jobs/money making gigs in 15 years is, in my opinion, plenty. What ways have you made money? Have you thought about how the collection of your experiences has influenced the work you do now? 

Hustle tools & resources i recommend

GRAMMARLY (BE A BETTER WRITER) I use Grammarly as a second pair of eyes to help me clean up and proofread my writing/typing. The best part is that it is free to use. You can install an extension on your web browser and it will check any writing you do online. While there is a paid premium version, you can get by with the free version for a long time. I only recently upgraded. If you want to know more about Grammarly, you can read my review.

30 Days or Less to Freelance Writing Success (to start freelance writing) Personally, I found the course, 30 Days or Less to Freelance Writing Success extremely helpful to get me started with freelance writing. It breaks down everything you need to do, step by step, so that by the time you get to pitching for jobs, you are prepared and successful. For me, the course paid for itself when I got my first freelance writing job. I now earn between $2,000 - $4,000 per month (check out my income reports) with freelance writing.

Lyft (to make money driving) Driving with Lyft is a great way to earn some extra cash. I love how easy it is to just turn on an app when I feel like driving and make some money. I wrote an entire post about driving for Lyft. It includes what you can expect during the application process, what it's like to actually drive and the many perks of driving with Lyft.  Get started driving for Lyft.

BookScouter (to make money selling your books) BookScouter allows you to enter your book's ISBN number and it compares the prices it would get from various sellers, making sure you fetch the most money possible for selling that book.

Contena (for Finding Freelance Writing Jobs) I used Contena when I was working my 9-5 and getting started freelance writing. It made it easy to find freelance writing jobs to pitch. While it's not a cheap Contena is definitely worth it if you don't have a ton of time to spend looking for freelance writing jobs to pitch. Contena pulls together pretty much all of the available freelance writing jobs out there into one place and will  notify you via email of ones in your niche. 

Rover (make money hanging with dogs) Rover is a website that connects pet sitters with pet owners. I did a video tutorial on how to use the site as pet sitter and the accompanying post goes over what makes Rover a great side hustle. Read and watch the post or get started petsitting.

Quickbooks Self-Employed (for managing Hustle Money) I use the QuickBooks Self Employed (BTW you'll get 50% off with my link) app to calculate my quarterly taxes so I know how much to set aside. Though keep in mind it only keeps up with federal taxes and you will need to set aside an additional amount for your state taxes. 

About the Author Elizabeth Stapleton

Elizabeth Stapleton is the founder and voice behind Less Debt More Wine and ElizabethStapleton.com. She is a Pinterest marketer, online entrepreneur, and recovering attorney whose writing has been featured on Entrepreneur.com, The Huffington Post, The Penny Hoarder, Budgets Are Sexy, Credit Sesame, and Magnify Money. Additionally, she has been quoted in articles on Business Insider, Student Loan Hero, and Nerd Wallet.

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