How I've Made Money in My Life

By - November, 2013

I am 49 years-old at the moment, and as I write this I'm self-employed, attempting to make this internet publishing business pay the bills like it used to (revenue is down, but there are always new things to try). Writing about different ways to generate income and profit is just one of the things I do for our business. I also have websites on backpacking, meditation, real estate, and various other subjects.

Because of the money-related websites, a couple years back I was invited to write a book on weird ways to make money by Wiley and Sons Publishing, and received a nice advance. You can probably find a link to the Amazon page for the book somewhere on this page (yes, my marketing skills are weak, which made it especially nice to have great publishing company helping me out). The introduction to the book is the closest thing I have to an autobiography, but it still covers only a couple dozen jobs and businesses I have had. This page has a fuller list, but without the stories. Later I will come back and link the various one-line descriptions of jobs, businesses and investments here to pages where I explain them in more detail.

I decided to start at the beginning, so here are some of the approximately one-hundred ways I've made money, starting at the age of eight. I include my best guess as to my age when I started each job, business, investment or other money-making activity, but many of these overlap in time. For example, while working a ten-year stint at various positions in a casino, I also rented out rooms in my home, bought and sold real estate, had a rental home, and bought and sold used cars. Also, for this list I include any way I have tried to make money, whether the attempt succeeded or not (but I did make some money with all but two or three of these). Let's get started...

I Started These at Age...

8 Years Old

House Cleaner - My parents paid me to do various cleaning jobs.

9 Years Old

Exterminator - My brothers and I received a penny for each fly killed one summer week at our family's cabin.

10 Years Old

Freelance Chef - I sold meals to my brothers so they wouldn't have to

Street Vendor - We sold artistic creations made of things found on the beach, as well as lemonade and cookies.

11 Years Old

Arms Dealer - I gathered the spent paper wads in my brothers wars and sold them back to them in the heat of the battle.

Contract Laborer - I did my brothers chores for them for a fee.

12 Years Old

Carnival Game Operator - I ran carnival games that always had the odds rigged in my favor, and was able to take a good chunk of the money my brothers and their friends earned from paper routes.

Investor - I opened my first bank account (by myself -- you could do that then) with $105 that I had saved, most of it in coins.

13 Years Old

Gambler - I bet on anything with friends and family, but only when I calculated that the odds were in my favor.

Casino Operator - I dealt blackjack and arranged other games for my brothers and their friends to bet money on -- with the odds in my favor, of course.

Banker - I held money for my brothers and loaned them money for interest.

Basketball Free-Thrower - I made money betting against anyone who was a worse shot than me.

Candy Vendor - I snuck candy into class in a hollow book and a jacket with pockets inside, buying it in bulk and selling it for a 100% markup.

Scavenger - I scavenged usable items from neighbors' garbage and sold what I could.

14 Years Old

Pornography Seller - I discovered there were dirty magazines being thrown out regularly in newspaper recycling bins, so I brought them to school to sell.

Pawn Shop Operator - I took collateral for loans and sold the things if the loan wasn't repaid on time, with interest.

Coin Roll Hunter - My older brother and I learned to buy coin rolls from the bank and search them for valuable silver dimes and quarters. You can read my more recent take on coin roll hunting here:

15 Years Old

Numismatist - I collected rare coins, and bought and sold them.

16 Years Old

Day Laborer - I did any job anyone would pay me for, including cleaning, washing cars, and picking up dog poop from yards. The work funded a cross-country hitchhiking trip.

17 Years Old

Dishwasher - My first job for a regular employer was as a dishwasher for an Elias Brothers Big Boy restaurant.

Bus Boy - I was promoted from dishwasher to busboy after a couple weeks.

Food Preparation - I was promoted from busboy to food prep after a few more weeks.

Cook - I was promoted to cook eventually, and made enough money to fund a hitchhiking trip to Mexico at age seventeen.

18 Years Old

Firewood Seller - I helped cut, split and deliver firewood in Michigan's Upper Peninsula, where I lived in a cabin for a couple years.

Live-In Baby Sitter - I watched the kids while my friends worked or looked for work.

Evergreen Bough Collector - A friend and I read that wreath-makers bought evergreen boughs, but after cutting 300 pounds of them we realized that we were only going to make $2 per hour at best, so we quit and had a bonfire.

19 Years Old

Fast Food Worker - I worked at an Arby's Roast beef restaurant.

20 Years Old

Restaurant Manager - I was actually a shift manager and then the assistant manager at Arby's, in charge of hiring and scheduling.

Loan Shark - I loaned money at high interest to friends, coworkers, and a real estate agent.

Check Cashing Service - I cashed checks for coworkers for a few dollars each, until the bank told me they no longer wanted me to bring in seven or eight second-party checks at a time.

Gift Marketer - I sold gifts from a catalog and wholesale items I bought, and tried to get employers to buy them for employee Christmas bonuses.

Marketing Business - I set up a discount-card promotion with a local high school sports team (the students would sell the cards), but the deal fell apart.

21 Years Old

Earring Seller - I bought earrings wholesale and placed racks in area businesses on consignment.

Real Estate Investor - I bought a lot and sold it for a profit after a few weeks. I did this again a few years later (and again after only a few weeks).

22 Years Old

Repo Man - My brother had a towing business and did auto repossession, paying me to help him steal the cars in the middle of the night.

Pizza Delivery Driver - I worked for a local pizza place, doing deliveries and later as closing manager.

23 Years Old

Process Server - An insurance company that was getting into the process-serving business hired me to investigate, locate and serve papers to defendants in lawsuits.

Newspaper Delivery Driver - I bundled newspapers and delivered them to coin-operated boxes and other locations.

Futures Market Speculator - Although I made money on some of my trades, options on futures contracts turned out to be a good way to lose money.

24 Years Old

Demolition Man - My parents bought a property with a an old house on it that needed to be torn down, so I tore it down.

Rummage Sale Vendor - I ran rummage sales and sold scavenged goods, things I bought wholesale, and snacks.

Collection Agent - I worked as a debt-collector for a small company that handled accounts for doctors, banks and jails (inmates had to pay for the time they had spent there).

Blackjack Dealer - I worked for ten years (Two different times) as a blackjack dealer at the casino on the reservation of the Grand Traverse Band of Ottawa and Chippewa Indians.

Roulette Croupier - I was also a roulette dealer or "croupier" at various times.

25 Years Old

Poker Dealer - When the tribe built a newer, bigger casino I went back to work for them and added to poker dealing to my resume.

26 Years Old

Real Estate Agent - I got my real estate license, sold a handful of homes (and a couple vacant lots), and decided that I didn't like the work.

Landscaper - I worked for a real estate investor and others doing landscaping jobs.

Property Researcher - I worked for a real estate investor, locating land for sale.

Temporary Agency Worker - I did many different things working for Manpower, Incorporated, some of which are listed below.

Convention Host - This was one of my temp-agency jobs.

Factory Worker - I lasted all of three days assembling muffler brackets, although they tell me I was the fastest worker there.

27 Years Old

Can and Bottle Collector - I collected returnable cans and bottles for the ten-cent deposit. The break room at the casino netted me about $1,700 in a little over a year.

Landlord - I bought a mobile home on a small lot for $16,000, and rented it out for $365 per month.

House Renovator - I worked for an investor friend, cleaning and fixing up houses.

Construction Worker - I worked on restaurants and other projects doing whatever didn't require too much in the way of professional skills.

Sample Distributor - This was another temp-agency gig.

28 Years Old

Boarding House Operator - I rented out rooms in my home by the week.

Scrap Metal Recycler - I occasionally rounded up aluminum and other metals to sell.

29 Years Old

Poker Player - I played poker for small stakes during breaks at work (the casino), winning about $1,600 or so in a year.

Chess Player - I bet on chess games at work and during sessions I arranged at home, winning most of the time.

Chauffeur - I drove for a local attorney (my father) for $50 per day, so he could work while traveling.

30 Years Old

Used Car Dealer - I was a partner with others who bought and sold cars (I put up the money for half of the profit).

31 Years Old

Home-Based Food Vendor - I set up a "grocery store" in a closet for my room renters, and sold soda as well.

32 Years Old

Parking Rental Business - A couple times I had room-renters who had more than one car (or, in one case, a car and a jet ski), so I charged a weekly fee for the extra parking.

33 Years Old

Stock Trader - Using limit orders (when you automatically buy or sell only if at a certain price), I bought 100 shares of a stock for $12 and sold for $14, for a $200 profit -- and discovered this when I returned home from work. That got me excited enough to invest more and eventually lose a couple grand.

34 Years Old

Newspaper Advertising Inserter - I was paid $100 every Saturday night to stuff the inserts into the Sunday paper.

Restaurant Equipment Installer - I was hired through the temp agency to install restaurant equipment in a new Outback Steakhouse.

35 Years Old

Drywall Installer - I worked a few weeks doing drywall installation and finishing in an apartment building that was being constructed near my home.

Carpet Cleaner - I worked as a carpet cleaner for $8 per hour.

Mover - This was another job through the temporary agency, moving a business from one location to another.

36 Years Old

Banquet Set-Up Worker - I worked at a resort for several weeks setting up tables, chairs and such for conventions and other events.

Product Packager - The temp agency sent me to a direct-mail fulfillment center for a couple weeks.

Courier - You usually don't get paid cash as an overseas carrier, but the company I worked for did give me heavily-discounted tickets to Ecuador for bringing car parts there (in four suitcases) and a plane prop back to Miami. I also met my future wife while in Quito.

37 Years Old

Slumlord - I rented out a shed as a bedroom for $50 per week (it had cost me $240 to build with mostly used lumber).

38 Years Old

Postal Worker - After I got married to the love of my life at 37 years old I decided more income would be nice, so I worked for the U.S. Postal Service part-time and seasonally for a couple years, sorting mail.

Flagman - One day was enough for this company that didn't even provide radios (I had no idea when the last car had passed on this busy stretch of highway -- it was chaos).

Thrift Store Worker - The job only paid $7.25 per hour, but I did get dibs on some cool stuff, and really cheap.

Special Needs Supervisor - When we moved to a beautiful but depressed little mountain town in Montana I got one of the "good jobs" taking care of adults with developmental disabilities; it paid $7.50 per hour.

39 Years Old

Tagua Seller - My wife Ana and I brought figurines made of tagua (vegetable ivory from a type of palm tree) back from a trip to Ecuador, and sold them at craft shows and flea markets.

Wreath Maker - Ana and I made wreaths from wild grape vines (which I gathered from the woods) and plastic flowers, and sold them in various ways.

Walking Stick Carver - I sold a couple hundred walking sticks that I hand-carved.

40 Years Old

Flea Market Vendor - The summer of 2004 was spent driving around Michigan, camping in our van, and selling reconditioned Barbie Dolls, used stuffed animals, walking sticks and forty other things at flea markets.

Internet Marketer - By September of 2004 we had our first websites online.

Article Writer - By early 2005 I discovered that writing free-distribution articles was the best way to promote our websites and drive traffic to them. We started making $5 and then $10 per day from our sites.

41 Years Old

Internet Publisher - I started writing and selling e-books on our sites, and expanded the ranges of what we put online (eventually fifty websites in a dozen or more niches).

42 Years Old

E-Zine Publisher - I started the Brainpower Newsletter (still published weekly eight years later), Unusual Ways to Make Money, and other "e-zines" as another way to drive traffic to our websites and sell products.

43 Years Old

E-Book Author - I began to write e-books (primarily as PDFs) and sell them.

44 Years Old

Self-Published Paperback Author - I wrote and self-published the paperback version of "Secrets of Lucky People."

45 Years Old

Overseas Book Sales - A Japanese company paid me for the rights to published "Secrets of Lucky People" in Japan.

46 Years Old

Video Creator - My wife did most of the technical work for our videos, which we put on YouTube and monetized with Google ads. They still bring in a little revenue every month.

47 Years Old

Traditional Non-Fiction Author - A senior editor Wiley and Sons Publishing in New York found my website,, and paid me a nice advance to write "101 Weird Ways to Make Money," which was released in the summer of 2011. Wiley arranged for interviews on Fox News and other media outlets, something I was unable to do with my three self-published paperbacks.

48 Years Old

Sign Holder - After we moved to Florida I discovered that temp agencies paid less in nominal terms (and perhaps 50% less adjusted for inflation) than 22 years earlier. I stood in the sun and waved a sign. I wrote about that experience, and about sign-holding opportunities in general here:

Construction Site Cleaner - This was another temp agency assignment for minimum wage, but the client at least paid us for the full eight hours when we worked only 5 or 6.

Condo Flipper - We bought the condo above ours to rent out, and decided to sell it for a small profit instead.

Electric Tram Driver -In Pelican Bay in Naples, Florida) owners have electric trams to take them to private restaurants and bars on the beach, past the alligators and other wildlife. At 48 I was the youngest of over 60 drivers.

Survey Participant - I gave it my all to see if I could make anything with online surveys. It was fun, but not worthwhile.

Age 49

Security and Safety Officer - I transferred to security at Pelican Bay, which was more of a member services job, and would be pleasant if not for the outdoor work in the summer.

Handyman - I worked for a general contractor installing towel racks and window blinds and doing whatever else was necessary for his clients.

Painter - On other jobs for the same contractor I was a painter.

Surrogate Juror - I was paid $150 to spend a day hearing and judging an actual lawsuit before it went to trial. You can read about that here:

Craigslist Vendor - I just sold something we recieved for free and advertised for free on Craigslist, for $45. This is something I might do again (we just found a beautiful wood dining room table sitting by a dumpster -- it's in our home now).

A Few More Money-Makers That Didn't Make the List

Here are a few other things I've done to earn money. I do not recall how old I was the first time I did them, but these were all regular activities at various times earlier in life.

Snow Shoveling - I often did this over the years when I was younger, preferring to get paid by the job rather than by the hour (I was quick).

Leaf Raking - This is another of the many jobs I had when I was younger.

House Sitting - A few times I have been paid to watch a home for someone when they were out of town.

Dog Sitting - I have taken care of dogs for a daily fee.

Pet Grooming - I don't get anything except feline complaints for brushing our cats' hair and teeth, but I have been paid to wash dogs quite a few times in the past.

Scrabble Competitor - Although I've won a bit from others, my mother was my primary Scrabble opponent when she was alive. We always played for 5-cents per point, and I won by 100 points at least once in a while.

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