How I've Made Money in My Life
By Steve Gillman - 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
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
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: http://www.everywaytomakemoney.com/coin-roll-hunting.html
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
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
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
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
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
Convention Host - This was one of my temp-agency
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
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
31 Years Old
Home-Based Food Vendor - I set up a "grocery
store" in a closet for my room renters, and sold soda as
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
34 Years Old
Newspaper Advertising Inserter - I was paid
$100 every Saturday night to stuff the inserts into the Sunday
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
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
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
45 Years Old
Overseas Book Sales - A Japanese company paid
me for the rights to published "Secrets of Lucky People"
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, unusualwaystomakemoney.com,
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
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
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: http://www.everywaytomakemoney.com/surrogate-juror.html
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
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.