Here’s How I Made $100K on the Side in 5 Years and Paid Off My Mortgage

side hustle
Photo from Derek Sall/Facebook

I was 25 years old. I had no savings, I had $18,000 in student loan debt, and I was earning just $33,000 a year in an expensive city. This was not how I pictured my life.

With a 3.7 GPA earning a Bachelor’s in Finance, shouldn’t I have been earning at least $70,000 at a prestigious bank somewhere? My millennial mindset was soon corrected when my first job involved proofing prices in catalogs — something I felt a chimp could do.

After just a few months of this mind-numbing job, I realized something had to give. I wanted out. I wanted something better. When all you can afford at the end of the day is a peanut butter and jelly sandwich, it’s a pretty clear sign you’re doing something wrong.

I needed more money, but I didn’t have the corporate experience to land a decent job (whoever decided that an entry-level position requires three years of experience… I have a bone to pick with you).

That’s when I decided to find a whole other avenue of income: side hustles. And I’ve never looked back.

1. Blogging

I knew that starting a website wasn’t going to make me much money initially, but I figured it was worth a try for a few months or so. Since at the time I was wasting my personal finance knowledge  on catalog proofing, I decided to start a personal finance blog called Life And My Finances.

In the first six months, I made a whopping $5. Literally pennies a day.

It was demoralizing. I knew other bloggers out there were raking in thousands of dollars a month, and my earnings were bupkis. Any sane person would have quit… but I’m sure glad I didn’t.

Over the course of the next six months, I continued writing and honing my craft — and earned more than $10,000. Since then, I’ve earned at least $1,000 a month.

How to try it for yourself:

  • To start your own blog, you’ll first need to sign up with a hosting company. Don’t get scared off! This isn’t as hard as it seems.
  • Be sure to choose a topic you find interesting, since you’ll likely write for many months without pay.
  • Choose a topic that will actually earn you money. Some of the top-earning blogs out there relate to:

    • Money
    • DIY projects
    • Health and fitness
    • Mommy wisdom

2. Freelance Writing

While my blog was sucking wind for those first six months, I quickly discovered I could generate traffic to my site and get paid for writing articles for other well-known sites.

At first, I had to offer my services for free. Then, once I built up a portfolio of articles on other sites, I could use these as fuel in my pitch for getting paid.

On average, I earned $25 per article (roughly 3 cents a word), which helped me bring home a few thousand bucks a year. Today, it’s not uncommon to earn $50 per article once you become a little more seasoned.

How to try it for yourself:

  • Start by building a long list of well-known blogs (I use the Alexa Toolbar to quickly identify popular pages — the lower the number, the better). Note their web address, the owners’ names and their email addresses. No idea where to start? Here’s a list of sites that pay $50 per article, sorted by topic.
  • Go through the list from top to bottom. Let them know you’re a new blogger who’d love to write a post for their site. Pitch them three or four relevant article ideas.
  • If they’re interested, write the best article of your life. This way they won’t hesitate to pay you and you’ll likely get tons of visitors to your site from the post.

3. Managing and Selling Display Advertising

In the good ol’ days (before my site was even any good), companies would offer to pay me $500 per year to display a simple ad in my site’s sidebar. I got five or six of these offers each month.

Money was good and life was easy. But, of course, that gravy train couldn’t last forever…

Today, ads are more difficult to come by and almost all blog owners need to rely on advertising agents, ranging from private individuals to larger entities like Link Vehicle, to send profitable deals their way.

At the three-year mark or so, I had a pretty solid list of advertising companies that wanted me to connect them with other bloggers.

It was a simple operation. I emailed my blogger buddies and told them I could help them make money. They’d keep 80% of the deal and I’d keep the other 20%.

Absolutely no one scoffed at this, and I suddenly became an advertising manager, earning roughly $2,000 a year with very little effort.

How to try it for yourself:

  • Get established and start making money through your site.
  • Keep a thorough list of companies that contact you about advertising.
  • Once you develop a list of 100 companies or more, start reaching out to other websites with ad deals for them to consider. Take your cut and start earning money!

4. Building and Selling Websites

Once you go through the pains of building your first website, doing it a second time is no big deal. Not only can you build it faster, but you can also build it better.

Almost immediately after I discovered that blogging could be insanely profitable, I started blog No. 2 and blog No. 3.

Each of these sites earned me an additional $500 a month for about a year, and then I sold them for $1,500 apiece when I wanted to move onto other things. It was a pretty easy way to earn an additional $10,000 on the side.

How to try it for yourself:

  • Build a .com site (these are taken way more seriously than .me, .biz, or even .net). Choose a name that clearly defines the site. If your site will be about passive income, put that in the name and URL!
  • Don’t sell your site on a website-selling page. Sell it to a fellow blogger. It will be far simpler, and you’ll earn more. Not sure how to do this? The trick is to start the friendship long before you want to sell a website. Comment on their site often, email them and praise them for their work. Don’t be disingenuous. Just be yourself!

5. Manual and Skilled Labor

You don’t have to be a writer or online whiz to make money. Another side hustle I worked involved simple manual labor. You just need to know where to look and how to get started.

When I was knocking out my debt, I came up with the business idea of an eco-friendly mowing service. This was basically me sweating my butt off while pushing around my reel mower (think 1950’s mowing).

I didn’t gain a ton of clients — in fact, one of them was my nephew… and another was my sister and her husband (talk about eating some humble pie) — but I still earned $25 an hour for each yard. Over the course of the summer, I pocketed a few hundred bucks.

If you’re interested in making thousands of dollars, look into businesses like:

  • Painting (interior or exterior)
  • Car repair
  • House cleaning
  • Moving services

How to try it for yourself:

  • Write down five solid skills
  • Rank them from high to low in terms of potential profits
  • Start spreading the word about your services through friends and family

Farewell, Debt. Hello, New Side Hustle!

Over the course of five years, I earned more than $100,000 with these side hustles. This income helped me pay off $18,000 in student debt and my entire mortgage.

Today, my wife and I live quite frugally and use the side income for real-estate investments.

But this isn’t about me — it’s about how working hard on the side can help you earn money to reach your own financial goals. What side hustle will you try?

Your Turn: How do you make money on the side? What side gigs have you tried?

This is a guest post from Derek Sall, an ordinary guy that stumbled into the extreme possibilities of side hustles. You can follow his journey at